Diltiazem hydrochloride |
![]() Last updated: 16/09/2025 |
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(Also known as: diltiazem HCl) |
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A non-dihydropyridine (non-DHP) veterinary drug | |
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Used in the treatment of atrial fibrillation, supraventricular tachycardias, hypertrophic cardiomyopathy and hypertension | |
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Dogs; Cats |
Approval status |
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Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Diltiazem hydrochloride exhibits both geometric (cis-trans) isomerism and chiral (optical) isomerism, due to the presence of two asymmetric carbon atoms at positions C-2 and C-3 of its benzothiazepine ring system. These centres allow for the formation of four stereoisomers: two cis and two trans, each with (R,R) and (S,S) configurations. The clinically used form is the d-cis-(2S,3S) isomer, which has been shown to possess optimal desirable pharmacokinetics. | |
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C₂₂H₂₇ClN₂O₄S | |
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CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC.Cl | |
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CC(=O)O[C@@H]1[C@@H](SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC.Cl | |
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HDRXZJPWHTXQRI-BHDTVMLSSA-N | |
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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 | |
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Yes |
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Common Name | Relationship | Link |
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diltiazem hydrochloride | - | ![]() |
diltiazem | Parent | ![]() |
General status |
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Vasodilator, Medicinal drug | |
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Unclassified substance | |
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Synthetic | |
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A calcium channel blocker | |
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[Voltage-dependent calcium channel gamma-1 subunit, Antagonist] | |
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33286-22-5 | |
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38411-61-9 | |
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251-443-3 | |
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62920 | |
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Cardiobascular system: Calcium channel blockers | |
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QC08DB01 | |
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No | |
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451.0 | |
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[(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate;hydrochloride | |
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White crystalline powder | |
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Commercial |
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Current | |||
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1960s, first synthesised Japan; 1971, first research published; 1982, first approvals for human use USA; 1990s, first vet use | |||
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Usually supplied in tablet form for oral administration | |||
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The production of diltiazem hydrochloride involves a multi-step synthesis centred around constructing its benzothiazepine ring system with precise stereochemistry. A key intermediate, O-desacetyldiltiazem, is first acetylated using acetic anhydride, triethylamine, and DMAP in dichloromethane under reflux conditions to form the acetylated lactam. This intermediate is then treated with anhydrous hydrogen chloride gas in methanol, adjusting the pH to around 2, which converts the compound into its hydrochloride salt form. The final product is precipitated by adding ether, filtered, and washed to yield diltiazem hydrochloride. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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465 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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231 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Decomposes before boiling | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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212 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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6.17 X 1002 | Calculated | - | |||||||
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2.79 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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8.90 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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740 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
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Aquatic ecotoxicology |
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15.0 | R4 R = Peer reviewed scientific publications Oryzias latipes4 = Verified data |
Moderate | ||||||||
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28.0 | R4 R = Peer reviewed scientific publications Daphnia magna4 = Verified data |
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General |
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High (class III) | - | - | ||||||||
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740 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Mouse4 = Verified data |
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Intraperitoneal LDLo = 220 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
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Intravenous LD₅₀ = 61 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
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Metabolised in the liver and excreted in the urine | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
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Health issues |
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May cause anorexia, vomiting, diarrhoea, abdominal pain, paralytic ileus and dyspepsia Teratogenic |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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diltiazem hydrochloride | ||
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Record last updated: | 16/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |