OXAPROZIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H15NO3
Molecular Weight	293.3166
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)CCC1=NC(=C(O1)C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=OFPXSFXSNFPTHF-UHFFFAOYSA-N

InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)

HIDE SMILES / InChI

Molecular Formula	C18H15NO3
Molecular Weight	293.3166
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201	Inhibitor 8,504		36.0 µM [IC50]
Cyclooxygenase-1 131	Inhibitor 8,504		2.2 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157	Primary	Approved 8,583	DAYPRO
Rheumatoid arthritis 320	Primary	Approved 8,583	DAYPRO
Juvenile rheumatoid arthritis 5	Primary	Approved 8,583	DAYPRO

C_max

Value	Dose	Analyte	Population
103 μg/mL	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
109 μg/mL	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
78.4 mg/L	0.6 g single, oral	OXAPROZIN plasma	Homo sapiens
129 mg/L	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
174 mg/L	1.8 g single, oral	OXAPROZIN plasma	Homo sapiens
239 mg/L	1.2 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens
280 mg/L	1.8 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
7042 μg × h/mL	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
7066 μg × h/mL	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
1290 mg × h/L	0.6 g single, oral	OXAPROZIN plasma	Homo sapiens
2240 mg × h/L	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
2970 mg × h/L	1.8 g single, oral	OXAPROZIN plasma	Homo sapiens
4210 mg × h/L	1.2 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens
4770 mg × h/L	1.8 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
50 h	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
48 h	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
58.3 h	0.6 g single, oral	OXAPROZIN plasma	Homo sapiens
54.9 h	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
47 h	1.8 g single, oral	OXAPROZIN plasma	Homo sapiens
41.4 h	1.2 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
0.13%	0.6 g single, oral	OXAPROZIN plasma	Homo sapiens
0.208%	1.2 g single, oral	OXAPROZIN plasma	Homo sapiens
0.305%	1.8 g single, oral	OXAPROZIN plasma	Homo sapiens
0.457%	1.2 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens
0.823%	1.8 g 1 times / day steady-state, oral	OXAPROZIN plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
1200 mg single, oral Highest studied dose	unhealthy, adult
1200 mg 1 times / day steady, oral Highest studied dose	healthy, adult
20 mg/kg single, oral Highest studied dose	unhealthy, children

Showing 1 to 3 of 3 entries

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1,193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747	CYP 303 UGT 219

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 749	inhibitor 4,027	yes [IC50 0.87 uM]
OAT1 730	inhibitor 4,027	yes [IC50 0.891 uM]

Showing 1 to 2 of 2 entries

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Drug as victim

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Target	Modality	Activity
CYP 303	substrate 4,014	yes
CYP2C9 1,193	substrate 4,014	yes
UGT 219	substrate 4,014	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7822	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7822
ChemicalBook	CB1272505	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1272505
eMolecules	593100	https://www.emolecules.com/cgi-bin/more?vid=593100
MolPort	MolPort-000-146-829	https://www.molport.com/shop/molecule-link/MolPort-000-146-829
ZINC	ZINC000049643479	http://zinc15.docking.org/substances/ZINC000049643479

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PubMed

Show entries

Title	Date	PubMed
Comparison of cyclooxygenase-1 and -2 inhibitory activities of various nonsteroidal anti-inflammatory drugs using human platelets and synovial cells.	1998 Apr 17	9650852
Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder.	2004 Aug	15324531
Oxaprozin: kinetic and dynamic profile in the treatment of pain.	2004 Aug	15324530
In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs.	2004 Dec 1	15528048
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs.	2004 Feb	15032311

Showing 1 to 5 of 31 entries

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Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Osteoarthritis Loading dose: 1200 mg to 1800 mg orally; not to exceed 26 mg/kg Maintenance dose: 1200 mg orally once a day Maximum dose: 1800 mg or 26 mg/kg orally per day, whichever is less, in divided doses

Route of Administration: Oral

In Vitro Use Guide

In arachidonic acid (AA)-induced rabbit platelet aggregation in vitro, oxaprozin exhibited a dose-dependent inhibitory effect with MIC 124.2 uM.