methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate

• ChemBase编号: 805
• 分子式: C22H38O5
• 平均质量: 382.53412
• 单一同位素质量: 382.27192432
• SMILES: O[C@H]1[C@@H]([C@@H](CCCCCCC(=O)OC)C(=O)C1)/C=C/CC(O)(CCCC)C
• Canonical SMILES: CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)(O)C
• InChI: InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
• InChIKey: OJLOPKGSLYJEMD-URPKTTJQSA-N

名称和登记号

名称

• IUPAC标准名: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
• IUPAC传统名: misoprostol
• 商标名: Arthrotec; Cytotec
• 别名: (±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1 methyl ester; Misoprostol; Misoprostolum [INN-Latin]; Misoprostol

登记号

• CAS号: 59122-46-2
• MDL号: MFCD00274550
• PubChem SID: 160964268; 24897117; 46505041
• PubChem CID: 5282381

理论计算性质

JChem

• Acid pKa: 14.680623
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.857755
• LogD (pH = 7.4): 3.857755
• Log P: 3.857755
• 摩尔折射率: 107.8798 cm^3
• 极化性: 42.359562 Å^3
• 极化表面积: 83.83 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.88
• LOG S: -4.37
• 溶解度: 1.64e-02 g/l

分子性质

理化性质

• 溶解度: >1.6 mg/mL at 25.0 oC
• 疏水性(logP): 3.6

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2810
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 60-61-25
• 安全公开号: 53-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H360
• GHS警示性声明: P201-P301 + P310-P308 + P313
• RID/ADR: UN 2810 6.1/PG 3
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... PTGIR(5739)

产品相关信息

• 纯度: ≥99% (TLC)

详细说明

DrugBank - DB00929

• Drug Groups: approved
• Description: A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. [PubChem]
• Indication: Indicated for the treatment of ulceration (duodenal, gastric and NSAID induced) and prophylaxis for NSAID induced ulceration.; Misoprostol is also indicated for other uses that are not approved in Canada, including the medical termination of an intrauterine pregnancy used alone or in combination with methotrexate,as well as the induction of labour in a selected population of pregnant women with unfavourable cervices. This indication is avoided in women with prior uterine surgery or cesarean surgery due to an increased risk of possible uterine rupture. Misoprostol is also used for the prevention or treatment of serious postpartum hemorrhage.
• Pharmacology: Misoprostol is a prostaglandin E1 (PGE1) analogue used for the treatment and prevention of stomach ulcers. When administered, misoprostol stimulates increased secretion of the protective mucus that lines the gastrointestinal tract and increases mucosal blood flow, thereby increasing mucosal integrity. It is sometimes co-prescribed with non-steroidal anti-inflammatory drugs (NSAIDs) to prevent the occurrence of gastric ulceration, a common adverse effect of the NSAIDs.
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly de-esterified to misoprostol acid. The de-esterified metabolite undergoes further metabolism by beta and omega oxidation; oxidation is followed by reduction of the ketone to yield prostaglandin F analogs.
• Absorption: Misoprostol is extensively absorbed.
• Half Life: 20-40 minutes
• Protein Binding: 85%
• Elimination: After a single oral dose of misoprostol to nursing mothers, misoprostol acid was excreted in breast milk.
• References: Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. [Pubmed] ; Coelho HL, Teixeira AC, Cruz Mde F, Gonzaga SL, Arrais PS, Luchini L, La Vecchia C, Tognoni G: Misoprostol: the experience of women in Fortaleza, Brazil. Contraception. 1994 Feb;49(2):101-10. [Pubmed] ; Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. [Pubmed] ; Rocha J: Brazil investigates drug's possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. [Pubmed] ; Gonzalez CH, Vargas FR, Perez AB, Kim CA, Brunoni D, Marques-Dias MJ, Leone CR, Correa Neto J, Llerena Junior JC, de Almeida JC: Limb deficiency with or without Mobius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy. Am J Med Genet. 1993 Aug 1;47(1):59-64. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M6807

Biochem/physiol Actions
Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration.
PGE1 analog prodrug which is rapidly de-esterified to active "misoprostolic acid". Cited for extremely wide-ranging therapeutic effects, including prevention of NSAID-induced gastric ulceration, regulation of immunologic cascades, inhibition of platelet-activating factor (PAF), treatment of ethanol- and acetaminophen-induced hepatotoxicity and hepatitis, and stimulation of cartilage repair after injury.1

参考文献

• Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. Pubmed
• Coelho HL, Teixeira AC, Cruz Mde F, Gonzaga SL, Arrais PS, Luchini L, La Vecchia C, Tognoni G: Misoprostol: the experience of women in Fortaleza, Brazil. Contraception. 1994 Feb;49(2):101-10. Pubmed
• Gonzalez CH, Vargas FR, Perez AB, Kim CA, Brunoni D, Marques-Dias MJ, Leone CR, Correa Neto J, Llerena Junior JC, de Almeida JC: Limb deficiency with or without Mobius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy. Am J Med Genet. 1993 Aug 1;47(1):59-64. Pubmed
• Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. Pubmed
• Rocha J: Brazil investigates drug's possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. Pubmed