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Antrafenine

July 24, 2017
Common Name

Antrafenine Description

Antrafenine is only found in individuals that have used or taken this drug. It 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 It is not widely used as it has largely been replaced by newer drugs.Antrafenine is believed to be associated with the inhibition of cyclooxygenase activity.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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source StakaneMeSH Antrafenine dihydrochlorideMeSH 2-(4-(m-Trifluoromethyl-phenyl)-1-piperazinyl)ethyl 2-(7-trifluoromethyl-4-quinolinylamino)benzoateMeSH

Chemical Formlia

C30H26F6N4O2 Average Molecliar Weight

588.5435 Monoisotopic Molecliar Weight

588.195995326 IUPAC Name

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

antrafenine CAS Registry Number

55300-30-6 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

InChI Identifier

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)

InChI Key

NWGGKKGAFZIVBJ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Diazinanes Direct Parent

Phenylpiperazines Alternative Parents

  • N-arylpiperazines
  • 4-aminoquinolines
  • Aminobenzoic acids and derivatives
  • Benzoic acid esters
  • Trifluoromethylbenzenes
  • Aniline and substituted anilines
  • Dialkylarylamines
  • Benzoyl derivatives
  • Aminopyridines and derivatives
  • N-alkylpiperazines
  • Vinylogous amides
  • Heteroaromatic compounds
  • Trialkylamines
  • Amino acids and derivatives
  • Carboxylic acid esters
  • Secondary amines
  • Azacyclic compounds
  • Monocarboxylic acids and derivatives
  • Hydrocarbon derivatives
  • Organic oxides
  • Organofluorides
  • Organooxygen compounds
  • Alkyl fluorides
  • Organopnictogen compounds

    • Substituents

  • Phenylpiperazine
  • N-arylpiperazine
  • Aminoquinoline
  • 4-aminoquinoline
  • Aminobenzoic acid or derivatives
  • Trifluoromethylbenzene
  • Benzoate ester
  • Quinoline
  • Benzoic acid or derivatives
  • Benzoyl
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aniline or substituted anilines
  • N-alkylpiperazine
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Secondary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alkyl halide
  • Alkyl fluoride
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

    Not Available Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility2.84e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0028 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Antrafenine Action PathwaySMP00693Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01419

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01419

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01419 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    61973 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Antrafenine NuGOwiki Link

    HMDB15488 Metagene Link

    HMDB15488 METLIN ID

    Not Available PubChem Compound

    68723 PDB ID

    Not Available ChEBI ID

    354983

    Product: VER-50590

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in peroxidase activity
    Specific function:
    Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
    Gene Name:
    PTGS2
    Uniprot ID:
    P35354
    Molecular weight:
    68995.625
    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:17607546 ]
    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 Dec;16(8):691-7. Epub 2007 Jul 2. [PubMed:17604186 ]
    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:17521299 ]
    4. White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. [PubMed:17612049 ]
    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:17532719 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in peroxidase activity
    Specific function:
    May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
    Gene Name:
    PTGS1
    Uniprot ID:
    P23219
    Molecular weight:
    68685.82
    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:7088753 ]
    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:6342700 ]
    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 Sep;42(9):779-85. Epub 2007 Jun 2. [PubMed:17541796 ]

    PMID: 26775841

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