Details of the Drug

General Information of Drug (ID: DMMUOLJ)

Drug Name
Varenicline
Synonyms CP 526555; Champix (TN); Chantix (TN); Varenicline (INN); 7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-h)(3)benzazepine; 7,8,9,10-tetrahydro-6h-6,10-methanoazepino[4,5-g]quinoxaline
Indication
Disease Entry ICD 11 Status REF
Drug dependence N.A. Approved [1]
Smoking dependence 6C4A.2 Approved [2]
Affected Organisms
Humans and other mammals
ATC Code
N07BA03: Varenicline
N07BA: Drugs used in nicotine dependence
N07B: DRUGS USED IN ADDICTIVE DISORDERS
N07: OTHER NERVOUS SYSTEM DRUGS
N: NERVOUS SYSTEM
S01XA28: Varenicline
S01XA: Other ophthalmologicals
S01X: OTHER OPHTHALMOLOGICALS
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 211.26
Logarithm of the Partition Coefficient (xlogp) 0.8
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
87% of drug becomes completely available to its intended biological destination(s) [4]
Elimination
92% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 24 hours [5]
Metabolism
The drug is metabolized via the kidneys []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.13524 micromolar/kg/day [6]
Water Solubility
The ability of drug to dissolve in water is measured as 0.2 mg/mL [3]
Chemical Identifiers
Formula
C13H13N3
IUPAC Name
5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene
Canonical SMILES
C1C2CNCC1C3=CC4=NC=CN=C4C=C23
InChI
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
InChIKey
JQSHBVHOMNKWFT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
170361
CAS Number
249296-44-4
UNII
W6HS99O8ZO
DrugBank ID
DB01273
TTD ID
D0LM4A
VARIDT ID
DR00237
ACDINA ID
D00722
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Neuronal acetylcholine receptor alpha-4/beta-2 (CHRNA4/B2) TTL1ATN ACHA4_HUMAN ; ACHB2_HUMAN Modulator [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [8]
Organic cation transporter 2 (SLC22A2) DT9IDPW S22A2_HUMAN Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Drug dependence
ICD Disease Classification
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Neuronal acetylcholine receptor alpha-4/beta-2 (CHRNA4/B2) DTT CHRNA4-CHRNB2 3.51E-10 -0.15 -0.61
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 8.54E-01 1.24E-02 7.20E-02
Organic cation transporter 2 (SLC22A2) DTP SLC22A2 8.22E-01 -1.05E-02 -3.83E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
FD&C blue no. 2 E00446 2723854 Colorant
Calcium hydrogenphosphate E00294 24441 Diluent
Carmellose sodium E00625 Not Available Disintegrant
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Triacetin E00080 5541 Humectant; Plasticizing agent; Solvent
⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Varenicline 0.5 mg tablet 0.5 mg Oral Tablet Oral
Varenicline 1 mg tablet 1 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Varenicline FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5459).
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 2006 drug approvals: finding the niche. Nat Rev Drug Discov. 2007 Feb;6(2):99-101.
8 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
9 Effect of human renal cationic transporter inhibition on the pharmacokinetics of varenicline, a new therapy for smoking cessation: an in vitro-in vivo study. Clin Pharmacol Ther. 2008 Apr;83(4):567-76.