ContaminantDB: Flurbiprofen

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (11)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:28 UTC

Update Date

2026-03-26 20:43:58 UTC

Accession Number

CHEM002254

Identification

Common Name

Flurbiprofen

Class

Small Molecule

Description

Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity. Oral formulations of flurbiprofen may be used for the symptomatic treatment of rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Analgesic
Anti-Inflammatory Agent
Anti-Inflammatory Agent, Non-Steroidal
Carbonic Anhydrase Inhibitor
Cyclooxygenase Inhibitor
Drug
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2-Fluoro-alpha-methyl-4-biphenylacetic acid	ChEBI
2-(2-Fluorobiphenyl-4-yl)propanoic acid	ChEBI
2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic acid	ChEBI
3-Fluoro-4-phenylhydratropic acid	ChEBI
Ansaid	ChEBI
(+-)-2-Fluoro-a-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-a-methyl-4-biphenylacetic acid	Generator
(+-)-2-Fluoro-alpha-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-α-methyl-4-biphenylacetate	Generator
(+-)-2-Fluoro-α-methyl-4-biphenylacetic acid	Generator
2-(2-Fluorobiphenyl-4-yl)propanoate	Generator
2-Fluoro-a-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-a-methyl-(1,1'-biphenyl)-4-acetic acid	Generator
2-Fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-α-methyl-(1,1'-biphenyl)-4-acetate	Generator
2-Fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid	Generator
3-Fluoro-4-phenylhydratropate	Generator
FLP	HMDB
Allergan brand OF flurbiprofen sodium	MeSH, HMDB
Apotex brand OF flurbiprofen	MeSH, HMDB
Klosterfrau brand OF flurbiprofen	MeSH, HMDB
Knoll brand OF flurbiprofen	MeSH, HMDB
Nu flurbiprofen	MeSH, HMDB
Ratiopharm brand OF flurbiprofen	MeSH, HMDB
Recordati brand OF flurbiprofen	MeSH, HMDB
Dobrofen	MeSH, HMDB
Flugalin	MeSH, HMDB
neo Artrol	MeSH, HMDB
novo Flurprofen	MeSH, HMDB
novo-Flurprofen	MeSH, HMDB
Nu-pharm brand OF flurbiprofen	MeSH, HMDB
Ocuflur	MeSH, HMDB
Cebutid	MeSH, HMDB
Flubiprofen	MeSH, HMDB
Flurbiprofen pfizer brand	MeSH, HMDB
Flurbiprofen sodium	MeSH, HMDB
Froben	MeSH, HMDB
Froben SR	MeSH, HMDB
Novopharm brand OF flurbiprofen	MeSH, HMDB
Nu-flurbiprofen	MeSH, HMDB
Ocufen	MeSH, HMDB
Pharm allergan brand OF flurbiprofen sodium	MeSH, HMDB
Pharm-allergan brand OF flurbiprofen sodium	MeSH, HMDB
Shire brand OF flurbiprofen	MeSH, HMDB
Sodium, flurbiprofen	MeSH, HMDB
ratio Flurbiprofen	MeSH, HMDB
Abbott brand OF flurbiprofen	MeSH, HMDB
apo Flurbiprofen	MeSH, HMDB
apo-Flurbiprofen	MeSH, HMDB
Cantabria brand OF flurbiprofen	MeSH, HMDB
Crookes brand OF flurbiprofen	MeSH, HMDB
Fluriproben	MeSH, HMDB
Nu pharm brand OF flurbiprofen	MeSH, HMDB
Pfizer brand OF flurbiprofen	MeSH, HMDB
Strefen	MeSH, HMDB
ratio-Flurbiprofen	MeSH, HMDB

Chemical Formula

C₁₅H₁₃FO₂

Average Molecular Mass

244.261 g/mol

Monoisotopic Mass

244.090 g/mol

CAS Registry Number

5104-49-4

IUPAC Name

2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoic acid

Traditional Name

flurbiprofen

SMILES

CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)

