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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 of DANAZOL

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
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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Palliative
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
Preventing
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
69.6 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
601 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.7 h
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

Overview

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Management of endometriosis and its impact on infertility.
2001 Aug
Therapies for the treatment of abnormal uterine bleeding.
2001 Dec
Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells.
2001 Feb
[Danazol--up-to-date aspect for endometriosis].
2001 Jan
Soluble ICAM-1 levels in the serum of endometriotic patients appear to be independent of medical treatment.
2001 Jul
Role of splenectomy in the treatment of myelodysplastic syndromes with peripheral thrombocytopenia: a report on six cases.
2001 Jun
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].
2001 May
[Pneumothorax during menstruation: a case report].
2001 May
[Danazol-induced hepatitis with functional deficit of the C1 inhibitor].
2001 Nov
[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome].
2001 Nov
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.
2001 Nov
Danazol mimics antigestagen action in first trimester termination of pregnancy.
2001 Nov
Danazol therapy in factor X deficiency.
2001 Sep
[Dysmenorrhea].
2001 Sep
Histomorphometric analysis: comparative study of manual and digital image analysis using reproductive organ as a model.
2002
Danazol for heavy menstrual bleeding.
2002
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding.
2002
Premenstrual syndrome.
2002 Apr
Microbial transformation of danazol.
2002 Apr
Risk factors for evolution of acquired aplastic anemia into myelodysplastic syndrome and acute myeloid leukemia after immunosuppressive therapy in children.
2002 Aug 1
Hysteroscopic endometrial destruction, optimum method for preoperative endometrial preparation: a prospective, randomized, multicenter evaluation.
2002 Jan-Mar
Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes.
2002 Jul
Pulsed high-dose dexamethasone therapy in children with chronic idiopathic thrombocytopenic purpura.
2002 Jul-Aug
Successful treatment of anemia in idiopathic myelofibrosis with recombinant human erythropoietin.
2002 Jun
Splenectomy for immune thrombocytopenic purpura: long-term results and treatment of postsplenectomy relapses.
2002 Jun
Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials.
2002 Jun
A randomized trial of danazol pretreatment prior to endometrial resection.
2002 Jun 10
Conventional medical therapies for endometriosis.
2002 Mar
[Acquired angioneurotic edema. Apropos of a case].
2002 Mar
The influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies.
2002 Mar
Hereditary angioedema with recurrent abdominal pain.
2002 Mar-Apr
Benign breast pain in women: a practical approach to evaluation and treatment.
2002 Spring
Patents

Sample Use Guides

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
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
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
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
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
WHO-VATC QG03XA01
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
NCI_THESAURUS C243
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
NCI_THESAURUS C2092
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
NDF-RT N0000000146
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
NCI_THESAURUS C2360
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
LIVERTOX 262
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
WHO-ATC G03XA01
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
NDF-RT N0000175824
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
Code System Code Type Description
CAS
17230-88-5
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
DRUG BANK
DB01406
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
241-270-1
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
RXCUI
3102
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY RxNorm
INN
2556
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1479
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
EVMPD
SUB06897MIG
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
EPA CompTox
17230-88-5
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
MESH
D003613
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
NCI_THESAURUS
C414
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
DRUG CENTRAL
779
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
USP_CATALOG
1162501
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M4081
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
DANAZOL
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
PUBCHEM
28417
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
IUPHAR
6942
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
FDA UNII
N29QWW3BUO
Created by admin on Fri Jun 25 20:56:59 UTC 2021 , Edited by admin on Fri Jun 25 20:56:59 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TARGET -> AGONIST
TARGET -> AGONIST
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METABOLITE -> PARENT
METABOLITE -> PARENT
3rd higest in plasma
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC