TEBANICLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11ClN2O
Molecular Weight	198.649
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(OC[C@H]2CCN2)C=N1

InChI

InChIKey=MKTAGSRKQIGEBH-SSDOTTSWSA-N

InChI=1S/C9H11ClN2O/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7/h1-2,5,7,11H,3-4,6H2/t7-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9580626 | https://www.ncbi.nlm.nih.gov/pubmed/9580627 | https://www.ncbi.nlm.nih.gov/pubmed/22386472

ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine] is a potent cholinergic neuronal nicotinic acetylcholine receptor (nAChR) ligand with analgesic properties. ABT-594 binds alpha-4/ beta-2 neuronal nAChRs acting as an agonist. ABT-594 is studying for the treatment of diabetic peripheral neuropathic pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha4/beta2 77 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9580626	Agonist 2752		55.0 pM [Ki]
Neuronal acetylcholine receptor; alpha4/beta2 77 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9580626	Inhibitor 8504		55.0 pM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetic peripheral neuropathic pain 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22328206 https://www.ncbi.nlm.nih.gov/pubmed/22145610 https://www.ncbi.nlm.nih.gov/pubmed/19632048 https://www.ncbi.nlm.nih.gov/pubmed/22386472	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
2.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19632048	300 μg 2 times / day multiple, oral dose: 300 μg route of administration: Oral experiment type: MULTIPLE co-administered:		TEBANICLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.73 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19632048	300 μg 2 times / day multiple, oral dose: 300 μg route of administration: Oral experiment type: MULTIPLE co-administered:		TEBANICLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
22.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19632048	300 μg 2 times / day multiple, oral dose: 300 μg route of administration: Oral experiment type: MULTIPLE co-administered:		TEBANICLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
25 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19632048	300 μg 2 times / day multiple, oral dose: 300 μg route of administration: Oral experiment type: MULTIPLE co-administered:		TEBANICLINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Pharmacological effects of nonselective and subtype-selective nicotinic acetylcholine receptor agonists in animal models of persistent pain.	2010-04	20167427
Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors.	2009-03-15	19232492
Morphine and ABT-594 (a nicotinic acetylcholine agonist) exert centrally mediated antinociception in the rat cyclophosphamide cystitis model of visceral pain.	2008-02	18088559
Ligands selective for alpha4beta2 but not alpha3beta4 or alpha7 nicotinic receptors generalise to the nicotine discriminative stimulus in the rat.	2007-02	17115136
3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity.	2005-03-15	15745813
ABT-594 (a nicotinic acetylcholine agonist): anti-allodynia in a rat chemotherapy-induced pain model.	2005-02-10	15713428
Modulators of nicotinic acetylcholine receptors as analgesics.	2004-01	14983978
Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats.	2000-04	10781917
ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization.	1998-05	9580626

Patents

Sample Use Guides

In Vivo Use Guide

Efficacy, safety and pharmacokinetics of ABT-594 in subjects with painful diabetic polyneuropathy were evaluated in a randomized, double-blind, placebo-controlled, parallel-group, multi-centre, 7-week Phase 2 study: subjects were approximately equally divided into four groups to receive BID regimens of placebo or 150, 225 and 300 ug of ABT-594. ABT-894 was evaluated in 2 separate randomized, double-blind, multicenter, placebo-controlled clinical trials in patients with diabetic peripheral neuropathic pain. Study 1 (280 patients randomized) tested 1, 2, and 4 mg ABT-894 twice daily compared with placebo and 60 mg duloxetine once per day over 8 weeks of treatment. Study 2 (124 patients randomized) tested 6 mg ABT-894 twice daily vs placebo for 8 weeks.

Route of Administration: Oral

In Vitro Use Guide

ABT-594 (30 uM) inhibits the release of calcitonin gene-related peptide from C-fibers terminating in the dorsal horn of the spinal cord, an effect mediated via nAChRs.

Name

Type

Language

ABT-165594

Preferred Name

English

TEBANICLINE

Official Name

English

ABT-594

Code

English

tebanicline [INN]

Common Name

English

TEBANICLINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73579