2017618 DiltiazemDrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)

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Identi cation

Name Diltiazem

Accession Number DB00343 (APRD00473)

Type Small Molecule

Groups Approved

Description A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem]

Structure H3 C O

CH3

O
O
(/structures/DB00343/image.svg)
S

N
CH3
N

H3 C

MOL (/structures/small_molecule_drugs/DB00343.mol) SDF (/structures/small_molecule_drugs/DB00343.sdf) 3D-SDF (/structures/small_molecule_drugs/DB00343.sdf?dim=3

PDB (/structures/small_molecule_drugs/DB00343.pdb) SMILES (/structures/small_molecule_drugs/DB00343.smiles) InChI (/structures/small_molecule_drugs/DB00343.inchi)

View 3D Structure (/structures/small_molecule_drugs/DB00343)

Synonyms (+)-cis-5-[2-(dimethylamino)Ethyl]-2,3-dihydro-3-hydroxy-2-(P-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate ester

(2S-cis)-3-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

(2S,3S)-5-(2-(dimethylamino)Ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate

Acetic acid (2S,3S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester

Diltiazem

Diltiazemum

External IDs Not Available

Product Ingredient UNII CAS InChI Key

Ingredients
Diltiazem hydrochloride OLH94387TE (http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=OLH94387TE) 33286- HDRXZJPWHTXQRI-
(/salts/DBSALT000865) 22-5 BHDTVMLSSA-N

Diltiazem malate 14Y6444DRP (http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=14Y6444DRP) 144604- IUSFTUWHKCSCDY-

(/salts/DBSALT001394) 00-2 QTKZZPNDSA-N

Diltiazem maleate 896626Q8XW (http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=896626Q8XW) 139492- WHBXLOWLFLTDMD-

(/salts/DBSALT002322) 78-7 WECFPGDBSA-N

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2017618 DiltiazemDrugBank

Approved
ID Pharmacology
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entriesReferences Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)
Prescription
Products
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Name Dosage Strength Route Labeller Marketing Start

Act Capsule, extended release 240 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem
CD

Act Capsule, extended release 300 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem
CD

Act Capsule, extended release 120 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem
CD

Act Capsule, extended release 180 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem
CD

Act Capsule, extended release 180 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem T

Act Capsule, extended release 240 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem T

Act Capsule, extended release 300 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem T

Act Capsule, extended release 360 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem T

Act Capsule, extended release 120 mg Oral Actavis Pharma Company 2011-10-06
Diltiazem T

Alti- Tablet 30 mg Oral Altimed Pharma Inc. 1990-12-31

diltiazem Tab
30mg

Showing 1 to 10 of 199 entries

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Approved Generic
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Prescription
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Marketing
Name Dosage Strength Route Labeller Start

Apo Diltiaz Tab 30mg Tablet 30 mg Oral Apotex Corporation 1988-12-3

Apo Diltiaz Tab 60mg Tablet 60 mg Oral Apotex Corporation 1988-12-3

Apo-diltiaz CD Capsule, extended release 120 mg Oral Apotex Corporation 1997-03-2

Apo-diltiaz CD Capsule, extended release 180 mg Oral Apotex Corporation 1997-03-2

Apo-diltiaz CD Capsule, extended release 240 mg Oral Apotex Corporation 1997-03-2

Apo-diltiaz CD - Cap Capsule, extended release 300 mg Oral Apotex Corporation 1996-09-1
300mg

Apo-diltiaz Injectable Liquid 5 mg Intravenous Apotex Corporation 2000-06-2

Apo-diltiaz SR - 90mg/src Capsule, extended release 90 mg Oral Apotex Corporation 1996-09-1

Apo-diltiaz SR - Src Capsule, extended release 120 mg Oral Apotex Corporation 1996-09-1
120mg

Apo-diltiaz SR - Src 60mg Capsule, extended release 60 mg Oral Apotex Corporation 1996-09-1

Showing 1 to 10 of 284 entries

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Approved Over the Not Available

Counter Products

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2017618 DiltiazemDrugBank

Unapproved/Other
ID Pharmacology
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Products
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Name Dosage Strength Route Labeller Marketing Start

Diltiazem Injection, solution 1 mg/mL Intravenous Cantrell Drug Company 2011-09-30

