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

• ChemBase ID: 805
• Molecular Formular: C22H38O5
• Molecular Mass: 382.53412
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
• IUPAC Traditional name: misoprostol
• Brand Name: Arthrotec; Cytotec
• Synonyms: (±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1 methyl ester; Misoprostol; Misoprostolum [INN-Latin]; Misoprostol

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.680623
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.857755
• LogD (pH = 7.4): 3.857755
• Log P: 3.857755
• Molar Refractivity: 107.8798 cm^3
• Polarizability: 42.359562 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.88
• LOG S: -4.37
• Solubility (Water): 1.64e-02 g/l

PROPERTIES

Physical Property

• Solubility: >1.6 mg/mL at 25.0 oC
• Hydrophobicity(logP): 3.6

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 60-61-25
• Safety Statements: 53-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H360
• GHS Precautionary statements: P201-P301 + P310-P308 + P313
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PTGIR(5739)

Product Information

• Purity: ≥99% (TLC)

DETAILS

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

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
• 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