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
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
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 |
DescriptionSources: http://products.sanofi.ca/en/cyclomen.pdfCurator'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
Sources: http://products.sanofi.ca/en/cyclomen.pdf
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DANAZOL Approved UseDanazol 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 Date8.395488E11 |
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Palliative | DANAZOL Approved UseDanazol 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 Date8.395488E11 |
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Preventing | DANAZOL Approved UseDanazol 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 Date8.395488E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [IC50 0.05 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 2.15 uM] | ||||
yes [Km 3.62 uM] | ||||
yes |
PubMed
Title | Date | PubMed |
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Danazol for pelvic pain associated with endometriosis. | 2001 |
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GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine. | 2001 Apr |
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The treatment of endometriosis. | 2001 Apr |
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Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine. | 2001 Apr 25 |
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Management of endometriosis and its impact on infertility. | 2001 Aug |
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Therapies for the treatment of abnormal uterine bleeding. | 2001 Dec |
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Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol. | 2001 Dec |
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Comparative effect of danazol and a GnRH agonist on monocyte chemotactic protein-1 expression by endometriotic cells. | 2001 Feb |
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Influence of drug treatment on survival of dogs with immune-mediated hemolytic anemia: 88 cases (1989-1999). | 2001 Feb 15 |
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[Pathological findings of endometriosis]. | 2001 Jan |
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[Endometriosis of the urinary tract]. | 2001 Jan |
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[Thoracic endometriosis]. | 2001 Jan |
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[Strategy of treatment for infertile women with endometriosis]. | 2001 Jan |
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[Low-dose danazol therapy in endometriosis]. | 2001 Jan |
|
Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether beta-cyclodextrins (SBE) and danazol-SBE inclusion complexes. | 2001 Jan 16 |
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Effectiveness of postoperative adjuvant therapy in improving reproductive outcome of endometriosis-associated infertility. | 2001 Jul |
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Soluble ICAM-1 levels in the serum of endometriotic patients appear to be independent of medical treatment. | 2001 Jul |
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Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group. | 2001 Jul-Aug |
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C1 esterase inhibitor: new preparation. A major advance in emergency treatment of hereditary angioneurotic oedema. | 2001 Jun |
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Role of splenectomy in the treatment of myelodysplastic syndromes with peripheral thrombocytopenia: a report on six cases. | 2001 Jun |
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Medical and surgical therapies for pain associated with endometriosis. | 2001 Mar |
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Postcoital contraception. | 2001 Mar |
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[Pneumothorax during menstruation: a case report]. | 2001 May |
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Allogeneic stem cell transplantation for Evans syndrome. | 2001 Nov |
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Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy. | 2001 Nov-Dec |
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A dynamic in vitro lipolysis model. II: Evaluation of the model. | 2001 Oct |
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Benign breast disease. | 2001 Sep |
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Histomorphometric analysis: comparative study of manual and digital image analysis using reproductive organ as a model. | 2002 |
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Danazol for heavy menstrual bleeding. | 2002 |
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Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy. | 2002 Apr |
|
Premenstrual syndrome. | 2002 Apr |
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Risk factors for evolution of acquired aplastic anemia into myelodysplastic syndrome and acute myeloid leukemia after immunosuppressive therapy in children. | 2002 Aug 1 |
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Endometriosis in an adolescent population: the severance hospital in Korean experience. | 2002 Feb |
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Expansion of trisomy 8 and Sweet syndrome in a prolonged course of aplastic anemia. | 2002 Jan |
|
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 |
|
Conventional medical therapies for endometriosis. | 2002 Mar |
|
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 |
|
Optimized conditions for MDCK permeability and turbidimetric solubility studies using compounds representative of BCS classes I-IV. | 2002 May |
|
Danazol-induced hepatocellular adenoma in patients with hereditary angio-oedema. | 2002 May |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10459439
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
Edited
Fri Jun 25 20:56:59 UTC 2021
by
admin
on
Fri Jun 25 20:56:59 UTC 2021
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Record UNII |
N29QWW3BUO
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000008241
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WHO-VATC |
QG03XA01
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NCI_THESAURUS |
C243
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NCI_THESAURUS |
C2092
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NDF-RT |
N0000000146
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NCI_THESAURUS |
C2360
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LIVERTOX |
262
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WHO-ATC |
G03XA01
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NDF-RT |
N0000175824
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DB01406
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M4081
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DANAZOL
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Related Record | Type | Details | ||
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TARGET -> AGONIST | |||
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TARGET -> AGONIST | |||
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
3rd higest in plasma
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MAJOR
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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