Diltiazem
- diltiazem
- 42399-41-7
- d-cis-Diltiazem
- Cardizem
- Dilcontin
- Create:2005-06-24
- Modify:2025-01-18
- Aldizem
- Cardil
- Cardizem
- CRD 401
- CRD-401
- CRD401
- Dilacor
- Dilacor XR
- Dilren
- Diltiazem
- Diltiazem Hydrochloride
- Diltiazem Malate
- Dilzem
- Tiazac
- diltiazem
- 42399-41-7
- d-cis-Diltiazem
- Cardizem
- Dilcontin
- Dilticard
- Endrydil
- Acalix
- Anoheal
- Dilzen
- Dilta-Hexal
- Incoril AP
- Diltiazemum
- Surazem
- Dilt-cd
- Dilacor-XR
- Cardil
- Dilren
- Tiazac
- (+)-cis-diltiazem
- (+)-diltiazem
- Diltiazemum [INN-Latin]
- Diltiazem free base
- (2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate
- Diltiazen
- Ditiaz
- HSDB 6528
- Diltiazem extended release
- UNII-EE92BBP03H
- EINECS 255-796-4
- EE92BBP03H
- Diltiazem (INN)
- D-(cis)-diltiazem
- BRN 3573079
- CHEBI:101278
- CHEMBL23
- DTXSID9022940
- 42399-41-7 (free base)
- (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
- [(2S,3S)-5-(2-dimethylaminoethyl)-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-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
- NCGC00024309-05
- DILTIAZEM [INN]
- Diltiazemum (INN-Latin)
- Diltiazem [INN:BAN]
- (+)-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-dihydro-1,5-benzothiazepin-3-yl] acetate
- DTXCID202940
- 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)-
- (+)-5-(2-(DIMETHYLAMINO)ETHYL)-CIS-2,3-DIHYDRO-3-HYDROXY-2-(P-METHOXYPHENYL)-1,5-BENZOTHIAZEPIN-4(5H)-ONE ACETATE (ESTER)
- 1,5-BENZOTHIAZEPIN-4(5H)-ONE, 3-(ACETYLOXY)-5-(U2-(DIMETHYLAMINO)ETHYL)-2,3-DIHYDRO-2-(4-METHOXYPHENYL)-, (+)-CIS-
- Surazem (TN)
- CAS-42399-41-7
- Cardizem (Hydrochloride)
- MK-793 (Malate)
- DTXSID50881104
- tetrahydrobenzo
- RG 83606 (Hydrochloride)
- (+)-cis-5-(2-(dimethylamino)ethyl)-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate ester
- (2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
- (2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo(b)(1,4)thiazepin-3-yl acetate
- (2S-cis)-3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
- 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)-
- 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
- C9F
- Diltiazem (Standard)
- Tocris-0685
- DILTIAZEM [MI]
- DITIAZ [VANDF]
- DILTIAZEM [HSDB]
- Prestwick0_000134
- Prestwick1_000134
- Prestwick2_000134
- Prestwick3_000134
- DILTIAZEM [VANDF]
- DILTIAZEM [WHO-DD]
- Lopac0_000327
- SCHEMBL17776
- BSPBio_000208
- BSPBio_001311
- BIDD:GT0548
- SPBio_002147
- BPBio1_000230
- GTPL2298
- HY-B0632R
- C05AE03
- C08DB01
- DTXCID30196864
- Bio1_000371
- Bio1_000860
- Bio1_001349
- HMS1791B13
- HMS1989B13
- HMS2089H09
- [b][1,4]thiazepin-3-yl acetate
- Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester
- cis-3-Acetoxy-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
- HY-B0632
- EINECS 260-060-0
- methoxyphenyl)-4-oxo-2,3,4,5-
- Tox21_110898
- AC-936
- BDBM50004704
- AKOS015897257
- Tox21_110898_1
- CCG-204422
- DB00343
- SDCCGSBI-0050315.P002
- NCGC00024309-02
- NCGC00024309-04
- NCGC00024309-06
- NCGC00024309-07
- NCGC00024309-08
- NCGC00024309-09
- NCGC00024309-10
- NCGC00024309-11
- NCGC00024309-17
- NCGC00024309-21
- NCGC00024309-27
- NCGC00024309-30
- (2S,3S)-5-[2-(dimethylamino)ethyl]-2-[4-(methyloxy)phenyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
- CS-0009567
- NS00068380
- ethyl 3-amino-1,2,4-triazole-1-carboxylate
- C06958
- D07845
- G12770
- (2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-
- A825887
- EN300-22049448
- Q422229
- W-106274
- BRD-K24023109-001-02-5
- BRD-K24023109-003-03-9
- BRD-K24023109-003-11-2
- BRD-K24023109-003-20-3
- BRD-K24023109-003-25-2
- BRD-K24023109-003-26-0
- 8-Chloro-1-methyl-6-phenyl-4H-2,3,5,10b-tetraaza-benzo[e]azulene
- (2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylacetate
- 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester(Diltiazem)Acetic acid
- Acetic acid (S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester
- Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester (Diltiazem)
- Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester(cis-(+)-Diltiazem)
- Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester; hydrochloride
- cis-Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester
- diltiazem;Acetic acid 5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester
193.96 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
180.56 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
194.75 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
193.4 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
178.02664 100
150.03224 56.70
72.07798 9.60
109.00677 9
137.05514 6.50
415.15645 100
178.02567 25.60
370.09726 9.90
312.09394 1.90
310.07944 1.30
178 100
415 20.82
179 7.11
370 6.31
312 5.11
178 100
150 8.21
179 5.91
137 5.11
180 4.30
- Diltiazem Hydrochloride (has salt form)
- Diltiazem Malate (has salt form)
- Diltiazem maleate (is active moiety of)
Use (kg; approx.) in Germany (2009): >5000
Use (kg) in USA (2002): 97800
Consumption (g per capita; approx.) in Germany (2009): 0.0611
Consumption (g per capita) in the USA (2002): 0.347
Excretion rate: 0.1
Calculated removal (%): 11.8
IMAP assessments - 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)-: Environment tier I assessment
IMAP assessments - 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)-: Human health tier I assessment
Diltiazem therapy is associated with a low rate of mild and transient elevations in serum aminotransferase levels which are usually asymptomatic and often resolve even with continuation of therapy. Clinically apparent, acute liver injury with jaundice due to diltiazem is rare and only isolated case reports have been published. In large case series of drug induced liver injury, calcium channel blockers are rarely mentioned. Most cases attributed to diltiazem have been marked by a short latency period (3 to 14 days) and features of hypersensitivity with fever, rash and eosinophilia. The pattern of liver injury was ranged from cholestatic to hepatocellular. Jaundice is often absent and usually mild. Autoantibody formation has not been described. Thus, liver injury from diltiazem is likely to be idiosyncratic in nature and is typically mild and self-limited with resolution within 4 to 8 weeks of stopping. Acute hepatic injury is listened as a possible adverse event in the diltiazem product label.
Likelihood score: C (probable but rare cause of clinically apparent liver injury).
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Based on limited data, amounts of diltiazem ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=HSUGRBWQSSZJOP-RTWAWAEBSA-N
- Australian Industrial Chemicals Introduction Scheme (AICIS)1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)-https://services.industrialchemicals.gov.au/search-assessments/
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/dl-cis-Diltiazemhttps://commonchemistry.cas.org/detail?cas_rn=56209-45-1
- ChemIDplusDiltiazem [INN:BAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0042399417cis-3-Acetoxy-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-onehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0056209451ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
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