HCl

Diltiazem Injection, solution .83 mg/mL Intravenous Cantrell Drug Company 2013-10-22
HCl

Showing 1 to 2 of 2 entries

International
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Brands
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Name Company

Acalix Roemmers

Adizem Mundipharma

Altiazem Lusofarmaco

Anoheal Not Available

Calcicard Not Available

Cartia Not Available

Dilacor Not Available

Dilacor-XR Watson

Dilcontin Modi-Mundipharma

Dilrene Sano

Showing 1 to 10 of 19 entries

Brand mixtures Not Available

Categories Antihypertensive Agents (/categories/DBCAT000410)

Benzazepines (/categories/DBCAT000451)
Benzothiazepine Derivatives (/categories/DBCAT002326)
Bradycardia-Causing Agents (/categories/DBCAT002703)
Calcium Channel Blockers (/categories/DBCAT000574)
Calcium Channel Blockers (Nondihydropyridine) (/categories/DBCAT003005)
Cardiovascular Agents (/categories/DBCAT000010)
Cardiovascular System (/categories/DBCAT002169)
Combined Inhibitors of CYP3A4 and P-glycoprotein (/categories/DBCAT002747)
Cytochrome P-450 CYP2C19 Substrates (/categories/DBCAT002638)
Cytochrome P-450 CYP2C8 Substrates (/categories/DBCAT002642)
Cytochrome P-450 CYP2C9 Inhibitors (/categories/DBCAT000489)
Cytochrome P-450 CYP2C9 Substrates (/categories/DBCAT002634)
Cytochrome P-450 CYP2D6 Inhibitors (/categories/DBCAT000911)
Cytochrome P-450 CYP2D6 Inhibitors (weak) (/categories/DBCAT002726)
Cytochrome P-450 CYP2D6 Substrates (/categories/DBCAT002623)
Cytochrome P-450 CYP3A Inhibitors (/categories/DBCAT000934)
Cytochrome P-450 CYP3A4 Inhibitors (moderate) (/categories/DBCAT002648)
Cytochrome P-450 CYP3A4 Substrates (/categories/DBCAT002646)
Hypotensive Agents (/categories/DBCAT002696)
Membrane Transport Modulators (/categories/DBCAT000128)
P-glycoprotein/ABCB1 Inhibitors (/categories/DBCAT002667)
P-glycoprotein/ABCB1 Substrates (/categories/DBCAT002668)
Selective Calcium Channel Blockers With Direct Cardiac Effects (/categories/DBCAT002327)
Vasodilator Agents (/categories/DBCAT000516)

UNII EE92BBP03H (http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=EE92BBP03H)

CAS number 42399-41-7

Weight Average: 414.518

Monoisotopic: 414.16132802

Chemical Formula C22H26N2O4S

InChI Key HSUGRBWQSSZJOP-RTWAWAEBSA-N

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2017618 DiltiazemDrugBank

InChI InChI=1S/C22H26N2O4S/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/t20-,2
ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)
IUPAC Name (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
Search drugs...
SMILES COC1=CC=C(C=C1)[C@@H]1SC2=CC=CC=C2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O

Pharmacology

Indication For the treatment of Hypertension

Structured Anal Fissures (/indications/DBCOND0031732)

Indications Anginal Pain (/indications/DBCOND0066917)
Atrial Flutter (/indications/DBCOND0080265)
Hypertensive (/indications/DBCOND0046062)
Nonvalvular Atrial Fibrillation (/indications/DBCOND0040606)
Paroxysmal Supraventricular Tachycardia (/indications/DBCOND0058642)
Chronic, stable Angina pectoris (/indications/DBCOND0020957)

Pharmacodynamics Diltiazem, a benzothiazepine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina
variant angina. Diltiazem is a non-dihydropyridine (DHP)member of the calcium channel blocker class, along with Verapamil. Diltiazem is similar to other peripheral v
the in ux of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating
interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smo
dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pr
afterload.

Mechanism of Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, diltiazem
action in ux of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the my
leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue.

Target Kind Pharmacological action Actions Organism UniProt ID

Voltage-dependent calcium channel gamma-1 subunit Protein yes inhibitor Human Q06432 (http://www.uniprot.org/unipro

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Absorption Diltiazem is well absorbed from the gastrointestinal tract but undergoes substantial hepatic rst-pass effect.

