Tìm theo
Levonorgestrel
Các tên gọi khác (27 ) :
  • (-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one
  • 13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
  • 13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one
  • 13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one
  • 17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one
  • 17-alpha-Ethynyl-13-ethyl-19-nortestosterone
  • 17-Ethynyl-18-methyl-19-nortestosterone
  • 17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
  • 17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
  • 17alpha-Ethynyl-18-homo-19-nortestosterone
  • 18-Methyl-17-alpha-ethynyl-19-nortestosterone
  • 18-Methylnorethisterone
  • d(-)-Norgestrel
  • Jadelle
  • Levonelle
  • Levonorgestrel
  • Lévonorgestrel
  • Levonorgestrelum
  • Levonova
  • Microlut
  • Microluton
  • Microval
  • Mirena
  • NorLevo
  • Plan b
  • Postinor
Hormon, Nội tiết tố
Thuốc Gốc
Small Molecule
CAS: 797-63-7
ATC: G03AC03, G03AD01
ĐG : 3M Health Care , http://www.3m.com
CTHH: C21H28O2
PTK: 312.4458
A synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H28O2
Phân tử khối
312.4458
Monoisotopic mass
312.20893014
InChI
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI Key
InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
IUPAC Name
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Name
levonorgestrel
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Độ tan chảy
240 °C
Độ hòa tan
2.05 mg/L
logP
3.8
logS
-4.7
pKa (strongest acidic)
17.91
pKa (Strongest Basic)
-1.5
PSA
37.3 Å2
Refractivity
92.03 m3·mol-1
Polarizability
36.73 Å3
Rotatable Bond Count
1
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Levonorgestrel 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. Levonorgestrel 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 with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral. 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 levonorgestrel 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 :
Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.
▧ Volume of Distribution :
* 260 L [Healthy Female Volunteers under Fasting Conditions] * 1.8 L/kg
▧ Protein binding :
55%
▧ Metabolism :
Hepatic
▧ Route of Elimination :
About 45% of levonorgestrel and its metabolites are excreted in the urine and about 32% are excreted in feces, mostly as glucuronide conjugates.
▧ Clearance :
* 7.7 +/- 2.7 L/h [Healthy Female Volunteers under Fasting Conditions]
Độc Tính : LD50 >5000 mg/kg (orally in rats)
Chỉ Định : For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
Tương Tác Thuốc :
  • Amobarbital Phenobarbital decreases the effect of levonorgestrel
  • Aprobarbital Phenobarbital decreases the effect of levonorgestrel
  • Artemether Artemether may decrease the effectiveness of levonorgestrel 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 levonorgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
  • Butabarbital Phenobarbital decreases the effect of levonorgestrel
  • Butalbital Phenobarbital decreases the effect of levonorgestrel
  • Butethal Phenobarbital decreases the effect of levonorgestrel
  • Carbamazepine Carbamazepine may decrease the contraceptive effect of levonorgestrel.
  • 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.
  • Dihydroquinidine barbiturate Phenobarbital decreases the effect of levonorgestrel
  • Ethotoin Phenytoin decreases the contraceptive effect
  • Fosphenytoin Phenytoin decreases the contraceptive effect
  • Heptabarbital Phenobarbital decreases the effect of levonorgestrel
  • Hexobarbital Phenobarbital decreases the effect of levonorgestrel
  • Mephenytoin Phenytoin decreases the contraceptive effect
  • Methohexital Phenobarbital decreases the effect of levonorgestrel
  • Methylphenobarbital Phenobarbital decreases the effect of levonorgestrel
  • Pentobarbital Phenobarbital decreases the effect of levonorgestrel
  • Phenobarbital Phenobarbital decreases the effect of levonorgestrel
  • Phenytoin Phenytoin decreases the contraceptive effect
  • Primidone Phenobarbital decreases the effect of levonorgestrel
  • Quinidine barbiturate Phenobarbital decreases the effect of levonorgestrel
  • Secobarbital Phenobarbital decreases the effect of levonorgestrel
  • Talbutal Phenobarbital decreases the effect of levonorgestrel
  • Thiopental Thiopental may decrease the effect of Levonorgestrel. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
  • Tretinoin Oral Tretinoin may decrease the effect of oral contraceptive, Levonorgestrel. An alternate form of contraception should be used during concomitant therapy.
  • Warfarin Levonorgestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if levonorgestrel is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Insert, extended release - Intrauterine
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Bayer
    Sản phẩm biệt dược : Jadelle
  • Công ty : Bayer
    Sản phẩm biệt dược : Levonelle
  • Công ty : Medopharm
    Sản phẩm biệt dược : Medonor
  • Công ty : Bayer
    Sản phẩm biệt dược : Microlut
  • Công ty : Wyeth
    Sản phẩm biệt dược : Microval
  • Công ty : Bayer
    Sản phẩm biệt dược : Mirena
  • Công ty : Schering
    Sản phẩm biệt dược : Neogest
  • Công ty : Watson
    Sản phẩm biệt dược : Next Choice
  • Công ty : Bayer
    Sản phẩm biệt dược : Norgeston
  • Công ty : Bayer
    Sản phẩm biệt dược : NorLevo
  • Công ty : Bayer
    Sản phẩm biệt dược : Norplant
  • Công ty : Teva
    Sản phẩm biệt dược : Plan B
  • Công ty : Gedeon Richter
    Sản phẩm biệt dược : Postinor
  • Công ty :
    Sản phẩm biệt dược : Skyla
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00367
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=13109
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508082
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C08149
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00950
ChemSpider
http://www.chemspider.com/Chemical-Structure.12560.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/51285-769-93
PharmGKB
http://www.pharmgkb.org/drug/PA450656
Wikipedia
http://en.wikipedia.org/wiki/Levonorgestrel
RxList
http://www.rxlist.com/cgi/generic2/norplant.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/pla1696.shtml
Drugs.com
http://www.drugs.com/cdi/levonorgestrel.html
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