(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol; 2-{[2-methyl-3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid

• ChemBase ID: 154241
• Molecular Formular: C21H28F3N3O7
• Molecular Mass: 491.4581296
• Monoisotopic Mass: 491.18793491
• SMILES: Cc1c(cccc1Nc1c(cccn1)C(=O)O)C(F)(F)F.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• Canonical SMILES: OC(=O)c1cccnc1Nc1cccc(c1C)C(F)(F)F.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
• InChI: InChI=1S/C14H11F3N2O2.C7H17NO5/c1-8-10(14(15,16)17)5-2-6-11(8)19-12-9(13(20)21)4-3-7-18-12;1-8-2-4(10)6(12)7(13)5(11)3-9/h2-7H,1H3,(H,18,19)(H,20,21);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1
• InChIKey: MGCCHNLNRBULBU-WZTVWXICSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol; 2-{[2-methyl-3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid
• IUPAC Traditional name: N-methyl-D(-)-glucamine; flunixin
• Synonyms: 2-[[2-Methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid meglumine salt; Banamine; Flunixin meglumine; 2-[[2-Methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid 1-Deoxy-1-(methylamino)-D-glucitol; 2-(2-Methyl-3-trifluoromethylanilino)nicotinic Acid N-Methyl-D-glucamine Salt; Equileve; Finadyne; Flunixin N-Methylglucamine; Sch 14714; Ilium Flunixil; NIH 10250; Flunixin Meglumine

Database IDs

• CAS Number: 42461-84-7
• EC Number: 255-836-0
• MDL Number: MFCD01725419
• PubChem SID: 162248380; 24724478
• PubChem CID: 39212

CALCULATED PROPERTIES

• Acid pKa: 1.8828834
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.3553996
• LogD (pH = 7.4): 1.985294
• Log P: 3.6344001
• Molar Refractivity: 70.9719 cm^3
• Polarizability: 25.446682 Å^3
• Polar Surface Area: 62.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: freely soluble; Methanol
• Apperance: White Solid; white to beige powder
• Melting Point: 135-137°C; 136.6-137.4 °C

Safety Information

• Storage Condition: Refrigerator
• RTECS: LZ4367000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H11F3N2O2·C7H17NO5

DETAILS

Sigma Aldrich - F0429

Application
Flunixin meglumine (IC50 = 1 nM) can be used as a drug for animals for the management of intestinal ischaemia, colic, and endotoxemia in horses.
Biochem/physiol Actions
COX1, COX2 and PLA2 inhibitor non-narcotic analgesic, anti-pyretic, anti-inflammatory.

Toronto Research Chemicals - F455400

Cyclooxigenase inhibitor. Anti-inflammatory; analgesic; antipyretic.

REFERENCES

• McLellan, R., et al.: Drug Metab. Dispos., 24, 1134 (1996)
• Hannan, P., et al.: Antimicrob. Agents Chemother., 41, 2037 (1996)
• Tasker, S., et al.: J. Microbiol. Methods., 56, 63 (1996)
• Regmi, N., et al.: J. Vet. Pharmacol. Therap., 28, 553 (1996)