Antifungal drug
Encyclopedia
An antifungal medication is a medication
used to treat fungal infection
s such as athlete's foot
, ringworm, candidiasis
(thrush), serious systemic infections such as cryptococcal
meningitis
, and others. Such drugs are usually obtained by a doctor's prescription
or purchased over-the-counter.
group of drugs is known to have caused anaphylaxis
.
There are also many drug interactions. Patients must read in detail the enclosed data sheet(s) of the medicine. For example, the azole antifungals such as ketoconazole or itraconazole
can be both substrates and inhibitors of the P-glycoprotein
, which (among other functions) excretes toxins and drugs into the intestines. Azole antifungals also are both substrates and inhibitors of the cytochrome P450 family CYP3A4
, causing increased concentration when administering, for example, calcium channel blockers, immunosuppressants, chemotherapeutic drugs, benzodiazepines, tricyclic antidepressants, macrolides and SSRIs.
is a molecule with multiple conjugated double bonds
. A polyene antifungal is a macrocyclic polyene with a heavily hydroxylated region on the ring opposite the conjugated system. This makes polyene antifungals amphiphilic. The polyene antimycotic
s bind with sterol
s in the fungal cell membrane
, principally ergosterol
. This changes the transition temperature (Tg) of the cell membrane, thereby placing the membrane in a less fluid, more crystalline state. As a result, the cell's contents including monovalent ions (K+, Na+, H+, and Cl-), small organic molecules leak and this is regarded one of the primary ways cell dies. Animal cells contain cholesterol
instead of ergosterol and so they are much less susceptible. However, at therapeutic doses, some amphotericin B may bind to animal membrane cholesterol, increasing the risk of human toxicity. Amphotericin B is nephrotoxic when given intravenously. As a polyene's hydrophobic chain is shortened, its sterol binding activity is increased. Therefore, further reduction of the hydrophobic chain may result in it binding to cholesterol, making it toxic to animals.
Azole antifungal drugs inhibit the enzyme lanosterol 14 α-demethylase; the enzyme necessary to convert lanosterol
to ergosterol. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.
Albaconazole
s may be used for systemic fungal infections in immunocompromised patients, they inhibit the synthesis of glucan
in the cell wall
via the enzyme 1,3-β glucan synthase:
Echinocandins are poorly absorbed when administered orally. When administered by injection they will reach most tissues and organs with concentrations sufficient to treat localized and systemic fungal infections.
Horopito
(Pseudowintera colorata) leaf - contains the anti-fungal compound polygodial
Israeli researchers
at Tel Aviv University
's Department of Plant Sciences published a study in 2009 indicating that carnivorous plant
s like the Venus flytrap contain compounds that may be useful in providing a new class of anti-fungal drugs for use in humans, for fungal infections that are resistant to current anti-fungal drugs.
and humans are eukaryote
s. Thus fungal and human cell
s are similar at the molecular level. This makes it more difficult to find or design drugs that target fungi without affecting human cells. As a consequence, many antifungal drugs cause side-effects
. Some of these side-effects can be life-threatening if the drugs are not used properly.
) are often found in anti-dandruff
shampoo
s. The antifungal drugs inhibit the yeast Malassezia globosa which encourages seborrhoeic dermatitis
and tinea versicolor
.
Medication
A pharmaceutical drug, also referred to as medicine, medication or medicament, can be loosely defined as any chemical substance intended for use in the medical diagnosis, cure, treatment, or prevention of disease.- Classification :...
used to treat fungal infection
Infection
An infection is the colonization of a host organism by parasite species. Infecting parasites seek to use the host's resources to reproduce, often resulting in disease...
s such as athlete's foot
Athlete's foot
Athlete's foot is a fungal infection of the skin that causes scaling, flaking, and itch of affected areas. It is caused by fungi in the genus Trichophyton and is typically transmitted in moist areas where people walk barefoot, such as showers or bathhouses...
, ringworm, candidiasis
Candidiasis
Thrush redirects here. For the hoof infection see Thrush .Candidiasis or thrush is a fungal infection of any of the Candida species , of which Candida albicans is the most common...
