SUPROFEN SODIUM

First approved in 1985

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H11O3S.Na
Molecular Weight	282.29
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC(C([O-])=O)C1=CC=C(C=C1)C(=O)C2=CC=CS2

InChI

InChIKey=ADTGIGSPQHDPLT-UHFFFAOYSA-M

InChI=1S/C14H12O3S.Na/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12;/h2-9H,1H3,(H,16,17);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891

Suprafen is a dual inhibitor of COX-1 and COX-2, which was used for the inhibition of intraoperative miosis. Suprafen was marketed under the name Profenal, however, it is no longer available in the USA.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 1 30 Target ID: P23219\|\|\|Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Inhibitor 8504		1.1 µM [IC50]
Prostaglandin G/H synthase 2 51 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Inhibitor 8504		8.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intraoperative miosis 2 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=4891	Preventing		Approved 8583	PROFENAL Approved Use Inhibition of miosis during intraocular surgery. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
18.95 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.43 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
26.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
21.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3243932	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6361789	unhealthy, > 18 years Health Status: unhealthy Age Group: > 18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6361789	Sources: https://pubmed.ncbi.nlm.nih.gov/6361789
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	Sources: https://pubmed.ncbi.nlm.nih.gov/3741528
400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	Other AEs: Nausea, Vomiting... Other AEs: Nausea (2 patients) Vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3741528

AEs

AE	Significance	Dose	Population
Nausea	2 patients	400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3741528
Vomiting	2 patients	400 mg single, oral Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3741528	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3741528

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193 inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 197

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B7 210	inhibitor 4027 Sources: https://link.springer.com/protocol/10.1385/1-59259-800-5:185 Page: 15.0	likely
CYP2C9 2497	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2610245/	yes [Ki 6.7 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1193	substrate 4014 Sources: https://www.ingentaconnect.com/content/ben/cmc/2009/00000016/00000027/art00003 Page: 2.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9362	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9362
ChemicalBook	CB2496867	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2496867
eMolecules	743277	https://www.emolecules.com/cgi-bin/more?vid=743277
MolPort	MolPort-001-791-811	https://www.molport.com/shop/molecule-link/MolPort-001-791-811
Selleck Chemicals	Suprofen(Profenal)	http://www.selleckchem.com/products/Suprofen(Profenal).html

PubMed

Title	Date	PubMed
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014-01	24085192
Single dose dipyrone for acute postoperative pain.	2010-09-08	20824835
Novel metabolic bioactivation mechanism for a series of anti-inflammatory agents (2,5-diaminothiophene derivatives) mediated by cytochrome p450 enzymes.	2010-09	20530221
Characterization of glutathione conjugates of duloxetine by mass spectrometry and evaluation of in silico approaches to rationalize the site of conjugation for thiophene containing drugs.	2010-08-16	20669986
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.	2010-08	20017213
Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid.	2009-08-13	19719267
Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism.	2009-05	19442216
Enantiomeric separation of acidic compounds by nano-liquid chromatography with methylated-beta-cyclodextrin as a mobile phase additive.	2009-05	19370733
Chemoenzymatic and microbial dynamic kinetic resolutions.	2009-04	18655180
Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection.	2009-01	18838506
Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development.	2009	19515014
New NSAIDs-NO hybrid molecules with antiproliferative properties on human prostatic cancer cell lines.	2008-08-15	18667313
Topical ocular delivery of NSAIDs.	2008-06	18437583
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008-02	18224312
Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure.	2007-06	17477341
Differential suppression of menstrual fluid prostaglandin F2a, prostaglandin E2, 6-keto prostaglandin F1a and thromboxane B2 by suprofen in women with primary dysmenorrhea.	2007-02	17259081
Nonaqueous capillary electrophoretic behavior of 2-aryl propionic acids in the presence of an achiral ionic liquid. A chemometric approach.	2007-01-05	17113588
Non-steroidal anti-inflammatory drugs for heavy bleeding or pain associated with intrauterine-device use.	2006-10-18	17054271
Enantiomeric separation of acidic compounds using single-isomer amino cyclodextrin derivatives in nonaqueous capillary electrophoresis.	2006-09	16892479
Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography.	2006-08	16634133
Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states.	2006-02	16472105
Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography.	2005-07-15	16013606
Intramolecular electron transfer between tyrosine and tryptophan photosensitized by a chiral pi,pi* aromatic ketone.	2005-05-20	15798972
Enantioseparation on mono(6A-n-allylamino-6A-deoxy)permethylated 3-cyclodextrin covalently bonded silica gel.	2004-12-03	15628124
Process modeling of the lipase-catalyzed dynamic kinetic resolution of (R, S)-suprofen 2,2,2-trifluoroethyl thioester in a hollow-fiber membrane.	2004-12	15645310
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.	2004-09-03	15453427
In vitro effects of risperidone and 9-hydroxy-risperidone on human platelet function, plasma coagulation, and fibrinolysis.	2004-08	15476907
Monolithic silica columns with chemically bonded tert-butylcarbamoylquinine chiral anion-exchanger selector as a stationary phase for enantiomer separations.	2004-05-21	15146914
Synthesis of precursor of anti-inflammatory agents by using highly reactive zinc.	2004-05	15468892
UV-induced drug release from photoactive REV sensitized by suprofen.	2004-04-16	15063031
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.	2004-02	14981683
Dextrans--potential polymeric drug carriers for suprofen.	2003-11	14664336
Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen.	2003-11	14570769
Topically applied vitamin C and cysteine derivatives protect against UVA-induced photodegradation of suprofen in ex vivo pigskin.	2003-04	12733644
Capillary electrochromatographic separation of non-steroidal anti-inflammatory drugs with a histidine bonded phase.	2002-12-27	12489886
Topical nonsteroidal anti-inflammatory therapy in ophthalmology.	2002-10-24	12592044
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002-04	12147041
Effects of suprofen on the isolated perfused rat kidney.	1992	1636026
The epidemiology of the acute flank pain syndrome from suprofen.	1989-12	2598570
Immune hemolytic anemia associated with tolmetin and suprofen.	1989-09	2773031
Renal effects of nonsteroidal anti-inflammatory drugs.	1988	3142236
Suprofen-induced acute renal failure.	1987-12	3424239
Suprofen and renal failure.	1987-05	3565984
Suprofen-induced transient flank pain and renal failure.	1987-04-16	3561450
Suprofen-related nephrotoxicity. A distinct clinical syndrome.	1987-02	3800183
Suprofen and acute renal failure.	1986-12	3777736
Suprofen-induced acute renal failure.	1986-11	3780418
Suprofen, acute renal failure, and hematuria.	1986-11	3767163
Skin sensitizing properties of arylalcanoic acids and their analogues.	1979-09	509935
Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils.	1978-11	712644

Patents

Sample Use Guides

In Vivo Use Guide

Administration of Profenal (1% solution of suprafen) begins the day before surgery: 2 drops every 4 hours. On the day of surgery two drops are placed in the eye 3, 2 and 1 hour before the procedure.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

SUPROFEN SODIUM

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-THIENYLCARBONYL)-, SODIUM SALT

Preferred Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-THIENYLCARBONYL)-, SODIUM SALT (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

23663698