MISOPROSTOL

Details

Stereochemistry	MIXED
Molecular Formula	C22H38O5
Molecular Weight	382.535
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OJLOPKGSLYJEMD-URPKTTJQSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00929
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/misoprostol.html

Misoprostol is a prostaglandin E1 (PGE1) analogue used for the treatment and prevention of stomach ulcers. When administered, misoprostol stimulates increased secretion of the protective mucus that lines the gastrointestinal tract and increases mucosal blood flow, thereby increasing mucosal integrity. It is sometimes co-prescribed with non-steroidal anti-inflammatory drugs (NSAIDs) to prevent the occurrence of gastric ulceration, a common adverse effect of the NSAIDs. Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. The activity of this receptor is mediated by G proteins which normally activate adenylate cyclase. The indirect inhibition of adenylate cyclase by Misoprostol may be dependent on guanosine-5’-triphosphate (GTP). The significant cytoprotective actions of misoprostol are related to several mechanisms. These include: 1. Increased secretion of bicarbonate, 2. Considerable decrease in the volume and pepsin content of the gastric secretions, 3. It prevents harmful agents from disrupting the tight junctions between the epithelial cells which stops the subsequent back diffusion of H+ ions into the gastric mucosa, 4. Increased thickness of mucus layer, 5. Enhanced mucosal blood flow as a result of direct vasodilatation, 6. Stabilization of tissue lysozymes/vascular endothelium, 7. Improvement of mucosal regeneration capacity, and 8. Replacement of prostaglandins that have been depleted as a result of various insults to the area. Misoprostol has also been shown to increase the amplitude and frequency of uterine contractions during pregnancy via selective binding to the EP-2/EP-3 prostanoid receptors. Misoprostol is indicated for the treatment of ulceration (duodenal, gastric and NSAID induced) and prophylaxis for NSAID induced ulceration. Misoprostol is also indicated for other uses that are not approved in Canada, including the medical termination of an intrauterine pregnancy used alone or in combination with methotrexate, as well as the induction of labour in a selected population of pregnant women with unfavourable cervices. This indication is avoided in women with prior uterine surgery or cesarean surgery due to an increased risk of possible uterine rupture. Misoprostol is also used for the prevention or treatment of serious postpartum hemorrhage. Misoprostol is sold under the brandname Cytotec among others.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid EP2 receptor 16 Target ID: CHEMBL1881 Sources: http://www.drugbank.ca/drugs/DB00929	Agonist 2470		3.74 µM [EC50]
Prostanoid EP3 receptor 10 Target ID: CHEMBL3710 Sources: http://www.drugbank.ca/drugs/DB00929	Agonist 2470		124.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastric ulcer 61 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019268s047lbl.pdf	Preventing		Approved 8043	Cytotec Approved Use Cytotec (misoprostol) is indicated for reducing the risk of NSAID (nonsteroidal antiinflammatory drugs, including aspirin)–induced gastric ulcers in patients at high risk of complications from gastric ulcer, e.g., the elderly and patients with concomitant debilitating disease, as well as patients at high risk of developing gastric ulceration, such as patients with a history of ulcer. Launch Date 5.9909761E11

C_max

Value	Dose	Analyte	Population
2.683 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, oral dose: 800 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
1.361 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, buccal dose: 800 μg route of administration: Buccal experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2.439 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
811 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019268s041lbl.pdf	300 μg single, oral dose: 300 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
2.019 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, oral dose: 800 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
2.073 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, buccal dose: 800 μg route of administration: Buccal experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
3.209 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
417 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019268s041lbl.pdf	300 μg single, oral dose: 300 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
1.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, oral dose: 800 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
0.837 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, buccal dose: 800 μg route of administration: Buccal experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
0.854 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27102981	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED
0.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019268s041lbl.pdf	300 μg single, oral dose: 300 μg route of administration: Oral experiment type: SINGLE co-administered:	MISOPROSTOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019268s041lbl.pdf			MISOPROSTOL serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12 mg single, oral Overdose Dose: 12 mg Route: oral Route: single Dose: 12 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17267868/	healthy, adolescent n = 1 Health Status: healthy Condition: induce abortion Age Group: adolescent Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17267868/	Disc. AE: Multiorgan failure... AEs leading to discontinuation/dose reduction: Multiorgan failure (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/17267868/
8400 mg single, oral Overdose Dose: 8400 mg Route: oral Route: single Dose: 8400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/	healthy, mean 28.8 years n = 1 Health Status: healthy Condition: induce abortion Age Group: mean 28.8 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/	Disc. AE: Abdominal pain, Vomiting... AEs leading to discontinuation/dose reduction: Abdominal pain (1 patient) Vomiting (1 patient) Diarrhea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/
50 ug 4 times / day steady, vaginal Recommended Dose: 50 ug, 4 times / day Route: vaginal Route: steady Dose: 50 ug, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 28.8 years n = 172 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 28.8 years Sex: F Population Size: 172 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	Other AEs: Diarrhea, Nausea... Other AEs: Diarrhea (1.7%) Nausea (9.3%) Vomiting (14%) Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
50 ug 6 times / day steady, oral Recommended Dose: 50 ug, 6 times / day Route: oral Route: steady Dose: 50 ug, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 29.1 years n = 167 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 29.1 years Sex: F Population Size: 167 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (9.6%) Vomiting (17.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
400 ug single, oral Dose: 400 ug Route: oral Route: single Dose: 400 ug Co-administed with:: mifepristone(600 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years n = 92 Health Status: healthy Condition: induce abortion Age Group: mean 30.2 years Sex: F Population Size: 92 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	Other AEs: Bleeding, Vomiting... Other AEs: Bleeding (68.2%) Vomiting (7.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/

