TEBANICLINE TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11ClN2O.C7H8O3S
Molecular Weight	370.851
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.ClC2=CC=C(OC[C@H]3CCN3)C=N2

InChI

InChIKey=JCPWIGCGJUGLJQ-OGFXRTJISA-N

InChI=1S/C9H11ClN2O.C7H8O3S/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7;1-6-2-4-7(5-3-6)11(8,9)10/h1-2,5,7,11H,3-4,6H2;2-5H,1H3,(H,8,9,10)/t7-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C9H11ClN2O
Molecular Weight	198.649
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 76 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9580626	Agonist 2678		55.0 pM [Ki]
Neuronal acetylcholine receptor; alpha4/beta2 76 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9580626	Inhibitor 8297		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 1132	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
ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization.	1998 May	9580626
Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats.	2000 Apr	10781917
ABT-594 (a nicotinic acetylcholine agonist): anti-allodynia in a rat chemotherapy-induced pain model.	2005 Feb 10	15713428
Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors.	2009 Mar 15	19232492
Pharmacological effects of nonselective and subtype-selective nicotinic acetylcholine receptor agonists in animal models of persistent pain.	2010 Apr	20167427

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:25:54 GMT 2023` Edited by `admin` on `Fri Dec 15 16:25:54 GMT 2023`
Record UNII	CP1A26546Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEBANICLINE TOSYLATE

Official Name

English

5-(((R)-2-AZETIDNYL)METHOXY)-2-CHLOROPYRIDINE MONO-P-TOLUENESULPHONATE

Systematic Name

English

TEBANICLINE TOSILATE

Common Name

English

PYRIDINE, 5-( (2R)-2-AZETIDINYLMETHOXY)-2-CHLORO-, MONO(4-METHYLBENZENESULPHONATE)

Common Name

English

A-16659447

Code

English

TEBANICLINE TOSYLATE [USAN]

Common Name

English

A-165594

Code

English

5-(((R)-2-AZETIDNYL)METHOXY)-2-CHLOROPYRIDINE MONO-P-TOLUENESULFONATE

Systematic Name

English

TEBANICLINE TOSYLATE [MI]

Common Name

English

PYRIDINE, 5-( (2R)-2-AZETIDINYLMETHOXY)-2-CHLORO-, MONO(4-METHYLBENZENESULFONATE)

Systematic Name

English

A-166594.47

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C73579