Danazol
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Also known as DanocrineNSC-270916WIN 17,757WIN-17757DanatrolSID26757819SID144205667SID49648394SID144212257SID170464884CO-ADD:0136764C0164824
Summary
Danazol (CHEMBL1479) is an approved small-molecule estrogen antagonist (ATC G03XA01) targeting AR; indicated across 12 conditions including breast fibrocystic disease and endometriosis.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: G03XA01
- Targets: 1 (AR)
- Indications: 12 conditions
- Clinical trials: 34
- Chemistry: 337.5 Da · C22H27NO2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1479 |
| Name | Danazol |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 28417 |
| ChEBI | CHEBI:4315 |
| ATC | G03XA01 |
| Molecular formula | C22H27NO2 |
| Molecular weight | 337.5 |
| InChIKey | POZRVZJJTULAOH-LHZXLZLDSA-N |
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
IUPAC name: (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
Pharmacological roles (ChEBI): anti-estrogen, estrogen antagonist, geroprotector.
Also known as: Danazol, Danocrine, NSC-270916, WIN 17,757, WIN-17757, danazol, Danatrol, DANAZOL, SID26757819, SID144205667, SID49648394, SID144212257
Patent coverage: 4,398 distinct patent families (16,256 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| AR | Androgen receptor | Agonist | 8 | P10275 |
Broader ChEMBL bioactivity targets: 26 (assay-derived). Sample: Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Glucocorticoid receptor, D(1A) dopamine receptor, Estrogen receptor, Progesterone receptor, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2A, Sodium-dependent serotonin transporter.
Bioactivity
ChEMBL activities: 33 potent at pChembl ≥ 5 of 51 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| SHBG | 8.2 | Kd | 6.31 | nM | CHEMBL_ACT_2155710 |
| P15207 | 8.1 | Ki | 7.99 | nM | CHEMBL_ACT_7711061 |
| CYP2J2 | 7.92 | IC50 | 12 | nM | CHEMBL_ACT_15445918 |
| P15207 | 7.92 | IC50 | 12 | nM | CHEMBL_ACT_7711060 |
| CYP2J2 | 7.72 | IC50 | 19 | nM | CHEMBL_ACT_15445917 |
| PGR | 7.72 | AC50 | 19 | nM | CHEMBL_ACT_25222847 |
| CYP2J2 | 7.7 | Ki | 20 | nM | CHEMBL_ACT_15445878 |
| P15207 | 7.64 | AC50 | 23 | nM | CHEMBL_ACT_25187313 |
| CYP2J2 | 7.11 | IC50 | 77 | nM | CHEMBL_ACT_15445916 |
| NR3C1 | 6.96 | AC50 | 111 | nM | CHEMBL_ACT_25175626 |
| CYP2C9 | 6.52 | IC50 | 300 | nM | CHEMBL_ACT_7708845 |
| CYP2C9 | 5.84 | IC50 | 1440 | nM | CHEMBL_ACT_15445906 |
| CYP2C8 | 5.71 | IC50 | 1950 | nM | CHEMBL_ACT_15447385 |
| NR3C1 | 5.71 | Ki | 1961 | nM | CHEMBL_ACT_7708876 |
| HTR2A | 5.6 | Ki | 2528 | nM | CHEMBL_ACT_7711037 |
| CYP2D6 | 5.56 | IC50 | 2740 | nM | CHEMBL_ACT_15445902 |
| ADRA2C | 5.46 | Ki | 3451 | nM | CHEMBL_ACT_7708790 |
| NR1I2 | 5.43 | AC50 | 3700 | nM | CHEMBL_ACT_25188008 |
| CHRM3 | 5.42 | Ki | 3762 | nM | CHEMBL_ACT_7708920 |
| NR3C1 | 5.37 | IC50 | 4314 | nM | CHEMBL_ACT_7708875 |
| ESR1 | 5.29 | Ki | 5083 | nM | CHEMBL_ACT_7708866 |
| SLC6A3 | 5.26 | Ki | 5436 | nM | CHEMBL_ACT_7708862 |
| SLC6A2 | 5.25 | Ki | 5651 | nM | CHEMBL_ACT_7708798 |
| SLC6A2 | 5.24 | IC50 | 5698 | nM | CHEMBL_ACT_7708797 |
| OPRM1 | 5.24 | Ki | 5715 | nM | CHEMBL_ACT_7710979 |
| OPRK1 | 5.21 | Ki | 6207 | nM | CHEMBL_ACT_7710977 |
| ADORA3 | 5.2 | Ki | 6309 | nM | CHEMBL_ACT_7706687 |
| SLC6A3 | 5.17 | IC50 | 6842 | nM | CHEMBL_ACT_7708861 |
| ADRA2A | 5.16 | Ki | 6873 | nM | CHEMBL_ACT_7708786 |
| SLC6A4 | 5.09 | Ki | 8193 | nM | CHEMBL_ACT_7711049 |
Target pathways
Aggregated over 1 target gene(s): AR.
