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
Urticaria and angioedema.	2001	11758115
Systemic capillary leak syndrome preceding plasma cell leukaemia.	2001	11713377
Danazol for pelvic pain associated with endometriosis.	2001	11687066
Management of endometriosis and its impact on infertility.	2001 Aug	11881858
Therapies for the treatment of abnormal uterine bleeding.	2001 Dec	12112970
Angioedema in the emergency department: a presentation of lymphoma.	2001 Dec	11903433
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.	2001 Dec	11754418
Danazol and limb-threatening arterial thrombosis: two case reports.	2001 Dec	11743571
C1 esterase inhibitor: new preparation. A major advance in emergency treatment of hereditary angioneurotic oedema.	2001 Jun	11718165
[Danazol-induced hepatitis with functional deficit of the C1 inhibitor].	2001 Nov	11862774
[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome].	2001 Nov	11855146
Allogeneic stem cell transplantation for Evans syndrome.	2001 Nov	11781654
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001 Nov	11757752
Eradication of Helicobacter pylori and improvement of hereditary angioneurotic oedema.	2001 Nov 17	11728547
Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy.	2001 Nov-Dec	11723415
Impairment of CYP3A4 capacity in patients receiving danazol therapy: examination on oxidative cortisol metabolism.	2001 Oct	11607885
Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus.	2001 Oct 15	11690572
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
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding.	2002	11869575
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.	2002 Apr	12071939
Premenstrual syndrome.	2002 Apr	12032448
Microbial transformation of danazol.	2002 Apr	11990425
Risk factors for evolution of acquired aplastic anemia into myelodysplastic syndrome and acute myeloid leukemia after immunosuppressive therapy in children.	2002 Aug 1	12130487
Endometriosis in an adolescent population: the severance hospital in Korean experience.	2002 Feb	11854932
Expansion of trisomy 8 and Sweet syndrome in a prolonged course of aplastic anemia.	2002 Jan	11902745
Danazol therapy in factor X deficiency: more questions than answers.	2002 Jan	11886468
Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases.	2002 Jan	11824975
Hormonal emergency contraception.	2002 Jan	11794429
Hysteroscopic endometrial destruction, optimum method for preoperative endometrial preparation: a prospective, randomized, multicenter evaluation.	2002 Jan-Mar	12002292
Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes.	2002 Jul	12115827
Pulsed high-dose dexamethasone therapy in children with chronic idiopathic thrombocytopenic purpura.	2002 Jul-Aug	12078864
Successful treatment of anemia in idiopathic myelofibrosis with recombinant human erythropoietin.	2002 Jun	12111781
Splenectomy for immune thrombocytopenic purpura: long-term results and treatment of postsplenectomy relapses.	2002 Jun	12107560
Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials.	2002 Jun	12042266
A randomized trial of danazol pretreatment prior to endometrial resection.	2002 Jun 10	12039468
[Ureteral endometriosis: urological features].	2002 Mar	12053448
The treatment of endometriosis: a review of the evidence.	2002 Mar	11949962
Conventional medical therapies for endometriosis.	2002 Mar	11949960
[Acquired angioneurotic edema. Apropos of a case].	2002 Mar	11928387
HIV-related thrombocytopenia.	2002 Mar	11914001
The influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies.	2002 Mar	11865961
Hereditary angioedema with recurrent abdominal pain.	2002 Mar-Apr	11990338
Danazol linked to ovarian cancer.	2002 May	12067790
Autoimmune acquired form of angioedema that responded to danazol therapy.	2002 May	12058892
Angioedema and acquired C1 esterase inhibitor deficiency.	2002 May	12058878
Optimized conditions for MDCK permeability and turbidimetric solubility studies using compounds representative of BCS classes I-IV.	2002 May	11988394
Danazol-induced hepatocellular adenoma in patients with hereditary angio-oedema.	2002 May	11983460
Benign breast pain in women: a practical approach to evaluation and treatment.	2002 Spring	11991427

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