Tìm theo
Desogestrel
Các tên gọi khác (3) :
  • 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
  • Cerazette
  • Desogestrelum
contraceptives oral synthetic, progestins
Thuốc Gốc
Small Molecule
CAS: 54024-22-5
ATC: G03AC09
ĐG : Organon Pharmaceuticals , http://www.organonshop.com
CTHH: C22H30O
PTK: 310.473
A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H30O
Phân tử khối
310.473
Monoisotopic mass
310.229665582
InChI
InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
InChI Key
InChIKey=RPLCPCMSCLEKRS-BPIQYHPVSA-N
IUPAC Name
(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
Traditional IUPAC Name
desogestrel
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]
Độ tan chảy
109-110
Độ hòa tan
3.01e-03 g/l
logP
4
logS
-5
pKa (strongest acidic)
17.99
pKa (Strongest Basic)
-1.5
PSA
20.23 Å2
Refractivity
95.73 m3·mol-1
Polarizability
37.54 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
1
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Desogestrel is used as a female contraceptive. Desogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Desogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
Cơ Chế Tác Dụng : A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem] Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like desogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
Dược Động Học :
▧ Absorption :
Following oral administration, the relative bioavailability of desogestrel, as measured by serum levels of etonogestrel, is approximately 84%. The absolute oral bioavailability is about 76%.
▧ Protein binding :
98.3%
▧ Metabolism :
Desogestrel is rapidly and completely metabolized by hydroxylation in the intestinal mucosa and on first pass through the liver. It is primarily metabolized to 3α-hydroxydesogestrel with small amounts of 3β-hydroxydesogestrel being formed. Both of these metabolites are then rapidly oxidized to its active metabolite, etonogestrel (3-ketodesogestrel). Other metabolites (e.g. 2-hydroxydesogestrel) with no pharmacologic action have also been identified. Desogestrel and some of its metabolites (e.g. 3β-hydroxydesogestrel, 15β-hydroxydesogestrel) may also undergo glucuronide and sulfate conjugation. Early in vitro studies demonstrated that CYP2C9 and possibly CYP2C19 were involved in the conversion of desogestrel to 3α-hydroxydesogestrel and 3β-hydroxydesogestrel (PMID 9864282); however, later clinical studies conducted in humans refuted this result (PMID 15963096). The latter study indicates that CYP3A4 plays an important role in metabolizing etonogestrel. Thus, strong CYP3A4 inhibitors or inducers could result in increased side effects or therapeutic failure, respectively.
▧ Half Life :
27.8±7.2 hours
Độc Tính : Symptoms of overdose include nausea and vaginal bleeding.
Chỉ Định : For the prevention of pregnancy in women who elect to use this product as a method of contraception.
Tương Tác Thuốc :
  • Artemether Artemether may decrease the effectiveness of desogestrel by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
  • Bexarotene Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of desogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
  • Colesevelam Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
  • Lamotrigine The oral contraceptive decreases the effect of lamotrigine
  • Thiopental Thiopental may decrease the effect of Desogestrel. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
  • Tretinoin Oral Tretinoin may decrease the effect of oral contraceptive, Desogestrel. An alternate form of contraception should be used during concomitant therapy.
  • Warfarin Desogestrol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if desogestrol is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral - 75 mcg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00304
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=40973
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505739
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07629
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02367
ChemSpider
http://www.chemspider.com/Chemical-Structure.37400.html
PharmGKB
http://www.pharmgkb.org/drug/PA449238
Wikipedia
http://en.wikipedia.org/wiki/Desogestrel
RxList
http://www.rxlist.com/cgi/generic/desest.htm
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