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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
DrugBank ID: DB09213
TTD ID: D06YPU
INTEDE ID: DR0468

Repurposed Drugs (RPD)

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.