(thrush), serious systemic infections such as cryptococcal
Cryptococcus
Cryptococcus is a genus of fungus. Species grow in culture as yeasts. The perfect forms or teleomorphs of Cryptococcus species are filamentous fungi in the genus Filobasidiella...
meningitis
Meningitis
Meningitis is inflammation of the protective membranes covering the brain and spinal cord, known collectively as the meninges. The inflammation may be caused by infection with viruses, bacteria, or other microorganisms, and less commonly by certain drugs...
, and others. Such drugs are usually obtained by a doctor's prescription
Prescription drug
A prescription medication is a licensed medicine that is regulated by legislation to require a medical prescription before it can be obtained. The term is used to distinguish it from over-the-counter drugs which can be obtained without a prescription...
or purchased over-the-counter.
Adverse effects
Apart from side-effects like liver-damage or affecting estrogen levels, many anti-fungal medicines can cause allergic reactions in people. For example, the azoleAzole
An azole is a class of five-membered nitrogen heterocyclic ring compounds containing at least one other non-carbon atom of either nitrogen, sulfur, or oxygen. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs with fewer...
group of drugs is known to have caused anaphylaxis
Anaphylaxis
Anaphylaxis is defined as "a serious allergic reaction that is rapid in onset and may cause death". It typically results in a number of symptoms including throat swelling, an itchy rash, and low blood pressure...
.
There are also many drug interactions. Patients must read in detail the enclosed data sheet(s) of the medicine. For example, the azole antifungals such as ketoconazole or itraconazole
Itraconazole
Itraconazole , invented in 1984, is a triazole antifungal agent that is prescribed to patients with fungal infections. The drug may be given orally or intravenously.-Medical uses:...
can be both substrates and inhibitors of the P-glycoprotein
P-glycoprotein
P-glycoprotein 1 also known as multidrug resistance protein 1 or ATP-binding cassette sub-family B member 1 or cluster of differentiation 243 is a glycoprotein that in humans is encoded by the ABCB1 gene...
, which (among other functions) excretes toxins and drugs into the intestines. Azole antifungals also are both substrates and inhibitors of the cytochrome P450 family CYP3A4
CYP3A4
Cytochrome P450 3A4 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. CYP3A4 is involved in the oxidation of the largest range of substrates of all the CYPs. As a result, CYP3A4 is present in...
, causing increased concentration when administering, for example, calcium channel blockers, immunosuppressants, chemotherapeutic drugs, benzodiazepines, tricyclic antidepressants, macrolides and SSRIs.
Polyene antifungals
A polyenePolyene
Polyenes are poly-unsaturated organic compounds that contain one or more sequences of alternating double and single carbon-carbon bonds. These double carbon-carbon bonds interact in a process known as conjugation, which results in an overall lower energy state of the molecule.Organic compounds with...
is a molecule with multiple conjugated double bonds
Conjugated system
In chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in compounds with alternating single and multiple bonds, which in general may lower the overall energy of the molecule and increase stability. Lone pairs, radicals or carbenium ions may be part of the...
. A polyene antifungal is a macrocyclic polyene with a heavily hydroxylated region on the ring opposite the conjugated system. This makes polyene antifungals amphiphilic. The polyene antimycotic
Polyene antimycotic
Polyene antimycotics, sometimes referred to as polyene antibiotics, are a class of antimicrobial polyene compounds that target fungi. These polyene antimycotics are typically obtained from some species of Streptomyces bacteria. The polyenes bind to ergosterol in the fungal cell membrane and...
s bind with sterol
Sterol
Sterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol...
s in the fungal cell membrane
Cell membrane
The cell membrane or plasma membrane is a biological membrane that separates the interior of all cells from the outside environment. The cell membrane is selectively permeable to ions and organic molecules and controls the movement of substances in and out of cells. It basically protects the cell...
, principally ergosterol
Ergosterol
Ergosterol is a sterol found in fungi, and named for ergot, a common name for the members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells...
