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Basic information
- CAS
4394-00-7- Standard SMILES
O=C(O)c1cccnc1Nc1cccc(C(F)(F)F)c1- InChIKey
JZFPYUNJRRFVQU-UHFFFAOYSA-N- Molecular formula
- C13H9F3N2O2
- Average molar mass
- 282.22 g/mol
- Monoisotopic mass
- 282.06161219
Overview
Niflumic acid is a member of pyridines and an aromatic carboxylic acid.
Names & identifiers
- Preferred name
- Niflumic Acid
- IUPAC
- 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid
- English name
- Niflumic acid
- Molecular formula
- C13H9F3N2O2
- Molecular weight
- 282.22
Names & synonyms
niflumic acid4394-00-7Acido niflumicoAcide niflumiqueNiflugelUP 832-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acidAcidum niflumicumDTXSID10233682-(3-(Trifluoromethyl)anilino)nicotinic acid2-[3-(Trifluoromethyl)anilino]nicotinic acidUP-83
Show more names
niflumicNifluminic acidACTOLsc1332ForenolDONALGINNIFLURILLandrumaNiflumate
4U5MP5IUD8NSC-758196DTXCID9033682-(3-[Trifluoromethyl]anilino)nicotinic acidAcid, Niflumic2-((3-(trifluoromethyl)phenyl)amino)pyridine-3-carboxylic acid2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylic acidRefChem:389149
Database identifiers
- CAS
4394-00-7- PubChem CID
- 4488
- DTXSID
DTXSID1023368- ChEMBL
CHEMBL63323
Properties
Computed structural propertiesFilling in
- XLogP
- 3.7
- Topological polar surface area
- 62.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
Drugs
Pharmaceuticals -> NSAIDs
Pharmaceuticals -> Listed in ZINC15
Pharmaceutical
Pharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic products
LogP4.43
Solubility8.83e-02 g/L
Human DrugsPharmaceuticals
Melting Point203 °C
Physical DescriptionSolid
Collision Cross Section
156.8 Ų [M+H]+ [CCS Type: TW]
159.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (56.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 99 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 07-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22710
Other Safety InformationIMAP assessments - 3-Pyridinecarboxylic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (56.6%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
NIFLUMIC ACID
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- QT2999100
- ridadr
- UN 2811 6.1/PG 3
Chemistry & industry
Pharmacology
ATC Code
M02AA17
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QM - Musculo-skeletal system
Protein Binding90% bound to plasma proteins.
PharmacodynamicsNiflumic acid, a nonsteroidal anti-inflammatory fenamate, is a Ca<sup>2+</sup>-activated Cl<sup>-</sup> channel blocker.
Mechanism of ActionNiflumic acid is able to inhibit both phospholipase A2 as well as COX-2, thereby acting as an antiinflamatory and pain reduction agent.
Biological Half-Life2.5 hours
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
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.
Absorption, Distribution and ExcretionWell absorbed following oral administration.
Cellular LocationsCytoplasm
Related reactions
7 records
Compound notes
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