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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:diltiazem
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Accession:CHEBI:101278 term browser browse the term
Definition:A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.
Synonyms:exact_synonym: (2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
 related_synonym: (+)-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-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;   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;   Formula=C22H26N2O4S;   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-,21+/m1/s1;   InChIKey=HSUGRBWQSSZJOP-RTWAWAEBSA-N;   SMILES=COc1ccc(cc1)[C@@H]1Sc2ccccc2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O;   d-cis-diltiazem;   diltiazemum
 alt_id: CHEBI:4602
 xref: CAS:42399-41-7;   DrugBank:DB00343;   Drug_Central:897;   HMDB:HMDB0014487;   KEGG:C06958;   KEGG:D07845;   LINCS:LSM-2523
 xref_mesh: MESH:D004110
 xref: PMID:11937779;   PMID:16651034;   PMID:19167257;   PMID:23687551;   PMID:24261918;   PMID:25122162;   PMID:8369596;   Patent:DE1805714;   Patent:DE3415035;   Patent:US3562257;   Patent:US4552695;   Reaxys:3573079;   VSDB:1863;   Wikipedia:Diltiazem
 cyclic_relationship: is_conjugate_base_of CHEBI:82812;   is_enantiomer_of CHEBI:82813


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diltiazem term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO Diltiazem inhibits the reaction [ABCB1 protein results in increased transport of Digoxin] CTD PMID:11895100 NCBI chr 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709 		JBrowse link
G Adrb1 adrenoceptor beta 1 affects response to substance ISO ADRB1 protein polymorphism affects the susceptibility to Diltiazem CTD PMID:22192668 NCBI chr 1:255,771,962...255,774,973
Ensembl chr 1:255,771,597...255,807,259 		JBrowse link
G Cacna1c calcium voltage-gated channel subunit alpha1 C multiple interactions ISO Diltiazem inhibits the reaction [Iron-Dextran Complex affects the expression of CACNA1C protein] CTD PMID:27095094 NCBI chr 4:151,764,138...152,379,454
Ensembl chr 4:151,764,138...152,379,648 		JBrowse link
G Cacna1f calcium voltage-gated channel subunit alpha1 F multiple interactions ISO Diltiazem inhibits the reaction [CACNA1F protein results in increased transport of Barium] CTD PMID:14744918 NCBI chr  X:14,868,096...14,896,413
Ensembl chr  X:14,868,024...14,896,413 		JBrowse link
G Cat catalase multiple interactions EXP Diltiazem inhibits the reaction [Streptozocin results in decreased activity of CAT protein] CTD PMID:15957552 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Col1a1 collagen type I alpha 1 chain multiple interactions ISO Diltiazem inhibits the reaction [Iron-Dextran Complex results in increased expression of COL1A1 protein] CTD PMID:27095094 NCBI chr10:79,883,622...79,900,625
Ensembl chr10:79,883,622...79,900,624 		JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases methylation
multiple interactions
decreases activity
affects metabolic processing		 ISO CYP3A4 protein results in decreased methylation of Diltiazem
Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Midazolam]; Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]; Diltiazem inhibits the reaction [CYP3A4 protein results in increased oxidation of 7-benzyloxy-4-trifluoromethylcoumarin]; potassium ferricyanide inhibits the reaction [Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Midazolam]]; potassium ferricyanide inhibits the reaction [Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]]; potassium ferricyanide inhibits the reaction [Diltiazem results in decreased activity of CYP3A4 protein]; potassium ferricyanide promotes the reaction [Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Midazolam]]; potassium ferricyanide promotes the reaction [Diltiazem inhibits the reaction [CYP3A4 protein results in increased hydroxylation of Testosterone]]
CYP3A4 protein affects the metabolism of Diltiazem		 CTD PMID:15286053 PMID:15499178 PMID:19299527 PMID:22652334 NCBI chr12:9,207,978...9,230,064
Ensembl chr12:9,015,383...9,285,008 		JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 affects metabolic processing
decreases methylation		 ISO CYP3A5 protein affects the metabolism of Diltiazem; CYP3A5 protein polymorphism affects the metabolism of Diltiazem
