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Identification
NameAntrafenine
Accession NumberDB01419
TypeSmall Molecule
GroupsApproved
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 It is not widely used as it has largely been replaced by newer drugs.

Structure
Thumb
Synonyms
SynonymLanguageCode
AntrafenineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
StakaneNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number55300-30-6
WeightAverage: 588.5435
Monoisotopic: 588.195995326
Chemical FormulaC30H26F6N4O2
InChI KeyNWGGKKGAFZIVBJ-UHFFFAOYSA-N
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)
IUPAC Name
2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
SMILES
FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Aminoquinoline
  • Quinoline
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Benzoic acid or derivatives
  • Substituted aniline
  • Dialkylarylamine
  • Benzoyl
  • N-alkylpiperazine
  • Aniline
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationAntrafenine is used as an anti-inflammatory and analgesic agent for the relief of mild to moderate pain.
PharmacodynamicsIts mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
Mechanism of actionAntrafenine is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Antrafenine Action PathwayDrug actionSMP00693
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.9132
Caco-2 permeable-0.5721
P-glycoprotein substrateSubstrate0.5792
P-glycoprotein inhibitor IInhibitor0.8917
P-glycoprotein inhibitor IIInhibitor0.9464
Renal organic cation transporterNon-inhibitor0.5702
CYP450 2C9 substrateNon-substrate0.8703
CYP450 2D6 substrateNon-substrate0.6674
CYP450 3A4 substrateNon-substrate0.5172
CYP450 1A2 substrateInhibitor0.7622
CYP450 2C9 substrateInhibitor0.7438
CYP450 2D6 substrateNon-inhibitor0.7155
CYP450 2C19 substrateInhibitor0.7394
CYP450 3A4 substrateInhibitor0.6383
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9305
Ames testNon AMES toxic0.6823
CarcinogenicityNon-carcinogens0.8812
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7506 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8133
hERG inhibition (predictor II)Inhibitor0.8583
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point88-90Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229.
Predicted Properties
PropertyValueSource
Water Solubility0.00284 mg/mLALOGPS
logP6.3ALOGPS
logP8.39ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.69ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.7 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.01 m3·mol-1ChemAxon
Polarizability55.48 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Giudicelli, D.P.R.L., Najer, H., Manory, P.M.J. and Dumas, A.P.F.; January 27,1976; assigned to Synthelabo US. Patent 3,935,229.

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Hassan SM, Olivesi A, Fish A, Turner P: A comparison of antrafenine and aspirin on platelet aggregation and frusemide-induced diuresis. Postgrad Med J. 1982 Jan;58(675):17-9. Pubmed
  2. Berry H, Coquelin JP, Gordon A, Seymour D: Antrafenine, naproxen and placebo in osteoarthritis: a comparative study. Br J Rheumatol. 1983 May;22(2):89-94. Pubmed
  3. James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 Inhibitors, Eicosanoid Synthesis and Clinical Outcomes: A Case Study of System Failure. Lipids. 2007 Jun 2;. Pubmed

2. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. Pubmed
  2. Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Jun 29;. Pubmed
  3. Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. Pubmed
  4. White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. Pubmed
  5. Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on July 24, 2007 02:34 / Updated on March 28, 2014 10:24