U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DANAZOL

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

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
Danazol and multiple hepatic adenomas: peculiar clinical findings in an acromegalic patient.
1999 Aug
Hepatocellular adenomas in patients taking danazol for hereditary angio-oedema.
1999 Mar 27
[Methimazole-induced aplastic anemia].
1999 Sep
[Spontaneous splenic rupture caused by spleen peliosis in a patient with autoimmune thrombocytopenic purpura treated with danazol].
2000 May 20
GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.
2001 Apr
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
The treatment of endometriosis.
2001 Apr
Sensory perineuritis presented as a mononeuritis multiplex associated with livedo vasculitis.
2001 Apr
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.
2001 Apr 25
Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain.
2001 Apr-Jun
Management of endometriosis and its impact on infertility.
2001 Aug
Influence of drug treatment on survival of dogs with immune-mediated hemolytic anemia: 88 cases (1989-1999).
2001 Feb 15
[Pathological findings of endometriosis].
2001 Jan
[Recto-vaginal endometriosis].
2001 Jan
[Strategy of treatment for infertile women with endometriosis].
2001 Jan
[Treatment for endometriosis with pain].
2001 Jan
[Combined treatment of endometriosis--medication and surgery].
2001 Jan
[Local administration of danazol on pelvic endometriosis and uterine adenomyosis].
2001 Jan
[Medical treatment of endometriosis: general approach].
2001 Jan
Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether beta-cyclodextrins (SBE) and danazol-SBE inclusion complexes.
2001 Jan 16
Cerebral venous thrombosis in a patient of paroxysmal nocturnal haemoglobinuria following aplastic anaemia.
2001 Jul
Role of splenectomy in the treatment of myelodysplastic syndromes with peripheral thrombocytopenia: a report on six cases.
2001 Jun
Pulmonary nocardiosis associated with idiopathic thrombocytopenic purpura.
2001 Mar
Medical and surgical therapies for pain associated with endometriosis.
2001 Mar
Postcoital contraception.
2001 Mar
[The evaluation of the effect of combined treatment (laparoscopic ante-fixation of the uterus and Danazol-therapy) in patients with endometriosis and retroflexion of the uterus].
2001 May
Interference by danazol with the Porter-Silber method for determination of urinary 17-hydroxycorticosteroids.
2001 May
Long-term outcomes after treatment for refractory immune thrombocytopenic purpura.
2001 May 3
[Danazol-induced hepatitis with functional deficit of the C1 inhibitor].
2001 Nov
Allogeneic stem cell transplantation for Evans syndrome.
2001 Nov
Treatment of autoimmune hemolytic anemias.
2001 Nov
Danazol mimics antigestagen action in first trimester termination of pregnancy.
2001 Nov
Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy.
2001 Nov-Dec
Danazol therapy in factor X deficiency.
2001 Sep
[Dysmenorrhea].
2001 Sep
Danazol for heavy menstrual bleeding.
2002
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
[Acquired angioneurotic edema. Apropos of a case].
2002 Mar
Danazol-induced hepatocellular adenoma in patients with hereditary angio-oedema.
2002 May
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.
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 [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
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
WHO-VATC QG03XA01
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
NCI_THESAURUS C243
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
NCI_THESAURUS C2092
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
NDF-RT N0000000146
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
NCI_THESAURUS C2360
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
LIVERTOX 262
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
WHO-ATC G03XA01
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
NDF-RT N0000175824
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
Code System Code Type Description
CAS
17230-88-5
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
DRUG BANK
DB01406
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-270-1
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
RXCUI
3102
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY RxNorm
INN
2556
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL1479
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
EVMPD
SUB06897MIG
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
CHEBI
4315
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
NSC
270916
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID2022880
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
MESH
D003613
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
NCI_THESAURUS
C414
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
RS_ITEM_NUM
1162501
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
DRUG CENTRAL
779
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
MERCK INDEX
M4081
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
DANAZOL
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
PUBCHEM
28417
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
SMS_ID
100000083436
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
IUPHAR
6942
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
DAILYMED
N29QWW3BUO
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY
FDA UNII
N29QWW3BUO
Created by admin on Thu Jul 06 10:58:20 UTC 2023 , Edited by admin on Thu Jul 06 10:58:20 UTC 2023
PRIMARY