Details of the Drug

General Information of Drug (ID: DMHMP05)

Drug Name
Carprofen
Synonyms
Carprofene; Carprofeno; Carprofenum; Imadyl; Ridamyl; Rimadyl; Carprofeno [Spanish]; C 5720; Ro 205720; C-5720; Carprofene [INN-French]; Carprofeno [INN-Spanish]; Carprofenum [INN-Latin]; Rimadyl (TN); Ro 20-5720; Carprofen (USAN/INN); Carprofen [USAN:INN:BAN]; Ro 20-5720/000; Ro-20-5720; Ro-20-5720/000; (+-)-6-Chloro-alpha-methylcarbazole-2-acetic acid; (+-)-isomer of carprofen; (+/-)-2-(3-chloro-9H-carbazol-7-yl)propanoic acid; (+/-)-6-Chloro-.alpha.-methylcarbazole-2-acetic acid; (-)-6-Chlor-alpha-methyl-2-carbazolessigsaeure; 2-(6-Chloro-9H-carbazol-2-yl)-propionic acid; 2-(6-Chloro-9H-carbazol-2-yl)propanoic acid; 6-Chlor-alpha-methyl-carbazol-2-essigsaeure; 6-Chlor-alpha-methyl-carbazol-2-essigsaeure [German]; 6-Chloro-alpha-methyl-9H-carbazole-2-acetic acid; 6-Chloro-alpha-methylcarbazole-2-acetic acid; 9H-Carbazole-2-acetic acid, 6-chloro-.al
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Approved [1], [2]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 273.71
Topological Polar Surface Area (xlogp) 4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The drug is rapidly and nearly completely orally absorbed [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.51 mL/min/kg [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 8 hours [4]
Metabolism
The drug is metabolized via the hepatic [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.001% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.22 L/kg [4]
Chemical Identifiers
Formula
C15H12ClNO2
IUPAC Name
2-(6-chloro-9H-carbazol-2-yl)propanoic acid
Canonical SMILES
CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O
InChI
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)
InChIKey
PUXBGTOOZJQSKH-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2581
ChEBI ID
CHEBI:364453
CAS Number
53716-49-7
DrugBank ID
DB00821
TTD ID
D0IT2X
INTEDE ID
DR1766
ACDINA ID
D00102

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 2B7 (UGT2B7)
Main DME 		DEB3CV1 UD2B7_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pain
ICD Disease Classification MG30-MG3Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF E00255 17730 Colorant
Carmellose sodium E00625 Not Available Disintegrant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water E00035 962 Solvent
⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Carprofen 100 mg tablet 100 mg Oral Tablet Oral
Carprofen 25 mg tablet 25 mg Oral Tablet Oral
Carprofen 75 mg tablet 75 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018550.
3 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Scaffold of the cyclooxygenase-2 (COX-2) inhibitor carprofen provides Alzheimer gamma-secretase modulators. J Med Chem. 2006 Dec 28;49(26):7588-91.
6 Enantioselective inhibition of carprofen towards UDP-glucuronosyltransferase (UGT) 2B7. Chirality. 2015 Mar;27(3):189-93.
7 Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22.
8 Determination of UDP-glucuronosyltransferase UGT2B7 activity in human liver microsomes by ultra-performance liquid chromatography with MS detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Jul 1;870(1):84-90.
9 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
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11 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
12 Pitavastatin: a review in hypercholesterolemia. Am J Cardiovasc Drugs. 2017 Apr;17(2):157-168.
13 Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9.
14 Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
15 Pharmacogenomics of statins: understanding susceptibility to adverse effects. Pharmgenomics Pers Med. 2016 Oct 3;9:97-106.
16 Maternal toxicity of nonsteroidal anti-inflammatory drugs as an important factor affecting prenatal development. Reprod Toxicol. 2009 Sep;28(2):239-44.
17 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
18 Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. Intern Med. 2007;46(13):1055-8.
19 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
20 Pfizer. Product Development Pipeline. March 31 2009.
21 Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. Exp Nephrol. 2001;9(6):387-96.
22 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
23 Flurbiprofen, a cyclooxygenase inhibitor, protects mice from hepatic ischemia/reperfusion injury by inhibiting GSK-3 signaling and mitochondrial permeability transition.Mol Med.2012 Sep 25;18:1128-35.
24 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.