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Danazol, sold under the brand name Danocrine among others, is a medication which is used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema, and other conditions.
The use of danazol is limited by masculinizing side effects such as acne, excessive hair growth, and voice deepening.
Danazol was discovered in 1963 and was introduced for medical use in 1971.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
4 Pharmacology
4.1 Pharmacodynamics
4.1.1 Modulation of steroid hormone receptors
4.1.2 Inhibition of steroidogenesis enzymes
4.1.3 Occupation and downregulation of carrier proteins
4.1.4 Antigonadotropic activity
4.1.5 Mechanism of action in endometriosis
4.1.6 Effects in men
4.2 Pharmacokinetics
5 Chemistry
6 History
7 Society and culture
7.1 Generic names
7.2 Brand names
7.3 Availability
8 Research
9 References
10 Further reading
Medical uses
Danazol is used primarily in the treatment of endometriosis. It has also been used – mostly off-label – for other indications, namely in the management of menorrhagia, fibrocystic breast disease, immune thrombocytopenic purpura, premenstrual syndrome, breast pain, and hereditary angioedema.
Available forms
Danazol comes in the form of 50, 100, and 200 mg oral capsules.
Contraindications
Danazol is contraindicated during pregnancy because it has the potential to virilize female fetuses. Women taking danazol should practice effective contraception to prevent pregnancy if sexually active.
Since danazol is metabolized by the liver, 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.
Side effects
See also: Anabolic steroid § Adverse effects
Androgenic side effects are of concern, as some women taking danazol may experience unwanted hair growth ( hirsutism ), acne, irreversible deepening of the voice, Some patients who use danazol experience weight gain and fluid retention. Due to its side effects, danazol is seldom prescribed continuously beyond six months.
The use of danazol for endometriosis has been linked to an increased risk of ovarian cancer.
Pharmacology
Pharmacodynamics
Danazol possesses a complex pharmacology, with multiple mechanisms of action.
Modulation of steroid hormone receptors
Danazol is described as a possessing high affinity for the androgen receptor (AR), moderate affinity for the progesterone receptor (PR) and glucocorticoid receptor (GR), and poor affinity for the estrogen receptor (ER).
Relative affinities (%) of danazol and metabolites
Steroid
PR
AR
ER
GR
MR
SHBG
CBG
Danazol
9
8
?
100 μM

0%
For reference, circulating concentrations of danazol are in the range of 2 μM at a dosage of 600 mg/day in women.
Occupation and downregulation of carrier proteins
Protein binding of testosterone in women
Group
Free
Albumin
SHBG
Normal (no danazol)
1%
39%
60%
Danazol treatment
3%
79%
18%
Danazol is known to bind to two steroid hormone carrier proteins: sex hormone-binding globulin (SHBG), which binds androgens and estrogens ; and corticosteroid-binding globulin (CBG), which binds progesterone and cortisol.
As can be seen, the percentage of free testosterone is tripled in women being treated with danazol.
It is noteworthy that 2-hydroxymethylethisterone, a major metabolite of danazol, circulates at concentrations 5–10 times greater than those of danazol and is twice as potent as danazol in displacing testosterone from SHBG.
Antigonadotropic activity
Via its weak progestogenic and androgenic activity, through activation of the PR and AR in the pituitary gland, danazol produces antigonadotropic effects.
Mechanism of action in endometriosis
Because danazol reduces estrogen production and levels,
Effects in men
In men, danazol has been found to inhibit gonadotropin secretion and markedly decrease testosterone levels, likely due to its actions as a steroidogenesis inhibitor and antigonadotropin.
Pharmacokinetics
The bioavailability of danazol is low.
Danazol is metabolized in the liver by enzymes such as CYP3A4.
Chemistry
See also: List of androgens/anabolic steroids and List of progestogens
Danazol, also known as 2,3-isoxazol-17α-ethynyltestosterone or as 17α-ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole, is a synthetic androstane steroid and a derivative of testosterone and ethisterone (17α-ethynyltestosterone).
History
Danazol was synthesized in 1963 by a team of scientists at Sterling Winthrop in Rensselaer, New York by a team that included Helmutt Neumann, Gordon Potts, W.T. Ryan, and Frederik W. Stonner.
Society and culture
Generic names
Danazol is the generic name of the drug and its INN, USAN, USP, BAN, DCF, DCIT, and JAN.
Brand names
Danazol is or has been marketed under many brand names throughout the world including Anargil, Azol, Benzol, Bonzol, Cyclolady, Cyclomen, Danal, Danalol, Danamet, Danamin, Danasin, Danatrol, Danazant, Danazol, Danocrine, Danodiol, Danogen, Danokrin, Danol, Danonice, Danoval, Danzol, Dogalact ( veterinary ), Dorink, Dzol, Ectopal, Elle, Gonablok, Gong Fu Yi Kang, Gynadom, Kodazol, Kupdina, Ladogal, Lozana, Mastodanatrol, Nazol, Norciden, Vabon, and Winobanin.
Availability
Danazol is available in the United States, Europe, and widely elsewhere throughout the world.
Research
Low-dose danazol has been investigated in the treatment of diabetic macular edema in a phase III clinical trial.
A 2016 phase I/II prospective study orally administered 800 mg per day to 27 patients with telomere diseases. The primary efficacy endpoint was a 20% reduction in the annual rate of telomere attrition measured. Toxic effects formed the primary safety endpoint. The study was halted early, after telomere attrition was reduced in all 12 patients who could be evaluated. 12 of 27 patients achieved the primary efficacy end point, 11 of whom increased telomere length at 24 months. Hematologic responses (secondary efficacy endpoint) occurred in 10 of 12 patients who could be evaluated at 24 months. Elevated liver-enzyme levels and muscle cramps (known adverse effects) of grade 2 or less occurred in 41% and 33% of the patients, respectively.

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