. This changes the transition temperature (Tg) of the cell membrane, thereby placing the membrane in a less fluid, more crystalline state. As a result, the cell's contents including monovalent ions (K+, Na+, H+, and Cl-), small organic molecules leak and this is regarded one of the primary ways cell dies. Animal cells contain cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...
instead of ergosterol and so they are much less susceptible. However, at therapeutic doses, some amphotericin B may bind to animal membrane cholesterol, increasing the risk of human toxicity. Amphotericin B is nephrotoxic when given intravenously. As a polyene's hydrophobic chain is shortened, its sterol binding activity is increased. Therefore, further reduction of the hydrophobic chain may result in it binding to cholesterol, making it toxic to animals.
- NatamycinNatamycinNatamycin , also known as pimaricin, is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. Natamycin has a very low solubility in water, however, natamycin is effective at very low levels. Most molds have an MIC of...
- 33 Carbons, binds well to ergosterol - Rimocidin
- FilipinFilipinFilipin is a chemical compound. It was isolated by chemists at the Upjohn company in 1955 from the mycelium and culture filtrates of a previously unknown actinomycete, Streptomyces filipinensis, that was discovered in a soil sample collected in the Philippine Islands. Thus the name Filipin. The...
- 35 Carbons, binds to cholesterol (toxic) - NystatinNystatinNystatin is a polyene antifungal medication to which many molds and yeast infections are sensitive, including Candida. Due to its toxicity profile, there are currently no injectable formulations of this drug on the US market...
- Amphotericin BAmphotericin BAmphotericin B is a polyene antifungal drug, often used intravenously for systemic fungal infections...
- Candicin
- HamycinHamycinHamycin is a polyene antimycotic organic compound described in India. It is a heptaene antifungal compound rather similar in chemical structure to amphotericin B except that it has an additional aromatic group bonded to the molecule. When pure, hamycin is a yellow, powdered solid...
Imidazole, triazole, and thiazole antifungals
Azole antifungal drugs inhibit the enzyme lanosterol 14 α-demethylase; the enzyme necessary to convert lanosterol
Lanosterol
Lanosterol is a tetracyclic triterpenoid, which is the compound from which all steroids are derived.-Role in creation of steroids:Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields...
to ergosterol. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.
Imidazoles
- MiconazoleMiconazoleMiconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes...
(trade name Micatin or Daktarin) - KetoconazoleKetoconazoleKetoconazole is a synthetic antifungal drug used to prevent and treat fungal skin infections, especially in immunocompromised patients such as those with AIDS or those on chemotherapy. Ketoconazole is sold commercially as an anti-dandruff shampoo, topical cream, and oral tablet.Ketoconazole is...
(trade names Nizoral, Fungoral and Sebizole) - ClotrimazoleClotrimazoleClotrimazole is an antifungal medication commonly used in the treatment of fungal infections such as vaginal yeast infections, oral thrush, and ringworm...
(trade names Lotrimin, Lotrimin AF and Canesten) - EconazoleEconazoleEconazole nitrate is an antifungal medication of the imidazole class. It is used as a cream under the brand names Spectazole , Ecostatin , Pevaryl and Pevisone to treat skin infections such as athlete's foot, tinea, pityriasis versicolor, ringworm, and jock itch...
- OmoconazoleOmoconazoleOmoconazole is an azole antifungal drug....
- BifonazoleBifonazoleBifonazole is an imidazole antifungal drug. Bifonazole is marketed by Bayer under the trade mark CANESPOR in ointment form.-Mechanism of action :...
- ButoconazoleButoconazoleButoconazole is an imidazole antifungal used in gynecology....
- FenticonazoleFenticonazoleFenticonazole is an azole antifungal drug, used locally as the nitrate in the treatment of vulvovaginal candidiasis.Antimicrobial Action...
- IsoconazoleIsoconazoleIsoconazole is an azole antifungal drug. Nigerian and British medical researchers found that for foot and vaginal infections, isoconazole has a similar effectiveness to clotrimazole....
- OxiconazoleOxiconazoleOxiconazole nitrate is an antifungal medication typically administered in a cream or lotion to treat skin infections such as athlete's foot, jock itch and ringworm...
- SertaconazoleSertaconazoleSertaconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream to treat skin infections such as athlete's foot....