Top Reactome pathways
23 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | AR |
| Signaling by Rho GTPases | 1 | AR |
| RHO GTPase Effectors | 1 | AR |
| Generic Transcription Pathway | 1 | AR |
| Cellular responses to stress | 1 | AR |
| SUMOylation | 1 | AR |
| SUMO E3 ligases SUMOylate target proteins | 1 | AR |
| HSP90 chaperone cycle for steroid hormone receptors (SHR) in the presence of ligand | 1 | AR |
| Nuclear Receptor transcription pathway | 1 | AR |
| Metabolism of proteins | 1 | AR |
| SUMOylation of intracellular receptors | 1 | AR |
| RHO GTPases activate PKNs | 1 | AR |
| Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3 | 1 | AR |
| Deubiquitination | 1 | AR |
| Ub-specific processing proteases | 1 | AR |
| Post-translational protein modification | 1 | AR |
| RNA Polymerase II Transcription | 1 | AR |
| Gene expression (Transcription) | 1 | AR |
| Transcriptional regulation by RUNX2 | 1 | AR |
| RUNX2 regulates osteoblast differentiation | 1 | AR |
| RUNX2 regulates bone development | 1 | AR |
| Cellular responses to stimuli | 1 | AR |
| Signaling by Rho GTPases, Miro GTPases and RHOBTB3 | 1 | AR |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| negative regulation of transcription by RNA polymerase II | 1 |
| MAPK cascade | 1 |
| in utero embryonic development | 1 |
| regulation of systemic arterial blood pressure | 1 |
| epithelial cell morphogenesis | 1 |
| transcription by RNA polymerase II | 1 |
| signal transduction | 1 |
| cell-cell signaling | 1 |
| spermatogenesis | 1 |
| single fertilization | 1 |
| positive regulation of cell population proliferation | 1 |
| negative regulation of cell population proliferation | 1 |
| male gonad development | 1 |
| positive regulation of gene expression | 1 |
| male somatic sex determination | 1 |
Indications & clinical
Indications
12 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| breast fibrocystic disease | 4 | MONDO:0005219 | EFO:0003014 |
| endometriosis | 4 | MONDO:0005133 | EFO:0001065 |
| infertility disorder | 3 | MONDO:0005047 | EFO:0000545 |
| autoimmune thrombocytopenic purpura | 2 | MONDO:0008558 | EFO:0007160 |
| myelodysplastic syndrome | 2 | MONDO:0018881 | EFO:0000198 |
| endometrium neoplasm | 2 | MONDO:0021251 | MONDO:0011962 |
| thrombotic thrombocytopenic purpura | 2 | MONDO:0018896 | MONDO:0018896 |
| aplastic anemia | 1 | MONDO:0015909 | HP:0001915 |
| dyskeratosis congenita | 1 | MONDO:0015780 | MONDO:0015780 |
| Fanconi anemia | 1 | MONDO:0019391 | MONDO:0019391 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 34.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 22 |
| PHASE1/PHASE2 | 5 |
| PHASE3 | 3 |
| PHASE4 | 1 |
| PHASE2/PHASE3 | 1 |
| PHASE1 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01779232 | PHASE4 | COMPLETED | Danazol Treatment in Endometriosis Women Before IVF |
| NCT03563664 | PHASE3 | COMPLETED | Effect of Danazol on Endometrial αvβ3 Integrin Expression in Patients With Unexplained Recurrent Implantation Failure |
