Podophyllin is a resinous powder obtained by precipitating an alcoholic tincture of the rhizome of
American MayapplePodophyllum peltatum is a herbaceous perennial plant in the family Berberidaceae, native to the eastern part of North America....
(Podophyllum peltatum) or
Podophyllum emodi by means of water acidified with
hydrochloric acidHydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong mineral acid and has major industrial uses. It is found naturally in gastric acid....
. It varies in color from grayish to bright yellow or greenish-brown, the first-named being the purest. It was commonly used against
genital wartGenital warts is a highly contagious sexually transmitted infection caused by some sub-types of human papillomavirus . It is spread through direct skin-to-skin contact during oral, genital, or anal sex with an infected partner...
s because it contains antiwart
lignanThe lignans are a group of chemical compounds found in plants, particularly in flax seed. Lignans are one of the major classes of phytoestrogens, which are estrogen-like chemicals and also act as antioxidants. The other classes of phytoestrogens are the isoflavones, and coumestans...
s, although podofilox, a purified form of the main active ingredient, has become recommended due to its higher efficacy and safety.
The powder is soluble in alcohol and strong solutions of
alkaliIn chemistry, an alkali is a basic, ionic salt of an alkali metal or alkaline earth metal element. Alkalis are best known for being bases that dissolve in water. Bases are compounds with a pH greater than 7. The adjective alkaline is commonly used in English as a synonym for base, especially for...
s, such as
ammoniaAmmonia is a compound of nitrogen and hydrogen with the formula NH
3. It is normally encountered as a gas with a characteristic pungent odor. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to foodstuffs and fertilizers...
.
Podophyllin is a resinous powder obtained by precipitating an alcoholic tincture of the rhizome of
American MayapplePodophyllum peltatum is a herbaceous perennial plant in the family Berberidaceae, native to the eastern part of North America....
(Podophyllum peltatum) or
Podophyllum emodi by means of water acidified with
hydrochloric acidHydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong mineral acid and has major industrial uses. It is found naturally in gastric acid....
. It varies in color from grayish to bright yellow or greenish-brown, the first-named being the purest. It was commonly used against
genital wartGenital warts is a highly contagious sexually transmitted infection caused by some sub-types of human papillomavirus . It is spread through direct skin-to-skin contact during oral, genital, or anal sex with an infected partner...
s because it contains antiwart
lignanThe lignans are a group of chemical compounds found in plants, particularly in flax seed. Lignans are one of the major classes of phytoestrogens, which are estrogen-like chemicals and also act as antioxidants. The other classes of phytoestrogens are the isoflavones, and coumestans...
s, although podofilox, a purified form of the main active ingredient, has become recommended due to its higher efficacy and safety.
The powder is soluble in alcohol and strong solutions of
alkaliIn chemistry, an alkali is a basic, ionic salt of an alkali metal or alkaline earth metal element. Alkalis are best known for being bases that dissolve in water. Bases are compounds with a pH greater than 7. The adjective alkaline is commonly used in English as a synonym for base, especially for...
s, such as
ammoniaAmmonia is a compound of nitrogen and hydrogen with the formula NH
3. It is normally encountered as a gas with a characteristic pungent odor. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to foodstuffs and fertilizers...
. Its composition is somewhat complex. There are certainly at least two
resinResin is a hydrocarbon secretion of many plants, particularly coniferous trees. It is valued for its chemical constituents and uses, such as varnishes and adhesives, as an important source of raw materials for organic synthesis, or for incense and perfume. Fossilized resins are the source of amber...
s in the powder (which is known officially as
Podophylli resina), one of them being soluble and the other insoluble in ether. Each of these contains an active substance, which can be obtained in crystalline form, and is known as
podophyllotoxinPodophyllotoxin, otherwise known as podofilox, is a non-alkaloid toxin in the lignan family. It is the main active antiwart component of podophyllin, an herbal extract of Podophyllum which used to be one of the main treatments for genital warts. It is more effective and safer than podophyllin...
. It is soluble in alcohol, ether, chloroform and boiling water.
Reactivity
Alkalis decompose it into picro-podophyllic acid and picro-podophyllin, minute traces of both of which occur in a free state in the rhizome. The acid is inert, but picro-podophyllin is the active principle.
