Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Diltiazem hydrochloride [USAN:USP:JAN]
RN: 33286-22-5
UNII: OLH94387TE
InChIKey: HDRXZJPWHTXQRI-BHDTVMLSSA-N

Note

  • A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.

Molecular Formula

  • C22-H26-N2-O4-S.Cl-H

Molecular Weight

  • 450.9843
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
  • Vasodilator (Coronary)

Names and Synonyms

Name of Substance

  • Diltiazem hydrochloride [USAN:USP:JAN]

Synonyms

  • (+)-5-(2-(Dimethylamino)ethyl)-cis-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate (ester) monohydrochloride
  • 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, monohydrochloride, (+)-cis-
  • Adizem
  • Adizem-CD
  • Altiazem
  • Altiazem Retard
  • Altiazem RR
  • Anginyl
  • Angitil
  • Angizem
  • Apo-diltiazem
  • Bi-Tildiem
  • Britiazim
  • Bruzem
  • Calcicard
  • Calnurs
  • Cardiazem
  • Cardil
  • Cardil Retard
  • Cardizem
  • Cardizem CD
  • Cardizem LA
  • Cardizem Retard
  • Cardizem SR
  • Carex
  • Cartia XT
  • Carzem
  • Cirilen
  • Cirilen AP
  • Citizen
  • Clarute
  • Coras
  • Corazet
  • CRD 401
  • CRD-401
  • Dazil
  • Deltazen
  • Diatal
  • Dil-Sonaramia
  • Dilacor
  • Dilacor XR
  • Dilacor XR Extended Release Capsules
  • Diladel
  • Dilatam
  • Dilatam 120
  • Dilatame
  • Dilcard
  • Dilem
  • Dilfar
  • Dilgard
  • Dilicardin
  • Dilpral
  • Dilren
  • Dilrene
  • Dilsal
  • Dilso
  • Dilt-CD
  • Dilt-XR
  • Diltahexal
  • Diltam
  • Diltan
  • Diltan SR
  • Diltelan
  • Diltia XT
  • Diltiasyn
  • Diltiazem AWD
  • Diltiazem Basics
  • Diltiazem chloridrate
  • Diltiazem Eu Rho
  • Diltiazem GNR
  • Diltiazem HCl
  • Diltiazem Henning
  • Diltiazem hydrochloride
  • Diltiazem Merck
  • Diltiazem MSD
  • Diltiazem Stada
  • Diltiazem UPSA
  • Diltiazem Verla
  • Diltiazem-Cophar
  • Diltiazem-GRY
  • Diltiazem-Isis
  • Diltiazem-Mepha
  • Diltikor
  • Diltime
  • Diltzac
  • Dilzem
  • Dilzem Retard
  • Dilzem RR
  • Dilzene
  • Dilzereal 90 Retard
  • Dilzicardin
  • Dinisor
  • Dinisor Retard
  • Doclis
  • Dodexen
  • Dodexen A.P.
  • Dolizem
  • Dyalac
  • EINECS 251-443-3
  • Entrydil
  • Etizen
  • Etyzen
  • Farmabes
  • Gadoserin
  • Hart
  • Helsibon
  • Herben
  • Herbesser
  • Herbesser 180 SR
  • Herbesser 60
  • Herbesser 90 SR
  • Hesor
  • Incoril
  • Iski
  • Iski-90 SR
  • Kaltiazen
  • Kardil
  • Lacerol
  • Levozem
  • Longazem
  • Lytelsen
  • Masdil
  • Metazem
  • Miocardie
  • Mono-Tildiem
  • Myonil
  • Myonil Retard
  • Novo-Diltazem
  • Oxycardil
  • Pazeadin
  • Pentilzeno
  • Poltiazem
  • Presoken
  • Presokin A. P.
  • RG 83606
  • Slozen
  • Surazem
  • Syn-Diltiazem
  • Tazem
  • Taztia XT
  • Tiadil
  • Tiaves
  • Tiazac
  • Tiazac extended release
  • Tilazem
  • Tilazem 90
  • Tilazem AS 60
  • Tilazem AS 90
  • Tildiem
  • Tildiem CR
  • Tildiem LA
  • Tildiem Retard
  • Trumsal
  • Ubicor
  • Uni Masdil
  • UNII-OLH94387TE
  • Verelan
  • Verelan PM
  • Viazem SR
  • Viazem XL
  • WL Diltiazem
  • Zildem
  • Ziruvate

Systematic Names

  • (2S-cis)-3-Acetoxy-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one monohydrochloride
  • 1,5-Benzothiazepin-4(5H)-one, 2,3-dihydro-3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-, monohydrochloride, cis-(+)-
  • 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, monohydrochloride, (+)-cis-

Superlist Names

  • Diltiazem hydrochloride
  • Tiazac

Registry Numbers

CAS Registry Number

  • 33286-22-5

FDA UNII

  • OLH94387TE

System Generated Number

  • 0033286225

Molecular Formulas

Molecular Formula

  • C22-H26-N2-O4-S.Cl-H

Molecular Formula Fragments

  • C22-H26-N2-O4-S
  • Cl-H
  • COMPONENT

Structure Descriptors

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

InChIKey

HDRXZJPWHTXQRI-BHDTVMLSSA-N

Smiles

Cl.COc1ccc(cc1)[C@@H]2Sc3ccccc3N(CCN(C)C)C(=O)[C@@H]2OC(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 40mg/kg (40mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 4843, 1987.
man LDLo oral 21mg/kg (21mg/kg) CARDIAC: PULSE RATE

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Postgraduate Medical Journal. Vol. 69, Pg. 474, 1993.
man TDLo oral 3429ug/kg/2D- (3.429mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Lancet. Vol. 341, Pg. 967, 1993.
man TDLo oral 15420ug/kg/7D (15.42mg/kg)   Archives of Internal Medicine. Vol. 151, Pg. 1869, 1991.
man TDLo oral 15420ug/kg/7D (15.42mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Archives of Internal Medicine. Vol. 151, Pg. 1869, 1991.
man TDLo oral 36mg/kg/13D-I (36mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" Gastroenterology. Vol. 88, Pg. 1260, 1985.
mouse LD50 intraperitoneal 177mg/kg (177mg/kg)   Journal of Medicinal Chemistry. Vol. 29, Pg. 820, 1986.
mouse LD50 intravenous 58mg/kg (58mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
mouse LD50 oral 508mg/kg (508mg/kg)   Journal of Medicinal Chemistry. Vol. 33, Pg. 2192, 1990.
mouse LD50 subcutaneous 260mg/kg (260mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TETANY
Japan Medical Gazette. Vol. 11(1), Pg. 12, 1974.
rat LD50 oral 560mg/kg (560mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat LD50 subcutaneous 520mg/kg (520mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
women LDLo oral 120mg/kg (120mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION Human & Experimental Toxicology. Vol. 13, Pg. 161, 1994.
women TDLo oral 7200ug/kg/2D- (7.2mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women TDLo oral 7200ug/kg (7.2mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women TDLo oral 8400ug/kg (8.4mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE
Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
women TDLo oral 18mg/kg (18mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women TDLo oral 18mg/kg (18mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women TDLo oral 19mg/kg (19mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Postgraduate Medical Journal. Vol. 64, Pg. 467, 1988.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 207.5-212 deg C   EXP
log P (octanol-water) 2.7 (none)   EXP
Water Solubility 12.3 mg/L 25 EST
Vapor Pressure 1.54E-11 mm Hg 25 EST
Henry's Law Constant 8.61E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.80E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.