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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

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
Urticaria and angioedema.
2001
Systemic capillary leak syndrome preceding plasma cell leukaemia.
2001
Danazol for pelvic pain associated with endometriosis.
2001
Management of endometriosis and its impact on infertility.
2001 Aug
Therapies for the treatment of abnormal uterine bleeding.
2001 Dec
Angioedema in the emergency department: a presentation of lymphoma.
2001 Dec
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.
2001 Dec
Danazol and limb-threatening arterial thrombosis: two case reports.
2001 Dec
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
C1 esterase inhibitor: new preparation. A major advance in emergency treatment of hereditary angioneurotic oedema.
2001 Jun
[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
Allogeneic stem cell transplantation for Evans syndrome.
2001 Nov
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.
2001 Nov
Treatment of autoimmune hemolytic anemias.
2001 Nov
Danazol mimics antigestagen action in first trimester termination of pregnancy.
2001 Nov
Eradication of Helicobacter pylori and improvement of hereditary angioneurotic oedema.
2001 Nov 17
Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy.
2001 Nov-Dec
Impairment of CYP3A4 capacity in patients receiving danazol therapy: examination on oxidative cortisol metabolism.
2001 Oct
Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus.
2001 Oct 15
Benign breast disease.
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
Danazol therapy for thrombocytopenia in patients with myelodysplastic syndromes.
2002
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.
2002 Apr
Premenstrual syndrome.
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
Endometriosis in an adolescent population: the severance hospital in Korean experience.
2002 Feb
Expansion of trisomy 8 and Sweet syndrome in a prolonged course of aplastic anemia.
2002 Jan
Danazol therapy in factor X deficiency: more questions than answers.
2002 Jan
Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases.
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
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
[Ureteral endometriosis: urological features].
2002 Mar
The treatment of endometriosis: a review of the evidence.
2002 Mar
Conventional medical therapies for endometriosis.
2002 Mar
[Acquired angioneurotic edema. Apropos of a case].
2002 Mar
HIV-related thrombocytopenia.
2002 Mar
Hereditary angioedema with recurrent abdominal pain.
2002 Mar-Apr
Danazol linked to ovarian cancer.
2002 May
Autoimmune acquired form of angioedema that responded to danazol therapy.
2002 May
Angioedema and acquired C1 esterase inhibitor deficiency.
2002 May
Danazol-induced hepatocellular adenoma in patients with hereditary angio-oedema.
2002 May
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.
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