Volume of Not Available

distribution

Protein binding 70%-80%

Metabolism
Diltiazem is metabolized by and acts as an inhibitor of the CYP3A4 enzyme.

Substrate Enzymes Product

Diltiazem N-Desmethyldiltiazem (/metabolites/DBMET00362)

Cytochrome P450 3A4 (/biodb/bio_entities/BE0002638)

Route of Not Available

elimination

Half life 3.0 - 4.5 hours

Clearance Not Available

Toxicity LD50=740mg/kg (orally in mice)

Affected organisms Humans and other mammals

Pathways Pathway Category SMPDB ID

Diltiazem Action Pathway Drug action SMP00359 (http://smpdb.ca/view/SMP00359?highlight[compounds][]=DB00343&highlight[proteins][]=DB00343)

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2017618 DiltiazemDrugBank

Pharmacogenomic
ID Pharmacology
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Effects/ADRs
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Interacting Allele
Gene/Enzyme name Genotype(s) De ning Change(s) Type(s) Description

Beta-1 --- (C;C) / (C;G) G > C (http://www.ncbi.nlm.nih.gov/SNP/snp_ref.cgi?rs=rs1801253) Effect Better response to

adrenergic Directly Studied drug therapy
receptor

Showing 1 to 1 of 1 entries

Interactions

Drug Interactions
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Drug Interaction

1,10-Phenanthroline (/drugs/DB02365) The metabolism of Diltiazem can be decreased when combined with 1,10-Phenanthroline.

2-HYDROXY-1,4- The risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with
NAPHTHOQUINONE Diltiazem.
(/drugs/DB04744)

3,4-Dichloroisocoumarin The metabolism of Diltiazem can be decreased when combined with 3,4-Dichloroisocoumarin.
(/drugs/DB04459)

4-(2- The metabolism of Diltiazem can be decreased when combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.
AMINOETHYL)BENZENESULFONYL
FLUORIDE (/drugs/DB07347)

7,8-DICHLORO-1,2,3,4- 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Diltiazem.

TETRAHYDROISOQUINOLINE
(/drugs/DB08550)

Abiraterone (/drugs/DB05812) The serum concentration of Diltiazem can be increased when it is combined with Abiraterone.

Acebutolol (/drugs/DB01193) The risk or severity of adverse effects can be increased when Diltiazem is combined with Acebutolol.

Acenocoumarol (/drugs/DB01418) The metabolism of Acenocoumarol can be decreased when combined with Diltiazem.

Acetaminophen (/drugs/DB00316) The metabolism of Acetaminophen can be decreased when combined with Diltiazem.

Acetazolamide (/drugs/DB00819) The risk or severity of adverse effects can be increased when Diltiazem is combined with Acetazolamide.

Showing 1 to 10 of 938 entries

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Food Interactions Avoid natural licorice.

Take this medication 30 minutes before meals.

References

Synthesis Kugita, H., Inoue, H., Ikezaki, M. and Takeo, S.; U.S. Patent 3,562,257; assigned to Tanabe Seiyaku Co.,Ltd., Japan.
Reference
US3562257 (https://www.google.com/?tbm=pts#q=3562257&tbm=pts)

General References Not Available

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2017618 DiltiazemDrugBank

External Links Resource Interactions Link Economics

ID Pharmacology References Trials Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)

Search drugs... Human Metabolome Database (HMDB) HMDB14487 (http://www.hmdb.ca/metabolites/HMDB14487)

KEGG Compound C06958 (http://www.genome.jp/dbget-bin/www_bget?cpd:C06958)

PubChem Compound 39186 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=39186)

PubChem Substance 46505667 (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505667)

ChemSpider 35850 (http://www.chemspider.com/Chemical-Structure.35850.html)

BindingDB 50004704 (http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50004704)

ChEBI 101278 (http://www.ebi.ac.uk/chebi/searchId.do?chebiId=101278)

ChEMBL CHEMBL23 (http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL23)

Therapeutic Targets Database DAP001262 (http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DAP001262)

PharmGKB PA449334 (http://www.pharmgkb.org/drug/PA449334)

