2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate

• ChemBase ID: 1227
• Molecular Formular: C30H26F6N4O2
• Molecular Mass: 588.5434592
• Monoisotopic Mass: 588.19599541
• SMILES: FC(F)(F)c1cc(N2CCN(CC2)CCOC(=O)c2c(Nc3c4c(ncc3)cc(cc4)C(F)(F)F)cccc2)ccc1
• Canonical SMILES: O=C(c1ccccc1Nc1ccnc2c1ccc(c2)C(F)(F)F)OCCN1CCN(CC1)c1cccc(c1)C(F)(F)F
• InChI: InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)
• InChIKey: NWGGKKGAFZIVBJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
• IUPAC Traditional name: @antrafenine; antrafenine
• Synonyms: 1,2-Dihydro-1-methyl5-methyl-d3-2-phenyl-3H-pyrazol-3-one; 2-Trideuteromethyl-3-methyl-1-phenyl-3-pyrazolin-5-one; Analgesine-d3; Anodynine-d3; Sedatine-d3; Antipyrine-d3; Antrafenine

Database IDs

• CAS Number: 55300-30-6; 65566-62-3
• PubChem SID: 46507354; 160964687
• PubChem CID: 68723
• CHEMBL: 345524
• Chemspider ID: 61973
• DrugBank ID: DB01419
• Unique Ingredient Identifier: 21FS93Y6OE
• Wikipedia Title: Antrafenine

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.689034
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 6.090569
• LogD (pH = 7.4): 8.219306
• Log P: 8.386885
• Molar Refractivity: 147.0059 cm^3
• Polarizability: 54.86143 Å^3
• Polar Surface Area: 57.7 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.3
• LOG S: -5.32
• Solubility (Water): 2.84e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Light Pink Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Metabolism: Hepatic
• Legal Status: Rx-only

DETAILS

DrugBank - DB01419

• Drug Groups: approved
• Description: Antrafenine is a piperazine derivative drug that acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen. It is not widely used as it has largely been replaced by newer drugs.
• Indication: Antrafenine is used as an anti-inflammatory and analgesic agent for the relief of mild to moderate pain.
• Pharmacology: Its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
• External Links: Wikipedia

Toronto Research Chemicals - A697502

Analgesic.

REFERENCES

• Vessel, E.S., et al.: Clin. Pharm. Ther., 26, 275 (1979)
• Farrell, G.C., et al.: Br. J. Clin. Pharmacol., 18, 559 (1979)