(trade name Ertaczo) - SulconazoleSulconazoleSulconazole nitrate is an antifungal medication of the imidazole class. It is available as a cream or solution to treat skin infections such as athlete's foot, ringworm, jock itch, and sun fungus....
- TioconazoleTioconazoleTioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names. Tioconazole ointments serve to treat women's vaginal yeast infections...
Triazoles
- FluconazoleFluconazoleFluconazole is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol. It is commonly marketed under the trade...
- ItraconazoleItraconazoleItraconazole , invented in 1984, is a triazole antifungal agent that is prescribed to patients with fungal infections. The drug may be given orally or intravenously.-Medical uses:...
- IsavuconazoleIsavuconazoleIsavuconazole is a triazole antifungal. Its prodrug, Isavuconazonium sulfate is currently in Phase III clinical trials....
- RavuconazoleRavuconazoleRavuconazole is a potent triazole antifungal, being developed by Bristol-Myers Squibb, that is currently in phase I/II clinical trials. . The drug has a shown to have a similar spectrum of activity to voriconazole, with an increased half-life. However, ravuconazole has limited activity against...
- PosaconazolePosaconazolePosaconazole is a triazole antifungal drug.Posaconazole is marketed in the United States, the European Union, and in other countries by Schering-Plough under the trade name Noxafil...
- VoriconazoleVoriconazoleVoriconazole is a triazole antifungal medication that is generally used to treat serious, invasive fungal infections. These are generally seen in patients who are immunocompromised, and include invasive candidiasis, invasive aspergillosis, and certain emerging fungal infections.-Invasive...
- TerconazoleTerconazoleTerconazole is an anti-fungal medication, primarily used to treat vaginal fungal infections.-References:*...
Albaconazole
Allylamines
Allylamines inhibit squalene epoxidase, another enzyme required for ergosterol synthesis:- TerbinafineTerbinafineTerbinafine hydrochloride is a...
(trade name Lamisil) - NaftifineNaftifineNaftifine is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis ....
(trade name Naftin) - ButenafineButenafineButenafine hydrochloride is a synthetic benzylamine antifungal, marketed under the trade names Mentax, Butop and is the active ingredient in Schering-Plough's Lotrimin Ultra. It is structurally related to synthetic allylamine antifungals such as terbinafine.-Pharmacology:Butenafine hydrochloride...
(trade name Lotrimin Ultra)
Echinocandins
EchinocandinEchinocandin
Echinocandins are antifungal drugs that inhibit the synthesis of glucan in the cell wall, probably via noncompetitive inhibition of the enzyme 1,3-β glucan synthase and are thus called penicillin of antifungals . Beta glucans are polymers which, linked in their tens of thousands, make up cell wall...
s may be used for systemic fungal infections in immunocompromised patients, they inhibit the synthesis of glucan
Glucan
A glucan molecule is a polysaccharide of D-glucose monomers linked by glycosidic bonds.Many beta-glucans are medically important.-Types:The following are glucans:-Alpha:...
in the cell wall
Cell wall
The cell wall is the tough, usually flexible but sometimes fairly rigid layer that surrounds some types of cells. It is located outside the cell membrane and provides these cells with structural support and protection, and also acts as a filtering mechanism. A major function of the cell wall is to...
via the enzyme 1,3-β glucan synthase:
- AnidulafunginAnidulafunginAnidulafungin or Eraxis is an antifungal drug originally manufactured and submitted for FDA approval by Vicuron Pharmaceuticals. Pfizer acquired the drug upon its acquisition of Vicuron in the fall of 2005. Pfizer gained approval by the Food and Drug Administration on February 21, 2006; it was...
- CaspofunginCaspofunginCaspofungin is an antifungal drug, the first of a new class termed the echinocandins from Merck & Co., Inc. It shows activity against infections with Aspergillus and Candida, and works by inhibiting the enzyme β-D-Glucan synthase and thereby disturbing the integrity of the fungal cell wall...
- Micafungin
Echinocandins are poorly absorbed when administered orally. When administered by injection they will reach most tissues and organs with concentrations sufficient to treat localized and systemic fungal infections.