| NCT04173494 | PHASE3 | COMPLETED | A Study of Momelotinib Versus Danazol in Symptomatic and Anemic Myelofibrosis Participants (MOMENTUM) |
| NCT04324060 | PHASE2/PHASE3 | UNKNOWN | A Randomized Trial of rhTPO Versus Placebo for Low/Intermediate-1 Risk MDS With Thrombocytopenia |
| NCT05697471 | PHASE3 | UNKNOWN | Comparisons of the Therapeutic Effects of Dienogest and Danazol on Endometriosis |
| NCT03312400 | PHASE2 | ACTIVE_NOT_RECRUITING | Low-Dose Danazol for the Treatment of Telomere Related Diseases |
| NCT04873102 | PHASE2 | RECRUITING | Danazol for Treatment of Cytopenias in Patients With Cirrhosis |
| NCT00003946 | PHASE2 | COMPLETED | Danazol in Treating Patients With Advanced or Recurrent Endometrial Cancer |
| NCT00744276 | PHASE2 | COMPLETED | A Study of Topical Danazol for the Treatment of Pain Associated With Fibrocystic Breast Disease |
| NCT00953771 | PHASE2 | TERMINATED | Safety Study of Danazol With Plasma Exchange and Steroids for the Treatment of Thrombotic Thrombocytopenic Purpura (TTP) |
| NCT01001598 | PHASE1/PHASE2 | TERMINATED | Safety and Efficacy Trial of Danazol in Patients With Fanconi Anemia or Dyskeratosis Congenita |
| NCT01105793 | PHASE2 | COMPLETED | An Open-Label, MultiCenter Evaluation of the Use of Topically Administered FP1198 in Subjects With Pain Associated With Cyclic Mastalgia |
| NCT01441037 | PHASE1/PHASE2 | COMPLETED | Danazol for Genetic Bone Marrow and Lung Disorders |
| NCT01667263 | PHASE2 | COMPLETED | The Combination of ATRA and Danazol as Second-line Treatment in Adult Immune Thrombocytopenia |
| NCT01732445 | PHASE2 | COMPLETED | Ruxolitinib Phosphate and Danazol in Treating Anemia in Patients With Myelofibrosis |
| NCT01821677 | PHASE2 | COMPLETED | A Safety and Efficacy Study of Oral Danazol (a Previously Approved Drug) in the Treatment of Diabetic Macular Edema. |
| NCT02002403 | PHASE2 | COMPLETED | Efficacy and Safety Study to Evaluate Two Doses of Oral DMI-5207 in Adult Subjects With Diabetic Macular Edema |
| NCT03352076 | PHASE2 | COMPLETED | Study to Determine Intraperitoneal,Tissue, Serum Concentrations of VML-0501 Following Five Days of Daily Vaginal Single Dose of VML-0501 (100 mg Danazol), in Comparison to Oral Danazol Capsules Daily 600 mg), in Women With Signs and Symptoms of Endometriosis Undergoing Laparoscopy |
| NCT03460808 | PHASE1/PHASE2 | UNKNOWN | The Combination of Atorvastatin, Acetylcysteine and Danazol as the Treatment of Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT03710356 | PHASE1/PHASE2 | UNKNOWN | Evaluating Efficacy and Safety of Danazol in Severe Hematologic or Pulmonary Disease Related to Telomeropathy |
| NCT04289207 | PHASE2 | UNKNOWN | Phase II Trial of Romiplostim With Danazol in Patients With Eltrombopag-resistant Immune Thrombocytopenia |
| NCT04481282 | PHASE2 | UNKNOWN | The Combination of Terbutaline and Danazol as the Treatment of Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT04638517 | PHASE2 | TERMINATED | The TELO-SCOPE Study: Attenuating Telomere Attrition With Danazol. Is There Scope to Dramatically Improve Health Outcomes for Adults and Children With Pulmonary Fibrosis |
