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

Molecular Formula	C14H11O3S
Molecular Weight	259.3
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

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 8297		1.1 µM [IC50]
Prostaglandin G/H synthase 2 48 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 8297		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 8429	PROFENAL Approved Use Inhibition of miosis during intraocular surgery. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

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 n = 41 Health Status: unhealthy Age Group: > 18 years Sex: M+F Population Size: 41 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 n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 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 n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 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 n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 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 n = 12 Health Status: healthy Age Group: adult Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/3741528

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037 inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 146

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B7 157	inhibitor 3277 Sources: https://link.springer.com/protocol/10.1385/1-59259-800-5:185 Page: 15.0	likely
CYP2C9 1819	inhibitor 3277 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 1037	substrate 3367 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
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
eMolecules	743277	https://www.emolecules.com/cgi-bin/more?vid=743277

PubMed

Title	Date	PubMed
Nonsteroid anti-inflammatory agents: regulators of the phagocytic secretion of lysosomal enzymes from guinea-pig neutrophils.	1978 Nov	712644
Skin sensitizing properties of arylalcanoic acids and their analogues.	1979 Sep	509935
Suprofen and acute renal failure.	1986 Dec	3777736
Suprofen-induced acute renal failure.	1986 Nov	3780418
Suprofen, acute renal failure, and hematuria.	1986 Nov	3767163
Suprofen-induced transient flank pain and renal failure.	1987 Apr 16	3561450
Suprofen-induced acute renal failure.	1987 Dec	3424239
Suprofen-related nephrotoxicity. A distinct clinical syndrome.	1987 Feb	3800183
Suprofen and renal failure.	1987 May	3565984
Renal effects of nonsteroidal anti-inflammatory drugs.	1988	3142236
The epidemiology of the acute flank pain syndrome from suprofen.	1989 Dec	2598570
Immune hemolytic anemia associated with tolmetin and suprofen.	1989 Sep	2773031
Single-dose dipyrone for acute postoperative pain.	2001	11687057
Protective effects of suprofen and its methyl ester against inactivation of rabbit kidney carbonyl reductase by phenylglyoxal.	2001 Nov	11916151
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Antibodies directed to drug epitopes to investigate the structure of drug-protein photoadducts. Recognition of a common photobound substructure in tiaprofenic acid/ketoprofen cross-photoreactivity.	2001 Nov	11712905
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002 Apr	12147041
Redox-sensitive interaction between KIAA0132 and Nrf2 mediates indomethacin-induced expression of gamma-glutamylcysteine synthetase.	2002 Apr 1	11909699
Capillary electrochromatographic separation of non-steroidal anti-inflammatory drugs with a histidine bonded phase.	2002 Dec 27	12489886
Effects of anti-inflammatory drugs and preservatives on morphologic characteristics and migration of canine corneal epithelial cells in tissue culture.	2002 Jun	12071871
Identification of drug-binding sites on human serum albumin using affinity capillary electrophoresis and chemically modified proteins as buffer additives.	2002 Mar	11920883
Differential binding mode of diverse cyclooxygenase inhibitors.	2002 Mar	11885959
[Cross-reaction potentials of ketoprofen].	2002 May 12	12063858
Topically applied vitamin C and cysteine derivatives protect against UVA-induced photodegradation of suprofen in ex vivo pigskin.	2003 Apr	12733644
Topical nonsteroidal anti-inflammatory therapy in ophthalmology.	2003 Mar-Apr	12592044
Dextrans--potential polymeric drug carriers for suprofen.	2003 Nov	14664336
Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen.	2003 Nov	14570769
Process modeling of the lipase-catalyzed dynamic kinetic resolution of (R, S)-suprofen 2,2,2-trifluoroethyl thioester in a hollow-fiber membrane.	2004 Dec	15645310
Enantioseparation on mono(6A-n-allylamino-6A-deoxy)permethylated 3-cyclodextrin covalently bonded silica gel.	2004 Dec 3	15628124
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.	2004 Feb	14981683
Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography.	2006 Aug	16634133
Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states.	2006 Feb	16472105
Non-steroidal anti-inflammatory drugs for heavy bleeding or pain associated with intrauterine-device use.	2006 Oct 18	17054271
Enantiomeric separation of acidic compounds using single-isomer amino cyclodextrin derivatives in nonaqueous capillary electrophoresis.	2006 Sep	16892479
Differential suppression of menstrual fluid prostaglandin F2a, prostaglandin E2, 6-keto prostaglandin F1a and thromboxane B2 by suprofen in women with primary dysmenorrhea.	2007 Feb	17259081
Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure.	2007 Jun	17477341
New NSAIDs-NO hybrid molecules with antiproliferative properties on human prostatic cancer cell lines.	2008 Aug 15	18667313
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008 Feb	18224312
Topical ocular delivery of NSAIDs.	2008 Jun	18437583
Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development.	2009	19515014
Chemoenzymatic and microbial dynamic kinetic resolutions.	2009 Apr	18655180
Photodegradation mechanism of nonsteroidal anti-inflammatory drugs containing thiophene moieties: suprofen and tiaprofenic acid.	2009 Aug 13	19719267
Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection.	2009 Jan	18838506
Binding of CYP2C9 with diverse drugs and its implications for metabolic mechanism.	2009 May	19442216
Enantiomeric separation of acidic compounds by nano-liquid chromatography with methylated-beta-cyclodextrin as a mobile phase additive.	2009 May	19370733
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.	2010 Aug	20017213
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 Aug 16	20669986
Novel metabolic bioactivation mechanism for a series of anti-inflammatory agents (2,5-diaminothiophene derivatives) mediated by cytochrome p450 enzymes.	2010 Sep	20530221
Single dose dipyrone for acute postoperative pain.	2010 Sep 8	20824835
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 Jan	24085192

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:39:18 GMT 2023` Edited by `admin` on `Sat Dec 16 11:39:18 GMT 2023`
Record UNII	S8LB9M91ST
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUPROFEN SODIUM

Common Name

English

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

Systematic Name

English

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

Common Name

English

Code System Code Type Description

PUBCHEM

23663698