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M6807

Sigma-Aldrich

Misoprostol

≥99% (HPLC)

Synonym(s):

(±)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1 methyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H38O5
CAS Number:
59122-46-2
Molecular Weight:
382.53
MDL number:
MFCD00274550
UNSPSC Code:
12352211
PubChem Substance ID:
24897117
NACRES:
NA.77

Quality Level

200

Assay

≥99% (HPLC)

form

liquid

functional group

ester

storage temp.

−20°C

SMILES string

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

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

InChI key

OJLOPKGSLYJEMD-URPKTTJQSA-N

Gene Information

human ... PTGER3(5733) , PTGIR(5739)

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Biochem/physiol Actions

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.
Cytoprotective PGE1 analog that prevents NSAID-induced gastric ulceration.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Ingrid Sääv et al.
Human reproduction (Oxford, England), 30(6), 1314-1322 (2015-04-04)
Can sublingual administration of misoprostol 1 h prior to vacuum aspiration be more effective than vaginal administration and as effective as either route three 3 h prior to surgery? Sublingually administered misoprostol is superior to vaginally administered misoprostol when given
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
Christina S Chu et al.
Journal of the Royal Society of Medicine, 105(8), 336-347 (2012-08-22)
This article describes and critically appraises clinical trials assessing misoprostol effectiveness in preventing primary postpartum haemorrhage (PPH) in home and community settings in low- and middle-income countries. Of 172 identified studies of misoprostol use in labour only six fulfilled the
V A Hundley et al.
BJOG : an international journal of obstetrics and gynaecology, 120(3), 277-285 (2012-11-30)
Using misoprostol to prevent postpartum haemorrhage (PPH) in home-birth settings remains controversial. To review the safety and effectiveness of oral misoprostol in preventing PPH in home-birth settings. The Cochrane Library, PubMed, and POPLINE were searched for articles published until 31
Deborah Bartz et al.
Obstetrics and gynecology, 122(1), 57-63 (2013-06-08)
To compare the efficacy and acceptability of buccal misoprostol or a synthetic osmotic cervical dilator for cervical preparation before same-day late first-trimester and early second-trimester surgical abortion. In this randomized, double-blind trial, we compared 400 micrograms of buccal misoprostol with
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