Drug Product Database 1926 (http://webprod5.hc-sc.gc.ca/dpd-bdpp/info.do?code=1926&lang=eng)

RxList http://www.rxlist.com/cgi/generic/diltiaz.htm (http://www.rxlist.com/cgi/generic/diltiaz.htm)

Drugs.com http://www.drugs.com/diltiazem.html (http://www.drugs.com/diltiazem.html)

PDRhealth http://www.pdrhealth.com/drug_info/rxdrugpro les/drugs/car1068.shtml (http://www.pdrhealth.com/drug_info/rxdrugpro les/d

Wikipedia Diltiazem (http://en.wikipedia.org/wiki/Diltiazem)

ATC Codes C05AE03

C05AE Muscle relaxants (/atc/C05AE)
C05A AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE (/atc/C05A)
C05 VASOPROTECTIVES (/atc/C05)
C CARDIOVASCULAR SYSTEM (/atc/C)
C08DB01
C08DB Benzothiazepine derivatives (/atc/C08DB)
C08D SELECTIVE CALCIUM CHANNEL BLOCKERS WITH DIRECT CARDIAC EFFECTS (/atc/C08D)
C08 CALCIUM CHANNEL BLOCKERS (/atc/C08)
C CARDIOVASCULAR SYSTEM (/atc/C)

AHFS Codes 24:28.92

PDB Entries Not Available

FDA label Not Available

MSDS Download (//s3-us-west-2.amazonaws.com/drugbank/msds/DB00343.pdf?1265922735) (73.2 KB)

Clinical Trials

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Clinical Trials
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Phase Status Purpose Conditions Count

1 Completed Not Drug Dependence 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0071404&phase=1&status=completed)

Available (/indications/DBCOND0071404)

1 Completed Not Healthy Volunteers 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0066957&phase=1&status=completed)

Available (/indications/DBCOND0066957)

1 Completed Not Nonvalvular Atrial Fibrillation 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0040606&phase=1&status=completed)

Available (/indications/DBCOND0040606)

1 Completed Basic Drug-induced QT Interval 1 (/drugs/DB00343/clinical_trials?

Science Prolongation conditions=DBCOND0079055%2CDBCOND0041775%2CDBCOND0031919&phase=1&purpose=b
(/indications/DBCOND0079055)
/ Pharmacodynamics
(/indications/DBCOND0041775)
/ Pharmacokinetics
(/indications/DBCOND0031919)

1 Completed Basic Healthy Volunteers 3 (/drugs/DB00343/clinical_trials?conditions=DBCOND0066957&phase=1&purpose=basic_science&

Science (/indications/DBCOND0066957)

1 Completed Basic Healthy; Adult; Volunteer; 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0044826&phase=1&purpose=basic_science&

Science Colchicine; Pharmacokinetics;
Diltiazem; Cytochrome p450
3A4; P-glycoprotein
(/indications/DBCOND0044826)

1 Completed Basic Thrombosis 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0020122&phase=1&purpose=basic_science&

Science (/indications/DBCOND0020122)

1 Completed Treatment Atherosclerosis 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0022749&phase=1&purpose=treatment&stat

(/indications/DBCOND0022749)

1 Completed Treatment CLARITHROMYCIN/DILTIAZEM 1 (/drugs/DB00343/clinical_trials?conditions=DBCOND0068438&phase=1&purpose=treatment&stat

[VA Drug Interaction]
(/indications/DBCOND0068438)

1 Completed Treatment Cardiovascular Disease (CVD) 1 (/drugs/DB00343/clinical_trials?

(/indications/DBCOND0057913) conditions=DBCOND0057913%2CDBCOND0035016%2CDBCOND0046062&phase=1&purpose=tr
/ Human Immunode ciency Virus
(HIV) Infections
(/indications/DBCOND0035016)
/ Hypertensive
(/indications/DBCOND0046062)