AEs

AE	Significance	Dose	Population
Multiorgan failure	grade 5, 1 patient Disc. AE	12 mg single, oral Overdose Dose: 12 mg Route: oral Route: single Dose: 12 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17267868/	healthy, adolescent n = 1 Health Status: healthy Condition: induce abortion Age Group: adolescent Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17267868/
Abdominal pain	1 patient Disc. AE	8400 mg single, oral Overdose Dose: 8400 mg Route: oral Route: single Dose: 8400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/	healthy, mean 28.8 years n = 1 Health Status: healthy Condition: induce abortion Age Group: mean 28.8 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/
Diarrhea	1 patient Disc. AE	8400 mg single, oral Overdose Dose: 8400 mg Route: oral Route: single Dose: 8400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/	healthy, mean 28.8 years n = 1 Health Status: healthy Condition: induce abortion Age Group: mean 28.8 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/
Vomiting	1 patient Disc. AE	8400 mg single, oral Overdose Dose: 8400 mg Route: oral Route: single Dose: 8400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/	healthy, mean 28.8 years n = 1 Health Status: healthy Condition: induce abortion Age Group: mean 28.8 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15223178/
Diarrhea	1.7%	50 ug 4 times / day steady, vaginal Recommended Dose: 50 ug, 4 times / day Route: vaginal Route: steady Dose: 50 ug, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 28.8 years n = 172 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 28.8 years Sex: F Population Size: 172 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
Vomiting	14%	50 ug 4 times / day steady, vaginal Recommended Dose: 50 ug, 4 times / day Route: vaginal Route: steady Dose: 50 ug, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 28.8 years n = 172 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 28.8 years Sex: F Population Size: 172 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
Nausea	9.3%	50 ug 4 times / day steady, vaginal Recommended Dose: 50 ug, 4 times / day Route: vaginal Route: steady Dose: 50 ug, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 28.8 years n = 172 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 28.8 years Sex: F Population Size: 172 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
Vomiting	17.4%	50 ug 6 times / day steady, oral Recommended Dose: 50 ug, 6 times / day Route: oral Route: steady Dose: 50 ug, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 29.1 years n = 167 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 29.1 years Sex: F Population Size: 167 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
Nausea	9.6%	50 ug 6 times / day steady, oral Recommended Dose: 50 ug, 6 times / day Route: oral Route: steady Dose: 50 ug, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/	healthy, mean 29.1 years n = 167 Health Status: healthy Condition: live term single cephalic fetus for indicated labor induction Age Group: mean 29.1 years Sex: F Population Size: 167 Sources: https://pubmed.ncbi.nlm.nih.gov/31923193/
Bleeding	68.2%	400 ug single, oral Dose: 400 ug Route: oral Route: single Dose: 400 ug Co-administed with:: mifepristone(600 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years n = 92 Health Status: healthy Condition: induce abortion Age Group: mean 30.2 years Sex: F Population Size: 92 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/
Vomiting	7.6%	400 ug single, oral Dose: 400 ug Route: oral Route: single Dose: 400 ug Co-administed with:: mifepristone(600 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years n = 92 Health Status: healthy Condition: induce abortion Age Group: mean 30.2 years Sex: F Population Size: 92 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1033	http://www.3bsc.com/index/pro_info.php?id=41938
AA Blocks	AA00E8MQ	https://www.aablocks.com/goods/Goods/detail?id=AA00E8MQ
AHH Chemical co.,ltd	MT-54309	http://www.ahhchemical.com/product/MT-54309.html
AK Scientific, Inc. (AKSCI)	67837	http://www.aksci.com/item_detail.php?cat=67837
Aaron Chemicals	AR00E9EI	http://www.aaronchem.com/59122-46-2
AbMole Bioscience	M3154	http://www.abmole.com/products/misoprostol.html
Acorn PharmaTech	ACN-052235	http://www.acornpharmatech.com/
Alfa Chemistry	AP59122462	https://reagents.alfa-chemistry.com/product/misoprostol-cas-59122-46-2-13661.html
Alfa Chemistry	59122-46-2	https://www.alfa-chemistry.com/misoprostol-cas-59122-46-2-item-292827.htm
Alsachim	1414	http://www.alsachim.com/product-C1879-glo.bal-view.html
Aurora Fine Chemicals LLC	A17.912.990	http://online.aurorafinechemicals.com/info?ID=A17.912.990
AvaChem Scientific	3052	http://www.avachem.com/productSearch.asp?3052
BLD Pharm	BD43199	http://www.bldpharm.com/products/59122-46-2.html
BioCrick	BCC5240	http://www.biocrick.com/Misoprostol-BCC5240.html
BioSynth	Q-201409	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201409.html
CSNpharm	CSN16851	https://www.csnpharm.com/products/misoprostol.html
Chem Scene	CS-2828	http://www.chemscene.com/59122-46-2.html
ChemMol	49404672	http://www.chemmol.com/chemmol/49404672.html
Chemspace	CSSB00020587567	https://chem-space.com/CSSB00020587567
DC Chemicals	DC31767	http://www.dcchemicals.com//product_show-Misoprostol.html
Excenen	EX-A1774	http://www.excenen.com/searchresultlist.php?id=59122-46-2
Glentham Life Sciences	GP2918	http://www.glentham.com/products/product/GP2918/
Lab Network	LN01288866	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01288866
MedChem Express	HY-B0610	https://www.medchemexpress.com/Misoprostol.html
MuseChem	I004214	https://www.musechem.com/product/I004214.html
MuseChem	M011584	https://www.musechem.com/product/M011584.html
OChem	4282	http://www.ocheminc.com/index.php?act=psearch&pid=122M462
Sigma-Aldrich	Y0000490_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0000490?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0001162_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0001162?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	M6807_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/m6807?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1444300_USP	https://www.sigmaaldrich.com/catalog/product/usp/1444300?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S535520	http://www.smolecule.com/products/s535520
THE BioTek	bt-275306	https://www.thebiotek.com/product/inhibitors/bt-275306
Tocris	2297	https://www.tocris.com/products/misoprostol_2297
eNovation Chemicals	D674574	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674574
eNovation Chemicals	D766208	https://www.enovationchem.com/ProductDetails.asp?ProductID=D766208
eNovation Chemicals	Y0974101	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974101
iChemical	EBD2197414	http://www.ichemical.com/products/59122-46-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Misoprostol in the treatment of duodenal ulcer. A multicenter double-blind placebo-controlled study.	1985 Nov	3932049
Evaluation of misoprostol cytoprotection of the bladder with cyclophosphamide (Cytoxan) therapy.	1986 Aug	3090278
The effect of misoprostol on base-line and stimulated acid secretion and on gastrin and histamine release in the totally isolated, vascularly perfused rat stomach.	1988 Aug	2459756
Neurosensory adverse effects after phenylbutazone and misoprostol combined treatment.	1989 Nov 25	2573801
Neurological adverse effects of naproxen and misoprostol combination.	1990 Oct	2125432
Overall safety of Arthrotec.	1992	1439622
Prostaglandins protect kidneys against ischemic and toxic injury by a cellular effect.	1992 Dec	1474766
Brazil investigates drug's possible link with birth defects.	1994 Sep 24	7950553
Protective effect of misoprostol on indomethacin induced renal dysfunction in elderly patients.	1995 Apr	7791169
The effect of misoprostol on indomethacin-induced renal dysfunction in well-compensated cirrhosis.	1995 Jul	8530800
The dose-dependent effect of misoprostol on indomethacin-induced renal dysfunction in well compensated cirrhosis.	1995 Sep	7661171
Misoprostol associated autonomic dysreflexia in a traumatic tetraplegic patient.	1996 Feb	8835039
Extemporaneous preparation of misoprostol gel for cervical ripening: a randomized trial.	1997 Dec	9397101
A comparison between two doses of intravaginal misoprostol and gemeprost for induction of second-trimester abortion.	1997 Dec	9397098
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.	1997 Sep	9298541
Use of misoprostol during pregnancy and Möbius' syndrome in infants.	1998 Jun 25	9637807
Timing of pain and bleeding after mifepristone-induced abortion.	2000 Dec	11239617
Prenatal exposure to misoprostol and vascular disruption defects: a case-control study.	2000 Dec 11	11186881
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.	2000 Jan 17	10634944
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.	2001 Mar 2	11164953
Side-effects of oral misoprostol in the third stage of labour--a randomised placebo-controlled trial.	2001 May	11455810
High rates of cramping with misoprostol administration for intrauterine insemination.	2001 May	11331658
Buccal versus intravaginal misoprostol administration for cervical ripening.	2002 Feb	11854640
Having an abortion using mifepristone and home misoprostol: a qualitative analysis of women's experiences.	2002 Jan-Feb	11990637
Comparison of abortions induced by methotrexate or mifepristone followed by misoprostol.	2002 May	11978292
Cognitive decline in administration of the nonsteroidal antiinflammatory drug loxoprofen with misoprostol in a 91-year-old Japanese woman.	2002 Oct	12366638
Effect of misoprostol and indomethacin on cyclooxygenase induction and eicosanoid production in carrageenan-induced air pouch inflammation in rats.	2002 Sep	12428691
Möbius sequence in children exposed in utero to misoprostol: neuropathological study of three cases.	2003 Dec	14745923
[Moebius syndrome due to the use of misoprostol. Case report].	2003 Jun	12815845
WHO multinational study of three misoprostol regimens after mifepristone for early medical abortion.	2004 Jul	15198763
Poland-Möbius syndrome and cocaine abuse: a relook at vascular etiology.	2005 Apr	15797189
Functional role of prostacyclin receptor in rat dorsal root ganglion neurons.	2005 Nov 18	16039053
Early dental management of patients with Mobius syndrome.	2006 Nov	17054764
Comparison of antinociceptive efficacy and gastroprotection between celecoxib and diclofenac plus misoprostol in rats.	2007	18605234
Comparative study of misoprostol vs dinoprostone for induction of labour.	2007 Jan-Mar	17877293
Misoprostol and pregnancy: risk of malformations.	2008 Apr	18516817
Cryptogenic stroke in the setting of intravaginal prostaglandin therapy for elective abortion.	2008 May	18378387
Prostaglandin analogue misoprostol attenuates neurotoxin 1-methyl-4-phenylpyridinium-induced mitochondrial damage and cell death in differentiated PC12 cells.	2008 Nov 25	18602972
Improved antiulcer and anticancer properties of a trans-resveratrol analog in mice.	2009 Mar	19066340
Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling.	2009 Mar 16	19273625
Acute coronary artery vasospasm associated with misoprostol for termination of pregnancy.	2010	20224253
Protective effect of anacardic acids from cashew (Anacardium occidentale) on ethanol-induced gastric damage in mice.	2010 Jan 5	19853593
Moebius syndrome and holoprosencephaly following exposure to misoprostol.	2010 Nov	20933185
Effects of misoprostol on cisplatin-induced renal damage in rats.	2011 Jul	21458517
Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors.	2011 Jul 28	21650226

Patents

Sample Use Guides

In Vivo Use Guide

The recommended adult oral dose of Cytotec (Misoprostol) for reducing the risk of NSAID-induced gastric ulcers is 200 mcg four times daily with food. If this dose cannot be tolerated, a dose of 100 mcg can be used

Route of Administration: Oral

In Vitro Use Guide

Antigen-evoked secretion of IFN-gamma by influenza hemagglutinin-specific mouse lymph node Th1 cells, that also express EP3Rs and EP4Rs, was increased a maximum of 10-fold by 10(-9) M misoprostol.

Name

Type

Language

MISOPROSTOL

Official Name

English

PROST-13-EN-1-OIC ACID, 11,16-DIHYDROXY-16-METHYL-9-OXO-, METHYL ESTER, (11.ALPHA.,13E)-(+/-)-

Common Name

English

MISOPROSTOL [MART.]

Common Name

English

MISOPROSTOL [HSDB]

Common Name

English

CYTOTEC

Brand Name

English

SC-29333

Code

English

MISOPROSTOL [USP-RS]

Common Name

English

MISOPROSTOL COMPONENT OF ARTHROTEC

Common Name

English

MISOPROSTOL [MI]

Common Name

English

MISOPROSTOL [INN]

Common Name

English

MISOPROSTOL [ORANGE BOOK]

Common Name

English

MISOPROSTOL [USP MONOGRAPH]

Common Name

English

MISOPROSTOL [VANDF]

Common Name

English

(+/-)-METHYL (1R,2R,3R)-3-HYDROXY-2-((E)-(4RS)-4-HYDROXY-4-METHYL-1-OCTENYL)-5-OXOCYCLOPENTANEHEPTANOATE

Systematic Name

English

MISOPROSTOL [USAN]

Common Name

English

MISOPROSTOL [WHO-DD]

Common Name

English

MISOPROSTOL [EP MONOGRAPH]

Common Name

English

ARTHROTEC COMPONENT MISOPROSTOL

Brand Name

English

MISOPROSTOL [JAN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007710