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M6932

Sigma-Aldrich

Misoprostol free acid

≥90%

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Synonym(s):
(±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1
Empirical Formula (Hill Notation):
C21H36O5
CAS Number:
112137-89-0
Molecular Weight:
368.51
MDL number:
MFCD00869984
UNSPSC Code:
12352211
PubChem Substance ID:
24897131
NACRES:
NA.25

Quality Level

200

Assay

≥90%

form

liquid

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

InChI

1S/C21H36O5/c1-3-4-13-21(2,26)14-9-11-17-16(18(22)15-19(17)23)10-7-5-6-8-12-20(24)25/h9,11,16-17,19,23,26H,3-8,10,12-15H2,1-2H3,(H,24,25)/b11-9+/t16-,17-,19-,21?/m1/s1

InChI key

CNWGPXZGIIOYDL-MKYGPDKMSA-N

Related Categories

Biochem/physiol Actions

Misoprostol is a synthetic prostaglandin E1 (PGE1) analogue use to prevent non steroidal anti inflammatory drug-induced (NSAID) gastric ulcers; as a labor inducing and postpartum hemorrhage treatment agent.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H361

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Marco Lazzaroni et al.
Drugs, 69(1), 51-69 (2009-02-06)
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 such damage by acid suppression. Proton pump inhibitors (PPIs) appear to be very effective
Dean Leduc et al.
Journal of obstetrics and gynaecology Canada : JOGC = Journal d'obstetrique et gynecologie du Canada : JOGC, 31(10), 980-993 (2009-11-28)
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 Society of Obstetricians and Gynaecologists of Canada (SOGC) clinical practice
A Elati et al.
BJOG : an international journal of obstetrics and gynaecology, 116 Suppl 1, 61-69 (2009-09-26)
Misoprostol, although originally introduced as a therapy for gastric ulcers, is now widely used in reproductive health. For some indications it is now the optimal choice, whilst for others it provides an important alternative, especially in low-resource settings. The optimal
D Y Graham et al.
Lancet (London, England), 2(8623), 1277-1280 (1988-12-03)
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). 420 patients with osteoarthritis and NSAID-associated abdominal pain were studied; they were receiving ibuprofen, piroxicam
Wendy R Sheldon et al.
Expert opinion on investigational drugs, 21(2), 235-250 (2012-01-12)
Uterotonic drugs are recommended for the prevention and treatment of postpartum hemorrhage (PPH), and oxytocin is considered the gold standard for both indications due to its established efficacy and safety. Unfortunately, access to oxytocin is still limited in many low-resource
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