ETOFENAMATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H18F3NO4
Molecular Weight	369.335
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCOCCOC(=O)C1=CC=CC=C1NC2=CC(=CC=C2)C(F)(F)F

InChI

InChIKey=XILVEPYQJIOVNB-UHFFFAOYSA-N

InChI=1S/C18H18F3NO4/c19-18(20,21)13-4-3-5-14(12-13)22-16-7-2-1-6-15(16)17(24)26-11-10-25-9-8-23/h1-7,12,22-23H,8-11H2

HIDE SMILES / InChI

Molecular Formula	C18H18F3NO4
Molecular Weight	369.335
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB08984
Curator's Comment: Description was created based on several sources, including http://www.mims.com/india/drug/info/etofenamate?mtype=generic https://www.ncbi.nlm.nih.gov/pubmed/6983482

Etofenamate is a non-steroidal anti-inflammatory drug (NSAID) used for the treatment of joint and muscular pain.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D04102	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D04102	Inhibitor 8504
lipoxygenase pathway 1 Target ID: GO:0019372 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2883093	Inhibitor 8504	53.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Muscle pain 7 Sources: http://www.mims.com/india/drug/info/etofenamate?type=full&mtype=generic#Actions	Palliative		Approved 8583	Etofenamate Approved Use Etofenamate is an NSAID applied topically for the relief of pain and inflammation associated with musculoskeletal, joint and soft tissue disorders.
Joint pain 1 Sources: http://www.mims.com/india/drug/info/etofenamate?type=full&mtype=generic#Actions	Palliative		Approved 8583	Etofenamate Approved Use Etofenamate is an NSAID applied topically for the relief of pain and inflammation associated with musculoskeletal, joint and soft tissue disorders.

C_max

Value	Dose	Co-administered	Analyte	Population
5810 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
31.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	230 mg single, topical dose: 230 mg route of administration: Topical experiment type: SINGLE co-administered:		FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
168100 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:	FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
449 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	230 mg single, topical dose: 230 mg route of administration: Topical experiment type: SINGLE co-administered:	FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
484 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	230 mg 2 times / day multiple, topical dose: 230 mg route of administration: Topical experiment type: MULTIPLE co-administered:	FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28561421/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		FLUFENAMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % single, topical Studied dose Dose: 2 % Route: topical Route: single Dose: 2 % Sources: https://pubmed.ncbi.nlm.nih.gov/6972853/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6972853/	Disc. AE: Eczema... AEs leading to discontinuation/dose reduction: Eczema Sources: https://pubmed.ncbi.nlm.nih.gov/6972853/
1 g single, intramuscular Highest studied dose Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/	healthy Health Status: healthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/	Other AEs: Headache, Burning skin... Other AEs: Headache Burning skin Injection site pain (20%) Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/

AEs

AE	Significance	Dose	Population
Eczema	Disc. AE	2 % single, topical Studied dose Dose: 2 % Route: topical Route: single Dose: 2 % Sources: https://pubmed.ncbi.nlm.nih.gov/6972853/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6972853/
Burning skin		1 g single, intramuscular Highest studied dose Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/	healthy Health Status: healthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/
Headache		1 g single, intramuscular Highest studied dose Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/	healthy Health Status: healthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/
Injection site pain	20%	1 g single, intramuscular Highest studied dose Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/	healthy Health Status: healthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28561421/

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Pharmacokinetic profile of an intradeltoid diclofenac injection in obese Indian volunteers.	2010-11-19	21311716
Etofenamate associated with Lyell syndrome: a case report.	2010-06	20586575
Influence of preemptive analgesia on pulmonary function and complications for laparoscopic cholecystectomy.	2009-12	19117121
Anti-inflammatory effects of locally applied enzyme-loaded ultradeformable vesicles on an acute cutaneous model.	2009-11	19839801
Efficacy of epicutaneous Diractin (ketoprofen in Transfersome gel) for the treatment of pain related to eccentric muscle contractions.	2009-09-21	19920930
Allergic and photoallergic contact dermartitis from etofenamate: study of 14 cases.	2009-08	19706053
Allergic contact dermatitis to etofenamate. Cross-reaction to other nonsteroidal anti-inflammatory drugs.	2008-02	18186756
[Etofenamate and the analgesic effect in the management of acute pain from spine in the emergency room].	2007-12-28	18159913
Topical etofenamate to facilitate venipuncture.	2007-10	18090116
[Results and assessment of photopatch testing in Spain: towards a new standard set of photoallergens].	2007-03	17397595
[Comparative clinical multicenter study to evaluate analgesic effectiveness of intramuscular etofenamate and diclofenac in patients with post-surgical pain].	2005-02-08	15694055
Intramuscular Etofenamate versus Diclofenac in the Relief of Renal Colic : A Randomised, Single-Blind, Comparative Study.	2003	17536883
Allergic contact dermatitis from etofenamate without cross-sensitization to other anthranilic acid derivatives.	2003	12771478
Comparative study of etofenamate and fentanyl for outpatient extracorporeal shockwave lithotripsy.	2001-12	11848431
Combined contact and photocontact allergic dermatitis to etofenamate in flogoprofen gel.	2001-12	11753896
Effects of some pharmacological agents on the survival of unipedicled venous flaps: an experimental study.	2001	11757060
Etofenamate levels in human serum and synovial fluid following iontophoresis.	2001	11455681

Patents

Sample Use Guides

In Vivo Use Guide

Intramuscular Pain and inflammation Adult: 1 g injected deeply in single doses. Topical/Cutaneous Pain and inflammation Adult: Apply 5% or 10% conc topically on affected area.

Route of Administration: Other

In Vitro Use Guide

PGE2 generation by rat peritoneal macrophages in MEM medium was dose-relatedly inhibited with etofenamate at the dosage range of 1 to 30 uM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:43:27 GMT 2025` Edited by `admin` on `Wed Apr 02 09:43:27 GMT 2025`
Record UNII	KZF0XM66JC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOFENAMATE

Official Name

English

BAY D 1107

Preferred Name

English

ETOFENAMATE [EP MONOGRAPH]

Common Name

English

ETOFENAMATE [MI]

Common Name

English

ETOFENAMATE [JAN]

Common Name

English

WHR-5020

Code

English

2-(2-HYDROXYETHOXY)ETHYL N-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)ANTHRANILATE

Systematic Name

English

TVX-485

Code

English

TVX485

Code

English

2-(2-HYDROXYETHOXY)ETHYL-N-(ALPHA,ALPHA,ALPHA-TRIFLUORO-M-TOLYL)ANTHRANILATE

Systematic Name

English

BENZOIC ACID, 2-((3-(TRIFLUOROMETHYL)PHENYL)AMINO)-, 2-(2-HYDROXYETHOXY)ETHYL ESTER

Systematic Name

English

BAYD-1107

Code

English

ETOFENAMATE [USAN]

Common Name

English

etofenamate [INN]

Common Name

English

ETOFENAMATE [MART.]

Common Name

English

BAY-D-1107

Code

English

Etofenamate [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

M02AA06