CYCLACILLIN

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB01000
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 Cyclacillin has been replaced by newer penicillin treatments.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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.drugbank.ca/drugs/DB01000	Binding Agent 1076
Solute carrier family 15 member 2 8 Target ID: CHEMBL1743125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7592745	Interacts 323	610.0 µM [IC50]
Oligopeptide transporter small intestine isoform 6 Target ID: CHEMBL4605 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7592745	Interacts 323	0.35 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.drugbank.ca/drugs/DB01000	Curative		Approved 8583	CYCLAPEN-W Approved Use For the treatment of bacterial infections caused by susceptible organisms. Launch Date 1979

C_max

Value	Dose	Analyte	Population
60.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3912193	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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

Value	Dose	Analyte	Population
62.6 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3912193	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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

T_1/2

Value	Dose	Analyte	Population
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3912193	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6576831	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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	PEPT1 60

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
PEPT1 60	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227492/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31444	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31444
eMolecules	35867682	https://www.emolecules.com/cgi-bin/more?vid=35867682
ZINC	ZINC000003830609	http://zinc15.docking.org/substances/ZINC000003830609

PubMed

Title	Date	PubMed
Topical formulations of serratiopeptidase: development and pharmacodynamic evaluation.	2010-01	20582192
Violacein-producing Collimonas sp. from the sea surface microlayer of costal waters in Trøndelag, Norway.	2009-11-12	20098599
Gender differences in kidney function.	2007-12	17638010
Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes.	2007-03	17120020
Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives.	2006-07	16597710
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.	2005-01	15567297
Efflux properties of basolateral peptide transporter in human intestinal cell line Caco-2.	2004-11	15340850
[Bacterial examination of sinusitis using antral puncture and irrigation].	2002-09	12400169
Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2.	1995-10-27	7592745
Sex- and species-related nephropathy of 6-(1-aminocyclohexanecarboxamido)penicillanic acid (cyclacillin) and its relationship to the metabolic disposition of the drug.	1974-07	4283678

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 `Mon Mar 31 17:45:03 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:03 GMT 2025`
Record UNII	72ZJ154X86
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYCLACILLIN

Official Name

English

CICLACILLIN

Preferred 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

CYCLACILLIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500