Carboprost
PubChem CID
5281075
Structure
Molecular Formula
Synonyms
- CARBOPROST
- 35700-23-3
- Carboprostum
- Prostin 15M
- (15S)-15-Methylprostaglandin F2alpha
Molecular Weight
368.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-11
Description
Carboprost is prostaglandin F2alpha 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. It has a role as an oxytocic and an abortifacient. It is functionally related to a prostaglandin F2alpha. It is a conjugate acid of a carboprost(1-).
Carboprost is a Prostaglandin Analog.
Carboprost is the (15S)-15 methyl analogue of naturally occurring prostaglandin F2 alpha (PGF2 alpha) with oxytocic activity. Mimicking endogenous PGF2 alpha, carboprost activates prostaglandin F receptor, a G-protein coupled receptor, on smooth muscle cells, thereby resulting in smooth muscle contractions. When administered intramuscularly on gravid subjects, this agent induces myometrium contractions, thereby initiating luteolysis and consequently parturition. Furthermore, carboprost's action on vascular smooth muscle and gastrointestinal tract sphincters leads to raised blood pressure and induces vomiting or diarrhea, respectively.
See also: Carboprost Tromethamine (has salt form).
Chemical Structure Depiction
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
DLJKPYFALUEJCK-IIELGFQLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C21H36O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)
59286-19-0
- 15 Methylprostaglandin F2alpha
- 15(S)-15-Methyl PGF2alpha
- 15-Methylprostaglandin F2alpha
- Carboprost
- CARBOPROST
- 35700-23-3
- Carboprostum
- Prostin 15M
- (15S)-15-Methylprostaglandin F2alpha
- 15-ME-PGF2-alpha
- UNII-7B5032XT6O
- 15-Methylprostaglandin F2-alpha
- (15S)-15-Methyl-PGF2alpha
- 7B5032XT6O
- 15-methyl-pgf2.alpha.
- 15(S)-Methylprostaglandin F2-alpha
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
- Carboprostum [INN-Latin]
- U 32921
- BRN 2949991
- U-32,921
- 15-methyl-15S-PGF2alpha
- CHEBI:3403
- DTXSID4022739
- (15S)-15-Methylprostaglandin F(sub 2alpha)
- 15-methylprostaglandin f2.alpha.
- (15s)-15-methyl-pgf2.alpha.
- U-32921
- 15-methyl-15S-Prostaglandin F2alpha
- 15(S)-15-methylprostaglandin F2alpha
- 15-Methyl prostaglandin F2alpha
- Carboprostum (INN-Latin)
- CARBOPROST (MART.)
- CARBOPROST [MART.]
- 15-METHYLPROSTAGLANDIN F2BETA, (15S)-
- (5Z,9-alpha,11-alpha,13E,15S)-9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic acid
- 9,11,15-Trihydroxy-15-methylprosta-5,13-dien-1-oic acid (5Z,9alpha,11alpha,13E,15S)-
- 59286-19-0
- 9S,11R,15S-trihydroxy-15-methyl-5Z,13E-prostadienoic acid
- (5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-15-methylprosta-5,13-dien-1-oic acid
- (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-oic acid
- Methyl-pgf2-alpha
- (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-3-methyl-1-octenyl))cyclopentyl)-5-heptenoic acid
- 15-Methyl-pgf2-alpha
- 15-Methyl PGF2-alpha
- 15(S)-15-methyl-PGF2alpha
- 15-Methyl-pgf2-alpha (alpha and beta)
- Carboprost [USAN:INN:BAN]
- 15 Methylprostaglandin F2alpha
- 15-Methylprostaglandin F2alpha
- 15(S)-15-Methyl pgf2-alpha
- (E,Z)-(1R,2R,3R,5S)-7-[3,5-Dihydroxy-2-[(3S)-(3-hydroxy-3-methyl-1-octenyl)]cyclopentyl]-5-heptenoic acid
- Carboprost (Standard)
- (15s)15 Methyl prostaglandin F2-alpha
- 15-methyl-PGF2?
- 15(S)-15-Methyl-prostaglandin F2-alpha
- CARBOPROST [MI]
- CARBOPROST [INN]
- Carboprost (USAN/INN)
- CARBOPROST [USAN]
- CARBOPROST [VANDF]
- CARBOPROST [WHO-DD]
- Prosta-5,13-dien-1-oic acid, 15-methyl-9,11,15-trihydroxy-, (5Z,9-alpha,11-alpha,13E,15S)-, (+-)-
- SCHEMBL433553
- DTXCID102739
- CHEMBL1237122
- G02AD04
- DLJKPYFALUEJCK-IIELGFQLSA-N
- GLXC-27444
- HMS3648F18
- LMFA03010080
- s9327
- AKOS027326498
- CCG-268274
- HY-128428R
- 15(S)-15-methyl Prostaglandin F2|A
- 1ST11428
- MS-25920
- Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-15-methyl-, (5Z,9.alpha.,11.alpha.,13E,15S)-
- Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-15-methyl-, (5Z,9alpha,11alpha,13E,15S)-
- HY-128428
- CS-0099506
- NS00127424
- C06872
- D02343
- G12369
- (15S)-15-METHYLPROSTAGLANDIN F2.ALPHA.
- SR-01000946499
- Q5038067
- SR-01000946499-1
- (15S)-15-METHYLPROSTAGLANDIN F(SUB 2.ALPHA.)
- (5Z,9.ALPHA.,11.ALPHA.,13E,15S)-9,11,15-TRIHYDROXY-15-METHYLPROSTA-5,13-DIEN-1-OIC ACID
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
368.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
368.25627424 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
368.25627424 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
98 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
473
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Fatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
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Same Connectivity Count
Same Parent, Connectivity Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Carboprost Tromethamine (has salt form)
Abortifacient Agents, Nonsteroidal
Non-steroidal chemical compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Nonsteroidal.)
Oxytocics
Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157) (See all compounds classified as Oxytocics.)
FDA UNII
7B5032XT6O
Active Moiety
CARBOPROST
Pharmacological Classes
Established Pharmacologic Class [EPC] - Prostaglandin Analog
Pharmacological Classes
Chemical Structure [CS] - Prostaglandins
FDA Pharmacology Summary
Carboprost is a Prostaglandin Analog.
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=DLJKPYFALUEJCK-IIELGFQLSA-N
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusCarboprost [USAN:INN:BAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=003570023315-Methyl-pgf2-alphahttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0059286190ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
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- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jsp
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- Metabolomics Workbench15-methyl-15S-PGF2alphahttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=2441
- Nature Chemistry
- NLM RxNorm TerminologyLICENSEThe RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.htmlcarboprosthttps://rxnav.nlm.nih.gov/id/rxnorm/2051
- NORMAN Suspect List ExchangeLICENSEData: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0https://creativecommons.org/licenses/by/4.0/NORMAN Suspect List Exchange Classificationhttps://www.norman-network.com/nds/SLE/
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- Wikidatacarboprosthttps://www.wikidata.org/wiki/Q5038067
- WikipediaAminoethylethanolaminehttps://en.wikipedia.org/wiki/AminoethylethanolamineCarboprosthttps://en.wikipedia.org/wiki/Carboprost
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- PubChem
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 391037055https://pubchem.ncbi.nlm.nih.gov/substance/391037055
- NCBI
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