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797-63-7 molecular structure
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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 ID: 251
Molecular Formular: C21H28O2
Molecular Mass: 312.44582
Monoisotopic Mass: 312.20893014
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
(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 Traditional name
norgestrel
plan b
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
Brand Name
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
Synonyms
(-)-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
(-)-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
CAS Number
797-63-7
6533-00-2
EC Number
212-349-8
MDL Number
MFCD00199013
PubChem SID
46508082
160963714
24897561
24857181
PubChem CID
13109

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.90929  H Acceptors
H Donor LogD (pH = 5.5) 3.6617966 
LogD (pH = 7.4) 3.6617966  Log P 3.6617966 
Molar Refractivity 92.0255 cm3 Polarizability 35.84699 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.25  LOG S -4.73 
Solubility (Water) 5.83e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2.05 mg/L expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
200-202°C expand Show data source
234-236°C expand Show data source
239-241 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -32°, c = 1 in chloroform expand Show data source
Hydrophobicity(logP)
3.499 expand Show data source
3.8 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
2-8°C expand Show data source
RTECS
JF8225000 expand Show data source
JF8259000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
60-20/21/22-40 expand Show data source
Safety Statements
22-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H312-H332-H351-H360 expand Show data source
GHS Precautionary statements
P201-P280-P308 + P313 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
rat ... Ar(24208) expand Show data source
Mechanism of Action
Progestogen expand Show data source
Purity
≥99% expand Show data source
95% expand Show data source
98% expand Show data source
Grade
analytical standard, for drug analysis expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Tocolytic expand Show data source
Used in oral contraceptives expand Show data source
Empirical Formula (Hill Notation)
C21H28O2 expand Show data source

DETAILS

DETAILS

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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • 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)
  • • Sopirak, A.M., et al.: Anal. Profiles Drug Subs., 4, 294 (1975)
  • • Dunson, T.R., et al.: Contraception, 48, 109 (1975)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 591C, (nmr)
  • • 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)
  • • Rosenberger, M. et al., Helv. Chim. Acta, 1971, 54, 2857, (synth)
  • • 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
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PATENTS

PATENTS

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