Flurbiprofen

Modify Date: 2024-01-02 16:48:39

Flurbiprofen Structure
Flurbiprofen structure
Common Name Flurbiprofen
CAS Number 5104-49-4 Molecular Weight 244.261
Density 1.2±0.1 g/cm3 Boiling Point 376.2±30.0 °C at 760 mmHg
Molecular Formula C15H13FO2 Melting Point 110-112 °C(lit.)
MSDS Chinese USA Flash Point 181.3±24.6 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Flurbiprofen


Flurbiprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity.Target: PGE synthaseFlurbiprofen, 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. Flurbiprofen may have unique pharmacological properties that reduce the accumulation of unfolded proteins and may represent a new class of drug for the fundamental treatment of obesity [1]. Flurbiprofen and its enantiomers selectively lower Aβ42 levels in broken cell γ-secretase assays, indicating that these compounds directly target the γ-secretase complex that generates Aβ from APP. Of the compounds tested, meclofenamic acid, racemic flurbiprofen, and the purified R and S enantiomers of flurbiprofen lowered Aβ42 levels to the greatest extent [2].

 Names

Name flurbiprofen
Synonym More Synonyms

 Flurbiprofen Biological Activity

Description Flurbiprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity.Target: PGE synthaseFlurbiprofen, 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. Flurbiprofen may have unique pharmacological properties that reduce the accumulation of unfolded proteins and may represent a new class of drug for the fundamental treatment of obesity [1]. Flurbiprofen and its enantiomers selectively lower Aβ42 levels in broken cell γ-secretase assays, indicating that these compounds directly target the γ-secretase complex that generates Aβ from APP. Of the compounds tested, meclofenamic acid, racemic flurbiprofen, and the purified R and S enantiomers of flurbiprofen lowered Aβ42 levels to the greatest extent [2].
Related Catalog
References

[1]. Hosoi, T., et al., Flurbiprofen ameliorated obesity by attenuating leptin resistance induced by endoplasmic reticulum stress. EMBO Mol Med, 2014.

[2]. Eriksen, J.L., et al., NSAIDs and enantiomers of flurbiprofen target gamma-secretase and lower Abeta 42 in vivo. J Clin Invest, 2003. 112(3): p. 440-9.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 376.2±30.0 °C at 760 mmHg
Melting Point 110-112 °C(lit.)
Molecular Formula C15H13FO2
Molecular Weight 244.261
Flash Point 181.3±24.6 °C
Exact Mass 244.089951
PSA 37.30000
LogP 4.11
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.568
Storage condition Store at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU8341000
CHEMICAL NAME :
4-Biphenylacetic acid, 2-fluoro-alpha-methyl-
CAS REGISTRY NUMBER :
5104-49-4
LAST UPDATED :
199512
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C15-H13-F-O2
MOLECULAR WEIGHT :
244.28
WISWESSER LINE NOTATION :
QVY1&R CF DR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
30 mg/kg/2W-I
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - headache Nutritional and Gross Metabolic - other changes
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 4,496,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14 mg/kg/7D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 112,550,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
117 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
108 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
640 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
890 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 49,98,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
550 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>385 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - sensory change involving peripheral nerve Sense Organs and Special Senses (Eye) - changes in refraction Behavioral - convulsions or effect on seizure threshold
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 9,2641,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 10,232,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
290 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,707,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
260 mg/kg/30D-I
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in other cell count (unspecified) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 10,2132,1976 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
REFERENCE :
PEREBL Pediatric Research. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1967- Volume(issue)/page/year: 22,567,1987

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements Missing Phrase - N15.00950417
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T,C
Risk Phrases R25
Safety Phrases S36/37/39-S45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS DU8341000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2916399090

 Synthetic Route

 Customs

HS Code 2916399090
Summary 2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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 Synonyms

froben
R-Flurbiprofen
R-(-)-Flurbiprofen
(2R)-2-(2-fluorobiphenyl-4-yl)propanoic acid
2-(2-Fluorobiphenyl-4-yl)propionic Acid
(-)-Flurbiprofen
(R)-Flurbiprofen
ANSAID
EINECS 225-827-6
(2R)-2-(2-Fluoro-1,1'-biphenyl-4-yl)propanoic acid
Cebutid
Stayban
fp70
(R)-2-Flubiprofen
MFCD00079303
ANSIDE
(R)-(−)-2-Fluoro-α-methyl-4-biphenylacetic acid
(2R)-2-(2-Fluoro-4-biphenylyl)propanoic acid
(R)-2-Flurbiprofen
[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (αR)-
Zepolas
Adfeed
Antadys
Flurbiprofen
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