SUPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H12O3S
Molecular Weight	260.308
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C2=CC=CS2

InChI

InChIKey=MDKGKXOCJGEUJW-UHFFFAOYSA-N

InChI=1S/C14H12O3S/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)

HIDE SMILES / InChI

Molecular Formula	C14H12O3S
Molecular Weight	260.308
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

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	Inhibitor 8,297		1.1 µM [IC50]
Prostaglandin G/H synthase 2 48	Inhibitor 8,297		8.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intraoperative miosis 2	Preventing		Approved 8,429	PROFENAL

C_max

Value	Dose	Co-administered	Analyte	Population
18.95 μg/mL	200 mg single, oral		SUPROFEN plasma	Homo sapiens
8.43 μg/mL	200 mg single, oral		SUPROFEN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
26.1 μg × h/mL	200 mg single, oral		SUPROFEN plasma	Homo sapiens
21.2 μg × h/mL	200 mg single, oral		SUPROFEN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
400 mg single, oral	unhealthy, > 18 years
600 mg single, oral Highest studied dose	healthy, adult
400 mg single, oral	healthy, adult	Other AEs: Nausea, Vomiting...

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AEs

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AE	Significance	Dose	Population
Nausea	2 patients	400 mg single, oral	healthy, adult
Vomiting	2 patients	400 mg single, oral	healthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1,037 inhibitor 1,767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 146

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B7 157	inhibitor 3,277	likely
CYP2C9 1,819	inhibitor 3,277	yes [Ki 6.7 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1,037	substrate 3,367	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Skin sensitizing properties of arylalcanoic acids and their analogues.	1979 Sep	509935
Suprofen and acute renal failure.	1986 Dec	3777736
Effects of suprofen on the isolated perfused rat kidney.	1992	1636026
Five cases of photocontact dermatitis due to topical ketoprofen: photopatch testing and cross-reaction study.	2001 Feb	11169173
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017

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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
Record UNII	988GU2F9PE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUPROFEN

Official Name

English

SUPROFEN [USAN]

Common Name

English

R-25061

Code

English

PROFENAL

Brand Name

English

NSC-303611

Code

English

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Classification Tree

Code System

Code

Propionic acid derivatives

WHO-VATC

QM01AE07

Propionic acid derivatives

WHO-ATC

M01AE07

Analgesic and Antipyretic

NCI_THESAURUS

C257

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Code System

Code

Type

Description

MERCK INDEX

m10404

PRIMARY

Merck Index

WIKIPEDIA

SUPROFEN

PRIMARY

INN

3586

PRIMARY

PUBCHEM

5359

PRIMARY

SMS_ID

100000082985

PRIMARY

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SUPROFEN, (S)-

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SUPROFEN, (R)-

ENANTIOMER -> RACEMATE


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SUPROFEN SODIUM

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Related Record

Type

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					988GU2F9PE

SUPROFEN

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

Drug as perpetrator