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Cilastatin

CHEBI:CHEBI_3697

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.

Chemical Information

Molecular Formula
C16H26N2O5S
Molecular Mass
358.45300
Charge
0
SMILES
CC1(C)C[C@@H]1C(=O)N\C(C(O)=O)=C/CCCCSC[C@H](N)C(O)=O
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
InChIKey
DHSUYTOATWAVLW-WFVMDLQDSA-N

Alternative Names

  • (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid
  • (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
  • (Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid
  • cilastatin
  • cilastatina
  • cilastatine
  • cilastatinum

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
2540
oboInOwl#hasDbXref
Wikipedia:Cilastatin
core#notation
CHEBI:3697

Additional References

Wikipedia:Cilastatin

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
2540
oboInOwl#hasDbXref
Wikipedia:Cilastatin
oboInOwl#hasAlternativeId
CHEBI:41538
oboInOwl#id
CHEBI:3697
core#notation
CHEBI:3697
listing_expiration_date
20251231
dosage_form
POWDER
marketing_start_date
20150824
product_type
BULK INGREDIENT
marketing_category
EXPORT ONLY
active_ingredient_strength
1 kg/kg
package_marketing_start_date
07-OCT-22
generic_name
Cilastatin Sodium
active_ingredient_name
CILASTATIN SODIUM
product_ndc
69806-0094
labeler_name
Merck Sharp & Dohme Corp.
spl_id
87a8ac0f-e586-447a-abf6-611db2a11f9f
package_ndc
69806-0094-0
package_description
1 CAN in 1 BOX (69806-0094-0) / 12 kg in 1 CAN
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_76926
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_59512
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http://www.w3.org/2002/07/owl#Class
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https://w3id.org/def/predibionto#has_side_effect22338
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http://purl.obolibrary.org/obo/CHEBI_59512
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t207592
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t3444752