ChemFOnt: Showing chemical card for Misoprostol (CFc000009372)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:29 UTC

Chemfont ID

CFc000009372

Molecule Identification

Common Name

Misoprostol

Definition

Misoprostol is only found in individuals that have used or taken this drug. It is a synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. [PubChem]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cytotec	Kegg
Apo-misoprostol	HMDB
Apotex brand OF misoprostol	HMDB
Glefos	HMDB
Misoprostol pfizer brand	HMDB
Misoprostol, (11alpha,13E,16R)-isomer	HMDB
Misoprostol, (11alpha.13E,16S)-isomer	HMDB
Misoprostol, (11beta,13E,16S)-isomer	HMDB
Apo misoprostol	HMDB
Grunenthal brand OF misoprostol	HMDB
Misoprostol grunenthal brand	HMDB
Misoprostol novopharm brand	HMDB
Misoprostol, (11alpha,13Z)-(+-)-isomer	HMDB
Misoprostol, (11beta,13E,16R)-isomer	HMDB
Misoprostol apotex brand	HMDB
Misoprostol, (11alpha,13E)-isomer	HMDB
Misoprostol, (11beta,13E)-(+-)-isomer	HMDB
Novo misoprostol	HMDB
Novo-misoprostol	HMDB
Novopharm brand OF misoprostol	HMDB
Pfizer brand OF misoprostol	HMDB

Chemical Formula

C₂₂H₃₈O₅

Average Molecular Weight

382.5341

Monoisotopic Molecular Weight

382.271924326

IUPAC Name

methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate

Traditional Name

misoprostol

CAS Registry Number

59122-46-2

SMILES

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

InChI Identifier

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

InChI Key

OJLOPKGSLYJEMD-URPKTTJQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Fatty acid ester
Fatty acid methyl ester
Cyclopentanol
Cyclic alcohol
Tertiary alcohol
Methyl ester
Secondary alcohol
Ketone
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015064)
Extracellular (HMDB: HMDB0015064)

Source

Exogenous

Exogenous (HMDB: HMDB0015064)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.88	ALOGPS
logP	3.86	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	107.88 m³·mol⁻¹	ChemAxon
Polarizability	45.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015064

DrugBank ID

DB00929

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Misoprostol

METLIN ID

Not Available

PubChem Compound

5282381

PDB ID

Not Available

ChEBI ID

122391

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Misoprostol (CFc000009372)

MOL for CFc000009372 (Misoprostol)

3D MOL for CFc000009372 (Misoprostol)

3D SDF for CFc000009372 (Misoprostol)

3D-SDF for CFc000009372 (Misoprostol)

PDB for CFc000009372 (Misoprostol)

3D PDB for CFc000009372 (Misoprostol)

SMILES for CFc000009372 (Misoprostol)

INCHI for CFc000009372 (Misoprostol)

Structure for CFc000009372 (Misoprostol)

3D Structure for CFc000009372 (Misoprostol)