Misoprostol acid

Names

[ Name ]:
Misoprostol acid

[Synonym ]:
Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, (11α,13E)-
(11α,13E)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid
Misoprostol Acid
MISOPROSTOL FREE ACID

Biological Activity

[Description]:

Misoprostol acid is an active metabolite of Misoprostol. Misoprostol is a synthetic analogue of prostaglandin E1 (PGE1), extensively absorbed, and undergoes rapid de-esterification to Misoprostol acid in the gastrointestinal tract after oral administration. Misoprostol can be used for non-steroidal anti-inflammatory drug-induced (NSAID) gastric ulcers[1]. Misoprostol is an oral agent used to induce labor[2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

Research Areas >> Inflammation/Immunology

[Target]

Prostaglandin E1 (PGE1)[1]

[In Vivo]

Unlike the Misoprostol, Misoprostol acid is detectable in plasma. Misoprostol is a lipophilic methyl ester prodrug and is readily metabolized to the free acid, which is the biologically active form. Misoprostol is used worldwide for a variety of indications in obstetrics and gynecology. Misoprostol has both gastric antisecretory and mucosal protective effects[1].

[References]

[1]. Vijaya Bharathi D, et al. Development and validation of highly sensitive method for determination of misoprostol free acid in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry: application to a clinical pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Sep 15;879(26):2827-33.

[2]. Schmidt-Hansen M, et al. Simultaneous compared to interval administration of mifepristone and misoprostol for medical abortion up to 10+0 weeks' gestation: a systematic review with meta-analyses. BMJ Sex Reprod Health. 2020 Feb 20. pii: bmjsrh-2019-200448.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
538.3±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₃₆O₅

[ Molecular Weight ]:
368.508

[ Flash Point ]:
293.4±26.6 °C

[ Exact Mass ]:
368.256287

[ PSA ]:
94.83000

[ LogP ]:
2.45

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.543

[ Storage condition ]:
−20°C

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335-H361

[ Precautionary Statements ]:
P261-P281-P301 + P310-P305 + P351 + P338

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R45

[ Safety Phrases ]:
53-22-36/37/39-45

[ RIDADR ]:
UN 2810 6

[ WGK Germany ]:
2

Articles

Active management of the third stage of labour: prevention and treatment of postpartum hemorrhage.

J. Obstet. Gynaecol. Can. 31 , 980-993, (2009)

To review the clinical aspects of postpartum hemorrhage (PPH) and provide guidelines to assist clinicians in the prevention and management of PPH. These guidelines are an update from the previous Soci...

Management of NSAID-induced gastrointestinal toxicity: focus on proton pump inhibitors.

Drugs 69 , 51-69, (2009)

The association between NSAIDs and the presence of upper gastrointestinal (GI) complications is well established. Evidence that acid aggravates NSAID-induced injury provides a rationale for minimizing...

Prevention of NSAID-induced gastric ulcer with misoprostol: multicentre, double-blind, placebo-controlled trial.

Lancet 2 , 1277, (1988)

A double-blind, placebo-controlled study was carried out to see whether the synthetic E prostaglandin, misoprostol, would prevent gastric ulcer induced by non-steroidal anti-inflammatory drugs (NSAIDs...