Showing 1 to 10 of 47 entries

Pharmacoeconomics

Manufacturers Biovail laboratories inc

Watson laboratories inc orida
Watson laboratories inc
Apotex inc
Actavis elizabeth llc
Kv pharmaceutical co
Mylan pharmaceuticals inc
Teva pharmaceuticals usa inc
Apotex inc etobicoke site
Biovail corp international
Biovail laboratories international srl
Apotex inc richmond hill
Baxter healthcare corp anesthesia and critical care
Bedford laboratories div ben venue laboratories inc
Hospira inc
International medication systems ltd
Taylor pharmacal co
Teva parenteral medicines inc
Apothecon inc div bristol myers squibb
Dava pharmaceuticals inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Teva pharmaceuticals usa
Merck and co inc

Packagers Abbott Laboratories Ltd. (http://www.abbott.com)

Actavis Group (http://www.actavis.com)
Advanced Pharmaceutical Services Inc.
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Akorn Inc. (http://www.akorn.com)
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Services Corp. Economics Properties Spectra
(http://www.amerisourcebergen.com) Taxonomy Targets (1) Enzymes (7) Transporters (1)

Search drugs... Apotex Inc. (http://www.apotex.com)

Apotheca Inc.
A-S Medication Solutions LLC (http://orders.a-smeds.com)
Atlantic Biologicals Corporation (http://www.atlanticbiologicals.com)
Baxter International Inc. (http://www.baxter.com)
Bedford Labs (http://www.bedfordlabs.com)
Ben Venue Laboratories Inc. (http://www.benvenue.com)
Biovail Pharmaceuticals (http://www.biovail.com)
Bracco Diagnostics Inc. (http://www.bracco.com)
Bryant Ranch Prepack (http://bryantranchprepack.com)
BTA Pharmaceuticals
Cardinal Health (http://www.cardinal.com)
Caremark LLC (http://www.caremark.com)
Comprehensive Consultant Services Inc.
Corepharma LLC (http://www.corepharma.com)
Dept Health Central Pharmacy
Direct Dispensing Inc.
DispenseXpress Inc.
Dispensing Solutions (http://www.drxdispensing.com)
Diversi ed Healthcare Services Inc. (http://www.dhscorp.com)
Driam Usa Inc.
Elan Pharmaceuticals Inc. (http://www.elan.com)
Ethex Corp. (http://www.ethex.com)
Ethypharm (http://www.ethypharm-pharmaceutical.com)
Forest Pharmaceuticals (http://www.forestpharm.com)
Gruppo Lepetit SPA
Heartland Repack Services LLC
Hl Moore Drug Exchange
Hospira Inc. (http://www.hospira.com)
Inwood Labs (http://www.inwoodlabs.com)
Ivax Pharmaceuticals
Kaiser Foundation Hospital
KV Pharmaceutical Co. (http://www.kvpharmaceutical.com)
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Long Wing International Inc. (http://www.longwing.net)
Major Pharmaceuticals (http://www.majorpharmaceuticals.com)
Mckesson Corp. (http://www.mckesson.com)
Medisca Inc. (http://www.medisca.com)
Meridian Medical Technologies Inc. (http://www.meridianmeds.com)
Murfreesboro Pharmaceutical Nursing Supply (http://www.unitdosesupply.com)
Mylan (http://www.mylan.com)
Neighborcare Repackaging Inc.
Neuman Distributors Inc.
Novex Pharma
Nucare Pharmaceuticals Inc. (http://www.nucarerx.com)
Palmetto Pharmaceuticals Inc. (http://www.palmettopharm.com)
PD-Rx Pharmaceuticals Inc. (http://www.pdrx.com)
Pharmaceutical Utilization Management Program VA Inc.
Pharmacy Service Center
Pharmedium (http://www.pharmedium.com)
Physicians Total Care Inc. (http://www.physicianstotalcare.com)
Preferred Pharmaceuticals Inc. (http://www.preferredpharmaceuticals.com)
Prepackage Specialists
Prepak Systems Inc. (http://www.prepaksys.com)
Prescript Pharmaceuticals (http://www.prescript.net)
Rebel Distributors Corp. (http://www.rebelrx.com)
Remedy Repack (http://www.remedyrepack.com)
Resource Optimization and Innovation LLC
Sandhills Packaging Inc. (http://www.sandhillspackaging.com)
Sano -Aventis Inc. (http://www.sano -aventis.com)
Southwood Pharmaceuticals (http://www.southwoodhealthcare.com)
Teva Pharmaceutical Industries Ltd. (http://www.tevapharm.com)
Ther-Rx Corp. (http://www.ther-rx.com)
Torpharm Inc.
Tya Pharmaceuticals
UDL Laboratories (http://www.udllabs.com)
Vangard Labs Inc.
Vetter Pharma Fertigung GmbH and Co. KG (http://www.vetter-pharma.com)
Watson Pharmaceuticals (http://www.watson.com)

