Details of the Drug

General Information of Drug (ID: DMFYBD0)

Drug Name
Dexibuprofen
Synonyms
(S)-(+)-Ibuprofen; 51146-56-6; DEXIBUPROFEN; S(+)-Ibuprofen; (S)-2-(4-Isobutylphenyl)propanoic acid; (S)-Ibuprofen; d-Ibuproten; (S)-(+)-2-(4-Isobutylphenyl)propionic acid; (+)-(S)-p-Isobutylhydratropic acid; Seractil; (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid; (S)-(+)-4-Isobutyl-alpha-methylphenylacetic acid; UNII-671DKG7P5S; S-(+)-ibuprofen; (2S)-2-(4-isobutylphenyl)propanoic acid; CHEMBL175; 671DKG7P5S; CHEBI:43415; (S)-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid; NCGC00016861-05
Indication
Disease Entry ICD 11 Status REF
Ankylosing spondylitis FA92.0 Approved [1]
Dysmenorrhea GA34.3 Approved [2]
Fever MG26 Approved [3]
Headache 8A80-8A84 Approved [4]
Osteoarthritis FA00-FA05 Approved [5]
Pain MG30-MG3Z Approved [3]
⏷ Show the Full List of Indication(s)
Affected Organisms
Humans and other mammals
ATC Code
M01AE14: Dexibuprofen
M01AE: Propionic acid derivatives
M01A: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M: MUSCULO-SKELETAL SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 206.28
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2.25-5 h [6]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.2 - 4.7 hours [6]
Chemical Identifiers
Formula
C13H18O2
IUPAC Name
(2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
Canonical SMILES
C[C@@H](C1=CC=C(C=C1)CC(C)C)C(=O)O
InChI
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/s1
InChIKey
HEFNNWSXXWATRW-JTQLQIEISA-N
Cross-matching ID
PubChem CID
39912
ChEBI ID
CHEBI:43415
CAS Number
51146-56-6
UNII
671DKG7P5S
DrugBank ID
DB09213
TTD ID
D06YPU
INTEDE ID
DR0468
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 (COX) TTK0943 PGH1_HUMAN ; PGH2_HUMAN Modulator [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [8]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [9]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [10]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [9]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [9]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DEF2WXN UD13_HUMAN Substrate [9]
Alpha-methylacyl-CoA racemase (AMACR) DEGKWJB AMACR_HUMAN Substrate [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 ADIDAC trial: analgesia with dexibuprofen versus ibuprofen in patients suffering from primary dysmenorrhea: a crossover trial. Gynecol Obstet Invest. 2009;67(1):25-31.
3 Efficacy and Safety of NSAIDs in Infants: A Comprehensive Review of the Literature of the Past 20 Years. Paediatr Drugs. 2022 Nov;24(6):603-655.
4 A comparative study of the pharmacokinetics of ibuprofen arginate versus dexibuprofen in healthy volunteers. Eur J Clin Pharmacol. 2006 Oct;62(10):849-54.
5 Comparison of safety, efficacy and tolerability of dexibuprofen and ibuprofen in the treatment of osteoarthritis of the hip or knee. Wien Klin Wochenschr. 2014 Jun;126(11-12):368-75.
6 Pharmacokinetic-pharmacodynamic model of newly developed dexibuprofen sustained release formulations. ISRN Pharm. 2012;2012:451481. doi: 10.5402/2012/451481. Epub 2012 Dec 6.
7 Comparison of the efficacy and tolerability of dexibuprofen and celecoxib in the treatment of osteoarthritis of the hip. Int J Clin Pharmacol Ther. 2003 Apr;41(4):153-64.
8 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
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.
10 PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106.
11 Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87.
12 Alpha-Methylacyl-CoA racemase (AMACR): metabolic enzyme, drug metabolizer and cancer marker P504S. Prog Lipid Res. 2013 Apr;52(2):220-30.