Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H12O2.C4H11NO3 |
| Molecular Weight | 333.3789 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CO)(CO)CO.OC(=O)CC1=CC=C(C=C1)C2=CC=CC=C2
InChI
InChIKey=SWKYVGAYFCGGRP-UHFFFAOYSA-N
InChI=1S/C14H12O2.C4H11NO3/c15-14(16)10-11-6-8-13(9-7-11)12-4-2-1-3-5-12;5-4(1-6,2-7)3-8/h1-9H,10H2,(H,15,16);6-8H,1-3,5H2
| Molecular Formula | C4H11NO3 |
| Molecular Weight | 121.135 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C14H12O2 |
| Molecular Weight | 212.2439 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Felbinac, an active metabolite of fenbufen, is two times more potent than the parent drug. Felbinac is used topically to alleviate pain in the joints and muscles caused by injury or inflammation (Trixam 3% gel or foam). The drug is believed to exert its action by inhibiting COX-2 protein.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7002162 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TRAXAM Approved UseTraxam Gel is used for the relief of pain in the joints and muscles caused by injury or inflammation. It is used for the treatment of the following conditions: sprains, strains, bruising, rheumatic or arthritic conditions, frozen shoulder, tennis elbow or other joint injuries. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1442 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
11.78 mg single, intravenous dose: 11.78 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2697 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
23.56 mg single, intravenous dose: 23.56 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5772 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg single, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
11947 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg single, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22043 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
164.92 mg single, intravenous dose: 164.92 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
34889 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
259.16 mg single, intravenous dose: 259.16 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
44879 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
377 mg single, intravenous dose: 377 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5817 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 1 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7530 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 3 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
11474 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 1 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
13568 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 3 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21230 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 1 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
26473 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 3 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.6 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
11.78 mg single, intravenous dose: 11.78 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10.7 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
23.56 mg single, intravenous dose: 23.56 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22.2 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg single, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
54 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg single, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
96 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
164.92 mg single, intravenous dose: 164.92 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
119 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
259.16 mg single, intravenous dose: 259.16 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
182 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
377 mg single, intravenous dose: 377 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 1 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
28 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 3 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
35 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 1 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
48 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 3 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
65 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 1 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
95 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 3 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
11.78 mg single, intravenous dose: 11.78 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
23.56 mg single, intravenous dose: 23.56 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg single, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg single, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
164.92 mg single, intravenous dose: 164.92 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
259.16 mg single, intravenous dose: 259.16 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
377 mg single, intravenous dose: 377 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 1 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.59 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
47.13 mg 3 times / day multiple, intravenous dose: 47.13 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 1 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
94.25 mg 3 times / day multiple, intravenous dose: 94.25 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 1 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32700191/ |
188.5 mg 3 times / day multiple, intravenous dose: 188.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FELBINAC plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g 2 times / day multiple, topical Recommended Dose: 1 g, 2 times / day Route: topical Route: multiple Dose: 1 g, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
1 g 4 times / day multiple, topical Recommended Dose: 1 g, 4 times / day Route: topical Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Rash | Disc. AE | 1 g 4 times / day multiple, topical Recommended Dose: 1 g, 4 times / day Route: topical Route: multiple Dose: 1 g, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Topical nonsteroidal anti-inflammatory drugs for the treatment of pain due to soft tissue injury: diclofenac epolamine topical patch. | 2010-11-10 |
|
| 2-(Biphenyl-4-yl)acetic acid (felbinac). | 2010-09-25 |
|
| Design, synthesis and evaluation of mutual prodrug of 4-biphenylacetic acid and quercetin tetramethyl ether (BPA-QTME) as gastrosparing NSAID. | 2010-06 |
|
| The suitability of tris(hydroxylmethyl) aminomethane (THAM) as a buffering system for hydroxypropyl methylcellulose (HPMC) hydrophilic matrices containing a weak acid drug. | 2010-03-15 |
|
| Incorporating multiple interventions in meta-analysis: an evaluation of the mixed treatment comparison with the adjusted indirect comparison. | 2009-09-21 |
|
| Validated LC-MS/MS assay for the determination of felbinac: Application to a preclinical pharmacokinetics study of felbinac trometamol injection in rat. | 2009-08-15 |
|
| Separation-oriented derivatization of native fluorescent compounds through fluorous labeling followed by liquid chromatography with fluorous-phase. | 2009-06-15 |
|
| Mechanisms of drug release in citrate buffered HPMC matrices. | 2009-03-31 |
|
| Cyclomaltoheptaose mixed esters of anti-inflammatory drugs and short-chain fatty acids and study of their enzymatic hydrolysis in vitro. | 2009-03-10 |
|
| Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents. | 2009 |
|
| Stepwise two-color laser photolysis studies of alpha-cleavage in highly excited triplet states of alpha-acyl-4-phenylphenols. | 2008-06 |
|
| Analgesic effect of percutaneously absorbed non-steroidal anti-inflammatory drugs: an experimental study in a rat acute inflammation model. | 2008-01-31 |
|
| Percutaneous penetration of felbinac after application of transdermal patches: relationship with pharmacological effects in rats. | 2008-01 |
|
| Synthesis and pharmacological evaluation of some dual-acting amino-alcohol ester derivatives of flurbiprofen and 2-[1,1'-biphenyl-4-yl]acetic acid: a potential approach to reduce local gastrointestinal toxicity. | 2006-11 |
|
| Changes in brain interleukin-1beta following the coadministration of norfloxacin with biphenylacetic acid in rats. | 2006-08-14 |
|
| Pharmaceutical quality control of acid and neutral drugs based on competitive self-assembly in amphiphilic systems. | 2006-01 |
|
| Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004-07-02 |
|
| Topical NSAIDs for acute pain: a meta-analysis. | 2004-05-17 |
|
| Synthetic applications of o- and p-halobenzyl sulfones as zwitterionic synthons: preparation of ortho-substituted cinnamates and biarylacetic acids. | 2002-07-26 |
|
| Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer. | 2002-06-04 |
|
| [Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration]. | 2002-06 |
|
| Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide. | 2001-11-21 |
|
| Inhibitory effect of quinolone antimicrobial and nonsteroidal anti-inflammatory drugs on a medium chain acyl-CoA synthetase. | 2001-08-01 |
|
| Effects of amino acids on the amidation of polyaromatic carboxylic acids by Bacillus cereus. | 2001-08 |
|
| Topical non-steroidal drugs are systemically absorbed and may cause renal disease. | 1999-01 |
|
| Role of nitric oxide in the convulsive seizures induced by fluoroquinolones coadministered with 4-biphenyl acetic acid. | 1997-11 |
|
| Quantitation of GABAA receptor inhibition required for quinolone-induced convulsions in mice. | 1994-11 |
|
| Biphenylacetate, but not theophylline, lethally interacts with ciprofloxacin in mice. | 1993-11 |
|
| Involvement of inhibitory and excitatory neurotransmitters in levofloxacin- and ciprofloxacin-induced convulsions in mice. | 1993-09 |
Sample Use Guides
The usual dose is about one inch or 2.5cm (which is about one gram) of gel rubbed into the affected area two to four times a day.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6782695
A 0.12 mM concentration of felbinac (BPAA) produces almost complete inhibition of arachidonate-induced aggregation of blood platelets.
| Substance Class |
Chemical
Created
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Edited
Tue Apr 01 21:55:52 GMT 2025
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| Record UNII |
HA8ZX3VG09
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| Record Status |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |
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