Details of the Drug

General Information of Drug (ID: DME2H5T)

Drug Name
Cilastatin
Synonyms
Cilastatina; Cilastatine; Cilastatinum; Cilastatin Monosodium Salt; Cilastatin acid; Cilastatina [Spanish]; Cilastatine [French]; Cilastatinum [Latin]; MK0791; Cilastatin (INN); Cilastatin [INN:BAN]; MK-791; (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1S)-2,2-dimethylcyclopropyl]carbonyl}amino)hept-2-enoic acid; (Z)-(S)-6-carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine; (Z)-7-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Indication
Disease Entry ICD 11 Status REF
Bacteremia 1A73 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Endometritis N.A. Approved [1]
Peritonitis N.A. Approved [1]
Pelvic inflammatory disease GA05 Investigative [1]
Therapeutic Class
Antibiotics
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 358.5
Logarithm of the Partition Coefficient (xlogp) -1
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The renal clearance of drug is 0.10-0.16 L/h/kg [4]
Elimination
Cilastatin is 70% excreted in the urine [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hour [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 59.78 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.6% [7]
Vd
The volume of distribution (Vd) of drug is 14.6-20.1 L [4]
Water Solubility
The ability of drug to dissolve in water is measured as 25 mg/mL [3]
Chemical Identifiers
Formula
C16H26N2O5S
IUPAC Name
(Z)-7-[(2R)-2-amino-2-carboxyethyl]sulfanyl-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
Canonical SMILES
CC1(C[C@@H]1C(=O)N/C(=C\\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C
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
Cross-matching ID
PubChem CID
6435415
ChEBI ID
CHEMBL766
CAS Number
82009-34-5
UNII
141A6AMN38
DrugBank ID
DB01597
TTD ID
D02GIU
VARIDT ID
DR00505
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dehydropeptidase I (DPEP1) TTYUENF DPEP1_HUMAN Inhibitor [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Cilastatin FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5166).
3 BDDCS applied to over 900 drugs
4 Balfour JA, Bryson HM, Brogden RN: Imipenem/cilastatin: an update of its antibacterial activity, pharmacokinetics and therapeutic efficacy in the treatment of serious infections. Drugs. 1996 Jan;51(1):99-136. doi: 10.2165/00003495-199651010-00008.
5 FDA: Recarbrio Label
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 Pharmacokinetic study of pleural fluid penetration of carbapenem antibiotic agents in chemical pleurisy. Respir Med. 2006 Feb;100(2):324-31.