It is a crystalline body, soluble only in concentrated alcohol. Hence the inutility of the pharmacopeial tinctura podophylli, which cannot be diluted before administration. The properties of podophyllin resin vary with the reaction of the tissue with which it is in contact; where this is acid the drug is inert, the picro-podophyllin being precipitated.
The resin does not affect the unbroken skin, but may be absorbed from a raw surface, and will then cause purging. When taken internally it is both a secretory and an excretory
cholagogueA cholagogue is a medicinal agent which promotes the discharge of bile from the system, purging it downward.In Patrick O'Brian's book The Post Captain which is set in the Napoleonic era, Stephen Maturin, one of the book's main characters and who is also a physician, naturalist and spy, sits in the...
, but so irritating and powerful that its use in cases of
jaundiceJaundice, also known as icterus , is a yellowish discoloration of the skin, the conjunctival membranes over the sclerae , and other mucous membranes caused by hyperbilirubinemia...
is generally undesirable. Its value, however, in certain cases of
constipationConstipation, costiveness, or irregularity is a condition of the digestive system in which a person experiences hard feces that are difficult to expel. This usually happens because the colon absorbs too much water from the food...
of hepatic origin is undeniable. It is largely used in patent medicines, usually as an auxiliary to
aloeAloe, also written Aloë, is a genus containing about four hundred species of flowering succulent plants. The most common and well known of these is Aloe vera, or "true aloe"....
s. The best method of prescribing podophyllin is in pill form.
Toxicity
In toxic doses podophyllin causes intense
enteritisIn medicine, enteritis refers to inflammation of the small intestine. It is most commonly caused by the ingestion of substances contaminated with pathogenic microorganisms. Symptoms include abdominal pain, cramping, diarrhea, dehydration and fever...
, with all its characteristic symptoms, and severe
depressionMajor depressive disorder is a mental disorder characterized by an all-encompassing low mood accompanied by low self-esteem, and loss of interest or pleasure in normally enjoyable activities...
, which may end in death. The treatment is
symptomA symptom is a departure from normal function or feeling which is noticed by a patient, indicating the presence of disease or abnormality...
atic, there being no specific antidote.
Even when podophyllin resin is used topically, it can be systemically absorbed into the body, and fatal and near-fatal reactions have been reported, particularly when it is used extensively or on mucous membranes. Neither podophyllin resin nor podofilox lotion or gel is used during pregnancy because these medications can be harmful to the fetus. The most common side effects near the application site are skin reactions, including burning, redness, pain, itching, swelling. There is some concern about the mutagenicity of some of the
flavonoidFlavonoids , also collectively known as Vitamin P and citrin, are a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:...
s in podophyllin.
Medical Applications
Podophyllin has been used to remove
genital wartGenital warts is a highly contagious sexually transmitted infection caused by some sub-types of human papillomavirus . It is spread through direct skin-to-skin contact during oral, genital, or anal sex with an infected partner...
s since its efficacy was first demonstrated in 1942, although the reliability of this early report has been questioned. This requires one application of podophyllin resin a week to the warts by a health professional, which is then washed off after 4 to 6 hours.
Petroleum jellyPetroleum jelly, petrolatum or soft paraffin, CAS number 8009-03-8, is a semi-solid mixture of hydrocarbons , originally promoted as a topical ointment for its healing properties...
, such as Vaseline, may be used to protect normal tissue near the warts from irritation. A health professional usually applies the resin once a week for at least 6 weeks or until warts disappear. It is unstable and therefore must be prepared shortly before use, which has possibly led to the lower efficacy shown in some clinical trials.
Podophyllin is also used to treat
Molluscum contagiosumMolluscum contagiosum is a viral infection of the skin or occasionally of the mucous membranes. MC has no animal reservoir, infecting only humans, as did smallpox. However, there are different pox viruses that infect many other mammals. The infecting human MC virus is a DNA poxvirus called the...
in the genital area. As the molluscum lesions can sometimes be quite numerous, scarring and
hypopigmentationHypopigmentation is the loss of skin color. It is caused by melanocyte or melanin depletion, or a decrease in the amino acid tyrosine, which is used by melanocytes to make melanin.-Associated conditions:It is seen in:*albinism...
become an issue with
cryosurgeryCryosurgery is the application of extreme cold to destroy abnormal or diseased tissue. The term comes from the Greek words cryo and surgery meaning "hand work" or "handiwork"....
.