DANAZOL

First approved in 1976

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 153	Agonist 2314	Hereditary Angioedema Types I and II

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fibrocystic Breast Disease 1	Palliative	Androgen Receptor	Approved 7777	DANAZOL
Endometriosis 33	Primary	Androgen Receptor	Approved 7777	DANAZOL
Hereditary Angioedema Types I and II 1	Preventing	Androgen Receptor	Approved 7777	DANAZOL
Bone marrow failure (in Fanconi anemia) 1			Approved (off-label) 7
Severe thrombocytopenia in MDS patients 1			Approved (off-label) 7

PubMed

Title	Date	PubMed
A report on alterations to the speaking and singing voices of four women following hormonal therapy with virilizing agents.	1999 Dec	10622516
[Methimazole-induced aplastic anemia].	1999 Sep	10544668
[Spontaneous splenic rupture caused by spleen peliosis in a patient with autoimmune thrombocytopenic purpura treated with danazol].	2000 May 20	10919136
Danazol for pelvic pain associated with endometriosis.	2001	11687066
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.	2001 Apr 25	11339285
[The chronic Philadelphia chromosome-negative myeloproliferative syndrome II. Clinical findings, diagnostics and treatment].	2001 Apr 30	11379260
Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain.	2001 Apr-Jun	11394422
Therapies for the treatment of abnormal uterine bleeding.	2001 Dec	12112970
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.	2001 Dec	11754418
Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells.	2001 Feb	11216879
Influence of drug treatment on survival of dogs with immune-mediated hemolytic anemia: 88 cases (1989-1999).	2001 Feb 15	11229506
[Endometriosis of the urinary tract].	2001 Jan	11235166
[Thoracic endometriosis].	2001 Jan	11235165
[Gastrointestinal endometriosis].	2001 Jan	11235164
[Strategy of treatment for infertile women with endometriosis].	2001 Jan	11235159
[Medical treatment of endometriosis: general approach].	2001 Jan	11235147
Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether beta-cyclodextrins (SBE) and danazol-SBE inclusion complexes.	2001 Jan 16	11165075
The success of laser laparoscopy in the treatment of endometriosis: a two-step analysis.	2001 Jan-Mar	11303991
Effectiveness of postoperative adjuvant therapy in improving reproductive outcome of endometriosis-associated infertility.	2001 Jul	11579612
Cerebral venous thrombosis in a patient of paroxysmal nocturnal haemoglobinuria following aplastic anaemia.	2001 Jul	11573565
[Two case reports of long-term treatment of endometriosis with cyproterone acetate].	2001 Mar	11340959
Pulmonary nocardiosis associated with idiopathic thrombocytopenic purpura.	2001 Mar	11310493
Medical and surgical therapies for pain associated with endometriosis.	2001 Mar	11268298
Postcoital contraception.	2001 Mar	11219237
[Endometriosis of the abdominal wall: diagnosis and treatment techniques].	2001 May	11526776
[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	11526760
Interference by danazol with the Porter-Silber method for determination of urinary 17-hydroxycorticosteroids.	2001 May	11392505
[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome].	2001 Nov	11855146
Allogeneic stem cell transplantation for Evans syndrome.	2001 Nov	11781654
Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus.	2001 Oct 15	11690572
[Postcoital emergency contraception].	2001 Sep	11594152
[Dysmenorrhea].	2001 Sep	11554049
Histomorphometric analysis: comparative study of manual and digital image analysis using reproductive organ as a model.	2002	12085619
Danazol therapy for thrombocytopenia in patients with myelodysplastic syndromes.	2002	12053153
Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy.	2002 Apr	12071939
Risk factors for evolution of acquired aplastic anemia into myelodysplastic syndrome and acute myeloid leukemia after immunosuppressive therapy in children.	2002 Aug 1	12130487
Danazol therapy in factor X deficiency: more questions than answers.	2002 Jan	11886468
Hormonal emergency contraception.	2002 Jan	11794429
Hysteroscopic endometrial destruction, optimum method for preoperative endometrial preparation: a prospective, randomized, multicenter evaluation.	2002 Jan-Mar	12002292
Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes.	2002 Jul	12115827
Pulsed high-dose dexamethasone therapy in children with chronic idiopathic thrombocytopenic purpura.	2002 Jul-Aug	12078864
Successful treatment of anemia in idiopathic myelofibrosis with recombinant human erythropoietin.	2002 Jun	12111781
Splenectomy for immune thrombocytopenic purpura: long-term results and treatment of postsplenectomy relapses.	2002 Jun	12107560
A randomized trial of danazol pretreatment prior to endometrial resection.	2002 Jun 10	12039468
[Ureteral endometriosis: urological features].	2002 Mar	12053448
Conventional medical therapies for endometriosis.	2002 Mar	11949960
[Acquired angioneurotic edema. Apropos of a case].	2002 Mar	11928387
The influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies.	2002 Mar	11865961
Danazol linked to ovarian cancer.	2002 May	12067790
Autoimmune acquired form of angioedema that responded to danazol therapy.	2002 May	12058892

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

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Name

Type

Language

DANAZOL

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