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6533-00-2 分子结构
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(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和InChIs

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

引用这个纪录

CBID:251 http://www.chembase.cn/molecule-251.html

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名称和登记号

名称和登记号

名称 登记号
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[8.7.0.02,7.011,15]heptadec-6-en-5-one
IUPAC传统名
norgestrel
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
plan b
商标名
Follistrel
Jadelle
Levlen
Levlen Ed
Levonova
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
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
别名
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
(-)-炔诺孕酮
D(-)-炔诺孕酮
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
Norgestrel
(-)-Norgestrel
(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
Dexnorgestrel (obsol.)
Mirena
D -Norgestrel
Levonorgestrel
Microval
Norgeston
(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
D-(-)-NORGESTREL
CAS号
6533-00-2
797-63-7
EC号
212-349-8
MDL号
MFCD00199013
PubChem SID
46508082
24897561
160963714
24857181
PubChem CID
13109

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.90929  质子受体
质子供体 LogD (pH = 5.5) 3.6617966 
LogD (pH = 7.4) 3.6617966  Log P 3.6617966 
摩尔折射率 92.0255 cm3 极化性 35.84699 Å3
极化表面积 37.3 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.25  LOG S -4.73 
溶解度 5.83e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
2.05 mg/L expand 查看数据来源
Chloroform expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
200-202°C expand 查看数据来源
234-236°C expand 查看数据来源
239-241 °C(lit.) expand 查看数据来源
比旋光度
[α]20/D -32°, c = 1 in chloroform expand 查看数据来源
疏水性(logP)
3.499 expand 查看数据来源
3.8 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
2-8°C expand 查看数据来源
RTECS编号
JF8225000 expand 查看数据来源
JF8259000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
60-20/21/22-40 expand 查看数据来源
安全公开号
22-36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H312-H332-H351-H360 expand 查看数据来源
GHS警示性声明
P201-P280-P308 + P313 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
相关基因信息
rat ... Ar(24208) expand 查看数据来源
生物活性机理
Progestogen expand 查看数据来源
纯度
≥99% expand 查看数据来源
95% expand 查看数据来源
98% expand 查看数据来源
级别
analytical standard, for drug analysis expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
应用领域
Tocolytic expand 查看数据来源
Used in oral contraceptives expand 查看数据来源
Empirical Formula (Hill Notation)
C21H28O2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank -  DB00367 external link
Item Information
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 external link
Drug information: approved
MP Biomedicals -  02155950 external link
(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)
Selleck Chemicals -  S1727 external link
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 -  N689500 external link
It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
Toronto Research Chemicals -  N689510 external link
An emergency contraceptive. Levonorgestrel is safe, tolerated and effective in emergency contraception in woman.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • Smith, H. et al., J.C.S., 1964, 4472, (synth)
  • Rufer, C. et al., Annalen, 1967, 702, 141, (synth, uv)
  • U.S. Pat., 1967, 3 338 925; CA, 68, 22142, (synth)
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  • Michnowicz, J. et al., Org. Mass Spectrom., 1972, 6, 765, (ms)
  • DeAngelis, N.J. et al., Acta Cryst. B, 1975, 31, 2040, (struct)
  • Sopirak, A. et al., Anal. Profiles Drug Subst., 1975, 4, 294, (rev)
  • Sauer, G. et al., Angew. Chem., Int. Ed., 1975, 14, 417, (synth)
  • Ranney, R.E., J. Toxicol. Environ. Health, 1977, 3, 139, (rev, metab)
  • Horvath, G. et al., Adv. Mass Spectrom., 1978, 7B, 1280, (ms)
  • Jones, R.C. et al., Int. J. Fertil., 1979, 24, 39, (props, enantiomers)
  • Delettre, J. et al., Acta Cryst. B, 1980, 36, 1505, (cryst struct)
  • Baier, H. et al., Helv. Chim. Acta, 1985, 68, 1054, (synth, cd, abs config, uv, ir, pmr)
  • Cleve, G. et al., Arzneim.-Forsch., 1986, 36, 784, (mol struct)
  • 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
  • Coukell, A.J. et al., Drugs, 1998, 55, 861-887, (rev)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NNQ500; NNQ520; NNQ525
  • 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
  • Sopirak, A.M., et al.: Anal. Profiles Drug Subs., 4, 294 (1975)
  • Dunson, T.R., et al.: Contraception, 48, 109 (1975)
  • Fotherby, K., et al.: J. Steroid Biochem., 19(1C), 817 (1983)
  • Stanczyk, F. Z., et al.: Contraception, 42, 67 (1983)
  • Bednarek, P., et al.: Drugs, 67, 2478 (1983)
  • http://en.wikipedia.org/wiki/Levonorgestrel
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专利

专利

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