Others
- PolygodialPolygodialPolygodial is an active constituent of Dorrigo Pepper, Mountain Pepper, Horopito, Canelo, Paracress and Water-pepper.Chemically it is a drimane-type sesquiterpene dialdehyde of formula C15H22O2.It elicits a warm and pungent flavour....
- strong and fast-acting in-vitro antifungal activity against Candida albicansCandida albicansCandida albicans is a diploid fungus that grows both as yeast and filamentous cells and a causal agent of opportunistic oral and genital infections in humans. Systemic fungal infections including those by C...
. - Benzoic acidBenzoic acidBenzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...
- has antifugal properties but must be combined with a keratolyticKeratolyticKeratolytic therapy is treatment to remove warts and other lesions in which the epidermis produces excess skin. In this therapy, acid medicine, such as salicylic acid is put on the lesion. Keratolytic therapy thins the skin on and around the lesion. It causes the outer layer of the skin to loosen...
agent such as in Whitfield's OintmentWhitfield's OintmentWhitfield's Ointment is salicylic acid and benzoic acid in a suitable base, such as lanolin or vaseline.The original ointment contains 3 % salicylic acid and 6 % benzoic acid, but other ratios are also used.... - Ciclopirox - (ciclopirox olamine), most useful against Tinea versicolour
- TolnaftateTolnaftateTolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin and Odor Eaters . Other brands are Absorbine, Aftate,...
(trade names Tinactin, Desenex and Aftate) - Undecylenic acidUndecylenic acidUndecylenic acid is an organic unsaturated fatty acid derived from castor oil. It is the common name of the 10-undecenoic acid, . It is used in the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas...
- an unsaturatedSaturation (chemistry)In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...
fatty acidFatty acidIn chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...
derived from natural castor oilCastor oilCastor oil is a vegetable oil obtained from the castor bean . Castor oil is a colorless to very pale yellow liquid with mild or no odor or taste. Its boiling point is and its density is 961 kg/m3...
; fungistatic as well as anti-bacterial and anti-viral - FlucytosineFlucytosineFlucytosine, or 5-fluorocytosine, a fluorinated pyrimidine analogue, is a synthetic antimycotic drug.It is structurally related to the cytostatic fluorouracil and to floxuridine. It is available in oral and in some countries also in injectable form. A common brand name is Ancobon. Flucytosine was...
or 5-fluorocytosine - an antimetaboliteAntimetaboliteAn antimetabolite is a chemical that inhibits the use of a metabolite, which is another chemical that is part of normal metabolism. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolates that interfere with the use of folic acid... - GriseofulvinGriseofulvinGriseofulvin is an antifungal drug that is administered orally. It is used both in animals and in humans, to treat fungal infections of the skin and nails...
- binds to polymerPolymerA polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...
ized microtubuleMicrotubuleMicrotubules are a component of the cytoskeleton. These rope-like polymers of tubulin can grow as long as 25 micrometers and are highly dynamic. The outer diameter of microtubule is about 25 nm. Microtubules are important for maintaining cell structure, providing platforms for intracellular...
s and inhibits fungal mitosisMitosisMitosis is the process by which a eukaryotic cell separates the chromosomes in its cell nucleus into two identical sets, in two separate nuclei. It is generally followed immediately by cytokinesis, which divides the nuclei, cytoplasm, organelles and cell membrane into two cells containing roughly... - HaloproginHaloproginHaloprogin is an antifungal drug used to treat athlete's foot and other fungal infections. It is marketed in creams under the trade names Halotex, Mycanden, Mycilan, and Polik.-Action:...
- discontinued due to the emergence of more modern antifungals with fewer side effects - Sodium bicarbonateSodium bicarbonateSodium bicarbonate or sodium hydrogen carbonate is the chemical compound with the formula Na HCO3. Sodium bicarbonate is a white solid that is crystalline but often appears as a fine powder. It has a slightly salty, alkaline taste resembling that of washing soda . The natural mineral form is...
(NaHCO3) - shown effective against green mold on citrus under refrigeration and powdery mildew on rose plants
Alternatives
Research conducted in 1996 indicated that the following substances or essential oils had anti-fungal properties:- Allicin - created from crushing garlic
- Tea tree oilTea tree oilTea tree oil, or melaleuca oil, is a pale yellow colour to nearly clear essential oil with a fresh camphoraceous odor. It is taken from the leaves of the Melaleuca alternifolia, which is native to the northeast coast of New South Wales, Australia...
