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Technical details about Varenicline, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Varenicline tartrate, 375815-87-5, (2s,3s)-2,3-dihydroxybutanedioic acid; 5,8,14-triazatetracyclo[10.3.1.0^{2,11}.0^{4,9}]hexadeca-2(11),3,5,7,9-pentaene, (2s,3s)-2,3-dihydroxybutanedioic acid;5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene, Akos026750167, As-35136
Molecular Formula
C17H19N3O6
Molecular Weight
361.3  g/mol
InChI Key
TWYFGYXQSYOKLK-WUUYCOTASA-N

A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3S)-2,3-dihydroxybutanedioic acid;5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene
2.1.2 InChI
InChI=1S/C13H13N3.C4H6O6/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1;5-1(3(7)8)2(6)4(9)10/h1-2,4-5,8-9,14H,3,6-7H2;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.0/s1
2.1.3 InChI Key
TWYFGYXQSYOKLK-WUUYCOTASA-N
2.1.4 Canonical SMILES
C1C2CNCC1C3=CC4=NC=CN=C4C=C23.C(C(C(=O)O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
C1C2CNCC1C3=CC4=NC=CN=C4C=C23.[C@H]([C@@H](C(=O)O)O)(C(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 6,7,8,9-tetrahydro-6,10-methano-6h-pyrazino(2,3-h)benzazepine

2. Champix

3. Varenicline

4. Varenicline Tartrate

2.2.2 Depositor-Supplied Synonyms

1. Varenicline Tartrate

2. 375815-87-5

3. (2s,3s)-2,3-dihydroxybutanedioic Acid; 5,8,14-triazatetracyclo[10.3.1.0^{2,11}.0^{4,9}]hexadeca-2(11),3,5,7,9-pentaene

4. (2s,3s)-2,3-dihydroxybutanedioic Acid;5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

5. Akos026750167

6. As-35136

7. A21286

8. Z1642292115

2.3 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 361.3 g/mol
Molecular Formula C17H19N3O6
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass361.12738533 g/mol
Monoisotopic Mass361.12738533 g/mol
Topological Polar Surface Area153 Ų
Heavy Atom Count26
Formal Charge0
Complexity388
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameChantix
PubMed HealthVarenicline (By mouth)
Drug ClassesSmoking Ceation Agent
Drug LabelCHANTIX tablets contain varenicline (as the tartrate salt), which is a partial agonist selective for 42 nicotinic acetylcholine receptor subtypes.Varenicline, as the tartrate salt, is a powder which is a white to off-white to slightly yellow soli...
Active IngredientVarenicline tartrate
Dosage FormTablet
RouteOral
Strengtheq 0.5mg base; eq 1mg base
Market StatusPrescription
CompanyPfizer

2 of 2  
Drug NameChantix
PubMed HealthVarenicline (By mouth)
Drug ClassesSmoking Ceation Agent
Drug LabelCHANTIX tablets contain varenicline (as the tartrate salt), which is a partial agonist selective for 42 nicotinic acetylcholine receptor subtypes.Varenicline, as the tartrate salt, is a powder which is a white to off-white to slightly yellow soli...
Active IngredientVarenicline tartrate
Dosage FormTablet
RouteOral
Strengtheq 0.5mg base; eq 1mg base
Market StatusPrescription
CompanyPfizer

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Nicotinic Agonists

Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)


Smoking Cessation Agents

Substances that facilitate the cessation of tobacco smoking. (See all compounds classified as Smoking Cessation Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Partial Cholinergic Nicotinic Agonists [MoA]; Partial Cholinergic Nicotinic Agonist [EPC]
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