CHEBI:3403 - carboprost

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ChEBI Name carboprost
ChEBI ID CHEBI:3403
Definition Prostaglandin F2α 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.
Supplier Information ChemicalBook:CB6501392, eMolecules:32453022, ZINC000016343305
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Carboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties. Carboprost's main use is to reduce postpartum bleeding during the obstetrical emergency of postpartum hemorrhage.
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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
InChIKey DLJKPYFALUEJCK-IIELGFQLSA-N
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).
abortifacient
A chemical substance that interrupts pregnancy after implantation.
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ChEBI Ontology
Outgoing carboprost (CHEBI:3403) has functional parent prostaglandin F2α (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)
IUPAC Name
(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-PGF2α ChemIDplus
(15S)-15-methylprostaglandin F2α ChemIDplus
15(S)-15-methyl-PGF2α ChemIDplus
15(S)-15-methylprostaglandin F2α ChemIDplus
Manual Xrefs Databases
4444532 ChemSpider
502 DrugCentral
C06872 KEGG COMPOUND
Carboprost Wikipedia
D02343 KEGG DRUG
DB00429 DrugBank
DE2121980 Patent
US3728382 Patent
View more database links
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
Last Modified
23 November 2020