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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
3.74 µM [EC50]
124.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Cytotec

Cmax

ValueDoseCo-administeredAnalytePopulation
2.683 ng/mL
800 μg single, oral
MISOPROSTOL plasma
Homo sapiens
1.361 ng/mL
800 μg single, buccal
MISOPROSTOL plasma
Homo sapiens
2.439 ng/mL
800 μg single, sublingual
MISOPROSTOL plasma
Homo sapiens
811 pg/mL
300 μg single, oral
MISOPROSTOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2.019 ng × h/mL
800 μg single, oral
MISOPROSTOL plasma
Homo sapiens
2.073 ng × h/mL
800 μg single, buccal
MISOPROSTOL plasma
Homo sapiens
3.209 ng × h/mL
800 μg single, sublingual
MISOPROSTOL plasma
Homo sapiens
417 pg × h/mL
300 μg single, oral
MISOPROSTOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.04 h
800 μg single, oral
MISOPROSTOL plasma
Homo sapiens
0.837 h
800 μg single, buccal
MISOPROSTOL plasma
Homo sapiens
0.854 h
800 μg single, sublingual
MISOPROSTOL plasma
Homo sapiens
0.5 h
300 μg single, oral
MISOPROSTOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
MISOPROSTOL serum
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
0E43V0BB57
Record Status Validated (UNII)
Record Version