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
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
Molecular Formula | C22H27NO2 |
Molecular Weight | 337.4553 |
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 |
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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 Date1996 |
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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 Date1996 |
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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 Date1996 |
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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Urticaria and angioedema. | 2001 |
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Systemic capillary leak syndrome preceding plasma cell leukaemia. | 2001 |
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Danazol for pelvic pain associated with endometriosis. | 2001 |
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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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Angioedema in the emergency department: a presentation of lymphoma. | 2001 Dec |
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Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol. | 2001 Dec |
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Danazol and limb-threatening arterial thrombosis: two case reports. | 2001 Dec |
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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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[Danazol-induced hepatitis with functional deficit of the C1 inhibitor]. | 2001 Nov |
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[The effectiveness of cyclosporin A in the treatment of autoimmune hemolytic anemia and Evans syndrome]. | 2001 Nov |
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Allogeneic stem cell transplantation for Evans syndrome. | 2001 Nov |
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Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia. | 2001 Nov |
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Eradication of Helicobacter pylori and improvement of hereditary angioneurotic oedema. | 2001 Nov 17 |
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Influence of vaginal danazol on uterine and brain perfusion during hormonal replacement therapy. | 2001 Nov-Dec |
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Impairment of CYP3A4 capacity in patients receiving danazol therapy: examination on oxidative cortisol metabolism. | 2001 Oct |
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Disease activity during the premenopausal and postmenopausal periods in women with systemic lupus erythematosus. | 2001 Oct 15 |
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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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Danazol therapy for thrombocytopenia in patients with myelodysplastic syndromes. | 2002 |
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Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding. | 2002 |
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Remission of transformed myelodysplastic syndrome with fibrosis after danazol therapy. | 2002 Apr |
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Premenstrual syndrome. | 2002 Apr |
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Microbial transformation of danazol. | 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 |
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Danazol therapy in factor X deficiency: more questions than answers. | 2002 Jan |
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Treatment of severe immune thrombocytopenia associated with systemic lupus erythematosus: 59 cases. | 2002 Jan |
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Hormonal emergency contraception. | 2002 Jan |
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Hysteroscopic endometrial destruction, optimum method for preoperative endometrial preparation: a prospective, randomized, multicenter evaluation. | 2002 Jan-Mar |
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Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes. | 2002 Jul |
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Pulsed high-dose dexamethasone therapy in children with chronic idiopathic thrombocytopenic purpura. | 2002 Jul-Aug |
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Successful treatment of anemia in idiopathic myelofibrosis with recombinant human erythropoietin. | 2002 Jun |
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Splenectomy for immune thrombocytopenic purpura: long-term results and treatment of postsplenectomy relapses. | 2002 Jun |
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Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials. | 2002 Jun |
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A randomized trial of danazol pretreatment prior to endometrial resection. | 2002 Jun 10 |
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[Ureteral endometriosis: urological features]. | 2002 Mar |
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The treatment of endometriosis: a review of the evidence. | 2002 Mar |
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Conventional medical therapies for endometriosis. | 2002 Mar |
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[Acquired angioneurotic edema. Apropos of a case]. | 2002 Mar |
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HIV-related thrombocytopenia. | 2002 Mar |
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The influence of hormones and pharmaceutical agents on DHEA and DHEA-S concentrations: a review of clinical studies. | 2002 Mar |
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Hereditary angioedema with recurrent abdominal pain. | 2002 Mar-Apr |
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Danazol linked to ovarian cancer. | 2002 May |
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Autoimmune acquired form of angioedema that responded to danazol therapy. | 2002 May |
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Angioedema and acquired C1 esterase inhibitor deficiency. | 2002 May |
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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 |
|
Benign breast pain in women: a practical approach to evaluation and treatment. | 2002 Spring |
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
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N0000008241
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NCI_THESAURUS |
C243
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C2092
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N0000000146
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C2360
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N0000175824
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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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