15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol

• ChemBase编号: 4450
• 分子式: C21H29NO2
• 平均质量: 327.46046
• 单一同位素质量: 327.21982917
• SMILES: CCC12CCC3C(C1CCC2(C#C)O)CCC1=C/C(=N\O)/CCC31
• Canonical SMILES: O/N=C\1/CCC2C(=C1)CCC1C2CCC2(C1CCC2(O)C#C)CC
• InChI: InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3
• InChIKey: ISHXLNHNDMZNMC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
• IUPAC传统名: 15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
• 商标名: Orthra Evra
• 别名: Norelgestromin

登记号

• CAS号: 53016-31-2
• PubChem SID: 160967882; 99443265
• PubChem CID: 13752005

理论计算性质

JChem

• Acid pKa: 11.466128
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.6694894
• LogD (pH = 7.4): 3.6712167
• Log P: 3.6712763
• 摩尔折射率: 95.8472 cm^3
• 极化性: 37.191574 Å^3
• 极化表面积: 52.82 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: 3.18
• LOG S: -4.73
• 溶解度: 6.05e-03 g/l

详细说明

DrugBank - DB06713

• Drug Groups: approved
• Description: Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.
• Indication: Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.
• Pharmacology: Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.
• References: Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [Pubmed] ; Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [Pubmed] ; Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. [Pubmed]
• External Links: Wikipedia

参考文献

• Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. Pubmed
• Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. Pubmed
• Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. Pubmed