Diltiazem malateProduct ingredient for Diltiazem

Name
Diltiazem malate
Drug Entry
Diltiazem

Diltiazem is a benzothiazepine derivative with antihypertensive and vasodilating properties. Approved in 1982 by the FDA, it is a member of the non-dihydropyridine calcium channel blockers drug class. It works through various mechanisms of action, but it primarily works by inhibiting the calcium influx into cardiac and vascular smooth muscle during depolarization.12 Compared to dihydropyridine drugs, such as nifedipine, that preferentially act on vascular smooth muscle and verapamil that directly acts on the heart muscle, diltiazem displays an intermediate specificity to target both the cardiac and vascular smooth muscle.8 Being a potent vasodilator, diltiazem is used clinically as an antihypertensive, anti-arrhythmic, and as an anti-anginal agent 9 for the management of cardiovascular conditions such as hypertension, chronic stable angina, atrial fibrillation, atrial flutter. Apart from its main FDA-approved indications, diltiazem has also been used for numerous off-label indications, such as anal fissures (in topical formulations), migraine prophylaxis, pulmonary hypertension, and rest-related cramps in the lower extremities.9 Typically available in extended-release oral and intravenous formulations, diltiazem is marketed under various brand names with Cardizem and Tiazac being the most common ones.

Accession Number
DBSALT001394
Structure
Synonyms
Not Available
External IDs
MK-793
UNII
14Y6444DRP
CAS Number
144604-00-2
Weight
Average: 548.61
Monoisotopic: 548.182851792
Chemical Formula
C26H32N2O9S
InChI Key
IUSFTUWHKCSCDY-QTKZZPNDSA-N
InChI
InChI=1S/C22H26N2O4S.C4H6O5/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;5-2(4(8)9)1-3(6)7/h5-12,20-21H,13-14H2,1-4H3;2,5H,1H2,(H,6,7)(H,8,9)/t20-,21+;2-/m10/s1
IUPAC Name
(2S)-2-hydroxybutanedioic acid; (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
SMILES
O[C@@H](CC(O)=O)C(O)=O.COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O
ChemSpider
2300948
ChEMBL
CHEMBL1200805
Predicted Properties
PropertyValueSource
Water Solubility0.0168 mg/mLALOGPS
logP3.09ALOGPS
logP2.73Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.86Chemaxon
pKa (Strongest Basic)8.18Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area59.08 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity114.37 m3·mol-1Chemaxon
Polarizability45.3 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon