(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 833
• Molecular Formular: C23H31NO3
• Molecular Mass: 369.49714
• Monoisotopic Mass: 369.23039386
• SMILES: O([C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=C/C(=N/O)/CC2)CC3)CC1)CC)C#C)C(=O)C
• Canonical SMILES: O/N=C/1\CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)OC(=O)C)CC
• InChI: InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
• InChIKey: KIQQMECNKUGGKA-NMYWJIRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate; (1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: norgestimate
• Brand Name: Ortho Cyclen-21; Ortho Cyclen-28; Ortho Tri-Cyclen; Ortho-Prefest
• Synonyms: (17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-Oxime; D-138; ORF-10131; Dexnorgestrel Acetime; Norgestimato [INN-Spanish]; Norgestimatum [INN-Latin]; Norgestimate

Database IDs

• CAS Number: 35189-28-7
• PubChem SID: 46507381; 160964296
• PubChem CID: 6540478

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.466128
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.1106176
• LogD (pH = 7.4): 4.1123424
• Log P: 4.112402
• Molar Refractivity: 104.9987 cm^3
• Polarizability: 41.020058 Å^3
• Polar Surface Area: 58.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.8
• LOG S: -4.84
• Solubility (Water): 5.31e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 230-232°C
• Hydrophobicity(logP): 4.8

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB00957

• Drug Groups: approved
• Description: Norgestimate is a form of progesterone, which is a female hormone important for the regulation of ovulation and menstruation. Norgestimate is used with estradiol to treat the symptoms of menopause.
• Indication: For the prevention of pregnancy
• Pharmacology: Norgestimate is used as a female contraceptive. Norgestimate 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. Norgestimate 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: GI tract/Hepatic
• Half Life: 12-30 hours
• External Links: Wikipedia; RxList

Toronto Research Chemicals - N686000

Progestogen. In combination with estrogen as oral contraceptive.

REFERENCES

• Hahn, D.W., et al.: Contraception, 16, 541 (1977)
• Weintraub, H.S., et al.: J. Pharm. Sci., 67, 1406 (1977)