L-cis-Diltiazem, cyclic nucleotide-gated channel blocker

Key facts

CAS number

42399-54-2

Purity

>97%

Form

Solid

form

Molecular weight

451 Da

Molecular formula

C₂₂H₂₇ClN₂O₄S

PubChem

198106

Nature

Synthetic

Solubility

Soluble in water to 100 mM

Biochemical name

Ent-diltiazem hydrochloride

Biological description

Selective inhibitor of cyclic nucleotide-gated (CNG) channels. Blocks rod-type CNGA1, olfactory-type CNGA2 and cone-type CNGA3, at micromolar concentrations. Optical isomer of diltiazem (ab120260). Protects against myocardial dysfunction in vitro.

Canonical smiles

CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC.Cl

Isomeric smiles

CC(=O)O[C@H]1[C@H](SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC.Cl

InChi

InChI=1S/C22H26N2O4S.ClH/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3;/h5-12,20-21H,13-14H2,1-4H3;1H/t20-,21+;/m0./s1

InChiKey

HDRXZJPWHTXQRI-JUDYQFGCSA-N

IUPAC Name

[(2R,3R)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate;hydrochloride