| NCT04807309 | PHASE1/PHASE2 | WITHDRAWN | PRETELL: PREvention of TELomere-related Complications After Lung Transplant |
| NCT04997811 | PHASE2 | UNKNOWN | Repurposed Drugs to Improve Haematological Responses in Myelodysplastic Syndromes |
| NCT05281068 | PHASE2 | UNKNOWN | The Combination of Iguratimod and Danazol as the Treatment of Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT05353673 | PHASE2 | UNKNOWN | The Combination of Sitagliptin and Danazol as the Treatment of Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT05471050 | PHASE2 | UNKNOWN | The Combination of Tacrolimus and Danazol as the Treatment of Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT05494307 | PHASE2 | UNKNOWN | The Combination of Terbutaline and Danazol as the Treatment of Corticosteroid-resistant/Relapse Immune Thrombocytopenia |
| NCT05852847 | PHASE2 | UNKNOWN | Low-dose Baricitinib Plus Danazol for Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT06176911 | PHASE2 | UNKNOWN | The Combination of Teriflunomide and Danazol for Steroid-resistant/Relapse Immune Thrombocytopenia |
| NCT07183787 | PHASE2 | COMPLETED | Letrozole vs Danazol for Endometriosis-Related Pain: Randomized Trial |
| NCT04757532 | PHASE1 | COMPLETED | Study of Exposure to Substances Prohibited by the World Anti-Doping Agency in Healthy Volunteers. |
| NCT04058678 | Not specified | COMPLETED | Effects of Telomerase Reactivation With Danazol in Ovarian Function. |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
130 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| MEGESTROL | ChEMBL + PubChem | Phase 4 (approved) | AR |
| ABIRATERONE | ChEMBL | Phase 4 (approved) | AR |
| APALUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | AR |
| BECLOMETHASONE DIPROPIONATE | ChEMBL | Phase 4 (approved) | AR |
| BETAMETHASONE | ChEMBL | Phase 4 (approved) | AR |
| BICALUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| BITHIONOL | ChEMBL | Phase 4 (approved) | AR |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | AR |
| BUDESONIDE | ChEMBL | Phase 4 (approved) | AR |
| CHLORMADINONE | ChEMBL | Phase 4 (approved) | AR |
| CLARITHROMYCIN | ChEMBL | Phase 4 (approved) | AR |
| CLASCOTERONE | ChEMBL | Phase 4 (approved) | AR |
| CLOCORTOLONE PIVALATE | ChEMBL | Phase 4 (approved) | AR |
| CLOMIPHENE | ChEMBL | Phase 4 (approved) | AR |
| CORTISONE | ChEMBL | Phase 4 (approved) | AR |
| CYCLOFENIL | ChEMBL | Phase 4 (approved) | AR |
| DAROLUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| DESOGESTREL | ChEMBL | Phase 4 (approved) | AR |
| DESOXIMETASONE | ChEMBL | Phase 4 (approved) | AR |
| DEXAMETHASONE | ChEMBL | Phase 4 (approved) | AR |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | AR |
| DIFLORASONE DIACETATE | ChEMBL | Phase 4 (approved) | AR |
| DORZOLAMIDE | ChEMBL | Phase 4 (approved) | AR |
