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Details

Stereochemistry ACHIRAL
Molecular Formula C22H26N2O4S.C4H4O4
Molecular Weight 530.59
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DILTIAZEM MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC=C(C=C1)[C@@H]2SC3=C(C=CC=C3)N(CCN(C)C)C(=O)[C@@H]2OC(C)=O

InChI

InChIKey=WHBXLOWLFLTDMD-WECFPGDBSA-N
InChI=1S/C22H26N2O4S.C4H4O4/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;5-3(6)1-2-4(7)8/h5-12,20-21H,13-14H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t20-,21+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C22H26N2O4S
Molecular Weight 414.518
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Diltiazem is a nondihydropyridines calcium channel blocker used in the treatment of hypertension, angina pectoris, and some types of arrhythmia. Diltiazem produces its antihypertensive effect primarily by relaxation of vascular smooth muscle and the resultant decrease in peripheral vascular resistance.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
21.0 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Calcium channel blockers for neuroleptic-induced tardive dyskinesia.
2001
[Dilren efficacy in postmyocardial infarction patients].
2001
Influence of diltiazem on the pharmacokinetics of amlodipine in elderly hypertensive patients.
2001 Apr
Effects of chlorthalidone and diltiazem on myocardial ischemia in elderly patients with hypertension and coronary artery disease.
2001 Apr
Effect of the calcium channel blockers nifedipine and diltiazem on pentylenetetrazole kindling-provoked amnesia in rats.
2001 Apr
Slowing the progression of renal disease in diabetic patients.
2001 Apr
Pharmacokinetics of cyclosporine in heart transplant recipients receiving metabolic inhibitors.
2001 Apr
Voltage-dependent calcium channels in the rat retina: involvement in NMDA-stimulated influx of calcium.
2001 Apr
Contribution of amiloride-insensitive pathways to alveolar fluid clearance in adult rats.
2001 Apr
A case of lichenoid purpura possibly caused by diltiazem hydrochloride.
2001 Feb
Susac's syndrome: beneficial effects of corticosteroid therapy in a Japanese case.
2001 Feb
Endothelin-1 enhances eicosanoids-induced coronary smooth muscle contraction by activating specific protein kinase C isoforms.
2001 Feb
Efficacy and safety of out-of-hospital self-administered single-dose oral drug treatment in the management of infrequent, well-tolerated paroxysmal supraventricular tachycardia.
2001 Feb
Diltiazem-associated photodistributed hyperpigmentation: a review of 4 cases.
2001 Feb
Calcium channel blocker D-cis-diltiazem does not slow retinal degeneration in the PDE6B mutant rcd1 canine model of retinitis pigmentosa.
2001 Feb 25
Pharmacological interventions of cyanide-induced cytotoxicity and DNA damage in isolated rat thymocytes and their protective efficacy in vivo.
2001 Feb 3
Diltiazem downregulates IL-12 production by human dendritic cells.
2001 Feb-Mar
Diltiazem affects human dendritic cell maturation.
2001 Feb-Mar
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells.
2001 Jan
Heart rate-lowering and -regulating effects of once-daily sustained-release diltiazem.
2001 Jan
Silent ischemic interval on exercise test is a predictor of response to drug therapy: a randomized crossover trial of metoprolol versus diltiazem in stable angina.
2001 Jan
Pharmacokinetic interaction between single oral doses of diltiazem and sirolimus in healthy volunteers.
2001 Jan
Design and evaluation of microcapsules of diltiazem hydrochloride.
2001 Jan-Feb
Protein kinase C activates store-operated Ca(2+) channels in human glomerular mesangial cells.
2001 Jul 13
Electrophysiological characteristics of rat gustatory cyclic nucleotide--gated channel expressed in Xenopus oocytes.
2001 Jun
Photostability and phototoxicity studies on diltiazem.
2001 Jun
Analysis of multicomponent formulations containing phenylpropanolamine hydrochloride, caffeine and diazepam by using LC.
2001 Jun
Adsorptive stripping voltammetric determination of antihypertensive agent: diltiazem.
2001 Jun
cAMP modulates the excitability of immortalized H=hypothalamic (GT1) neurons via a cyclic nucleotide gated channel.
2001 Jun
Smooth muscle relaxation and local hydraulic impedance properties of the aorta.
2001 Jun
Calcium signaling pathways utilized by P2X receptors in freshly isolated preglomerular MVSMC.
2001 Jun
Contraction of human colonic circular smooth muscle cells is inhibited by the calcium channel blocker pinaverium bromide.
2001 Jun
An alternative method to the evaluation of similarity factor in dissolution testing.
2001 Jun 4
