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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014573
Secondary Accession Numbers
  • HMDB14573
Metabolite Identification
Common NameCarboprost Tromethamine
DescriptionCarboprost Tromethamine is only found in individuals that have used or taken this drug. It is a nonsteroidal abortifacient agent that is effective in both the first and second trimesters of pregnancy. [PubChem]Carboprost is a synthetic prostaglandin. It binds the prostaglandin E2 receptor, causing myometrial contractions, casuing the induction of labour or the expulsion of the placenta. Prostaglandins occur naturally in the body and act at several sites in the body including the womb (uterus). They act on the muscles of the womb, causing them to contract.
Structure
Data?1582753194
Synonyms
ValueSource
(15S)-15-Methyl-PGF2alphaChEBI
(15S)-15-Methylprostaglandin F2alphaChEBI
15(S)-15-Methyl-PGF2alphaChEBI
15(S)-15-Methylprostaglandin F2alphaChEBI
CarboprostumChEBI
(15S)-15-Methyl-PGF2aGenerator
(15S)-15-Methyl-PGF2αGenerator
(15S)-15-Methylprostaglandin F2aGenerator
(15S)-15-Methylprostaglandin F2αGenerator
15(S)-15-Methyl-PGF2aGenerator
15(S)-15-Methyl-PGF2αGenerator
15(S)-15-Methylprostaglandin F2aGenerator
15(S)-15-Methylprostaglandin F2αGenerator
(15S)-15-Methyl-PGF2alpha tromethamine saltHMDB
(15S)-15-Methylprostaglandin F2alpha tromethamineHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9alpha,11beta,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-OateHMDB
15(S)-15-Methyl-PGF2alpha tromethamine saltHMDB
15(S)-15-Methylprostaglandin F2alpha tromethamineHMDB
Carboprost trometamolHMDB
(15S)-15-Methyl-PGF2a tromethamine saltHMDB
(15S)-15-Methyl-PGF2α tromethamine saltHMDB
(15S)-15-Methylprostaglandin F2a tromethamineHMDB
(15S)-15-Methylprostaglandin F2α tromethamineHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9a,11b,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-OateHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9a,11b,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-Oic acidHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9alpha,11beta,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-Oic acidHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9α,11β,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-OateHMDB
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9α,11β,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-Oic acidHMDB
15(S)-15-Methyl-PGF2a tromethamine saltHMDB
15(S)-15-Methyl-PGF2α tromethamine saltHMDB
15(S)-15-Methylprostaglandin F2a tromethamineHMDB
15(S)-15-Methylprostaglandin F2α tromethamineHMDB
15-Methylprostaglandin F2alpha-tromethamineHMDB
Prostin m-15HMDB
Chemical FormulaC21H36O5
Average Molecular Weight368.514
Monoisotopic Molecular Weight368.256274259
IUPAC Name(5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name15(S)-15-methyl-PGF2α
CAS Registry Number58551-69-2
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
InChI Identifier
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
InChI KeyDLJKPYFALUEJCK-WJDSMEDOSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point95 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.062 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
logP4.29ALOGPS
logP2.89ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity105.11 m³·mol⁻¹ChemAxon
Polarizability43.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+205.42630932474
DeepCCS[M-H]-203.0330932474
DeepCCS[M-2H]-236.22730932474
DeepCCS[M+Na]+211.33830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carboprost TromethamineCCCCC[C@](C)(O)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O4350.3Standard polar33892256
Carboprost TromethamineCCCCC[C@](C)(O)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O2714.0Standard non polar33892256
Carboprost TromethamineCCCCC[C@](C)(O)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O2878.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carboprost Tromethamine,1TMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2949.5Semi standard non polar33892256
Carboprost Tromethamine,1TMS,isomer #2CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O2782.3Semi standard non polar33892256
Carboprost Tromethamine,1TMS,isomer #3CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2765.4Semi standard non polar33892256
Carboprost Tromethamine,1TMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2828.6Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2826.8Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #2CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2807.4Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #3CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2885.4Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2709.7Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #5CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2728.7Semi standard non polar33892256
Carboprost Tromethamine,2TMS,isomer #6CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2712.8Semi standard non polar33892256