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Dosage forms
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Form Route Strength

Capsule, extended release Oral 90 mg

Capsule, extended release Oral 60 mg

Tablet, coated Oral 120 mg/1

Tablet, coated Oral 90 mg/1

Capsule Oral 240 mg/1

Capsule, extended release Oral 120 mg

Capsule, extended release Oral 180 mg

Capsule, extended release Oral 240 mg

Capsule, extended release Oral 300 mg

Liquid Intravenous 5 mg

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Prices
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Unit description Cost

Cormax 0.05% Solution 50ml Bottle 81.6USD

Cormax 0.05% Solution 25ml Bottle 45.99USD

Cormax 0.05% Cream 15 gm Tube 43.98USD

Diltiazem hcl 100 mg vial 9.54USD

Diltiazem hcl powder 8.42USD

Cardizem CD 360 mg 24 Hour Capsule 7.94USD

Cardizem cd 360 mg capsule 7.63USD

Cardizem CD 300 mg 24 Hour Capsule 7.3USD

Cardizem LA 420 mg 24 Hour tablet 5.56USD

Cardizem CD 240 mg 24 Hour Capsule 5.48USD

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Patents
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Patent Number Pediatric Extension Approved Expires (estimated)

CA2111085 (https://patents.google.com/patent/CA2111085) No 1999-04-27 2012-06-25

CA2307547 (https://patents.google.com/patent/CA2307547) No 2007-08-14 2020-05-04

US5286497 (https://patents.google.com/patent/US5286497) No 1994-05-20 2011-05-20

US6923984 (https://patents.google.com/patent/US6923984) No 2001-02-25 2021-02-25

US7108866 (https://patents.google.com/patent/US7108866) No 1999-12-17 2019-12-17

Showing 1 to 5 of 5 entries

Properties

State Solid

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Experimental Property Value Source

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)
Properties
Search drugs... melting point (C) 187-188 Kugita, H., Inoue, H., Ikezaki, M. and Takeo, S.; U.S. Patent 3,562,257; assigned to Tanabe Seiyaku Co.,Ltd.,
Japan.

water solubility 465 mg/L (at 25 C) MCFARLAND,JW ET AL. (2001)

logP 2.8 Not Available

Caco2 permeability -4.38 ADME Research, USCD

Predicted Property Value Source

Properties
Water Solubility 0.0168 mg/mL ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 3.09 ALOGPS (http://www.vcclab.org/lab/alogps/)

logP 2.73 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#logp_logd)

logS -4.4 ALOGPS (http://www.vcclab.org/lab/alogps/)

pKa (Strongest Acidic) 12.86 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

pKa (Strongest Basic) 8.18 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

Physiological Charge 1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-predictors/#pka)

Hydrogen Acceptor Count 4 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

Hydrogen Donor Count 0 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#h_bond)

2
Polar Surface Area 59.08 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topolgical_surface)

Rotatable Bond Count 7 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

Refractivity 114.37 m3mol-1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#refractivity)

3
Polarizability 43.65 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Number of Rings 3 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/property-calculations/#topology_analysis)

Bioavailability 1 ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Rule of Five Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Ghose Filter Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

Veber's Rule Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

MDDR-like Rule Yes ChemAxon (http://www.chemaxon.com/products/calculator-plugins/molecular-modelling/#polarization)

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Predicted ADMET Property Interactions

ID Pharmacology References Trials Economics Properties Spectra Value
Taxonomy Targets (1) Enzymes (7) Transporters (1)
features
Search drugs... Human Intestinal Absorption +
Blood Brain Barrier +

