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Merck
CN

M6807

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
NACRES:
NA.77
PubChem Substance ID:
24897117
UNSPSC Code:
12352211
MDL number:
MFCD00274550

Key Documents

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Product Name

Misoprostol, ≥99% (HPLC)

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

SMILES string

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

InChI key

OJLOPKGSLYJEMD-URPKTTJQSA-N

assay

≥99% (HPLC)

form

liquid

functional group

ester

storage temp.

−20°C

Quality Level

200

Gene Information

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

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Biochem/physiol Actions

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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H360

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000496724
0000496724
0000468801
0000468801
0000454886

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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
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
Jeffrey Michael Smith et al.
BMC pregnancy and childbirth, 13, 44-44 (2013-02-21)
Hemorrhage continues to be a leading cause of maternal death in developing countries. The 2012 World Health Organization guidelines for the prevention and management of postpartum hemorrhage (PPH) recommend oral administration of misoprostol by community health workers (CHWs). However, there
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