| DROSPIRENONE | ChEMBL | Phase 4 (approved) | AR |
| DYDROGESTERONE | ChEMBL | Phase 4 (approved) | AR |
| ENZALUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| EPLERENONE | ChEMBL | Phase 4 (approved) | AR |
| ESTRADIOL | ChEMBL | Phase 4 (approved) | AR |
| ESTRADIOL CYPIONATE | ChEMBL | Phase 4 (approved) | AR |
| ESTRADIOL VALERATE | ChEMBL | Phase 4 (approved) | AR |
| ESTRIOL | ChEMBL | Phase 4 (approved) | AR |
| ESTRONE | ChEMBL | Phase 4 (approved) | AR |
| ETHINYL ESTRADIOL | ChEMBL | Phase 4 (approved) | AR |
| ETHYNODIOL DIACETATE | ChEMBL | Phase 4 (approved) | AR |
| ETONOGESTREL | ChEMBL | Phase 4 (approved) | AR |
| FLUMETHASONE PIVALATE | ChEMBL | Phase 4 (approved) | AR |
| FLUOCINOLONE ACETONIDE | ChEMBL | Phase 4 (approved) | AR |
| FLUOCINONIDE | ChEMBL | Phase 4 (approved) | AR |
| FLUOXYMESTERONE | ChEMBL | Phase 4 (approved) | AR |
| FLURANDRENOLIDE | ChEMBL | Phase 4 (approved) | AR |
| FLUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| FLUTICASONE FUROATE | ChEMBL | Phase 4 (approved) | AR |
| FLUTICASONE PROPIONATE | ChEMBL | Phase 4 (approved) | AR |
| HALCINONIDE | ChEMBL | Phase 4 (approved) | AR |
| HALOBETASOL PROPIONATE | ChEMBL | Phase 4 (approved) | AR |
| HEXACHLOROPHENE | ChEMBL | Phase 4 (approved) | AR |
| HEXESTROL | ChEMBL | Phase 4 (approved) | AR |
| HYDROCORTISONE | ChEMBL | Phase 4 (approved) | AR |
| INDOMETHACIN | ChEMBL | Phase 4 (approved) | AR |
| LEVONORGESTREL | ChEMBL | Phase 4 (approved) | AR |
| MEDROXYPROGESTERONE | ChEMBL | Phase 4 (approved) | AR |
| METHYLPREDNISOLONE | ChEMBL | Phase 4 (approved) | AR |
| MIFEPRISTONE | ChEMBL | Phase 4 (approved) | AR |
| MOMETASONE FUROATE | ChEMBL | Phase 4 (approved) | AR |
| NILUTAMIDE | ChEMBL | Phase 4 (approved) | AR |
| NOMEGESTROL | ChEMBL | Phase 4 (approved) | AR |
| NORETHINDRONE | ChEMBL | Phase 4 (approved) | AR |
| NORETHYNODREL | ChEMBL | Phase 4 (approved) | AR |
| OXANDROLONE | ChEMBL | Phase 4 (approved) | AR |
Related Atlas pages
- Genes: AR
- Diseases: breast fibrocystic disease, endometriosis, infertility disorder
- Drugs: Megestrol, Abiraterone, Apalutamide, Aripiprazole, Beclomethasone Dipropionate, Betamethasone, Bicalutamide, Bithionol, Bromhexine, Budesonide, Chlormadinone, Clarithromycin, Clascoterone, Clocortolone Pivalate, Clomiphene, Cortisone, Cyclofenil, Darolutamide, Desogestrel, Desoximetasone, Dexamethasone, Diethylstilbestrol, Diflorasone Diacetate, Dorzolamide, Drospirenone, Dydrogesterone, Enzalutamide, Eplerenone, Estradiol, Estradiol Cypionate, Estradiol Valerate, Estriol, Estrone, Ethinyl Estradiol, Ethynodiol Diacetate, Etonogestrel, Flumethasone Pivalate, Fluocinolone Acetonide, Fluocinonide, Fluoxymesterone, Flurandrenolide, Flutamide, Fluticasone Furoate, Fluticasone Propionate, Halcinonide, Halobetasol Propionate, Hexachlorophene, Hexestrol, Hydrocortisone, Indomethacin, Levonorgestrel, Medroxyprogesterone, Methylprednisolone, Mifepristone, Mometasone Furoate, Nilutamide, Norethindrone, Norethynodrel, Oxandrolone