- ISO 4730 ("Oil of Melaleuca, Terpinen-4-ol type") - Citronella oilCitronella oilCitronella oil is one of the essential oils obtained from the leaves and stems of different species of Cymbopogon. The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol and geraniol...
- obtained from the leaves and stems of different species of CymbopogonCymbopogonCymbopogon is a genus of about 55 species of grasses, native to warm temperate and tropical regions of the Old World and Oceania. It is a tall perennial grass...
(Lemon grass) - IodineIodineIodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
- Lugol's iodineLugol's iodineLugol's iodine, also known as Lugol's solution, first made in 1829, is a solution of elemental iodine and potassium iodide in water, named after the French physician J.G.A. Lugol. Lugol's iodine solution is often used as an antiseptic and disinfectant, for emergency disinfection of drinking water,... - olive leafOlive leafOlive leaf is the leaf of the olive tree . While olive oil is well known for its flavor and health benefits, the leaf has been used medicinally in various times and places. Natural olive leaf and olive leaf extracts , are now marketed as an anti-aging, immunostimulator and an antibiotic...
- orange oilOrange oilOrange oil is an essential oil produced by cells inside the rind of an orange fruit. In contrast to most essential oils, it is extracted as a by-product of orange juice production by centrifugation, producing a cold-pressed oil...
- palmarosa oilCymbopogon martiniiCymbopogon martinii is a species of grass in the lemon grass genus best known by the common name palmarosa. Other common names include Indian geranium and rosha or rosha grass. This perennial grass is native to southeast Asia, especially India , and it is cultivated for its oil...
- patchouliPatchouliPatchouli is a species from the genus Pogostemon and a bushy herb of the mint family, with erect stems, reaching two or three feet in height and bearing small, pale pink-white flowers...
- lemon myrtle
- Neem Seed Oil
- Coconut OilCoconut oilCoconut oil is an edible oil extracted from the kernel or meat of matured coconuts harvested from the coconut palm . Throughout the tropical world, it has provided the primary source of fat in the diets of millions of people for generations. It has various applications in food, medicine, and industry...
- medium chain triglycerideTriglycerideA triglyceride is an ester derived from glycerol and three fatty acids. There are many triglycerides, depending on the oil source, some are highly unsaturated, some less so....
s in the oil have antifungal activities - ZincZincZinc , or spelter , is a metallic chemical element; it has the symbol Zn and atomic number 30. It is the first element in group 12 of the periodic table. Zinc is, in some respects, chemically similar to magnesium, because its ion is of similar size and its only common oxidation state is +2...
- in dietary supplements or natural food sources, including pumpkin seeds and chick peas - SeleniumSeleniumSelenium is a chemical element with atomic number 34, chemical symbol Se, and an atomic mass of 78.96. It is a nonmetal, whose properties are intermediate between those of adjacent chalcogen elements sulfur and tellurium...
- in dietary supplements or natural food sources, particularly Brazil nuts
Horopito
Horopito
Horopito may refer to:*Horopito, the name of two plant species in the Pseudowintera genus in the Māori language*Horopito, New Zealand, a location in the North Island of New Zealand...
(Pseudowintera colorata) leaf - contains the anti-fungal compound polygodial
Polygodial
Polygodial is an active constituent of Dorrigo Pepper, Mountain Pepper, Horopito, Canelo, Paracress and Water-pepper.Chemically it is a drimane-type sesquiterpene dialdehyde of formula C15H22O2.It elicits a warm and pungent flavour....
Israeli researchers
Science and technology in Israel
Science and technology in Israel is one of the country's most developed sectors. The percentage of Israelis engaged in scientific and technological inquiry, and the amount spent on research and development in relation to gross domestic product , is amongst the highest in the world...
at Tel Aviv University
Tel Aviv University
Tel Aviv University is a public university located in Ramat Aviv, Tel Aviv, Israel. With nearly 30,000 students, TAU is Israel's largest university.-History:...
