General Information of Drug (ID: DM23D7J)

Drug Name
Tiaprofenic acid
Synonyms
Surgam; Tiaprofensaeure; Acide tiaprofenique; Acido tiaprofenico; Acidum tiaprofenicum; Surgam SR; FC 3001; RU 15060; Acide tiaprofenique [INN-French]; Acido tiaprofenico [INN-Spanish]; Acidum tiaprofenicum [INN-Latin]; Apo-Tiaprofenic Tablets; Dom-tiaprofenic; Surgam (TN); Surgamyl (TN); Tiaprofen (TN); Tiaprofenic acid (JAN/INN); Tiaprofenic-200-Tab; Tiaprofenic-300-Tab; Tiaprofenic acid [INN:BAN:DCF:JAN]; Alpha-methyl-5-benzoyl-2-thienylacetic acid; 2-(5-Benzyl-2-thienyl)propionsaeure; 2-(5-benzoylthiophen-2-yl)propanoic acid; 2-[5-(phenylcarbonyl)-2-thienyl]propanoic acid; 5-Benzoyl-alpha-methyl-2-thiopheneacetic acid; 5-benzoyl-alpha-methylthiophene-2-acetic acid
Indication
Disease Entry ICD 11 Status REF
Osteoarthritis FA00-FA05 Approved [1]
Pain MG30-MG3Z Approved [2]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 260.31
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability
The bioavailability of drug is 90% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.62 mL/min/kg [4]
Elimination
2.5% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.5 - 2.5 hours [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 38.41515 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.015% [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 0.08 L/kg [4]
Chemical Identifiers
Formula
C14H12O3S
IUPAC Name
2-(5-benzoylthiophen-2-yl)propanoic acid
Canonical SMILES
CC(C1=CC=C(S1)C(=O)C2=CC=CC=C2)C(=O)O
InChI
InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17)
InChIKey
GUHPRPJDBZHYCJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5468
ChEBI ID
CHEBI:32221
CAS Number
33005-95-7
DrugBank ID
DB01600
TTD ID
D0S7VO
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Carbonyl reductase 1 (CBR1) OTQ3A541 CBR1_HUMAN Biotransformations [7]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [8]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Biotransformations [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Osteoarthritis
ICD Disease Classification FA00-FA05
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

References

1 Tiaprofenic acid. A reappraisal of its pharmacological properties and use in the management of rheumatic diseases. Drugs. 1995 Dec;50(6):1050-75.
2 Drug information of Tiaprofenic acid, 2008. eduDrugs.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Effects of tiaprofenic acid on the concentration and metabolism of proteoglycans in normal and degenerating canine articular cartilage. J Clin Pharmacol. 1990 Sep;30(9):808-14.
7 Reductive metabolism of tiaprofenic acid by the human liver and recombinant carbonyl reducing enzymes. Chem Biol Interact. 2017 Oct 1;276:121-126. doi: 10.1016/j.cbi.2017.03.006. Epub 2017 Mar 18.
8 Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
9 Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J Pharmacol Exp Ther. 1993 Jan;264(1):475-9.