CHEBI:3403 - carboprost

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ChEBI Name carboprost
Definition Prostaglandin F in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of pregnancy.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H36O5
Net Charge 0
Average Mass 368.514
Monoisotopic Mass 368.25627
InChI InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
SMILES CCCCC[C@](C)(O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
A chemical substance that interrupts pregnancy after implantation.
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ChEBI Ontology
Outgoing carboprost (CHEBI:3403) has functional parent prostaglandin F (CHEBI:15553)
carboprost (CHEBI:3403) has role abortifacient (CHEBI:50691)
carboprost (CHEBI:3403) has role oxytocic (CHEBI:36063)
carboprost (CHEBI:3403) is a hydroxy monocarboxylic acid (CHEBI:35868)
carboprost (CHEBI:3403) is conjugate acid of carboprost(1−) (CHEBI:59205)
Incoming carboprost(1−) (CHEBI:59205) is conjugate base of carboprost (CHEBI:3403)
(5Z,13E,15S)-9α,11α,15-trihydroxy-15-methylprosta-5,13-dien-1-oic acid
INNs Sources
carboprost WHO MedNet
carboprost WHO MedNet
carboprost WHO MedNet
carboprostum WHO MedNet
Synonyms Sources
(15S)-15-methyl-PGF ChemIDplus
(15S)-15-methylprostaglandin F ChemIDplus
15(S)-15-methyl-PGF ChemIDplus
15(S)-15-methylprostaglandin F ChemIDplus
Manual Xrefs Databases
4444532 ChemSpider
502 DrugCentral
Carboprost Wikipedia
DB00429 DrugBank
DE2121980 Patent
US3728382 Patent
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Registry Numbers Types Sources
2949991 Beilstein Registry Number Beilstein
35700-23-3 CAS Registry Number KEGG COMPOUND
35700-23-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15104835 PubMed citation Europe PMC
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Last Modified
23 November 2020