InChI Key

SYTBZMRGLBWNTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Fluorobenzene
Halobenzene
Aryl halide
Aryl fluoride
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organofluoride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

fluorobiphenyl (CHEBI:5130 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

non-narcotic analgesic

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	110-111°C
Boiling Point	Not Available
Solubility	8 mg/L (at 22°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.94	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.29 m³·mol⁻¹	ChemAxon
Polarizability	25.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2940000000-9f5fff7c7dd3930840ab	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fft-9531000000-d8e1afedb8496d7ccae1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-0900000000-1c9889f5fc33443c7b3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-0900000000-1791423706be24cc354b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0229-3920000000-b822873abe0cc77b6500	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-0900000000-1791423706be24cc354b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-0900000000-1c9889f5fc33443c7b3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-2900000000-d74a9b309815da3ba05d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-0900000000-be4ed0fe252134b8d5d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0290000000-a84327eef03dc68e08c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0890000000-8fb4c7dcd6ef32ab325b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ba-2910000000-570b59a950d65dd4631e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-68c52b6d3396c526a75c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-1950000000-7014af9c0d6f2fc23c18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-5910000000-9a60410e16b662ddcff0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-cbd4141a005693f2c6aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0940000000-f30f7aa21a68a7f1ab95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0900000000-2bf6ee99259baef46083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0910000000-b3fba75f1be1c305f3d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-f48dedd82d182cffdfbf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fi0-0900000000-150de333ffe505b0359d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.

Mechanism of Toxicity

Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity.

Metabolism

Hepatic. Cytochrome P450 2C9 plays an important role in the metabolism of flurbiprofen to its major metabolite, 4’-hydroxy-flurbiprofen. The 4’-hydroxy-flurbiprofen metabolite showed little anti-inflammatory activity in animal models of inflammation. Route of Elimination: Flurbiprofen is poorly excreted into human milk. Following dosing with flurbiprofen, less than 3% of flurbiprofen is excreted unchanged in the urine, with about 70% of the dose eliminated in the urine as parent drug and metabolites. Renal elimination is a significant pathway of elimination of flurbiprofen metabolites. Half Life: R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours

Toxicity Values

LD50: 10 mg/kg (Oral, Dog) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Flurbiprofen tablets are indicated for the acute or long-term symptomatic treatment of rheumatoid arthritis, osteorarthritis and anklosing spondylitis. It may also be used to treat pain associated with dysmenorrhea and mild to moderate pain accompanied by inflammation (e.g. bursitis, tendonitis, soft tissue trauma). Topical ophthalmic formulations may be used pre-operatively to prevent intraoperative miosis.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of a flurbiprofen overdose may include nausea, vomiting, stomach pain, dizziness, drowsiness, black or bloody stools, coughing up blood, urinating less than usual or not at all, shallow breathing, fainting, or coma.

Treatment

Patients should be managed by symptomatic and supportive care following overdose with a nonsteroidal anti-inflammatory drug. There are no specific antidotes. Emesis and/or activated charcoal (60 to 100 g in adults, 1 to 2 g/kg in children) and/or osmotic cathartic may be indicated in patients seen within 4 hours of ingestion with symptoms, or following a large overdose (5 to 10 times the usual dose). Forced diuresis, alkalization of urine, hemodialysis, or hemoperfusion may not be useful due to high protein binding. (8)

Concentrations

Not Available

External Links

DrugBank ID

DB00712

HMDB ID

HMDB0258727

FooDB ID

FDB002154

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Flurbiprofen

Chemspider ID

3277

ChEBI ID

5130

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Yutaka Mizushima, Hiroyuki Okamoto, Shigetoshi Sugio, Kazumasa Yokoyama, Tadakazu Suyama, Masao Tohno, Makoto Okumura, Yoshiaki Konishi, Kiyonoshin Ichikawa, Katsuhiro Uchida, “Flurbiprofen derivative ophthalmic preparation.” U.S. Patent US5171566, issued January, 1984.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12859660

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17562170

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19588427

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=27746736

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=27832658

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28147361

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=28298171

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28402193

Flurbiprofen (CHEM002254)

Structure for CHEM002254: Flurbiprofen