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

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

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 167 Target ID: CHEMBL1871 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Agonist 2662

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 8360	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 8.395488E11
Fibrocystic breast disease 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Palliative	Approved 8360	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 8.395488E11
Hereditary angioedema 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Preventing	Approved 8360	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 8.395488E11

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 1709	inhibitor 1752	inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2J2 16 CYP1A2 1509 CYP2C19 1463 CYP3A 211	CYP2J2 56 CYP2C8 688 CYP2C19 985 CYP1A2 1032 CYP1A1 348 CYP2A6 523 CYP2B6 660 FMO 35

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1875	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	no
CYP2J2 19	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes [IC50 0.05 uM]
CYP1A2 1673	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C19 1537	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C9 1803	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP3A 295	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 348	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
FMO 35	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2J2 56	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 2.15 uM]
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 3.62 uM]
CYP2D6 1193	substrate 3326 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
ZINC	ZINC000003881958	http://zinc15.docking.org/substances/ZINC000003881958
eMolecules	2726153	https://www.emolecules.com/cgi-bin/more?vid=2726153
eMolecules	30512482	https://www.emolecules.com/cgi-bin/more?vid=30512482

PubMed

Title	Date	PubMed
Systemic capillary leak syndrome preceding plasma cell leukaemia.	2001	11713377
The possible anti-inflammatory role of circulating human leukocyte antigen levels in women with endometriosis after treatment with danazol and leuprorelin acetate depot.	2001 Apr	11405553
Sensory perineuritis presented as a mononeuritis multiplex associated with livedo vasculitis.	2001 Apr	11311480
[Recto-vaginal endometriosis].	2001 Jan	11235163
[Strategy of treatment for infertile women with endometriosis].	2001 Jan	11235159
[Low-dose danazol therapy in endometriosis].	2001 Jan	11235154
[Danazol--up-to-date aspect for endometriosis].	2001 Jan	11235153
Soluble ICAM-1 levels in the serum of endometriotic patients appear to be independent of medical treatment.	2001 Jul	11438377
Role of splenectomy in the treatment of myelodysplastic syndromes with peripheral thrombocytopenia: a report on six cases.	2001 Jun	11417482
[Two case reports of long-term treatment of endometriosis with cyproterone acetate].	2001 Mar	11340959
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].	2001 May	11526776
[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
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001 Nov	11757752
Danazol mimics antigestagen action in first trimester termination of pregnancy.	2001 Nov	11604193
Eradication of Helicobacter pylori and improvement of hereditary angioneurotic oedema.	2001 Nov 17	11728547
Impairment of CYP3A4 capacity in patients receiving danazol therapy: examination on oxidative cortisol metabolism.	2001 Oct	11607885
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
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
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 influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies.	2002 Mar	11865961
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

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 `Thu Jul 06 10:58:20 UTC 2023` Edited by `admin` on `Thu Jul 06 10:58:20 UTC 2023`
Record UNII	N29QWW3BUO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

DANOCRINE

Brand 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