CAS 4394-00-7|2-(alpha,alpha,alpha-Trifluoro-m-toluidino)nicotinic acid|2-(3-(Trifluoromethyl)anilino)nicotinic acid|Flogovital|Acide niflumique [inn-french]|NFA|2-(3-Trifluoromethyl-phenylamino)-ni...

General Information

Structure

Molecular Formula

C₁₃H₉F₃N₂O₂

Molecular Mass

282.2179696

Exact Mass

282.0616122

Charge

InChI

InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)

InChIKey

JZFPYUNJRRFVQU-UHFFFAOYSA-N

Canonic Smiles

OC(=O)c1cccnc1Nc1cccc(c1)C(F)(F)F

Isomeric Smiles

FC(F)(F)c1cc(Nc2ncccc2C(=O)O)ccc1

Calculated Properties

JChem

Acid pKa

1.8800513

H Acceptors

H Donor

LogD (pH = 5.5)

2.8410227

LogD (pH = 7.4)

1.4721208

Log P

3.1187294

Molar Refractivity

65.9307

Polarizability

23.710608

Polar Surface Area

62.22

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

4.33

LOG S

-3.5

Solubility (Water)

8.83e-02 g/l

Data Source

Names and Identifiers

Synonyms

2-(alpha,alpha,alpha-Trifluoro-m-toluidino)nicotinic acid2-(3-(Trifluoromethyl)anilino)nicotinic acidAcide niflumique [inn-french]NFA2-(3-Trifluoromethyl-phenylamino)-nicotinic acidLopac-N-06302-[(3-Trifluoromethyl)Phenyl]Amino-3-Pyridine-Carboxylic AcidNiflumic AcidAcido niflumico [inn-spanish]Niflumate2-(3-(Trifluoromethyl)-phenyl)aminonicotinic acidNifluminic acidNFL2-[3-(Trifluoromethyl)anilino]nicotinic acidAcidum niflumicum [inn-latin]ActolForenolNiflurilLandruma2-[alpha,alpha,alpha-trifluoro-m-toluidino]-nicotinic acid2-((3-(Trifluoromethyl)phenyl)amino)nicotinic acid2-(α,α,α-Trifluoro-m-toluidino)nicotinic acidNiflumic acidUP 83FlogovitalActol (analgesic)Donalgin2-[[3-(Trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid

Brand Name

FlogovitalActolNiflurilForenolNiflamLandruma

IUPAC Traditional name

niflumic acid

IUPAC name

2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid

Names and Identifiers

Registration numbers

CAS Number

4394-00-7

PubChem SID

4650465724278582160967552

PubChem CID

4488

MDL Number

MFCD00010569

EC Number

224-516-2

Registration numbers

Properties

Physical Property

Solubility

0.019 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Sparingly Soluble in DMSO and Methanol

Hydrophobicity(logP)

4.43 [TAKACS-NOVAK,K ET AL. (1995)]

Melting Point

194-205°C

199-204°C

Apperance

Light Yellow Solid

Pharmacology Properties

human ... PTGS1(5742)

GABA Receptor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

N0630

Biochem/physiol Actions
Selective cyclooxygenase-2 (COX-2) inhibitor.

DrugBank

DB04552

Drug Groups

approved

Description

An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis. [PubChem]

Indication

Used in the treatment of rheumatoid arthritis.

Pharmacology

Niflumic acid, a nonsteroidal anti-inflammatory fenamate, is a Ca²⁺-activated Cl^- channel blocker.

Toxicity

Oral, mouse: LD₅₀ = 350 mg/kg; Oral, rat: LD₅₀ = 250 mg/kg

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

Well absorbed following oral administration.

Half Life

2.5 hours

Protein Binding

90% bound to plasma proteins.

References

• Criddle DN, de Moura RS, Greenwood IA, Large WA: Inhibitory action of niflumic acid on noradrenaline- and 5-hydroxytryptamine-induced pressor responses in the isolated mesenteric vascular bed of the rat. Br J Pharmacol. 1997 Mar;120(5):813-8. [Pubmed]

TRC

N457500

Anti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor.

Molecule Details

References

PubChem Literature

From Data Sources

• Boissier, et al.: Therapie, 26, 211 (1969)

• Sorenson, J.R.J., et al.: J. Med. Chem., 19, 135 (1969)

• Johnson, J.L., et al.: Arch. Biochem.

• Glasson, et al.: Biochem, Pharmacol., 18, 633 (1969)

• Barnett, J., et al.: Biochim. Biophys. Acta, 1209, 130 (1969)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

FlogovitalActolNiflurilForenolNiflamLandruma

IUPAC Traditional name

niflumic acid

IUPAC name

2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid

Registration numbers

CAS Number

4394-00-7

PubChem SID

4650465724278582160967552

PubChem CID

MDL Number

EC Number

Molecule Details

N0630

Biochem/physiol Actions
Selective cyclooxygenase-2 (COX-2) inhibitor.

DrugBank

DB04552

Drug Groups

approved

Description

An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis. [PubChem]

Indication

Used in the treatment of rheumatoid arthritis.

Pharmacology

Niflumic acid, a nonsteroidal anti-inflammatory fenamate, is a Ca²⁺-activated Cl^- channel blocker.

Toxicity

Oral, mouse: LD₅₀ = 350 mg/kg; Oral, rat: LD₅₀ = 250 mg/kg

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Absorption

Well absorbed following oral administration.

Half Life

2.5 hours

Protein Binding

90% bound to plasma proteins.

References

TRC

N457500

Anti-inflammatory. Selective cyclooxygenase-2 (COX-2) inhibitor.

References

PubChem Literature

From Data Sources

• Boissier, et al.: Therapie, 26, 211 (1969)

• Sorenson, J.R.J., et al.: J. Med. Chem., 19, 135 (1969)

• Johnson, J.L., et al.: Arch. Biochem.

• Glasson, et al.: Biochem, Pharmacol., 18, 633 (1969)

• Barnett, J., et al.: Biochim. Biophys. Acta, 1209, 130 (1969)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Solubility

0.019 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Sparingly Soluble in DMSO and Methanol

Hydrophobicity(logP)

4.43 [TAKACS-NOVAK,K ET AL. (1995)]

Melting Point

194-205°C

199-204°C

Apperance

Light Yellow Solid

Pharmacology Properties

human ... PTGS1(5742)

GABA Receptor

Molecule

ID:4120