Diltiazem hydrochlorideProduct ingredient for Diltiazem

Name
Diltiazem hydrochloride
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
DBSALT000865
Structure
Synonyms
Diltiazem HCl
UNII
OLH94387TE
CAS Number
33286-22-5
Weight
Average: 450.98
Monoisotopic: 450.1380062
Chemical Formula
C22H27ClN2O4S
InChI Key
HDRXZJPWHTXQRI-BHDTVMLSSA-N
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+;/m1./s1
IUPAC Name
(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride
SMILES
Cl.COC1=CC=C(C=C1)[C@@H]1SC2=C(C=CC=C2)N(CCN(C)C)C(=O)[C@@H]1OC(C)=O
KEGG Drug
D00616
PubChem Compound
62920
ChemSpider
56639
ChEBI
645509
ChEMBL
CHEMBL1697
Wikipedia
Diltiazem
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 Count7Chemaxon
Refractivity114.37 m3·mol-1Chemaxon
Polarizability43.73 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon