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

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

Molecular Formula	C22H38O5
Molecular Weight	382.535
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

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 20 Target ID: CHEMBL1881 Sources: http://www.drugbank.ca/drugs/DB00929	Agonist 2752		3.74 µM [EC50]
Prostanoid EP3 receptor 11 Target ID: CHEMBL3710 Sources: http://www.drugbank.ca/drugs/DB00929	Agonist 2752		124.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastric ulcer 74 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019268s047lbl.pdf	Preventing		Approved 8583	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 1988

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
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
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
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
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
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
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
0.854 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
0.837 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
0.5 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 Health Status: healthy Age Group: adolescent Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 29.1 years Sex: F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years Health Status: healthy Age Group: mean 30.2 years Sex: F 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 Health Status: healthy Age Group: adolescent Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 28.8 years Sex: F 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 Health Status: healthy Age Group: mean 29.1 years Sex: F 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 Health Status: healthy Age Group: mean 29.1 years Sex: F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years Health Status: healthy Age Group: mean 30.2 years Sex: F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/10640161/	healthy, mean 30.2 years Health Status: healthy Age Group: mean 30.2 years Sex: F 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
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/
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
Alfa Chemistry	59122-46-2	https://www.alfa-chemistry.com/misoprostol-cas-59122-46-2-item-292827.htm
Alfa Chemistry	AP59122462	https://reagents.alfa-chemistry.com/product/misoprostol-cas-59122-46-2-13661.html
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
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
BLD Pharm	BD43199	http://www.bldpharm.com/products/59122-46-2.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
CSNpharm	CSN16851	https://www.csnpharm.com/products/misoprostol.html
DC Chemicals	DC31767	http://www.dcchemicals.com//product_show-Misoprostol.html
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
Excenen	EX-A1774	http://www.excenen.com/searchresultlist.php?id=59122-46-2
Glentham Life Sciences	GP2918	http://www.glentham.com/products/product/GP2918/
iChemical	EBD2197414	http://www.ichemical.com/products/59122-46-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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	1444300_USP	https://www.sigmaaldrich.com/catalog/product/usp/1444300?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	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
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

PubMed

Title	Date	PubMed
Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors.	2011-07-28	21650226
Effects of misoprostol on cisplatin-induced renal damage in rats.	2011-07	21458517
Moebius syndrome and holoprosencephaly following exposure to misoprostol.	2010-11	20933185
Protective effect of anacardic acids from cashew (Anacardium occidentale) on ethanol-induced gastric damage in mice.	2010-01-05	19853593
Acute coronary artery vasospasm associated with misoprostol for termination of pregnancy.	2010	20224253
Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling.	2009-03-16	19273625
Improved antiulcer and anticancer properties of a trans-resveratrol analog in mice.	2009-03	19066340
Prostaglandin analogue misoprostol attenuates neurotoxin 1-methyl-4-phenylpyridinium-induced mitochondrial damage and cell death in differentiated PC12 cells.	2008-11-25	18602972
Möbius syndrome in a neonate after mifepristone and misoprostol elective abortion failure.	2008-06	18460590
Cryptogenic stroke in the setting of intravaginal prostaglandin therapy for elective abortion.	2008-05	18378387
Misoprostol and pregnancy: risk of malformations.	2008-04	18516817
Comparative study of misoprostol vs dinoprostone for induction of labour.	2007-09-20	17877293
Acute hemolytic anemia with acanthocytosis associated with high-dose misoprostol for medical abortion.	2007-09	17084939
Comparison of antinociceptive efficacy and gastroprotection between celecoxib and diclofenac plus misoprostol in rats.	2007	18605234
Early dental management of patients with Mobius syndrome.	2006-11	17054764
A randomized study comparing efficacy and patient satisfaction in medical or surgical treatment of miscarriage.	2006-08	16764872
Role of periaqueductal grey prostaglandin receptors in formalin-induced hyperalgesia.	2006-01-13	16360148
Functional role of prostacyclin receptor in rat dorsal root ganglion neurons.	2005-11-18	16039053
Poland-Möbius syndrome and cocaine abuse: a relook at vascular etiology.	2005-04	15797189
WHO multinational study of three misoprostol regimens after mifepristone for early medical abortion.	2004-07	15198763
Möbius sequence in children exposed in utero to misoprostol: neuropathological study of three cases.	2003-12	14745923
[Moebius syndrome due to the use of misoprostol. Case report].	2003-06	12815845
Autism and Möbius sequence: an exploratory study of children in northeastern Brazil.	2003-06	12806493
Cognitive decline in administration of the nonsteroidal antiinflammatory drug loxoprofen with misoprostol in a 91-year-old Japanese woman.	2002-10	12366638
Effect of misoprostol and indomethacin on cyclooxygenase induction and eicosanoid production in carrageenan-induced air pouch inflammation in rats.	2002-09	12428691
Having an abortion using mifepristone and home misoprostol: a qualitative analysis of women's experiences.	2002-05-07	11990637
Use of misoprostol during pregnancy and Möbius' syndrome in infants.	1998-06-25	9637807
Extemporaneous preparation of misoprostol gel for cervical ripening: a randomized trial.	1997-12	9397101
A comparison between two doses of intravaginal misoprostol and gemeprost for induction of second-trimester abortion.	1997-12	9397098
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.	1997-09	9298541
Misoprostol associated autonomic dysreflexia in a traumatic tetraplegic patient.	1996-02	8835039
The dose-dependent effect of misoprostol on indomethacin-induced renal dysfunction in well compensated cirrhosis.	1995-09	7661171
The effect of misoprostol on indomethacin-induced renal dysfunction in well-compensated cirrhosis.	1995-07	8530800
Protective effect of misoprostol on indomethacin induced renal dysfunction in elderly patients.	1995-04	7791169
Brazil investigates drug's possible link with birth defects.	1994-09-24	7950553
RU486: the French experience.	1994-06	7962459
Misoprostol: the experience of women in Fortaleza, Brazil.	1994-02	8143449
Limb deficiency with or without Möbius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy.	1993-08-01	8368254
The Brazilian experience with Cytotec.	1993-07-01	8212093
Misoprostol and illegal abortion in Rio de Janeiro, Brazil.	1993-05-15	8098402
Prostaglandins protect kidneys against ischemic and toxic injury by a cellular effect.	1992-12	1474766
Overall safety of Arthrotec.	1992	1439622
Misoprostol-induced urinary incontinence.	1991-11	1940783
Delirium in an elderly woman possibly associated with administration of misoprostol.	1991-02	1905439
H2-receptor antagonist-refractory ulcer: its pathophysiology and treatment.	1991	1682356
Neurological adverse effects of naproxen and misoprostol combination.	1990-10	2125432
Neurosensory adverse effects after phenylbutazone and misoprostol combined treatment.	1989-11-25	2573801
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.	1988-08	2459756
Evaluation of misoprostol cytoprotection of the bladder with cyclophosphamide (Cytoxan) therapy.	1986-08	3090278
Misoprostol in the treatment of duodenal ulcer. A multicenter double-blind placebo-controlled study.	1985-11	3932049

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:51 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:51 GMT 2025`
Record UNII	0E43V0BB57
Record Status	`FAILED`
Record Version

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Name

Type

Language

MISOPROSTOL

Official Name

English

ARTHROTEC COMPONENT MISOPROSTOL

Preferred 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 [WHO-DD]

Common Name

English

MISOPROSTOL [USP-RS]

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 [EP MONOGRAPH]

Common Name

English

MISOPROSTOL [JAN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007710