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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015398
Secondary Accession Numbers
  • HMDB15398
Metabolite Identification
Common NameVarenicline
DescriptionVarenicline is a prescription medication used to treat smoking addiction. This medication is the first approved nicotinic receptor partial agonist. Specifically, varenicline is a partial agonist of the alpha4/beta2 subtype of the nicotinic acetylcholine receptor. In addition it acts on alpha3/beta4 and weakly on alpha3beta2 and alpha6-containing receptors. A full agonism was displayed on alpha7-receptors.
Structure
Data?1582753292
Synonyms
ValueSource
7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-H)(3)benzazepineChEBI
VareniclinaChEBI
VareniclinumChEBI
CP-526,555HMDB
Varenicline tartrateHMDB
6,7,8,9-Tetrahydro-6,10-methano-6H-pyrazino(2,3-H)benzazepineHMDB
Tartrate, vareniclineHMDB
ChampixHMDB
ChantixHMDB
Chemical FormulaC13H13N3
Average Molecular Weight211.2624
Monoisotopic Molecular Weight211.110947431
IUPAC Name(1R,12S)-5,8,14-triazatetracyclo[10.3.1.0²,¹¹.0⁴,⁹]hexadeca-2,4,6,8,10-pentaene
Traditional Namechantix
CAS Registry Number249296-44-4
SMILES
[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21
InChI Identifier
InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+
InChI KeyJQSHBVHOMNKWFT-DTORHVGOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Diazanaphthalene
  • Quinoxaline
  • Indane
  • Azepine
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Pyrazine
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.088 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM151.030932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP1.39ALOGPS
logP1.01ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.81 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.3 m³·mol⁻¹ChemAxon
Polarizability23.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.84531661259
DarkChem[M-H]-150.96331661259
DeepCCS[M-2H]-183.44330932474
DeepCCS[M+Na]+158.86630932474
AllCCS[M+H]+147.232859911
AllCCS[M+H-H2O]+143.232859911
AllCCS[M+NH4]+151.032859911
AllCCS[M+Na]+152.132859911
AllCCS[M-H]-153.532859911
AllCCS[M+Na-2H]-153.032859911
AllCCS[M+HCOO]-152.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Varenicline[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C212961.4Standard polar33892256
Varenicline[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C212160.0Standard non polar33892256
Varenicline[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C212126.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Varenicline,1TMS,isomer #1C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C122255.8Semi standard non polar33892256
Varenicline,1TMS,isomer #1C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C122251.5Standard non polar33892256
Varenicline,1TMS,isomer #1C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C122791.8Standard polar33892256
Varenicline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C122497.2Semi standard non polar33892256
Varenicline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C122509.9Standard non polar33892256
Varenicline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C123013.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Varenicline GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-1910000000-6dbc451aea83e1d014b62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Varenicline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 10V, Positive-QTOFsplash10-03di-0190000000-4f145434c13b3afcb5332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 20V, Positive-QTOFsplash10-03di-0590000000-9e05cfabbf6c1eb096b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 40V, Positive-QTOFsplash10-0159-3900000000-82a1aaedcfa4ad0c47d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 10V, Negative-QTOFsplash10-03di-0090000000-213d1987d097fb210ee12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 20V, Negative-QTOFsplash10-03di-0190000000-c719b55058a71a2359952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 40V, Negative-QTOFsplash10-01po-3930000000-7accc44141f8030a7a2b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 10V, Positive-QTOFsplash10-03di-0090000000-151eb25ddf9df2d6bfbe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 20V, Positive-QTOFsplash10-03di-0090000000-151eb25ddf9df2d6bfbe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 40V, Positive-QTOFsplash10-0lz9-0920000000-ff0909b76eb139f2276a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 10V, Negative-QTOFsplash10-03di-0090000000-4dafdcd63f1115768fe92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 20V, Negative-QTOFsplash10-03di-0090000000-4dafdcd63f1115768fe92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Varenicline 40V, Negative-QTOFsplash10-0a4i-0190000000-1ec0bedd3eb5b1bc40342021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01273 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01273 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01273
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVarenicline
METLIN IDNot Available
PubChem Compound5310966
PDB IDQMR
ChEBI ID84500
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 References
  1. Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD 3rd, O'Neill BT: Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem. 2005 May 19;48(10):3474-7. [PubMed:15887955 ]
  2. Obach RS, Reed-Hagen AE, Krueger SS, Obach BJ, O'Connell TN, Zandi KS, Miller S, Coe JW: Metabolism and disposition of varenicline, a selective alpha4beta2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos. 2006 Jan;34(1):121-30. Epub 2005 Oct 12. [PubMed:16221753 ]
  3. Kuehn BM: FDA speeds smoking cessation drug review. JAMA. 2006 Feb 8;295(6):614. [PubMed:16467225 ]
  4. Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
  5. Jorenby DE, Hays JT, Rigotti NA, Azoulay S, Watsky EJ, Williams KE, Billing CB, Gong J, Reeves KR: Efficacy of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, vs placebo or sustained-release bupropion for smoking cessation: a randomized controlled trial. JAMA. 2006 Jul 5;296(1):56-63. [PubMed:16820547 ]