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
CHEMBL43415
CAS Number
51146-56-6
UNII
671DKG7P5S
DrugBank ID
DB09213
TTD ID
D06YPU
INTEDE ID
DR0468
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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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.