U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23N3O4S
Molecular Weight 341.426
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLACILLIN

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=HGBLNBBNRORJKI-WCABBAIRSA-N
InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H23N3O4S
Molecular Weight 341.426
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cyclacillin is a cyclohexylamido analog of penicillanic acid. It is used for the treatment of bacterial infections caused by susceptible organisms. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin has been replaced by newer penicillin treatments.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
610.0 µM [IC50]
0.35 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CYCLAPEN-W

Cmax

ValueDoseCo-administeredAnalytePopulation
60.1 mg/L
1500 mg single, oral
CYCLACILLIN plasma
Homo sapiens
25.6 μg/mL
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens
27 μg/mL
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
62.6 mg × h/L
1500 mg single, oral
CYCLACILLIN plasma
Homo sapiens
42 μg × h/mL
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens
44 μg × h/mL
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.9 h
1500 mg single, oral
CYCLACILLIN plasma
Homo sapiens
0.7 h
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens
0.79 h
25 mg/kg 3 times / day steady-state, oral
CYCLACILLIN serum
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The MIC values for cyclacillin were: 31.25 ug/ml (Salmonella typhosa), 62.5 ug/ml (Salmonella enteritidis, paratyphi A), 0.98-7.8 ug/ml (Staphylococcus aureus), 125 ug/ml (Escherichia coli).
Substance Class Chemical
Record UNII
72ZJ154X86
Record Status Validated (UNII)
Record Version