CYP3A5 protein results in decreased methylation of Diltiazem		 CTD PMID:15499178 PMID:16024008 NCBI chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422 		JBrowse link
G Drd1 dopamine receptor D1 multiple interactions ISO Diltiazem inhibits the reaction [SCH 23390 binds to DRD1 protein] CTD PMID:9533112 NCBI chr17:10,540,440...10,544,971
Ensembl chr17:10,540,558...10,545,002 		JBrowse link
G Drd2 dopamine receptor D2 multiple interactions ISO Diltiazem inhibits the reaction [Raclopride binds to DRD2 protein] CTD PMID:9533112 NCBI chr 8:49,708,927...49,772,876
Ensembl chr 8:49,708,927...49,772,875 		JBrowse link
G Fth1 ferritin heavy chain 1 multiple interactions ISO Diltiazem inhibits the reaction [Iron-Dextran Complex results in increased expression of FTH1 protein] CTD PMID:27095094 NCBI chr 1:206,627,142...206,629,430
Ensembl chr 1:206,627,103...206,725,424 		JBrowse link
G Hamp hepcidin antimicrobial peptide multiple interactions ISO Diltiazem promotes the reaction [Iron-Dextran Complex results in increased expression of HAMP mRNA] CTD PMID:27095094 NCBI chr 1:86,170,926...86,172,865
Ensembl chr 1:86,170,901...86,172,891 		JBrowse link
G Hsf1 heat shock transcription factor 1 decreases activity ISO Diltiazem results in decreased activity of HSF1 protein CTD PMID:34170685 NCBI chr 7:108,196,040...108,223,011
Ensembl chr 7:108,196,056...108,223,011 		JBrowse link
G Il12a interleukin 12A multiple interactions
decreases expression		 ISO Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12A promoter]; Diltiazem inhibits the reaction [Lipopolysaccharides results in increased expression of [IL12A protein binds to IL12B protein]]; Diltiazem inhibits the reaction [Lipopolysaccharides results in increased expression of IL12A mRNA]
Diltiazem results in decreased expression of IL12A mRNA		 CTD PMID:15652234 NCBI chr 2:152,965,769...152,973,035
Ensembl chr 2:152,965,769...152,972,734 		JBrowse link
G Il12b interleukin 12B multiple interactions
decreases expression		 ISO Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12B promoter]; Diltiazem inhibits the reaction [Lipopolysaccharides results in increased expression of [IL12A protein binds to IL12B protein]]; Diltiazem inhibits the reaction [Lipopolysaccharides results in increased expression of IL12B mRNA]
Diltiazem results in decreased expression of IL12B mRNA		 CTD PMID:15652234 NCBI chr10:28,888,832...28,903,802
Ensembl chr10:28,893,008...28,902,903 		JBrowse link
G Kcnk10 potassium two pore domain channel subfamily K member 10 multiple interactions ISO Diltiazem inhibits the reaction [KCNK10 protein results in increased transport of Potassium] CTD PMID:16075240 NCBI chr 6:117,690,052...117,826,120
Ensembl chr 6:117,694,222...117,825,695 		JBrowse link
G Kcnk2 potassium two pore domain channel subfamily K member 2 multiple interactions ISO Diltiazem inhibits the reaction [KCNK2 protein results in increased transport of Potassium] CTD PMID:16075240 NCBI chr13:100,766,101...100,963,435
Ensembl chr13:100,766,113...100,963,435 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions EXP Diltiazem affects the reaction [Amphetamine results in increased phosphorylation of MAPK1 protein] CTD PMID:15329393 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions EXP Diltiazem affects the reaction [Amphetamine results in increased phosphorylation of MAPK3 protein] CTD PMID:15329393 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mapk8 mitogen-activated protein kinase 8 decreases activity EXP Diltiazem results in decreased activity of MAPK8 protein CTD PMID:11937779 NCBI chr16:8,638,897...8,721,960
Ensembl chr16:8,638,924...8,721,981 		JBrowse link
G Mmp13 matrix metallopeptidase 13 multiple interactions EXP Diltiazem promotes the reaction [ferrous sulfate results in increased expression of MMP13 protein] CTD PMID:27095094 NCBI chr 8:4,497,960...4,508,239
Ensembl chr 8:4,497,960...4,508,239 		JBrowse link
G Nfkb1 nuclear factor kappa B subunit 1 affects localization
multiple interactions		 ISO Diltiazem affects the localization of NFKB1 protein
[Diltiazem co-treated with Lipopolysaccharides] affects the localization of NFKB1 protein; Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12A promoter]; Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12B promoter]; Diltiazem results in decreased activity of [NFKB1 protein binds to RELA protein]		 CTD PMID:15652234 NCBI chr 2:224,016,214...224,132,135
