Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11ClN2O.ClH |
| Molecular Weight | 235.11 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.ClC1=CC=C(OC[C@H]2CCN2)C=N1
InChI
InChIKey=GYVARJONEFSAJB-OGFXRTJISA-N
InChI=1S/C9H11ClN2O.ClH/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7;/h1-2,5,7,11H,3-4,6H2;1H/t7-;/m1./s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| 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 |
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.
Originator
Approval Year
Cmax
| 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 |
|
| Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors. | 2009-03-15 |
|
| Morphine and ABT-594 (a nicotinic acetylcholine agonist) exert centrally mediated antinociception in the rat cyclophosphamide cystitis model of visceral pain. | 2008-02 |
|
| Ligands selective for alpha4beta2 but not alpha3beta4 or alpha7 nicotinic receptors generalise to the nicotine discriminative stimulus in the rat. | 2007-02 |
|
| 3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity. | 2005-03-15 |
|
| ABT-594 (a nicotinic acetylcholine agonist): anti-allodynia in a rat chemotherapy-induced pain model. | 2005-02-10 |
|
| Modulators of nicotinic acetylcholine receptors as analgesics. | 2004-01 |
|
| Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats. | 2000-04 |
|
| 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 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
48U2WUT775
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| Record Status |
Validated (UNII)
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| Record Version |
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203564-54-9
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m10497
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48U2WUT775
Created by
admin on Mon Mar 31 22:24:38 GMT 2025 , Edited by admin on Mon Mar 31 22:24:38 GMT 2025
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