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Biological and Environmental Research Ontology
| Preferred Name | cilastatin | |
| Synonyms |
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid cilastatine cilastatina (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid (Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine cilastatinum cilastatin (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid |
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| Definitions |
The thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_3697 |
|
| alternative term |
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid cilastatine cilastatina (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid (Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine cilastatinum cilastatin (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
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| bearer of |
http://purl.obolibrary.org/obo/CHEBI_37670 http://purl.obolibrary.org/obo/CHEBI_76926 |
|
| charge |
0
|
|
| database_cross_reference |
Patent:EP72014 Drug_Central:640 DrugBank:DB01597 Patent:EP48025 PMID:3495664 KEGG:D07698 Beilstein:6895069 PDBeChem:CIL Patent:EP48301 KEGG:C01675 Reaxys:6895069 Wikipedia:Cilastatin CAS:82009-34-5
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|
| definition |
The thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products. Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4.
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|
| formula |
C16H26N2O5S
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|
| has_alternative_id |
CHEBI:41538 CHEBI:143261 CHEBI:109454
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|
| has_exact_synonym |
(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
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|
| has_obo_namespace |
chebi_ontology
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| has_related_synonym |
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid cilastatine cilastatina (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid (Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine cilastatinum cilastatin
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|
| id |
CHEBI:3697
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| in_subset | ||
| inchi |
InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1
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|
| inchikey |
DHSUYTOATWAVLW-WFVMDLQDSA-N
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| is_conjugate_acid_of | ||
| label |
cilastatin
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|
| mass |
358.45300
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|
| monoisotopicmass |
358.15624
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|
| notation |
CHEBI:3697
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|
| prefLabel |
cilastatin
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| RO_0000087 |
http://purl.obolibrary.org/obo/CHEBI_37670 http://purl.obolibrary.org/obo/CHEBI_76926 |
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| smiles |
CC1(C)C[C@@H]1C(=O)N\C(C(O)=O)=C/CCCCSC[C@H](N)C(O)=O
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|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_83824 http://purl.obolibrary.org/obo/CHEBI_16385 |
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