's Department of Plant Sciences published a study in 2009 indicating that carnivorous plant
Carnivorous plant
Carnivorous plants are plants that derive some or most of their nutrients from trapping and consuming animals or protozoans, typically insects and other arthropods. Carnivorous plants appear adapted to grow in places where the soil is thin or poor in nutrients, especially nitrogen, such as acidic...
s like the Venus flytrap contain compounds that may be useful in providing a new class of anti-fungal drugs for use in humans, for fungal infections that are resistant to current anti-fungal drugs.
Mechanism of action
Antifungals work by exploiting differences between mammalian and fungal cells to kill the fungal organism without dangerous effects on the host. Unlike bacteria, both fungiFungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...
and humans are eukaryote
Eukaryote
A eukaryote is an organism whose cells contain complex structures enclosed within membranes. Eukaryotes may more formally be referred to as the taxon Eukarya or Eukaryota. The defining membrane-bound structure that sets eukaryotic cells apart from prokaryotic cells is the nucleus, or nuclear...
s. Thus fungal and human cell
Cell (biology)
The cell is the basic structural and functional unit of all known living organisms. It is the smallest unit of life that is classified as a living thing, and is often called the building block of life. The Alberts text discusses how the "cellular building blocks" move to shape developing embryos....
s are similar at the molecular level. This makes it more difficult to find or design drugs that target fungi without affecting human cells. As a consequence, many antifungal drugs cause side-effects
Adverse effect (medicine)
In medicine, an adverse effect is a harmful and undesired effect resulting from a medication or other intervention such as surgery.An adverse effect may be termed a "side effect", when judged to be secondary to a main or therapeutic effect. If it results from an unsuitable or incorrect dosage or...
. Some of these side-effects can be life-threatening if the drugs are not used properly.
Anti-dandruff shampoos
Antifungal agents (such as ketoconazoleKetoconazole
Ketoconazole is a synthetic antifungal drug used to prevent and treat fungal skin infections, especially in immunocompromised patients such as those with AIDS or those on chemotherapy. Ketoconazole is sold commercially as an anti-dandruff shampoo, topical cream, and oral tablet.Ketoconazole is...
) are often found in anti-dandruff
Dandruff
Dandruff is the shedding of dead skin cells from the scalp . Dandruff is sometimes caused by frequent exposure to extreme heat and cold. As it is normal for skin cells to die and flake off, a small amount of flaking is normal and common; about 487,000 cells/cm2 get released normally after...
shampoo
Shampoo
Shampoo is a hair care product used for the removal of oils, dirt, skin particles, dandruff, environmental pollutants and other contaminant particles that gradually build up in hair...
s. The antifungal drugs inhibit the yeast Malassezia globosa which encourages seborrhoeic dermatitis
Seborrhoeic dermatitis
Seborrhoeic dermatitis is an inflammatory skin disorder affecting the scalp, face, and torso. Typically, seborrheic dermatitis presents with scaly, flaky, itchy, and red skin. It particularly affects the sebaceous-gland-rich areas of skin...
and tinea versicolor
Tinea versicolor
Tinea versicolor is a condition characterized by a rash on the trunk and proximal extremities. Recent research has shown that the majority of Tinea versicolor is caused by the Malassezia globosa fungus, although Malassezia furfur is responsible for a small number of cases...
.
