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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17ClN3O5S.Na.H2O
Molecular Weight 475.878
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOXACILLIN SODIUM

SMILES

O.[Na+].CC1=C(C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C([O-])=O)C(=NO1)C4=CC=CC=C4Cl

InChI

InChIKey=KCUWTKOTPIUBRI-VICXVTCVSA-M
InChI=1S/C19H18ClN3O5S.Na.H2O/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23;;/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1

HIDE SMILES / InChI
Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.881
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Cloxacillin is a derivative of penicillin for the treatment of broad spectrum of bacterial infections. The drug exerts its action by inhiiting bacterial beta-lactamase (penicillin-binding proteins).

CNS Activity

CNS Penetrant
2588
Sources: www.ncbi.nlm.nih.gov/pubmed/25582344
Curator's Comment: Cloxacillin does not significantly cross the blood brain barrier.

Originator

Approval Year

1965
159
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8583
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1277730/
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CLOXACILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
310 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1277730/
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CLOXACILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
43 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1277730/
2 g single, intravenous
dose: 2 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CLOXACILLIN serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
12 g 1 times / day steady, intravenous
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: steady
Dose: 12 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28786715/
unhealthy, 21 years
Health Status: unhealthy
Age Group: 21 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28786715/
Disc. AE: Agranulocytosis...
AEs leading to
discontinuation/dose reduction:
Agranulocytosis (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28786715/
12 g 1 times / day multiple, intravenous
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 12 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/29665445/
unhealthy, 66 - 80 years
Health Status: unhealthy
Age Group: 66 - 80 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29665445/
Disc. AE: Acute kidney injury...
AEs leading to
discontinuation/dose reduction:
Acute kidney injury (23 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/29665445/
9.8 g 1 times / day multiple, intravenous
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
Other AEs: Neutropenia, Rash...
Other AEs:
Neutropenia (2 patients)
Rash (4 patients)
Fever (5 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
AEs

AEs

AESignificanceDosePopulation
Agranulocytosis 1 patient
Disc. AE
12 g 1 times / day steady, intravenous
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: steady
Dose: 12 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28786715/
unhealthy, 21 years
Health Status: unhealthy
Age Group: 21 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/28786715/
Acute kidney injury 23 patients
Disc. AE
12 g 1 times / day multiple, intravenous
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 12 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/29665445/
unhealthy, 66 - 80 years
Health Status: unhealthy
Age Group: 66 - 80 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29665445/
Neutropenia 2 patients
9.8 g 1 times / day multiple, intravenous
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
Rash 4 patients
9.8 g 1 times / day multiple, intravenous
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
Fever 5 patients
9.8 g 1 times / day multiple, intravenous
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/10090118/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
PEPT1
27

OAT3
747

OAT1
725

OAT4
150

BSEP
550
PEPT1
60

P-gp
2052

PEPT2
37
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
PEPT1
29
 weak [Ki 3000 uM]
OAT3
749
 yes [IC50 13 uM]
OAT4
150
 yes [IC50 21 uM]
BSEP
554
 yes [IC50 41.6 uM]
OAT1
730
 yes [IC50 550 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 likely
yes (pharmacogenomic study)
Comment: Compared with the other groups, carriers of the 1236CC genotype had a significantly lower mean Cloxacillin Cmax (−53%; P = 0.013) and AUC0−∞ (−40%; P = 0.044), and a significantly higher mean apparent oral clearance (35%; P = 0.013).
PEPT2
37
 moderate [Ki 950 uM]
PEPT1
60
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:49566
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49566
ChemicalBook
CB7163623
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7163623
MolPort
MolPort-006-110-156
https://www.molport.com/shop/molecule-link/MolPort-006-110-156
ZINC
ZINC000003875417
http://zinc15.docking.org/substances/ZINC000003875417
PubMed

