(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: 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

NAMES AND DATABASE IDS

Names

• 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[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: norgestrel; plan b; (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.90929
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6617966
• LogD (pH = 7.4): 3.6617966
• Log P: 3.6617966
• Molar Refractivity: 92.0255 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.25
• LOG S: -4.73
• Solubility (Water): 5.83e-03 g/l

PROPERTIES

Physical Property

• Solubility: 2.05 mg/L; Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 200-202°C; 234-236°C; 239-241 °C(lit.)
• Optical Rotation: [α]20/D -32°, c = 1 in chloroform
• Hydrophobicity(logP): 3.499; 3.8

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• RTECS: JF8225000; JF8259000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H312-H332-H351-H360
• GHS Precautionary statements: P201-P280-P308 + P313
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Ar(24208)
• Mechanism of Action: Progestogen

Product Information

• Purity: ≥99%; 95%; 98%
• Grade: analytical standard, for drug analysis
• Salt Data: Free Base
• Application(s): Tocolytic; Used in oral contraceptives
• Empirical Formula (Hill Notation): C21H28O2

DETAILS

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.

REFERENCES

• 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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• Dunson, T.R., et al.: Contraception, 48, 109 (1975)
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• DeAngelis, N.J. et al., Acta Cryst. B, 1975, 31, 2040, (struct)
• Sopirak, A. et al., Anal. Profiles Drug Subst., 1975, 4, 294, (rev)
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• Ranney, R.E., J. Toxicol. Environ. Health, 1977, 3, 139, (rev, metab)
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• 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