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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H26N2O5S
Molecular Weight 358.453
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CILASTATIN

SMILES

CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C(O)=O)C(O)=O

InChI

InChIKey=DHSUYTOATWAVLW-WFVMDLQDSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H26N2O5S
Molecular Weight 358.453
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

PRIMAXIN® is a combination of cilastatin and imipenem. Cilastatin is a specific and reversible renal dehydropeptidase-I inhibitor. Imipenem is a penem antibacterial drug. Since the antibiotic, imipenem, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to block the metabolism and thus the inactivation of imipenem so that antibacterial levels of imipenem can be attained in the urine. However, cilastatin in and of itself does not have any antibacterial activity. It also prevents the metabolism of leukotriene D4 to leukotriene E4 through the inhibition of leukotriene D4 dipeptidase.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.73 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PRIMAXIN
PubMed

PubMed

TitleDatePubMed
Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids.
1987 Jun
The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA.
1995 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Cilastatin attenuates cisplatin-induced proximal tubular cell damage.
2010 Aug
Patents

Sample Use Guides

In Vivo Use Guide
For adult patients with normal renal function (creatinine clearance of greater than or equal to 90 mL/min), the recommended PRIMAXIN® dosage regimens are: 500 mg every 6 hours OR 1000 mg every 8 hours OR 1000 mg every 6 hours.
Route of Administration: Intravenous
In Vitro Use Guide
Imipenem hydrolysis by both enzymes (human dehydropeptidase I and cphA from Aeromonas hydrophila) was seen to be cilastatin sensitive. The 50% inhibitory concentrations were 0.3 +/- 0.01 and 178 +/- 11 uM (n = 8), respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:03 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:03 UTC 2019
Record UNII
141A6AMN38
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CILASTATIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CILASTATIN [WHO-DD]
Common Name English
CILASTATIN [VANDF]
Common Name English
CILASTATIN [MI]
Common Name English
CILASTATIN [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C783
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NDF-RT N0000175513
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
NDF-RT N0000175514
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.1 (IMI/CIL)
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
LIVERTOX 207
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
Code System Code Type Description
WIKIPEDIA
CILASTATIN
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
INN
5457
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
NCI_THESAURUS
C61679
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
CAS
82009-34-5
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
ChEMBL
CHEMBL766
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
RXCUI
2540
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY RxNorm
MESH
D015377
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
EVMPD
SUB06264MIG
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
ECHA (EC/EINECS)
279-875-8
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
EPA CompTox
82009-34-5
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
DRUG BANK
DB01597
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
IUPHAR
5166
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
MERCK INDEX
M3544
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY Merck Index
PUBCHEM
6435415
Created by admin on Mon Oct 21 19:50:03 UTC 2019 , Edited by admin on Mon Oct 21 19:50:03 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY