BENOXAPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H12ClNO3
Molecular Weight	301.724
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C(O)=O)C1=CC2=C(OC(=N2)C3=CC=C(Cl)C=C3)C=C1

InChI

InChIKey=MITFXPHMIHQXPI-UHFFFAOYSA-N

InChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C16H12ClNO3
Molecular Weight	301.724
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

BENOXAPROFEN is an anti-inflammatory drug indicated for the treatment of arthritis. It was marketed under the brand name ORAFLEX® in the US and as OPREN® in Europe by Eli Lilly and Company. In 1982 Eli Lilly voluntarily withdrew BENOXAPROFEN from the market due to postmarketing reports of severe liver toxicity in patients who took it.

Originator

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Arachidonate 5-lipoxygenase 49	Inhibitor 8,297		149.0 µM [IC50]
Bile salt export pump 15	Inhibitor 8,297		99.1 µM [IC50]

C_max

Value	Dose	Co-administered	Analyte	Population
43 μg/mL	100 mg 2 times / day multiple, oral		BENOXAPROFEN plasma	Homo sapiens
94 μg/mL	300 mg 2 times / day steady-state, rectal		BENOXAPROFEN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
503 μg × h/mL	100 mg single, oral		BENOXAPROFEN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.84 h	100 mg single, oral		BENOXAPROFEN plasma	Homo sapiens
38 h	300 mg 2 times / day steady-state, rectal		BENOXAPROFEN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
600 mg 1 times / day steady, oral Recommended	unhealthy, 35 years (rage: 26-43 years)	Disc. AE: Photosensitivity...
900 mg 1 times / day steady, oral Highest studied dose	unhealthy, 54,9 years (range: 18-86 years)

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AEs

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AE	Significance	Dose	Population
Photosensitivity	11 patient Disc. AE	600 mg 1 times / day steady, oral Recommended	unhealthy, 35 years (rage: 26-43 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A1 108 CYP1A2 701 CYP4A1 17

Drug as perpetrator

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Target	Modality	Activity
CYP1A1 218	inducer 1,573	yes
CYP1A2 1,692	inducer 1,573	yes
CYP4A1 25	inducer 1,573	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:76114	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76114
eMolecules	35875742	https://www.emolecules.com/cgi-bin/more?vid=35875742

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PubMed

Show entries

Title	Date	PubMed
Toxic optic neuropathy caused by benoxaprofen.	1981 Jul 18	6789963
[Vasculitis caused by benoxaprofen].	1983 Oct 8	6645654
Interaction of benoxaprofen with rat erythrocytes: effects on oxidative metabolism and membrane ATPase activities.	1986 Nov	2947294
In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils.	1988	2849922
Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways.	2007 Oct	17880178