Clinical outcomes of aneurysmal subarachnoid hemorrhage patients treated with oral diltiazem and limited intensive care management.
2001 Mar
Effect of simvastatin on vascular smooth muscle responsiveness: involvement of Ca(2+) homeostasis.
2001 Mar
Positive and negative contractile effects of somatostatin-14 on rat ventricular cardiomyocytes.
2001 Mar
Effect of angiotensin II on venodilator response to nitroglycerin.
2001 Mar
Differential efficacy of L- and T-type calcium channel blockers in preventing tachycardia-induced atrial remodeling in dogs.
2001 Mar
Effect of magnesium stearate or calcium stearate as additives on dissolution profiles of diltiazem hydrochloride from press-coated tablets with hydroxypropylmethylcellulose acetate succinate in the outer shell.
2001 Mar 23
Inhibition by nifedipine of adherence- and activated macrophage-induced death of human gingival fibroblasts.
2001 Mar 9
Inhibitory effects of TA-993 and its metabolite MB3 on platelet activation induced by collagen and U-46619 in human platelets.
2001 May
Randomized trial of rhythm or rate control in atrial fibrillation: the Pharmacological Intervention in Atrial Fibrillation Trial (PIAF).
2001 May
Diltiazem treatment does not alter renal function after thoracic surgery.
2001 May
Calcium-channel antagonists and nitrates in coronary artery bypass patients receiving radial artery grafts.
2001 May
Trimetazidine for stable angina pectoris.
2001 May
Ca2+-dependent exocytosis of L-glutamate by alphaTC6, clonal mouse pancreatic alpha-cells.
2001 May
Calcium-dependent effects of melatonin inhibition of glutamatergic response in rat striatum.
2001 May
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.
2001 May
Characterization of drug release from diltiazem-loaded polylactide microspheres prepared using sodium caseinate and whey protein as emulsifying agents.
2001 May-Jun
Study of processing parameters influencing the properties of diltiazem hydrochloride microspheres.
2001 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
When used as monotherapy, reasonable starting doses are 180 to 240 mg once daily, although some patients may respond to lower doses. Maximum antihypertensive effect is usually observed by 14 days of chronic therapy; therefore, dosage adjustments should be scheduled accordingly. The usual dosage range studied in clinical trials was 240 to 360 mg once daily. Individual patients may respond to higher doses of up to 480 mg once daily. Dosages for the treatment of angina should be adjusted to each patient's needs, starting with a dose of 120 or 180 mg once daily. Individual patients may respond to higher doses of up to 480 mg once daily. When necessary, titration may be carried out over a 7- to 14-day period.
Route of Administration: Oral
In Vitro Use Guide
Tissue homogenate of cerebral cortext and heart containing calcium channel receptors was used in a radioligand-binding assays. Cerebral cortices of male SD rats were homogenized. Hearts were also removed, perfused through aorta with ice-cold saline solution, and homogenized. Subsequently, the cardiac homogenates were filtered through four layers of cloth. Both cortical and cardiac homogenates were washed 5 times by centrifugation for 10 min at 48000 g. The final pelle was resuspended to a conc. of 50 mg of original wet tissue wt/mL of buffer and stored at -70°C. Tissue homogenate (200 uL) was incubated for 90 min in a dark room at 0°C with 100 uL of [3H]nitreddipine (3x10^-10M, 87 Ci/mmol) and 100 uL of the test compound dissolved in DMSO in 50 mM of Na-Hepes buffer, pH 7.4. The incubations were stopped by adding 4 mL of cold buffer followed by rapid filtratoin through glass fiber filter disks. The samples were subsequently washed 3 times with 4.5 mL of the same buffer and placed into scintill. vials. Diltiazem inhibited binding of [3H]nitrendipine with Ki of 21 nM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 18:36:27 UTC 2019
Edited
by admin
on Tue Oct 22 18:36:27 UTC 2019
Record UNII
896626Q8XW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DILTIAZEM MALEATE
VANDF  
Common Name English
DILTIAZEM MALEATE [VANDF]
Common Name English
1,5-BENZOTHIAZEPIN-4(5H)-ONE, 3-(ACETYLOXY)-5-(2-(DIMETHYLAMINO)ETHYL)-2,3-DIHYDRO-2-(4-METHOXYPHENYL)-, (2S,3S)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
67938926
Created by admin on Tue Oct 22 18:36:27 UTC 2019 , Edited by admin on Tue Oct 22 18:36:27 UTC 2019
PRIMARY
CAS
139492-78-7
Created by admin on Tue Oct 22 18:36:27 UTC 2019 , Edited by admin on Tue Oct 22 18:36:27 UTC 2019
PRIMARY
RXCUI
314592
Created by admin on Tue Oct 22 18:36:27 UTC 2019 , Edited by admin on Tue Oct 22 18:36:27 UTC 2019
PRIMARY RxNorm
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ACTIVE MOIETY