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
- External Links
- Predicted Properties
Property Value Source Water Solubility 0.0168 mg/mL ALOGPS logP 3.09 ALOGPS logP 2.73 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 12.86 Chemaxon pKa (Strongest Basic) 8.18 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 59.08 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 114.37 m3·mol-1 Chemaxon Polarizability 43.73 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon