DANAZOL

First approved in 1976

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27NO2
Molecular Weight	337.4553
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=POZRVZJJTULAOH-LHZXLZLDSA-N

InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H27NO2
Molecular Weight	337.4553
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://products.sanofi.ca/en/cyclomen.pdf
Curator's Comment: description was created based on several sources, including https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d, www.ncbi.nlm.nih.gov/pubmed/1606119

Danazol is a synthetic derivative of ethisterone which is approved by FDA for the treatment of endometriosis, fibrocystic breast disease and for preventing hereditary angioedema. It is believed that the in vivo therapeutic effect is achieved through activating androgen receptors. Danazol has teratogenic effects.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Endometriosis 32 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Primary	Approved 8583	DANAZOL Approved Use Danazol is indicated for the treatment of endometriosis amenable to hormonal management; for the treatment of fibrocystic Breast Disease and for the prevention of attacks of angioedema of all types (cutaneous, abdominal, laryngeal) in males and females. Launch Date 1996
Fibrocystic breast disease 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Palliative	Approved 8583	DANAZOL Approved Use Danazol is indicated for the treatment of endometriosis amenable to hormonal management; for the treatment of fibrocystic Breast Disease and for the prevention of attacks of angioedema of all types (cutaneous, abdominal, laryngeal) in males and females. Launch Date 1996
Hereditary angioedema 6 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Preventing	Approved 8583	DANAZOL Approved Use Danazol is indicated for the treatment of endometriosis amenable to hormonal management; for the treatment of fibrocystic Breast Disease and for the prevention of attacks of angioedema of all types (cutaneous, abdominal, laryngeal) in males and females. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
69.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017557s033s039s040s041s042lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		DANAZOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
601 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017557s033s039s040s041s042lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		DANAZOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.7 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017557s033s039s040s041s042lbl.pdf	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		DANAZOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2J2 33 CYP1A2 2153 CYP2C19 2057 CYP3A 227	CYP2J2 71 CYP2C8 810 CYP2C19 1119 CYP1A2 1197 CYP1A1 389 CYP2A6 626 CYP2B6 776 FMO 34

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	no
CYP2J2 36	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes [IC50 0.05 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
FMO 34	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 2.15 uM]
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 3.62 uM]
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4315	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4315
ChemicalBook	CB9463336	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9463336
eMolecules	2726153	https://www.emolecules.com/cgi-bin/more?vid=2726153
eMolecules	30512482	https://www.emolecules.com/cgi-bin/more?vid=30512482
ZINC	ZINC000003881958	http://zinc15.docking.org/substances/ZINC000003881958

