cilastatin

Also known as MK 0791, (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, (L)-7-(2-amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid

Cilastatin inhibits the human enzyme dehydropeptidase.

Chemical data

Formula: C16H26N2O5S
Molecular weight: 358.5 g/mol
IUPAC name: (Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
SMILES: CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C
InChIKey: DHSUYTOATWAVLW-WFVMDLQDSA-N
XLogP: -1
Polar surface area: 155 Å²
H-bond donors: 4
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1985
Admin. routes: parenteral
Indications: infection, osteomyelitis, urinary tract infection, bacterial pneumonia

via ChEMBL · EBI

Research

2,028 papers

via PubMed

Wikidata facts

Mass: 358.156243
Has use: medication

Show 7 more facts

subject has role: protease inhibitor
chemical formula: C₁₆H₂₆N₂O₅S
medical condition treated: bacterial infectious disease
World Health Organisation international non-proprietary name: cilastatin
isomeric SMILES: CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C
canonical SMILES: CC1(CC1C(=O)NC(=CCCCCSCC(C(=O)O)N)C(=O)O)C
Commons category: Cilastatin

Sources (3)

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Encyclopedic overview

2 sections

Contents

Uses
References

{{Drugbox | Watchedfields = changed | verifiedrevid = 460036539 | IUPAC_name = (Z)-7-[(2R)-2-Amino-3-hydroxy-3-oxopropyl]sulfanyl-2-{[(1S)-2,2-dimethylcyclopropanecarbonyl]amino}hept-2-enoic acid | image = Cilastatin.svg | image_class = skin-invert-image | width = 200 | alt = | image2 = Cilastatin ball-and-stick.png | image_class2 = bg-transparent | alt2 =

Excerpted from Wikipedia’s “cilastatin” article, available under the CC BY-SA 4.0 licence.

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