U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3(N)CCCCC3)C(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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68003493

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 Cyclacillin has been replaced by newer penicillin treatments.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

Curator's Comment: Alburn, H.E., Grant, N.H. and Fletcher, H. III; US.Patent 3,194,802; assigned to American Home Products Corporation.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CYCLAPEN-W

Approved Use

For the treatment of bacterial infections caused by susceptible organisms.

Launch Date

1979
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.1 mg/L
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
25.6 μg/mL
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
27 μg/mL
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
62.6 mg × h/L
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
42 μg × h/mL
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
44 μg × h/mL
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.9 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.7 h
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
0.79 h
25 mg/kg 3 times / day steady-state, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CYCLACILLIN serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Sex- and species-related nephropathy of 6-(1-aminocyclohexanecarboxamido)penicillanic acid (cyclacillin) and its relationship to the metabolic disposition of the drug.
1974 Jul
Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2.
1995 Oct 27
[Bacterial examination of sinusitis using antral puncture and irrigation].
2002 Sep
Efflux properties of basolateral peptide transporter in human intestinal cell line Caco-2.
2004 Nov
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
2005 Jan
Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives.
2006 Jul
Gender differences in kidney function.
2007 Dec
Violacein-producing Collimonas sp. from the sea surface microlayer of costal waters in Trøndelag, Norway.
2009 Nov 12
Patents

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
Created
by admin
on Fri Dec 15 15:03:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:43 GMT 2023
Record UNII
72ZJ154X86
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLACILLIN
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
CICLACILLIN [MART.]
Common Name English
Ciclacillin [WHO-DD]
Common Name English
6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Systematic Name English
CYCLACILLIN [USAN]
Common Name English
WY-4508
Code English
CYCLAPEN-W
Brand Name English
ciclacillin [INN]
Common Name English
CYCLACILLIN [ORANGE BOOK]
Common Name English
NSC-88789
Code English
VASTCILLIN
Brand Name English
CYCLACILLIN [VANDF]
Common Name English
CICLACILLIN [JAN]
Common Name English
CICLACILLIN
INN   MART.   WHO-DD  
INN  
Official Name English
CYCLACILLIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9022861
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
RXCUI
2968
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PRIMARY RxNorm
INN
2764
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PRIMARY
ChEMBL
CHEMBL1200356
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PRIMARY
MESH
D003493
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-470-8
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PRIMARY
CHEBI
31444
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PRIMARY
CAS
3485-14-1
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PRIMARY
FDA UNII
72ZJ154X86
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
DRUG CENTRAL
632
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
PUBCHEM
19003
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
WIKIPEDIA
CICLACILLIN
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
IUPHAR
4817
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
NSC
88789
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
EVMPD
SUB06232MIG
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
DRUG BANK
DB01000
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
MERCK INDEX
m3965
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY Merck Index
SMS_ID
100000088593
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
NCI_THESAURUS
C47464
Created by admin on Fri Dec 15 15:03:43 GMT 2023 , Edited by admin on Fri Dec 15 15:03:43 GMT 2023
PRIMARY
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