PubMed

Title	Date	PubMed
Risk factors for evolution of acquired aplastic anemia into myelodysplastic syndrome and acute myeloid leukemia after immunosuppressive therapy in children.	2002-08-01	12130487
Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes.	2002-07	12115827
Pulsed high-dose dexamethasone therapy in children with chronic idiopathic thrombocytopenic purpura.	2002-06-25	12078864
A randomized trial of danazol pretreatment prior to endometrial resection.	2002-06-10	12039468
Successful treatment of anemia in idiopathic myelofibrosis with recombinant human erythropoietin.	2002-06	12111781
Splenectomy for immune thrombocytopenic purpura: long-term results and treatment of postsplenectomy relapses.	2002-06	12107560
Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials.	2002-06	12042266
Hysteroscopic endometrial destruction, optimum method for preoperative endometrial preparation: a prospective, randomized, multicenter evaluation.	2002-05-11	12002292
Hereditary angioedema with recurrent abdominal pain.	2002-05-07	11990338
Danazol linked to ovarian cancer.	2002-05	12067790
Autoimmune acquired form of angioedema that responded to danazol therapy.	2002-05	12058892
Angioedema and acquired C1 esterase inhibitor deficiency.	2002-05	12058878
Optimized conditions for MDCK permeability and turbidimetric solubility studies using compounds representative of BCS classes I-IV.	2002-05	11988394
Danazol-induced hepatocellular adenoma in patients with hereditary angio-oedema.	2002-05	11983460
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.	2002-04	12071939
Premenstrual syndrome.	2002-04	12032448
Microbial transformation of danazol.	2002-04	11990425
[Ureteral endometriosis: urological features].	2002-03	12053448
The treatment of endometriosis: a review of the evidence.	2002-03	11949962
Conventional medical therapies for endometriosis.	2002-03	11949960
[Acquired angioneurotic edema. Apropos of a case].	2002-03	11928387
HIV-related thrombocytopenia.	2002-03	11914001
The influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies.	2002-03	11865961
Endometriosis in an adolescent population: the severance hospital in Korean experience.	2002-02	11854932
Expansion of trisomy 8 and Sweet syndrome in a prolonged course of aplastic anemia.	2002-01	11902745
Danazol therapy in factor X deficiency: more questions than answers.	2002-01	11886468
Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases.	2002-01	11824975
Hormonal emergency contraception.	2002-01	11794429
Histomorphometric analysis: comparative study of manual and digital image analysis using reproductive organ as a model.	2002	12085619
Danazol for heavy menstrual bleeding.	2002	12076401
Danazol therapy for thrombocytopenia in patients with myelodysplastic syndromes.	2002	12053153
Benign breast pain in women: a practical approach to evaluation and treatment.	2002	11991427
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding.	2002	11869575
Therapies for the treatment of abnormal uterine bleeding.	2001-12	12112970
Angioedema in the emergency department: a presentation of lymphoma.	2001-12	11903433
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.	2001-12	11754418
Danazol and limb-threatening arterial thrombosis: two case reports.	2001-12	11743571
Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy.	2001-11-28	11723415
Eradication of Helicobacter pylori and improvement of hereditary angioneurotic oedema.	2001-11-17	11728547
[Danazol-induced hepatitis with functional deficit of the C1 inhibitor].	2001-11	11862774
[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome].	2001-11	11855146
Allogeneic stem cell transplantation for Evans syndrome.	2001-11	11781654
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001-11	11757752
Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus.	2001-10-15	11690572
Impairment of CYP3A4 capacity in patients receiving danazol therapy: examination on oxidative cortisol metabolism.	2001-10	11607885
Management of endometriosis and its impact on infertility.	2001-08	11881858
C1 esterase inhibitor: new preparation. A major advance in emergency treatment of hereditary angioneurotic oedema.	2001-06	11718165
Urticaria and angioedema.	2001	11758115
Systemic capillary leak syndrome preceding plasma cell leukaemia.	2001	11713377
Danazol for pelvic pain associated with endometriosis.	2001	11687066

Patents

Sample Use Guides

In Vivo Use Guide

Endometriosis: In moderate to severe disease, a starting dose of 800 mg given in two divided doses is recommended. For mild cases, an initial daily dose of 200 mg to 400 mg given in two divided doses is recommended. Fibrocystic Breast Disease: The total daily dosage of danazol for fibrocystic breast disease ranges from 100 mg to 400 mg given in two divided doses depending upon patient response. Hereditary Angioedema: It is recommended that the patient be started on 200 mg, two or three times a day.

Route of Administration: Oral

In Vitro Use Guide

Undissolved danazol significantly inhibited endometrial cell growth even at less than 100 ng/ml. At 500 ng/ml of fully dissolved danazol, which is the therapeutic dose, danazol solution inhibited leukemic cell growth but not endometrial cell growth.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:02 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:02 GMT 2025`
Record UNII	N29QWW3BUO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DANOCRINE

Preferred Name

English

DANAZOL

Official Name

English

NSC-270916

Code

English

DANAZOL [USP-RS]

Common Name

English

17.ALPHA.-PREGNA-2,4-DIEN-20-YNO(2,3)-DISOXAZOL-17-OL

Common Name

English

Danazol [WHO-DD]

Common Name

English

DANAZOL [VANDF]

Common Name

English

DANAZOL [USAN]

Common Name

English

DANAZOL [MART.]

Common Name

English

DANAZOL [ORANGE BOOK]

Common Name

English

DANAZOL [JAN]

Common Name

English

DANAZOL [USP MONOGRAPH]

Common Name

English

danazol [INN]

Common Name

English

DANAZOL [MI]

Common Name

English

PREGNA-2,4-DIEN-20-YNO(2,3-D)ISOXAZOL-17-OL,(17.ALPHA.)-

Common Name

English

WIN-17757

Code

English

WIN 17,757

Code

English

Classification Tree Code System Code

NDF-RT

N0000008241