Ensembl chr 2:224,016,214...224,110,404 		JBrowse link
G Rela RELA proto-oncogene, NF-kB subunit multiple interactions ISO Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12A promoter]; Diltiazem inhibits the reaction [[NFKB1 protein binds to RELA protein] which binds to IL12B promoter]; Diltiazem results in decreased activity of [NFKB1 protein binds to RELA protein] CTD PMID:15652234 NCBI chr 1:202,925,001...202,935,484
Ensembl chr 1:202,924,945...202,935,484 		JBrowse link
G Ren renin increases expression ISO Diltiazem results in increased expression of REN protein CTD PMID:2222951 NCBI chr13:44,796,260...44,807,491
Ensembl chr13:44,796,091...44,807,489 		JBrowse link
G RT1-Db1 RT1 class II, locus Db1 affects expression ISO Diltiazem affects the expression of HLA-DRB1 mRNA CTD PMID:25811541 NCBI chr20:4,548,664...4,558,237
Ensembl chr20:4,548,666...4,558,258 		JBrowse link
G RT1-Ha RT1 class II, locus Ha affects expression ISO Diltiazem affects the expression of HLA-DPA1 mRNA CTD PMID:25811541 NCBI chr20:4,760,631...4,770,662
Ensembl chr20:4,760,118...4,770,244 		JBrowse link
G Slc11a2 solute carrier family 11 member 2 multiple interactions ISO Diltiazem inhibits the reaction [Iron-Dextran Complex results in increased expression of SLC11A2 protein] CTD PMID:27095094 NCBI chr 7:131,503,076...131,540,246
Ensembl chr 7:131,503,081...131,540,145 		JBrowse link
G Slc22a1 solute carrier family 22 member 1 multiple interactions ISO Diltiazem inhibits the reaction [SLC22A1 protein results in increased uptake of 1-Methyl-4-phenylpyridinium] CTD PMID:21641380 NCBI chr 1:48,076,657...48,103,679
Ensembl chr 1:48,076,666...48,103,678 		JBrowse link
G Slc22a4 solute carrier family 22 member 4 multiple interactions ISO Diltiazem inhibits the reaction [SLC22A4 protein results in increased uptake of Tetraethylammonium] CTD PMID:21641380 NCBI chr10:38,133,333...38,179,932
Ensembl chr10:38,133,322...38,179,720 		JBrowse link
G Star steroidogenic acute regulatory protein multiple interactions ISO Diltiazem promotes the reaction [Cyclic AMP results in increased expression of STAR protein] CTD PMID:19822634 NCBI chr16:66,267,094...66,274,368
Ensembl chr16:66,264,807...66,271,672 		JBrowse link
G Timp1 TIMP metallopeptidase inhibitor 1 multiple interactions EXP Diltiazem inhibits the reaction [ferrous sulfate results in increased expression of TIMP1 protein] CTD PMID:27095094 NCBI chr  X:1,212,969...1,217,714
Ensembl chr  X:1,212,972...1,217,664 		JBrowse link
Term paths to the root
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Term Annotations click to browse term
  CHEBI ontology 19874
    role 19844
      biological role 19842
        pharmacological role 19072
          antagonist 17233
            calcium channel blocker 7164
              diltiazem 31
Path 2
Term Annotations click to browse term
  CHEBI ontology 19874
    subatomic particle 19872
      composite particle 19872
        hadron 19872
          baryon 19872
            nucleon 19872
              atomic nucleus 19872
                atom 19872
                  main group element atom 19811
                    p-block element atom 19811
                      carbon group element atom 19751
                        carbon atom 19748
                          organic molecular entity 19748
                            heteroorganic entity 19505
                              organochalcogen compound 19268
                                organooxygen compound 19184
                                  carbon oxoacid 18654
                                    carboxylic acid 18651
                                      carboacyl group 17694
                                        univalent carboacyl group 17694
                                          carbamoyl group 17545
                                            carboxamide 17545
                                              lactam 8389
                                                5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate 31
                                                  diltiazem 31
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