Danazol

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Danazol

Danazol is a derivative of the synthetic steroid

Steroid

A steroid is a terpenoid lipid characterized by a carbon skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion.Steroids vary by the functional groups attached to these rings and the oxidation state of the rings....
ethisterone

Ethisterone

Ethisterone is a progestagen hormone.The first orally active progestin, ethisterone , the 17a-ethynyl radical analog of testosterone, was chemical synthesis in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering in Berlin and marketed in Germany in 1939 as Proluton C and by Schering-Plough in the...
, a modified testosterone

Testosterone

Testosterone is a steroid hormone from the androgen group. In mammals, testosterone is primarily secreted in the testis of males and the ovaries of females, although small amounts are also secreted by the adrenal glands....
. Also known as 17alpha-ethinyl testosterone. Before becoming available as a generic drug

Generic drug

A generic drug is a medication which isproduced and distributed without patent protection. The generic drug may still have a patent on the formulation but not on the active ingredient....
, Danazol was marketed as Danocrine in the United States. It was approved by the U.S. Food and Drug Administration

Food and Drug Administration

The U.S. Food and Drug Administration is an Government agency of the United States Department of Health and Human Services and is responsible for regulating and supervising the safety of foods, dietary supplements, Medications, vaccines, Biopharmaceutical, blood transfusion, medical devices, Electromagnetic radiation-emitting devices, veteri...
(FDA) as the first drug to specifically treat endometriosis

Endometriosis

Endometriosis is a medical condition in women in which endometrial cells are deposited in areas outside the uterine cavity. The uterine cavity is lined by endometrial cells, which are under the influence of female hormones....
in the early 1970s. Although effective for endometriosis, its use is limited by its masculinizing side-effects.

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Chemistry

The agent is fat-soluble. It is an isoxazole

Isoxazole

Isoxazole is an azole with an oxygen atom next to the nitrogen.Isoxazoles are found in some natural products, such as ibotenic acid. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib ....
of testosterone with isolated weak androgenic activity and no estrogenic or progestagenic effects.

Method of action

Danazol inhibits ovarian steroidogenesis resulting in decreased secretion of estradiol and may increase androgens. Pituitary hormones are largely unaffected although luteinizing hormone (LH

Luteinizing hormone

Luteinizing hormone is a hormone produced by the anterior pituitary gland.* In the female, an acute rise of LH ? the LH surge ? triggers ovulation....
) may be slightly elevated.

Indications

Danazol has been used - mostly off-label - for other indications, namely in the management of menorrhagia

Menorrhagia

Menorrhagia is an abnormally heavy and prolonged menstruation at regular intervals. Causes may be due to abnormal blood clotting, disruption of normal hormonal regulation of periods or disorders of the endometrium lining of the uterus....
, fibrocystic breast disease, immune thrombocytopenic purpura, breast pain (mastodynia) and of hereditary angioedema

Hereditary angioedema

Hereditary angioedema presents in the second to fourth decade, and is characterized by local swelling in subcutaneous tissues.In hereditary angioedema, specific stimuli that have previously led to attacks may need to be avoided in the future....
. Though danazol prevents pregnancy, it is not licenced for use as a contraceptive agent.

Side-effects

Androgenic side effects are of concern, because in sensitive female patients, danazol can enhance unwanted hair growth, leading to hirsutism

Hirsutism

Hirsutism or Frazonism or is defined as excessive and increased hair growth in women in locations where the occurrence of terminal hair normally is minimal or absent....
. On rare occasion, it can deepen the voice. Other possible side effects include acne

Acne vulgaris

Acne vulgaris is a skin condition caused by changes in the pilosebaceous units . Severe acne is inflammation, but acne can also manifest in noninflammatory forms....
and oily skin. Because danazol is metabolized by the liver

Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
, it cannot be used by patients with liver disease, and in patients receiving long-term therapy, liver function must be monitored on a periodic basis. Some patients who use danazol experience weight gain and fluid retention. Due to these limitations, danazol is seldom prescribed continuously beyond six months.

The use of danazol for endometriosis has been linked to an increased risk of ovarian cancer. Patients with endometriosis have specific risk factors for ovarian cancer so this may not apply for other uses.

Danazol has, like most other androgenic agents, been linked with an increased risk of liver tumors. These are generally benign.

Unlike GnRH agonists, danazol does not induce osteoporosis

Osteoporosis

Osteoporosis is a disease of bone that leads to an increased risk of bone fracture. In osteoporosis the bone mineral density is reduced, bone microarchitecture is disrupted, and the amount and variety of collagen proteins in bone is altered....
. Also, symptoms of hot flushes tend to be less common or severe.

Contraindications

Danazol is contraindicated in pregnancy because it could masculinize a female fetus.