DANAZOL

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,678

Conditions

Condition	Modality	Highest Phase	Product
Endometriosis 32	Primary	Approved 8,429	DANAZOL
Fibrocystic breast disease 1	Palliative	Approved 8,429	DANAZOL
Hereditary angioedema 3	Preventing	Approved 8,429	DANAZOL

C_max

Value	Dose	Co-administered	Analyte	Population
69.6 ng/mL	400 mg single, oral		DANAZOL plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
601 ng × h/mL	400 mg single, oral		DANAZOL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.7 h	400 mg single, oral		DANAZOL plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	inhibitor 1,767	inhibitor 1,852 substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2J2 16 CYP1A2 1,524 CYP2C19 1,478 CYP3A 214	CYP2J2 56 CYP2C8 693 CYP2C19 991 CYP1A2 1,054 CYP1A1 349 CYP2A6 543 CYP2B6 664 FMO 35

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP2D6 1,891	inhibitor 3,277	no
CYP2J2 19	inhibitor 3,277	yes [IC50 0.05 uM]
CYP1A2 1,692	inhibitor 3,277	yes
CYP2C19 1,553	inhibitor 3,277	yes
CYP2C9 1,819	inhibitor 3,277	yes

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Drug as victim

Show entries

Target	Modality	Activity
CYP1A1 349	substrate 3,367	no
CYP1A2 1,054	substrate 3,367	no
CYP2A6 543	substrate 3,367	no
CYP2B6 664	substrate 3,367	no
CYP2C19 991	substrate 3,367	no

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Sourcing

Sourcing

Show entries

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

Showing 1 to 5 of 5 entries

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PubMed

Show entries

Title	Date	PubMed
Systemic capillary leak syndrome preceding plasma cell leukaemia.	2001	11713377
Sensory perineuritis presented as a mononeuritis multiplex associated with livedo vasculitis.	2001 Apr	11311480
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
[Thoracic endometriosis].	2001 Jan	11235165

Showing 1 to 5 of 11 entries

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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.