Caco-2 permeable +

P-glycoprotein substrate Substrate

P-glycoprotein inhibitor I Inhibitor

P-glycoprotein inhibitor II Inhibitor

Renal organic cation transporter Non-inhibitor

CYP450 2C9 substrate Non-substrate

CYP450 2D6 substrate Substrate

CYP450 3A4 substrate Substrate

CYP450 1A2 substrate Non-inhibitor

CYP450 2C9 inhibitor Non-inhibitor

CYP450 2D6 inhibitor Non-inhibitor

CYP450 2C19 inhibitor Non-inhibitor

CYP450 3A4 inhibitor Inhibitor

CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity

Ames test Non AMES toxic

Carcinogenicity Non-carcinogens

Biodegradation Not ready biodegradable

Rat acute toxicity 2.4130 LD50, mol/kg

hERG inhibition (predictor I) Weak inhibitor

hERG inhibition (predictor II) Inhibitor

ADMET data is predicted using admetSAR (http://lmmd.ecust.edu.cn:8000), a free tool for evaluating chemical ADMET properties.
(23092397 (http://www.ncbi.nlm.nih.gov/pubmed/23092397))

Spectra

Mass Spec (NIST) Not Available

Spectra Spectrum Splash Key

Type Description (http://splash. ehnlab.ucdavis.edu/)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 10V, Positive
MS/MS (/spectra/ms_ms/99498)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 20V, Positive
MS/MS (/spectra/ms_ms/99499)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 40V, Positive
MS/MS (/spectra/ms_ms/99500)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 10V, Negative
MS/MS (/spectra/ms_ms/164640)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 20V, Negative
MS/MS (/spectra/ms_ms/164641)

Predicted Predicted LC-MS/MS Not Available

LC- Spectrum - 40V, Negative
MS/MS (/spectra/ms_ms/164642)

MS Mass Spectrum (Electron splash10-0ab9-9200000000- View in MoNA (http://mona. ehnlab.ucdavis.edu/#/spectra/splash/splash10-0ab9-920000

Ionization) b1095b8fe5973d23fdd6
(/spectra/ei_ms/750)

Taxonomy

Description This compound belongs to the class of organic compounds known as benzothiazepines. These are organic compounds containing a benzene fused to a thiazepine ring
nitrogen atom and a sulfur atom replacing two carbon atoms).

Kingdom Organic compounds (http://classy re.wishartlab.com/tax_nodes/C0000000)

Super Class Organoheterocyclic compounds (http://classy re.wishartlab.com/tax_nodes/C0000002)

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Class Benzothiazepines (http://classy re.wishartlab.com/tax_nodes/C0000317)

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)
Sub Class Not Available
Search drugs...
Direct Parent Benzothiazepines (http://classy re.wishartlab.com/tax_nodes/C0000317)

Alternative Parents Phenoxy compounds (http://classy re.wishartlab.com/tax_nodes/C0004742) / Methoxybenzenes (http://classy re.wishartlab.com/tax_nodes/C0004113)

Anisoles (http://classy re.wishartlab.com/tax_nodes/C0000138) / Alkyl aryl ethers (http://classy re.wishartlab.com/tax_nodes/C0000128) /
Alkylarylthioethers (http://classy re.wishartlab.com/tax_nodes/C0003863) / Tertiary carboxylic acid amides (http://classy re.wishartlab.com/tax_nodes/C000
Trialkylamines (http://classy re.wishartlab.com/tax_nodes/C0002239) / Amino acids and derivatives (http://classy re.wishartlab.com/tax_nodes/C0000347)
Lactams (http://classy re.wishartlab.com/tax_nodes/C0000160) / Carboxylic acid esters (http://classy re.wishartlab.com/tax_nodes/C0001238)

Substituents Benzothiazepine / Phenoxy compound / Aryl thioether / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / Alkylarylthioether / Monocyclic benzen
show 22 more

Molecular Aromatic heteropolycyclic compounds

Framework

External 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate (CHEBI:101278 (http://www.ebi.ac.uk/chebi/searchId

