U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C22H38O5
Molecular Weight 382.5341
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MISOPROSTOL

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 382.5341
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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

1986
103
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2637
 3.74 µM [EC50]
Agonist
2637
 124.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8307
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
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
Neurological adverse effects of naproxen and misoprostol combination.
1990 Oct
Delirium in an elderly woman possibly associated with administration of misoprostol.
1991 Feb
Overall safety of Arthrotec.
1992
Limb deficiency with or without Möbius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy.
1993 Aug 1
The Brazilian experience with Cytotec.
1993 Jul-Aug
Misoprostol: the experience of women in Fortaleza, Brazil.
1994 Feb
The effect of misoprostol on indomethacin-induced renal dysfunction in well-compensated cirrhosis.
1995 Jul
Misoprostol associated autonomic dysreflexia in a traumatic tetraplegic patient.
1996 Feb
Extemporaneous preparation of misoprostol gel for cervical ripening: a randomized trial.
1997 Dec
A comparison between two doses of intravaginal misoprostol and gemeprost for induction of second-trimester abortion.
1997 Dec
Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.
1997 Sep
Use of misoprostol during pregnancy and Möbius' syndrome in infants.
1998 Jun 25
Side-effects of oral misoprostol in the third stage of labour--a randomised placebo-controlled trial.
2001 May
High rates of cramping with misoprostol administration for intrauterine insemination.
2001 May
Buccal versus intravaginal misoprostol administration for cervical ripening.
2002 Feb
Effect of misoprostol and indomethacin on cyclooxygenase induction and eicosanoid production in carrageenan-induced air pouch inflammation in rats.
2002 Sep
WHO multinational study of three misoprostol regimens after mifepristone for early medical abortion.
2004 Jul
Improved antiulcer and anticancer properties of a trans-resveratrol analog in mice.
2009 Mar
Acute coronary artery vasospasm associated with misoprostol for termination of pregnancy.
2010
Protective effect of anacardic acids from cashew (Anacardium occidentale) on ethanol-induced gastric damage in mice.
2010 Jan 5
Moebius syndrome and holoprosencephaly following exposure to misoprostol.
2010 Nov
Patents

Patents

JP2001039876A
13

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 Fri Dec 16 17:42:20 UTC 2022
Edited
by admin
on Fri Dec 16 17:42:20 UTC 2022
Record UNII
0E43V0BB57
Record Status Validated (UNII)
Record Version
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Name Type Language
MISOPROSTOL
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
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 [WHO-DD]
Common Name 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 [EP MONOGRAPH]
Common Name English
ARTHROTEC COMPONENT MISOPROSTOL
Brand Name English
MISOPROSTOL [JAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007710
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-ATC G02AD06
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 22.1 (MIF/MIS)
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NDF-RT N0000007710
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-ATC A02BB01
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
LIVERTOX 644
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NDF-RT N0000175785
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NCI_THESAURUS C2080
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-VATC QA02BB01
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
FDA ORPHAN DRUG 186604
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NCI_THESAURUS C29701
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-VATC QM01AE56
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NDF-RT N0000007710
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
NCI_THESAURUS C78568
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-ATC M01AE56
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-VATC QG02AD06
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 22.1
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C1313
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
EVMPD
SUB08998MIG
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
LACTMED
Misoprostol
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
MESH
D016595
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
MERCK INDEX
M7563
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1444300
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
DAILYMED
0E43V0BB57
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
DRUG CENTRAL
1817
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
HSDB
3573
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
INN
5154
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
IUPHAR
1936
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
WIKIPEDIA
MISOPROSTOL
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
RXCUI
42331
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY RxNorm
PUBCHEM
5282381
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
DRUG BANK
DB00929
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
CAS
59122-46-2
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
CHEBI
63610
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
ChEMBL
CHEMBL606
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
FDA UNII
0E43V0BB57
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
EPA CompTox
DTXSID7020897
Created by admin on Fri Dec 16 17:42:20 UTC 2022 , Edited by admin on Fri Dec 16 17:42:20 UTC 2022
PRIMARY
Related Record Type Details
Structure of MISOPROSTOL
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of MISOPROSTOL
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
Structure of MISOPROSTOL ACID
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of 8-EPIMISOPROSTOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 12-EPIMISOPROSTOL
IMPURITY -> PARENT
12-Epimisoprostol consists of two diastereomers that are separated under these conditions; integrate both peaks together for the impurity calculations
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of MISOPROSTOL B
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of NORPROSTOL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of 12-EPIMISOPROSTOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MISOPROSTOL A
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.13
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MISOPROSTOL B
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 8-EPIMISOPROSTOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of NORPROSTOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 11-EPIMISOPROSTOL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of MISOPROSTOL A
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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