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Merck
CN

SML4099

ABT-639

≥98% (HPLC)

Synonym(s):

(R)-4-Chloro-2-fluoro-N-(2-fluorophenyl)-5-(octahydropyrrolo[1,2-a]pyrazine-2-carbonyl)benzenesulfonamide, 4-Chloro-2-fluoro-N-(2-fluorophenyl)-5-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide, ABT 639, ABT639

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About This Item

Empirical Formula (Hill Notation):
C20H20ClF2N3O3S
CAS Number:
Molecular Weight:
455.91
MDL number:
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Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

Fc1c(cc(c(c1)Cl)C(=O)N3C[C@@H]4N(CC3)CCC4)[S](=O)(=O)Nc2c(cccc2)F

InChI key

AGPIHNZOZNKRGT-CYBMUJFWSA-N

Biochem/physiol Actions

Orally active, peripherally acting, potent and Cav3.2-selective T-type calcium channel blocker with antinociception efficacy in vivo.

ABT-639 is an orally active, peripherally acting, potent and Cav3.2-selective T-type calcium channel blocker (hCav3.2 IC50 = 2 μM vs. >30 μM against Cav3.1/Cav3.3) that attenuates low-voltage-activated (LVA) currents in rat DRG neurons (IC50 = 7.6 μM). ABT-639 exhibits antinociception efficacy in a rat knee joint pain model (ED50 = 2 mg/kg, p.o.), and increases tactile allodynia thresholds in multiple models of neuropathic pain in vivo (10-100 mg/kg, p.o.) with no adverse effects on hemodynamic or psychomotor function even at doses as high as 300 mg/kg.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Elodie Picard et al.
British journal of pharmacology, 176(7), 950-963 (2019-02-05)
Abdominal pain associated with low-grade inflammation is frequently encountered in irritable bowel syndrome (IBS) and inflammatory bowel disease (IBD) during remission. Current treatments are not very effective and new therapeutic approaches are needed. The role of CaV 3.2 channels, which
Qingwei Zhang et al.
ACS medicinal chemistry letters, 6(6), 641-644 (2015-06-24)
The discovery of a novel peripherally acting and selective Cav3.2 T-type calcium channel blocker, ABT-639, is described. HTS hits 1 and 2, which have poor metabolic stability, were optimized to obtain 4, which has improved stability and oral bioavailability. Modification
Michael F Jarvis et al.
Biochemical pharmacology, 89(4), 536-544 (2014-04-15)
Activation of T-type Ca²⁺ channels contributes to nociceptive signaling by facilitating action potential bursting and modulation of membrane potentials during periods of neuronal hyperexcitability. The role of T-type Ca²⁺ channels in chronic pain is supported by gene knockdown studies showing

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