DANAZOL

First approved in 1976

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H27NO2
Molecular Weight	337.4561
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C#C[C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=Cc5c(C[C@]4(C)[C@@]3([H])CC[C@@]21C)cno5)O

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	337.4561
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 163 Target ID: CHEMBL1871 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Agonist 2470

Conditions

Condition	Modality	Highest Phase	Product
Endometriosis 30 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f2c9b713-aafc-49ca-866e-334d9b5c2e2d	Primary	Approved 8043	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 8043	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 8043	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 1601	inhibitor 1604	inhibitor 1702 substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2J2 16 CYP1A2 1383 CYP2C19 1325 CYP3A 191	CYP2J2 53 CYP2C8 634 CYP2C19 910 CYP1A2 972 CYP1A1 325 CYP2A6 485 CYP2B6 616 FMO 33

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1738	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	no
CYP2J2 19	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes [IC50 0.05 uM]
CYP1A2 1532	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C19 1392	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP2C9 1648	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes
CYP3A 271	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26048912/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 325	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP1A2 972	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2A6 485	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2B6 616	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C19 910	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2C8 634	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
FMO 33	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	no
CYP2J2 53	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 2.15 uM]
CYP3A4 1601	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19923256/	yes [Km 3.62 uM]
CYP2D6 1118	substrate 3113 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
Management of endometriosis and its impact on infertility.	2001 Aug	11881858
Therapies for the treatment of abnormal uterine bleeding.	2001 Dec	12112970
Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells.	2001 Feb	11216879
[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
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].	2001 May	11526776
[Pneumothorax during menstruation: a case report].	2001 May	11526763
[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
Danazol therapy in factor X deficiency.	2001 Sep	11554940
[Dysmenorrhea].	2001 Sep	11554049
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
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding.	2002	11869575
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
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
Conventional medical therapies for endometriosis.	2002 Mar	11949960
[Acquired angioneurotic edema. Apropos of a case].	2002 Mar	11928387
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
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 `Fri Jun 25 20:56:59 UTC 2021` Edited by `admin` on `Fri Jun 25 20:56:59 UTC 2021`
Record UNII	N29QWW3BUO
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DANAZOL

Official Name

English

NSC-270916

Code

English

DANAZOL [WHO-DD]

Common Name

English

DANAZOL [USP-RS]

Common Name

English

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

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