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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:00:47 UTC
HMDB IDHMDB0014959
Secondary Accession Numbers
  • HMDB14959
Metabolite Identification
Common NameCarprofen
DescriptionCarprofen is a non-steroidal anti-inflammatory drug (NSAID) that is used by veterinarians as a supportive treatment for the relief of arthritic symptoms in geriatric dogs. Carprofen was previously used in human medicine for over 10 years (1985-1995). It was generally well tolerated, with the majority of adverse effects being mild, such as gastro-intestinal pain and nausea, similar to those recorded with aspirin and other non-steroidal anti-inflammatory drugs. It is no longer marketed for human usage, after being withdrawn on commercial grounds. [Wikipedia ]
Structure
Data?1582753242
Synonyms
ValueSource
(+-)-6-Chloro-alpha-methylcarbazole-2-acetic acidChEBI
(+/-)-2-(3-chloro-9H-carbazol-7-yl)propanoic acidChEBI
2-(6-Chloro-9H-carbazol-2-yl)-propionic acidChEBI
6-Chloro-alpha-methyl-9H-carbazole-2-acetic acidChEBI
CarprofeneChEBI
CarprofenoChEBI
CarprofenumChEBI
RimadylKegg
(+-)-6-Chloro-a-methylcarbazole-2-acetateGenerator
(+-)-6-Chloro-a-methylcarbazole-2-acetic acidGenerator
(+-)-6-Chloro-alpha-methylcarbazole-2-acetateGenerator
(+-)-6-Chloro-α-methylcarbazole-2-acetateGenerator
(+-)-6-Chloro-α-methylcarbazole-2-acetic acidGenerator
(+/-)-2-(3-chloro-9H-carbazol-7-yl)propanoateGenerator
2-(6-Chloro-9H-carbazol-2-yl)-propionateGenerator
6-Chloro-a-methyl-9H-carbazole-2-acetateGenerator
6-Chloro-a-methyl-9H-carbazole-2-acetic acidGenerator
6-Chloro-alpha-methyl-9H-carbazole-2-acetateGenerator
6-Chloro-α-methyl-9H-carbazole-2-acetateGenerator
6-Chloro-α-methyl-9H-carbazole-2-acetic acidGenerator
2-(6-Chloro-9H-carbazol-2-yl)propanoic acidHMDB
6-Chloro-alpha-methylcarbazole-2-acetic acidHMDB
(R)-Isomer OF carprofenHMDB
(S)-Isomer OF carprofenHMDB
Carprofen, (S)-isomerHMDB
(+-)-Isomer OF carprofenHMDB
Carprofen, (+-)-isomerHMDB
Carprofen, (R)-isomerHMDB
Chemical FormulaC15H12ClNO2
Average Molecular Weight273.714
Monoisotopic Molecular Weight273.05565634
IUPAC Name2-(6-chloro-9H-carbazol-2-yl)propanoic acid
Traditional Namecarprofen
CAS Registry Number53716-49-7
SMILES
CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1
InChI Identifier
InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)
InChI KeyPUXBGTOOZJQSKH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassCarbazoles
Direct ParentCarbazoles
Alternative Parents
Substituents
  • Carbazole
  • Indole
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0038 g/LNot Available
LogP3.8Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP10(4.09) g/LALOGPS
logP10(3.88) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Acidic)4.42ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.16 m³·mol⁻¹ChemAxon
Polarizability28.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carprofen,1TMS,#1CC(C(=O)O[Si](C)(C)C)C1=CC=C2C(=C1)[NH]C1=CC=C(Cl)C=C122804.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Carprofen,1TMS,#2CC(C(=O)O)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C)C2=C12740.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Carprofen,1TBDMS,#1CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C2C(=C1)[NH]C1=CC=C(Cl)C=C123013.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Carprofen,1TBDMS,#2CC(C(=O)O)C1=CC=C2C3=CC(Cl)=CC=C3N([Si](C)(C)C(C)(C)C)C2=C12924.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2290000000-8e764c2da7663d646e652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carprofen GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9066000000-a8e76536064f58e75c0b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carprofen , positive-QTOFsplash10-0006-2910000000-d2961d6d33669b09ac4d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 10V, Positive-QTOFsplash10-00di-0090000000-bbfca556ca844825bcaa2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 20V, Positive-QTOFsplash10-0kdi-0090000000-e1ce007088ba090130792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 40V, Positive-QTOFsplash10-0ufr-1390000000-fc5022b898e71ff8c6b12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 10V, Negative-QTOFsplash10-00di-0090000000-6740a199277a7baa3bb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 20V, Negative-QTOFsplash10-00b9-0090000000-44c304e6c89130ee3c8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 40V, Negative-QTOFsplash10-0wbc-6790000000-894ded030da574fd900f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 10V, Positive-QTOFsplash10-05fr-0090000000-31993c6f749285c221f52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 20V, Positive-QTOFsplash10-004i-0090000000-7153ca460f92875f99cb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 40V, Positive-QTOFsplash10-004i-0490000000-c63ce88239e47609a5fe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 10V, Negative-QTOFsplash10-004i-0090000000-b0a34778cae3fe8a802d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 20V, Negative-QTOFsplash10-0059-5090000000-3f0a01f697769e871da52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carprofen 40V, Negative-QTOFsplash10-001i-9020000000-95a620ddb1bb04bf15da2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00821 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00821 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00821
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2483
KEGG Compound IDC18364
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarprofen
METLIN IDNot Available
PubChem Compound2581
PDB IDNot Available
ChEBI ID364453
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 ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. [PubMed:10895904 ]
  2. Brideau C, Van Staden C, Chan CC: In vitro effects of cyclooxygenase inhibitors in whole blood of horses, dogs, and cats. Am J Vet Res. 2001 Nov;62(11):1755-60. [PubMed:11703020 ]
  3. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
  4. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
  5. Narlawar R, Perez Revuelta BI, Haass C, Steiner H, Schmidt B, Baumann K: Scaffold of the cyclooxygenase-2 (COX-2) inhibitor carprofen provides Alzheimer gamma-secretase modulators. J Med Chem. 2006 Dec 28;49(26):7588-91. [PubMed:17181139 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]