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
Danazol for pelvic pain associated with endometriosis.	2001	11687066
GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.	2001 Apr	11442791
The treatment of endometriosis.	2001 Apr	11332005
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.	2001 Apr 25	11339285
Management of endometriosis and its impact on infertility.	2001 Aug	11881858
Therapies for the treatment of abnormal uterine bleeding.	2001 Dec	12112970
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.	2001 Dec	11754418
Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells.	2001 Feb	11216879
Influence of drug treatment on survival of dogs with immune-mediated hemolytic anemia: 88 cases (1989-1999).	2001 Feb 15	11229506
[Pathological findings of endometriosis].	2001 Jan	11235174
[Endometriosis of the urinary tract].	2001 Jan	11235166
[Thoracic endometriosis].	2001 Jan	11235165
[Strategy of treatment for infertile women with endometriosis].	2001 Jan	11235159
[Low-dose danazol therapy in endometriosis].	2001 Jan	11235154
Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether beta-cyclodextrins (SBE) and danazol-SBE inclusion complexes.	2001 Jan 16	11165075
Effectiveness of postoperative adjuvant therapy in improving reproductive outcome of endometriosis-associated infertility.	2001 Jul	11579612
Soluble ICAM-1 levels in the serum of endometriotic patients appear to be independent of medical treatment.	2001 Jul	11438377
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.	2001 Jul-Aug	11600235
C1 esterase inhibitor: new preparation. A major advance in emergency treatment of hereditary angioneurotic oedema.	2001 Jun	11718165
Role of splenectomy in the treatment of myelodysplastic syndromes with peripheral thrombocytopenia: a report on six cases.	2001 Jun	11417482
Medical and surgical therapies for pain associated with endometriosis.	2001 Mar	11268298
Postcoital contraception.	2001 Mar	11219237
[Pneumothorax during menstruation: a case report].	2001 May	11526763
Allogeneic stem cell transplantation for Evans syndrome.	2001 Nov	11781654
Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy.	2001 Nov-Dec	11723415
A dynamic in vitro lipolysis model. II: Evaluation of the model.	2001 Oct	11576829
Benign breast disease.	2001 Sep	11594256
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
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.	2002 Apr	12071939
Premenstrual syndrome.	2002 Apr	12032448
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
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
Conventional medical therapies for endometriosis.	2002 Mar	11949960
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

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

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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