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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:42 UTC
HMDB IDHMDB0015488
Secondary Accession Numbers
  • HMDB15488
Metabolite Identification
Common NameAntrafenine
DescriptionAntrafenine 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 It is not widely used as it has largely been replaced by newer drugs.Antrafenine is believed to be associated with the inhibition of cyclooxygenase activity.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
Data?1582753302
Synonyms
ValueSource
StakaneHMDB
Antrafenine dihydrochlorideHMDB
2-(4-(m-Trifluoromethyl-phenyl)-1-piperazinyl)ethyl 2-(7-trifluoromethyl-4-quinolinylamino)benzoateHMDB
Chemical FormulaC30H26F6N4O2
Average Molecular Weight588.5435
Monoisotopic Molecular Weight588.195995326
IUPAC Name2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
Traditional Nameantrafenine
CAS Registry Number55300-30-6
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 KeyNWGGKKGAFZIVBJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • 1,3-thiazol-2-amine
  • Heteroaromatic compound
  • Azole
  • Thiazole
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Thioether
  • Hemithioaminal
  • Carboxylic acid derivative
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Azacycle
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0028 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP10(6.3) g/LALOGPS
logP10(8.39) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Acidic)16.69ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.7 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.01 m³·mol⁻¹ChemAxon
Polarizability55.48 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AntrafenineFC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC13930.9Standard polar33892256
AntrafenineFC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC13860.8Standard non polar33892256
AntrafenineFC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC13938.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Antrafenine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C123779.6Semi standard non polar33892256
Antrafenine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C123666.7Standard non polar33892256
Antrafenine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C124401.0Standard polar33892256
Antrafenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C123946.8Semi standard non polar33892256
Antrafenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C123806.6Standard non polar33892256
Antrafenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C124435.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Antrafenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar3-2192010000-e78886973a64ef0f77a82017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 10V, Positive-QTOFsplash10-052r-0064090000-3a3f873837b9e36277d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 20V, Positive-QTOFsplash10-0ap0-0195020000-e202288f4207ee95fde82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 40V, Positive-QTOFsplash10-014r-2193000000-1ddcbe94c38041fd4dc22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 10V, Negative-QTOFsplash10-000i-0064090000-8a59aea448acc191e90e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 20V, Negative-QTOFsplash10-000i-0094040000-13fea3df8f430bfbfe672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 40V, Negative-QTOFsplash10-000i-1292000000-3163db928f680ec695632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 10V, Positive-QTOFsplash10-000i-0003090000-0643995e1083964892272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 20V, Positive-QTOFsplash10-000i-0035090000-f556108a82ce93cbeeaf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 40V, Positive-QTOFsplash10-014i-0967110000-57099b829a8b1b90d12e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 10V, Negative-QTOFsplash10-000i-0000090000-b2a5859050c4c7f5552e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 20V, Negative-QTOFsplash10-000i-0022090000-f345c715233f7ff4d3862021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antrafenine 40V, Negative-QTOFsplash10-01p9-0193000000-c5d889108558dc0c03f42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01419 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01419 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01419
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID61973
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntrafenine
METLIN IDNot Available
PubChem Compound68723
PDB IDNot Available
ChEBI ID354983
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]