Danazol

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Cat Number

API0232314

CAS Number

17230-88-5

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CAS Number

17230-88-5

EINECS

241-270-1

Storage

Store at room temperature

Synonyms

Danocrine; Chronogyn; Danol; Winobanin; Danazolum; Cyclomen

Molecular Formula

C22H27NO2

Molecular Weight

337.5

Smiles

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5

Appearance

White to light yellow crystalline powder

Melting Point

224.4-226.8°C

Boiling Point

473.76°C (Estimate)

Relative Density

1.0909 (Estimate)

General Description

Danazol is a synthetic steroid with a 17α-ethinyl group, derived from 17α-ethinyltestosterone. Its chemical structure is 17α-ethinyl-17β-hydroxy-4,6-androstadien-3-one. Danazol is a white to off-white crystalline powder, practically insoluble in water but soluble in organic solvents. It is a weak androgen with both antigonadotropic and antiglucocorticoid properties.

Mechanism of Action

Danazol acts by suppressing the release of gonadotropins (LH and FSH) from the pituitary gland through a negative feedback mechanism. This leads to a decrease in ovarian estrogen production and a reduction in the growth of endometrial tissue. The drug also has a direct effect on the endometrium, causing atrophy and reducing the symptoms of endometriosis.

Application

Danazol is indicated for the treatment of endometriosis, particularly for the management of pelvic pain and infertility, and for the prevention of recurrence after surgery. It is also used for the treatment of fibrocystic breast disease and hereditary angioedema. The drug is effective in reducing pain and improving fertility, but it is associated with significant androgenic side effects.

Danazol, a non‑chemotherapeutic drug, induced caspase‑dependent apoptosis and cytotoxicity in chronic lymphocytic leukemia cells via both mitochondrial and receptor pathways. It showed synergy with cladribine, an additive effect with fludarabine, and infra‑additivity with bendamustine. Efficacy did not differ by prognostic markers. Danazol may be a potential therapeutic agent for CLL, alone or in combination with purine analogs.

Fig. 1 Percentage of leukemic cells with expression of active caspase-3 (aCas3) in 24-h cultures with danazol (10 μM), fludarabine (1 μg/ml), and both drugs. (Podhorecka M, et al., 2016)

References

Podhorecka M, et al. Danazol induces apoptosis and cytotoxicity of leukemic cells alone and in combination with purine nucleoside analogs in chronic lymphocytic leukemia. Ann Hematol. 2016;95(3):425-435.

In a phase 1‑2 study of danazol (800 mg/day for 24 months) in 27 patients with telomere diseases, telomere attrition was reduced in all 12 evaluable patients. Unexpectedly, 92% had telomere elongation at 24 months (mean increase 386 bp). Hematologic responses occurred in 83% at 24 months. Adverse effects (elevated liver enzymes, muscle cramps) were grade ≤2. Danazol leads to telomere elongation in telomere diseases.

Fig. 2 Hematologic Response in Patients Treated with Danazol, According to Mutation. (Townsley DM, et al., 2016)

References

Townsley DM, et al. Danazol Treatment for Telomere Diseases. N Engl J Med. 2016;374(20):1922-1931.

Does Danazol require protection from light during long-term storage?

Yes, it is photosensitive. Light exposure can cause photodegradation and discoloration of the isoxazole ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Danazol?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate oxidation.

Is Danazol stable in capsule formulations with standard excipients?

Yes, when formulated with standard excipients and protected from moisture.

How is the impurity danazol 17β-hydroxy (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.