| Agent | Trade names | Medical applications |
| Ketoconazole Ketoconazole Ketoconazole is a synthetic antifungal drug used to prevent and treat fungal skin infections, especially in immunocompromised patients such as those with AIDS or those on chemotherapy. Ketoconazole is sold commercially as an anti-dandruff shampoo, topical cream, and oral tablet.Ketoconazole is... |
Nizoral, Fungoral and Sebizole | Preliminary findings, research and studies including the completion of a small controlled clinical trial have produced data suggesting that ketoconazole shampoo is effective as a hair loss treatment in men with androgenic alopecia. Larger controlled clinical studies are still needed to evaluate the ideal dosage, formulation, and to determine the routine of treatment for this condition, thus ketoconazole shampoo is not FDA approved for this indication. |
| Ciclopirox olamine | Loprox | The cream and lotion form of this agent is used to treat fungal infections of the skin. The lacquer form is used as part of a treatment plan to treat fungal infections of the nails. The shampoo form of this medication is used to treat and prevent dandruff or to treat seborrhoeic dermatitis. |
| Piroctone olamine Piroctone olamine Piroctone olamine, also known as Octopirox and piroctone ethanolamine, is a compound sometimes used in the treatment of fungal infections. Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone.... |
Octopirox and Nivea Complete Control | Piroctone olamine is sometimes used as an anti fungal agent, and it often used in dandruff shampoos in lieu of zinc. Piroctone Olamine is said to be less toxic than other anti-dandruff agents, often bypassing some of the normal FDA warnings, but still must be used with care, and only externally. |
| Zinc pyrithione Zinc pyrithione Zinc pyrithione is a coordination complex of zinc. This colourless solid is used as an antifungal and antibacterial agent. This coordination complex, which has many names, was first reported in the 1930s.- Structure of the compound :... |
Head & Shoulders Head & Shoulders Head & Shoulders is a brand of anti-dandruff shampoo produced by Procter & Gamble. Head & Shoulders Classic Clean Shampoo is the top-selling shampoo in the United States by dollar sales.- History :... , Johnson and Johnson ZP-11, Clinic All Clear, Pantene Pro V and Sikkai Powder |
An antifungal and antibacterial agent first reported in the 1930s. Zinc pyrithione is best known for its use in the treatment of dandruff and seborrhoeic dermatitis. It also has antibacterial properties and is effective against many pathogens from the streptococcus and staphylococcus class. Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea, and vitiligo. |
| Selenium sulfide Selenium sulfide Selenium disulfide is an inorganic compound with the approximate formula SeS2. Both sulfur and selenium catenate readily, and mixtures of selenium and sulfur likewise give rise to numerous "alloys"... |
Selsun Blue Selsun Blue Selsun Blue is an over-the-counter brand of dandruff shampoo now owned by Sanofi-Aventis. First made by Abbott Laboratories, the brand was bought in Chattem in 2002. Chattem was acquired by Sanofi-Aventis in 2010. Selsun Blue has been marketed as a more effective alternative to brand leader Head &... , Head & Shoulders Head & Shoulders Head & Shoulders is a brand of anti-dandruff shampoo produced by Procter & Gamble. Head & Shoulders Classic Clean Shampoo is the top-selling shampoo in the United States by dollar sales.- History :... and Vichy Dercos Anti-Dandruff Shampoo |
Selenium sulfide is available as a 1% and 2.5% lotion and shampoo. In some countries, the higher strength preparations requires a doctors prescription. The shampoo is used to treat dandruff and seborrhea of the scalp, and the lotion is used to treat tinea versicolor, a fungal infection of the skin. |
| Tar Tar Tar is modified pitch produced primarily from the wood and roots of pine by destructive distillation under pyrolysis. Production and trade in tar was a major contributor in the economies of Northern Europe and Colonial America. Its main use was in preserving wooden vessels against rot. The largest... |
Neutrogena T-Gel T-Gel T/Gel is a medicated shampoo produced by Neutrogena. It reduces psoriasis, dandruff, seborrheic dermatitis, and DHT levels. It has a limited antiandrogen effect, and is used by some people to slow hair loss... |
Is effective as a therapeutic treatment to control scalp itching and flaking symptomatic of scalp psoriasis, eczema, seborrhoeic dermatitis and dandruff. |
| Tea tree oil Tea tree oil Tea tree oil, or melaleuca oil, is a pale yellow colour to nearly clear essential oil with a fresh camphoraceous odor. It is taken from the leaves of the Melaleuca alternifolia, which is native to the northeast coast of New South Wales, Australia... |
Dr. Bronner's Castile Soap | Is used topically as an ingredient in creams, ointments, lotions, soaps, and shampoos. In addition to antifungal properties, tea tree oil has antiseptic, antibacterial, and antiviral actions. It is effective against bacteria, viruses, fungal infections, mites (such as scabies), and lice (such as head lice). |
External links
- Antifungal Drugs - Detailed information on antifungals from the Fungal Guide written by Drs. R. Thomas and K. Barber