Carboprost Tromethamine,3TMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2781.8Semi standard non polar33892256
Carboprost Tromethamine,3TMS,isomer #2CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2818.7Semi standard non polar33892256
Carboprost Tromethamine,3TMS,isomer #3CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2800.6Semi standard non polar33892256
Carboprost Tromethamine,3TMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2676.6Semi standard non polar33892256
Carboprost Tromethamine,4TMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C[C@H](O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2786.5Semi standard non polar33892256
Carboprost Tromethamine,1TBDMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3208.7Semi standard non polar33892256
Carboprost Tromethamine,1TBDMS,isomer #2CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O2999.3Semi standard non polar33892256
Carboprost Tromethamine,1TBDMS,isomer #3CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2984.8Semi standard non polar33892256
Carboprost Tromethamine,1TBDMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3099.7Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3322.3Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #2CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3300.1Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #3CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3413.3Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O3179.6Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #5CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3226.1Semi standard non polar33892256
Carboprost Tromethamine,2TBDMS,isomer #6CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3211.7Semi standard non polar33892256
Carboprost Tromethamine,3TBDMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3477.1Semi standard non polar33892256
Carboprost Tromethamine,3TBDMS,isomer #2CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3543.4Semi standard non polar33892256
Carboprost Tromethamine,3TBDMS,isomer #3CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3523.7Semi standard non polar33892256
Carboprost Tromethamine,3TBDMS,isomer #4CCCCC[C@](C)(O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3393.5Semi standard non polar33892256
Carboprost Tromethamine,4TBDMS,isomer #1CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3663.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carboprost Tromethamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 10V, Positive-QTOFsplash10-0f89-0019000000-469c4f055dd8640d06562019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 20V, Positive-QTOFsplash10-0pir-3479000000-a2bf44c4779ddafa22e12019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 40V, Positive-QTOFsplash10-0a4i-9431000000-4cd08b28f65942f82a8f2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 10V, Negative-QTOFsplash10-014j-0009000000-0751716629d46123df5f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 20V, Negative-QTOFsplash10-0002-1009000000-9b8fd264ed555f063c552019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 40V, Negative-QTOFsplash10-0a4i-9832000000-e358a421e5147fd23f362019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 10V, Negative-QTOFsplash10-014i-0009000000-d7fcbcd2c6a4296d75632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 20V, Negative-QTOFsplash10-014i-0039000000-3af47f29f3af094136d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 40V, Negative-QTOFsplash10-0059-8493000000-451afab9ad9860c63a6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 10V, Positive-QTOFsplash10-0f89-0029000000-75709a7ac64508bf58a32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 20V, Positive-QTOFsplash10-0839-8694000000-adcb2e24cc481753347a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboprost Tromethamine 40V, Positive-QTOFsplash10-05mo-9610000000-d11b176c30fc2456a6fc2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00429 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00429 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26333214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarboprost
METLIN IDNot Available
PubChem Compound35023177
PDB IDNot Available
ChEBI ID3403
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:
PTGER1
Uniprot ID:
P34995
Molecular weight:
41800.7
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Hay A, Wood S, Olson D, Slater DM: Labour is associated with decreased expression of the PGF2alpha receptor (PTGFR) and a novel PTGFR splice variant in human myometrium but not decidua. Mol Hum Reprod. 2010 Oct;16(10):752-60. doi: 10.1093/molehr/gaq046. Epub 2010 Jun 2. [PubMed:20519365 ]
  3. Tsuboi K, Ichikawa A: [Reproduction physiology and prostanoids]. Nihon Yakurigaku Zasshi. 2001 Apr;117(4):267-73. [PubMed:11338376 ]
  4. Carrasco MP, Asboth G, Phaneuf S, Lopez Bernal A: Activation of the prostaglandin FP receptor in human granulosa cells. J Reprod Fertil. 1997 Nov;111(2):309-17. [PubMed:9462300 ]