Product Name

Misoprostol

CAS Number

59122-46-2

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Product Name:
Misoprostol
CAS Number:
59122-46-2
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.
Mode of Action:

Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. The activity of this receptor is mediated by G proteins which normally activate adenylate cyclase. The indirect inhibition of adenylate cyclase by Misoprostol may be dependent on guanosine-5ê-triphosphate (GTP). The significant cytoprotective actions of misoprostol are related to several mechanisms. These include: 1. Increased secretion of bicarbonate, 2. Considerable decrease in the volume and pepsin content of the gastric secretions, 3. It prevents harmful agents from disrupting the tight junctions between the epithelial cells which stops the subsequent back diffusion of H+ ions into the gastric mucosa, 4. Increased thickness of mucus layer, 5. Enhanced mucosal blood flow as a result of direct vasodilatation, 6. Stabilization of tissue lysozymes/vascular endothelium, 7. Improvement of mucosal regeneration capacity, and 8. Replacement of prostaglandins that have been depleted as a result of various insults to the area. Misoprostol has also been shown to increase the amplitude and frequency of uterine contractions during pregnancy via selective binding to the EP-2/EP-3 prostanoid receptors.

Pharmacodynamics:

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.

Metabolism:

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.

IUPAC:
methyl 7-[(1R, 2R, 3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
ATC:
A02BB01
PubChem:
5282381
DrugBank:
DB00929 (APRD00037)
Formula:
C15H15NO2S
Molecular Mass:
382.5341
Synonyms:
Misoprostolum [INN-Latin]
SMILES:
CCCCC(C)(O)CC=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
AHFS Code:
56:28.3
InChi:
OJLOPKGSLYJEMD-URPKTTJQSA-N
General Reference:
General Reference:

  1. Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. Pubmed
  2. 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
  3. Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. Pubmed
  4. Rocha J: Brazil investigates drugês possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. Pubmed
  5. 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

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