(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

• ChemBase编号: 251
• 分子式: C21H28O2
• 平均质量: 312.44582
• 单一同位素质量: 312.20893014
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CC(=O)CC2)CC3)CC1)CC)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• 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
• InChIKey: WWYNJERNGUHSAO-XUDSTZEESA-N

名称和登记号

名称

• IUPAC标准名: (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; (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC传统名: norgestrel; plan b; (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• 商标名: Alesse; Alpha-Norgestrel; Component of Lo/Ovral; Component of Ovral; DL-Norgestrel; LD Norgestrel; Ld Norgestrel [French]; Lo/Ovral; Logynon; Methylnorethindrone; Microgynon; Microlut; Monovar; NOG; Neogest; Norgeston; Norgestrel [Progestins]; Norgestrel [Usan:Ban:Inn:Jan]; Norgestrelum [INN-Latin]; Ovral; Ovran; Postinor; Stediril; Tetragynon; Trinordiol; Levora-21; Levora-28; Logynon Ed; Malloside; Microgest Ed; Microgyn; Microgynon 21; Microgynon 28; Microgynon 30 Ed; Microgynon Cd; Microlution; Microval; Minivlar 30; Mirena; Monofeme 28; Norplant; Neogynon 21; Nordet; Nordette; Nordette 21; Nordette 28; Norplant 2; Norplant II; Ovral-Lo; Ovranette; Ovrette; Plan B; Rigevidon 21+7; Stediril 30; Tri-Levlen; Tri-Levlen 21; Triagynon; Triciclor; Trifeme 28; Trigoa; Trinordiol 21; Trinordiol 28; Trivora; Levonelle; NorLevo; Postinor-2; 72-HOURS; Follistrel; Jadelle; Levlen; Levlen Ed; Levonova
• 别名: (-)-炔诺孕酮; 18,19-双失碳孕甾-4-烯-20-炔基-3-酮; 18,19-双失碳-13β-乙基-17β-羟基-孕甾-4-烯-20-炔基-3-酮; 左旋甲基炔诺酮; 左炔诺孕酮; 甲基炔诺酮; D(-)-炔诺孕酮; (-)-Norgestrel; Norgestrel; (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; (17α)-(+/-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one; (+/-)-13-Ethyl-17α-ethynyl-17-hydroxygon-4-en-3-one; (+/-)-Norgestrel; DL-Norgestrel; FH 122A; Methylnorethindrone; Monovar; Neogest; Ovrette; Postinor; SH 70850; SH 850; Wy 3707; 17-Ethynyl-18-methyl-19-nortestosterone; (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one; Levonorgestrel; Dexnorgestrel; Microlut; Microval; Norgeston; Levonorgestrelum [INN-Latin]; SOH-075; Levonorgestrel; Levonelle; D-Norgestrel; Levonova; 18,19-Dinor-13β-ethyl-17 β hydroxy-4-pregnen-20-yn-3-one; 18,19-Dinor-4-pregnen-20-yn-3-one; 13β-Ethyl-17α-ethynyl-17 β-hydroxygon-4-en-3-one; D-(-)-NORGESTREL; D(-)-Norgestrel; Dexnorgestrel (obsol.); Mirena; D -Norgestrel; Levonorgestrel

登记号

• CAS号: 6533-00-2; 797-63-7
• EC号: 212-349-8
• MDL号: MFCD00199013
• PubChem SID: 160963714; 24897561; 46508082; 24857181
• PubChem CID: 13109

理论计算性质

JChem

• Acid pKa: 17.90929
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.6617966
• LogD (pH = 7.4): 3.6617966
• Log P: 3.6617966
• 摩尔折射率: 92.0255 cm^3
• 极化性: 35.84699 Å^3
• 极化表面积: 37.3 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.25
• LOG S: -4.73
• 溶解度: 5.83e-03 g/l

分子性质

理化性质

• 溶解度: 2.05 mg/L; Chloroform; Methanol
• 外观: White Solid
• 熔点: 200-202°C; 234-236°C; 239-241 °C(lit.)
• 比旋光度: [α]20/D -32°, c = 1 in chloroform
• 疏水性(logP): 3.499; 3.8

安全信息

• 保存条件: -20°C; -20°C Freezer; 2-8°C
• RTECS编号: JF8225000; JF8259000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 60-20/21/22-40
• 安全公开号: 22-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H312-H332-H351-H360
• GHS警示性声明: P201-P280-P308 + P313
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Ar(24208)
• 生物活性机理: Progestogen

产品相关信息

• 纯度: ≥99%; 95%; 98%
• 级别: analytical standard, for drug analysis
• 成盐信息: Free Base
• 应用领域: Tocolytic; Used in oral contraceptives
• Empirical Formula (Hill Notation): C21H28O2

详细说明

MP Biomedicals - 02155950

(18,19-Dinor-13β-ethyl-17β hydroxy-4-pregnen-20-yn-3-one; 18,19-Dinor-4-pregnen-20-yn-3-one; 13β-Ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one)

DrugBank - DB00367

• Drug Groups: approved; investigational
• Description: 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.
• Indication: For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
• Pharmacology: 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.
• Toxicity: LD50 >5000 mg/kg (orally in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.
• Protein Binding: 55%
• Elimination: About 45% of levonorgestrel and its metabolites are excreted in the urine and about 32% are excreted in feces, mostly as glucuronide conjugates.
• Distribution: * 260 L [Healthy Female Volunteers under Fasting Conditions]; * 1.8 L/kg
• Clearance: * 7.7 +/- 2.7 L/h [Healthy Female Volunteers under Fasting Conditions]
• References: Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [Pubmed] ; Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

DrugBank - DB00506

Drug information: approved

Selleck Chemicals - S1727

Research Area: Endocrinology
Biological Activity:
Levonorgestrel(Levonelle) is a synthetic progestogen used as an active ingredient in some hormonal contraceptives. It is a hormonally active levorotatory enantiomer of the racemic mixture norgestrel. It is a gonane progestin derived from 19-nortestosterone. [1]

Toronto Research Chemicals - N689510

An emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman.

Toronto Research Chemicals - N689500

It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.

参考文献

• Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. Pubmed
• Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. Pubmed
• http://en.wikipedia.org/wiki/Levonorgestrel
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• Stanczyk, F. Z., et al.: Contraception, 42, 67 (1983)
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• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6287; 6288
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1190
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