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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
Amanda Selk et al.
Obstetrics and gynecology, 118(4), 941-949 (2011-09-22)
To estimate the benefits and harms of misoprostol use for cervical dilation in patients undergoing operative hysteroscopy. We searched MEDLINE, EMBASE, and the Cochrane Central Register of Controlled Trials (from inception to February 2011). We also searched trial registries, other
C W Ho et al.
Alimentary pharmacology & therapeutics, 37(8), 819-824 (2013-02-26)
Poor adherence to gastroprotective agents (GPAs) is common among users of nonsteroidal anti-inflammatory drugs (NSAIDs) or low-dose aspirin (ASA). There are little data on the utilization of GPAs among NSAID and ASA users complicated by ulcer bleeding. To study the
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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