Tìm theo
Danazol
Các tên gọi khác (3) :
  • Cyclomen
  • Danazolum
  • Danocrine
Hormon, Nội tiết tố
Thuốc Gốc
Small Molecule
CAS: 17230-88-5
ATC: G03XA01
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C22H27NO2
PTK: 337.4553
A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H27NO2
Phân tử khối
337.4553
Monoisotopic mass
337.204179113
InChI
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
InChI Key
InChIKey=POZRVZJJTULAOH-LHZXLZLDSA-N
IUPAC Name
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol
Traditional IUPAC Name
danazol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3
Độ tan chảy
224.2-226.8
Độ hòa tan
1.76e-02 g/l
logP
0.51
logS
-4.3
pKa (strongest acidic)
17.59
pKa (Strongest Basic)
0.25
PSA
46.26 Å2
Refractivity
98.54 m3·mol-1
Polarizability
38.56 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.
Cơ Chế Tác Dụng : A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem] As a gonadotropin inhibitor, danazol suppresses the pituitary-ovarian axis possibly by inhibiting the output of pituitary gonadotropins. Danazol also depresses the preovulatory surge in output of follicle-stimulating hormone (FSH) and luteinizing hormone (LH), thereby reducing ovarian estrogen production. Danazol may also directly inhibits ovarian steroidogenesis; bind to androgen, progesterone, and glucocorticoid receptors; bind to sex-hormone-binding globulin and corticosteroid-binding globulin; and increases the metabolic clearance rate of progesterone. Another mechanism of action by which danazol may use to facilitate regression of endometriosis is by decreasing IgG, IgM, and IgA concentrations, as well as phospholipid and IgG isotope autoantibodies. In the treatment of endometriosis, as a consequence of suppression of ovarian function, danazol causes both normal and ectopic endometrial tissues to become inactive and atrophic. This leads to anovulation and associated amenorrhea. In fibrocystic breast disease, the exact mechanism of action of danazol is unknown, but may be related to suppressed estrogenic stimulation as a result of decreased ovarian production of estrogen. A direct effect on steroid receptor sites in breast tissue is also possible. This leads to a disappearance of nodularity, relief of pain and tenderness, and possibly changes in the menstrual pattern. In terms of hereditary angioedema, danazol corrects the underlying biochemical deficiency by increasing serum concentrations of the deficient C1 esterase inhibitor, resulting in increased serum concentrations of the C4 component of the complement system. (Source: PharmGKB)
Dược Động Học :

▧ Metabolism :
Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.
▧ Half Life :
Approximately 24 hours.
Chỉ Định : For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.
Tương Tác Thuốc :
  • Acenocoumarol The androgen, danazol, may increase the anticoagulant effect of acenocoumarol.
  • Anisindione The androgen, danazol, may increase the anticoagulant effect of anisindione.
  • Carbamazepine Danazol may decrease the metabolism of carbamazepine. Monitor for changes in the therapeutic and adverse effects of carbamazepine if danazol is initiated, discontinued or dose changed.
  • Cyclosporine The androgen, danazol, may increase the effect and toxicity of cyclosporine.
  • Dicoumarol The androgen, danazol, may increase the anticoagulant effect of dicumarol.
  • Exenatide Monitor therapy due to reduced hypoglycemic effect of exenatide.
  • Insulin Aspart Monitor therapy due to decreased hypoglycemic effect of insulin aspart.
  • Lovastatin Risk of severe myopathy/rhabdomyolysis with this combination
  • Tacrolimus Danazol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Danazol therapy is initiated, discontinued or altered.
  • Warfarin Danazol may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if danazol is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Capsule - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Cyclomen 100 mg Capsule
    Giá bán buôn : USD >1.45
    Đơn vị tính : capsule
  • Biệt dược thương mại : Danazol 50 mg capsule
    Giá bán buôn : USD >1.95
    Đơn vị tính : capsule
  • Biệt dược thương mại : Cyclomen 200 mg Capsule
    Giá bán buôn : USD >2.31
    Đơn vị tính : capsule
  • Biệt dược thương mại : Danazol 100 mg capsule
    Giá bán buôn : USD >2.92
    Đơn vị tính : capsule
  • Biệt dược thương mại : Danocrine 200 mg capsule
    Giá bán buôn : USD >4.53
    Đơn vị tính : capsule
  • Biệt dược thương mại : Danazol 200 mg capsule
    Giá bán buôn : USD >5.2
    Đơn vị tính : capsule
  • Biệt dược thương mại : Danazol powder
    Giá bán buôn : USD >21.42
    Đơn vị tính : g
  • Biệt dược thương mại : Cyclomen 50 mg Capsule
    Giá bán buôn : USD >0.98
    Đơn vị tính : capsule
Nhà Sản Xuất
  • Công ty : Sanofi
    Sản phẩm biệt dược : Cyclomen
  • Công ty : Sanofi
    Sản phẩm biệt dược : Danocrine
  • Công ty : Sanofi
    Sản phẩm biệt dược : Danol
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01406
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=28417
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506475
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00289
ChemSpider
http://www.chemspider.com/Chemical-Structure.26436.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0024-0305-60
PharmGKB
http://www.pharmgkb.org/drug/PA164749056
Wikipedia
http://en.wikipedia.org/wiki/Danazol
RxList
http://www.rxlist.com/cgi/generic/danazol.htm
Drugs.com
http://www.drugs.com/cdi/danazol.html
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