Fenbufen

HCID 3335CAS 36330-85-5
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(O)CCC(=O)c1ccc(-c2ccccc2)cc1
InChIKey
ZPAKPRAICRBAOD-UHFFFAOYSA-N
Molecular formula
C16H14O3
Average molar mass
254.28 g/mol
Monoisotopic mass
254.09429431

Overview

Fenbufen is a member of biphenyls and a 4-oxo monocarboxylic acid. It has a role as a non-steroidal anti-inflammatory drug.

Names & identifiers

Preferred name
Fenbufen
IUPAC
4-oxo-4-(4-phenylphenyl)butanoic acid
English name
Fenbufen
Molecular formula
C16H14O3
Molecular weight
254.29

Names & synonyms

fenbufen36330-85-54-(4-Biphenylyl)-4-oxobutyric acid3-(4-Biphenylylcarbonyl)propionic acid3-(4-Phenylbenzoyl)propionic acidFenbufene4-(biphenyl-4-yl)-4-oxobutanoic acidFenbufenumgamma-Oxo(1,1'-biphenyl)-4-butanoic acidCL-822043-(4-Biphenylcarbonyl)propionic acidDTXSID9023043
Show more names
4-([1,1'-Biphenyl]-4-yl)-4-oxobutanoic acidbufemidcl82204napanolcinopalCinopolenbufenlederfenFenbufen CRS
NSC-757812CL 82,2049815R1WR9B(1,1'-BIPHENYL)-4-BUTANOIC ACID, gamma-OXO-DTXCID703043CHEBI:315994-[1,1'-biphenyl-4-yl]-4-oxobutanoic acid4-(1,1'-biphenyl-4-yl)-4-oxobutanoic acid

Database identifiers

CAS
36330-85-5
PubChem CID
3335
DTXSID
DTXSID9023043
ChEMBL
CHEMBL277522
ChEBI
CHEBI:31599
UNII
9815R1WR9B
EC Number
252-979-0
Nikkaji
J3.182H

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
19

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP2.91
Human DrugsPharmaceuticals
Melting Point185-187
Collision Cross Section150.36 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
184 · 184-187 °C (lit.)
Boiling point
357.5 °C · 357.5°C (rough estimate)
Density
1.1565 · 1.1565 (rough estimate)
refractive index
1.56 · 1.5600 (estimate)
storage temp.
2 · 2-8°C
solubility
Very slightly soluble in water, slightly soluble in acetone, in ethanol (96 per cent) and in methylene chloride.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Other Safety InformationIMAP assessments - [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
DV1761000
ridadr
UN 2811 6.1/PG 3
hs_code
2918300090
Toxicity
LD50 in various strains of mice, rats (mg/kg): 795-1673, 200-720 orally; 506-811, 265-575 i.p. (Bolte)

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

MeSH Pharmacological Classification · 2 items

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 4 items

DescriptionFenbufen has been found to be an effective, well-tolerated drug for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Fenbufen is prepared by the Friedel-Crafts (aluminum chloride – nitrobenzene) acylation of biphenyl with succinic anhydride. The compound is metabolized in humans first to 4-hydroxy-4-biphenylbutyric acid (tmax 2.5 h) then to 4-biphenyl acetic acid (tmax 7.5 h). Both metabolites are more active than fenbufen itself and circulate for several hours (t1/2 10 h). This slow conversion of fenbufen to active metabolites having relatively long plasma half-lives allows for once a day dosing with this agent.

UsesCyclo-oxygenase inhibitor; analgesic; anti-inflammatory

Usesmuscle relaxant (smooth)

General DescriptionFenbufen belongs to the class of non-steroidal anti-inflammatory drugs, widely used as an antipyretic and analgesic in medical applications. Its mode of action involves the inhibition of cyclooxygenase enzyme and thereby prevents the synthesis of certain prostaglandins.

Upstream & downstream products

Downstream products

Suppliers50 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海策嵘生物科技有限公司[email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

Additional notes

DefinitionChEBI: Fenbufen is a member of biphenyls and a 4-oxo monocarboxylic acid. It has a role as a non-steroidal anti-inflammatory drug.

Related reactions

15 records
New reaction record

Linked notes

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