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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 of TEBANICLINE

SMILES

ClC1=NC=C(OC[C@H]2CCN2)C=C1

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

Molecular Formula C9H11ClN2O
Molecular Weight 198.649
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
55.0 pM [Ki]
55.0 pM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 ng/mL
300 μg 2 times / day multiple, oral
TEBANICLINE plasma
Homo sapiens
2.73 ng/mL
300 μg 2 times / day multiple, oral
TEBANICLINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
22.9 ng × h/mL
300 μg 2 times / day multiple, oral
TEBANICLINE plasma
Homo sapiens
25 ng × h/mL
300 μg 2 times / day multiple, oral
TEBANICLINE plasma
Homo sapiens

PubMed

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
Record UNII
9KX8NKV538
Record Status Validated (UNII)
Record Version