Descriptors

Targets

1. Voltage-dependent calcium channel gamma-1 subunit (/biodb/polypeptides/Q06432) Details (/biodb/polypeptides/Q06432)

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor

General Function:
Voltage-gated calcium channel activity
Speci c Function:
This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive
Ca(2+) channel may function only as a multiple subunit complex.
Gene Name:
CACNG1
Uniprot ID:
Q06432 (http://www.uniprot.org/uniprot/Q06432)
Molecular Weight:
25028.105 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
[PubMed:17139284 (http://www.ncbi.nlm.nih.gov/pubmed/17139284)]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
[PubMed:17016423 (http://www.ncbi.nlm.nih.gov/pubmed/17016423)]
3. Budriesi R, Ioan P, Carosati E, Cruciani G, Zhorov BS, Chiarini A: Ligands of diltiazem binding site: an overview of some chemotypes. Mini Rev Med Chem. 2009 Oct;9(12):1379-
88. [PubMed:19929811 (http://www.ncbi.nlm.nih.gov/pubmed/19929811)]
4. Romero M, Sanchez I, Pujol MD: New advances in the eld of calcium channel antagonists: cardiovascular effects and structure-activity relationships. Curr Med Chem
Cardiovasc Hematol Agents. 2003 Jun;1(2):113-41. [PubMed:15320693 (http://www.ncbi.nlm.nih.gov/pubmed/15320693)]

Enzymes

1. Cytochrome P450 3A4 (/biodb/polypeptides/P08684) Details (/biodb/polypeptides/P08684)

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate inhibitor

General Function:
Vitamin d3 25-hydroxylase activity

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Speci c Function:
CytochromesID P450
Pharmacology
are a groupInteractions References
of heme-thiolate Trials
monooxygenases. Economics PropertiesthisSpectra
In liver microsomes, enzyme isTaxonomy
involved in anTargets (1) Enzymes (7)
NADPH-dependent Transporters
electron (1)
transport
pathway.
Search drugs... It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-
hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684 (http://www.uniprot.org/uniprot/P08684)
Molecular Weight:
57342.67 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome
P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24.
[PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]
2. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and
CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 (http://www.ncbi.nlm.nih.gov/pubmed/12124305)]
3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

2. Cytochrome P450 3A5 (/biodb/polypeptides/P20815) Details (/biodb/polypeptides/P20815)

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate inhibitor

General Function:
Oxygen binding
Speci c Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport
pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815 (http://www.uniprot.org/uniprot/P20815)
Molecular Weight:
57108.065 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome
P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24.
[PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]
2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

3. Cytochrome P450 3A7 (/biodb/polypeptides/P24462) Details (/biodb/polypeptides/P24462)

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate inhibitor

General Function:
Oxygen binding
Speci c Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport
pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:

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P24462 (http://www.uniprot.org/uniprot/P24462)
ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy Targets (1) Enzymes (7) Transporters (1)
Molecular Weight:
57525.03
Search drugs... Da

References

1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link (http://medicine.iupui.edu/clinpharm/ddis/table.asp)]

4. Cytochrome P450 2C19 (/biodb/polypeptides/P33261) Details (/biodb/polypeptides/P33261)

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate

General Function:
Steroid hydroxylase activity
Speci c Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates,
diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261 (http://www.uniprot.org/uniprot/P33261)
Molecular Weight:
55930.545 Da

References

1. Kosuge K, Jun Y, Watanabe H, Kimura M, Nishimoto M, Ishizaki T, Ohashi K: Effects of CYP3A4 inhibition by diltiazem on pharmacokinetics and dynamics of diazepam in
relation to CYP2C19 genotype status. Drug Metab Dispos. 2001 Oct;29(10):1284-9. [PubMed:11560871 (http://www.ncbi.nlm.nih.gov/pubmed/11560871)]
2. McGinnity DF, Parker AJ, Soars M, Riley RJ: Automated de nition of the enzymology of drug oxidation by the major human drug metabolizing cytochrome P450s. Drug Metab
Dispos. 2000 Nov;28(11):1327-34. [PubMed:11038161 (http://www.ncbi.nlm.nih.gov/pubmed/11038161)]

5. Cytochrome P450 2D6 (/biodb/polypeptides/P10635) Details (/biodb/polypeptides/P10635)

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate inhibitor

General Function:
Steroid hydroxylase activity
Speci c Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics,
adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635 (http://www.uniprot.org/uniprot/P10635)
Molecular Weight:
55768.94 Da

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome
P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24.
[PubMed:19934256 (http://www.ncbi.nlm.nih.gov/pubmed/19934256)]

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