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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H24N2O5S.Na.H
Molecular Weight 380.435
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CILASTATIN SODIUM

SMILES

[H+].[Na+].CC1(C)C[C@@H]1C(=O)N\C(=C/CCCCSC[C@H](N)C([O-])=O)C([O-])=O

InChI

InChIKey=QXPBTTUOVWMPJN-QBNHLFMHSA-M
InChI=1S/C16H26N2O5S.Na/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);/q;+1/p-1/b12-6-;/t10-,11+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C16H24N2O5S
Molecular Weight 356.437
Charge -2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Molecular Formula H
Molecular Weight 1.0079
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Primary TargetPharmacologyConditionPotency
0.73 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PRIMAXIN

AUC

ValueDoseCo-administeredAnalytePopulation
82.19 mg × h/L
500 mg 4 times / day multiple, intravenous
CILASTATIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
500 mg 4 times / day multiple, intravenous
CILASTATIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

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
Record UNII
5428WXZ74M
Record Status Validated (UNII)
Record Version