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

C[C@]12CC[C@H]3[C@@H](CCC4=CC5=C(C[C@]34C)C=NO5)[C@@H]1CC[C@@]2(O)C#C

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
Stereochemistry ABSOLUTE
Additional Stereochemistry
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

PubMed

PubMed

TitleDatePubMed
A report on alterations to the speaking and singing voices of four women following hormonal therapy with virilizing agents.
1999 Dec
[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
Danazol for pelvic pain associated with endometriosis.
2001
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.
2001 Apr 25
[The chronic Philadelphia chromosome-negative myeloproliferative syndrome II. Clinical findings, diagnostics and treatment].
2001 Apr 30
Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain.
2001 Apr-Jun
Therapies for the treatment of abnormal uterine bleeding.
2001 Dec
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.
2001 Dec
Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells.
2001 Feb
Influence of drug treatment on survival of dogs with immune-mediated hemolytic anemia: 88 cases (1989-1999).
2001 Feb 15
[Endometriosis of the urinary tract].
2001 Jan
[Thoracic endometriosis].
2001 Jan
[Gastrointestinal endometriosis].
2001 Jan
[Strategy of treatment for infertile women with endometriosis].
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
The success of laser laparoscopy in the treatment of endometriosis: a two-step analysis.
2001 Jan-Mar
Effectiveness of postoperative adjuvant therapy in improving reproductive outcome of endometriosis-associated infertility.
2001 Jul
Cerebral venous thrombosis in a patient of paroxysmal nocturnal haemoglobinuria following aplastic anaemia.
2001 Jul
[Two case reports of long-term treatment of endometriosis with cyproterone acetate].
2001 Mar
Pulmonary nocardiosis associated with idiopathic thrombocytopenic purpura.
2001 Mar
Medical and surgical therapies for pain associated with endometriosis.
2001 Mar
Postcoital contraception.
2001 Mar
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].
2001 May
[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
[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome].
2001 Nov
Allogeneic stem cell transplantation for Evans syndrome.
2001 Nov
Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus.
2001 Oct 15
[Postcoital emergency contraception].
2001 Sep
[Dysmenorrhea].
2001 Sep
Histomorphometric analysis: comparative study of manual and digital image analysis using reproductive organ as a model.
2002
Danazol therapy for thrombocytopenia in patients with myelodysplastic syndromes.
2002
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.
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
Danazol therapy in factor X deficiency: more questions than answers.
2002 Jan
Hormonal emergency contraception.
2002 Jan
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
A randomized trial of danazol pretreatment prior to endometrial resection.
2002 Jun 10
[Ureteral endometriosis: urological features].
2002 Mar
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
Danazol linked to ovarian cancer.
2002 May
Autoimmune acquired form of angioedema that responded to danazol therapy.
2002 May
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 Tue Oct 22 00:31:16 UTC 2019
Edited
by admin
on Tue Oct 22 00:31:16 UTC 2019
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 [USP]
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 [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 Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
WHO-VATC QG03XA01
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
NCI_THESAURUS C243
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
NCI_THESAURUS C2092
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
NDF-RT N0000000146
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
NCI_THESAURUS C2360
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
LIVERTOX 262
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
WHO-ATC G03XA01
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
NDF-RT N0000175824
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
Code System Code Type Description
CAS
17230-88-5
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
DRUG BANK
DB01406
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
ECHA (EC/EINECS)
241-270-1
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
RXCUI
3102
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY RxNorm
INN
2556
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
ChEMBL
CHEMBL1479
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
EVMPD
SUB06897MIG
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
EPA CompTox
17230-88-5
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
MESH
D003613
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
NCI_THESAURUS
C414
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
MERCK INDEX
M4081
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
DANAZOL
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
PUBCHEM
28417
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
IUPHAR
6942
Created by admin on Tue Oct 22 00:31:16 UTC 2019 , Edited by admin on Tue Oct 22 00:31:16 UTC 2019
PRIMARY
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