PubMed

TitleDatePubMed
[Treatment of mastitis in general practice].
2003-11-06
Empyema thoracis: a 10-year comparative review of hospitalised children from south Asia.
2003-11
AmpC cephalosporinase hyperproduction in Acinetobacter baumannii clinical strains.
2003-10
Large-volume sample stacking combined with separation by 2-hydroxypropyl-beta-cyclodextrin for analysis of isoxyzolylpenicillins by capillary electrophoresis.
2003-09
Case 1--a 65-year-old female patient presented to Kijabe Mission Hospital with a complaint of left thigh swelling.
2003-08-22
[Drying off cows: a comparative study with two dry cow products].
2003-08-15
NmcA carbapenem-hydrolyzing enzyme in Enterobacter cloacae in North America.
2003-08
Pattern of aerobic bacteria with their drug susceptibility of surgical inpatients.
2003-07
Suspected chlamydial keratoconjunctivitis in British cattle.
2003-06-21
Use of antibiotic-loaded polymethyl methacrylate beads in the management of musculoskeletal sepsis--a retrospective study.
2003-06
Risk of anaphylaxis in a hospital population in relation to the use of various drugs: an international study.
2003-05-08
Lucio's phenomenon.
2003-05
Infective endocarditis and cardiac surgery in intravenous drug abusers and HIV-1 infected patients.
2003-05
Neonatal Staphylococcal scalded skin syndrome complicating ileal atresia.
2003-05
[Vesicular/pustular lesions in a patient with atopic dermatitis].
2003-05
Determination of organochlorine pesticides in agricultural soil with special reference to gamma-HCH degradation by Pseudomonas strains.
2003-05
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.
2003-04-12
Staphylococcus aureus subcutaneous abscess complicating acupuncture: need for implementation of proper infection control guidelines.
2003-04
[Relapsing Staphylococcus lugdunensis septic arthritis associated with a knee prosthesis].
2003-04
[Community-acquired necrotizing pneumonia associated with bacteriemia and metastatic septic foci].
2003-04
A severity score for complicated skin and soft tissue infections derived from phase III studies of linezolid.
2003-04
Folliculitis decalvans--a retrospective study in a tertiary referred centre, over five years.
2003-02
[Simultaneous determination of five penicillins in muscle, liver and kidney from slaughtered animals using liquid chromatography coupled with electrospray ionization tandem mass spectrometry].
2003-02
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.
2003-02
Occurrence and detection of AmpC beta-lactamases among Gram-negative clinical isolates using a modified three-dimensional test at Guru Tegh Bahadur Hospital, Delhi, India.
2003-02
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.
2003-02
Efficacy of intramammary tilmicosin and risk factors for cure of Staphylococcus aureus infection in the dry period.
2003-01
Comparison of beta-lactamases of classes A and D: 1.5-A crystallographic structure of the class D OXA-1 oxacillinase.
2003-01
Acute bacterial skin infections in pediatric medicine: current issues in presentation and treatment.
2003
Dicloxacillin: a higher risk than cloxacillin for infusion phlebitis.
2003
[Therapeutic effect of some antibiotics on experimental staphylococcal infection and its correlation with in vitro activity of antibiotics in sub-inhibitory concentration against Staphylococcus aureus strains].
2003
Field trials on the prophylaxis of intramammary infections in pregnant heifers.
2003
Confirmatory analysis of beta-lactam antibiotics in kidney tissue by liquid chromatography/electrospray ionization selective reaction monitoring ion trap tandem mass spectrometry.
2003
Clinical study of 44 cases of Staphylococcus aureus meningitis.
2002-12
Bilateral renal abscesses in a healthy child.
2002-12
Effect of proguanil interaction on bioavailability of cloxacillin.
2002-12
[Impact of regulatory measures in the trends of community consumption of antibiotics in Chile].
2002-11
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.
2002-11
Impact of an antibiotic policy on antibiotic use in a paediatric department. Individual based follow-up shows that antibiotics were chosen according to diagnoses and bacterial findings.
2002-11
Antibiogram and beta-lactamase production of Staphylococcus aureus isolates from different human clinical specimens in Edo State, Nigeria.
2002-10-31
The effect of an intramammary teat seal on new intramammary infections.
2002-10
Bullous reaction in leprosy: a rare phenomenon.
2002-09
Prevalence of coagulase-negative staphylococci in bovine mastitis in Zimbabwe.
2002-06
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.
2002-05
Pathogenic agents of chronic suppurative otitis media in Ilorin, Nigeria.
2002-04
Influence of failure of primary wound healing on subsequent recurrence of pilonidal sinus. combined prospective study and randomised controlled trial.
2002
[Effect of subinhibitory levels of selected antibiotics on susceptibility of Staphylococcus aureus strains to phagocytosis and killing by rabbit granulocytes].
2002
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.
2001-09
[Reversible renal failure in female patients with acute interstitial nephritis caused by cloxacillin].
1992-12-07
Cloxacillin-induced acute tubulo interstitial nephritis.
1992-10
Patents

Patents

20010007157
7
JP2003507080A
4
JP2003515526A
470

Sample Use Guides

In Vivo Use Guide
Recommended dose for adults is 500 mg four times a day, one for 2-10 y.o. Kids is 250 mg four times a day, children younger than 2 y.o. should take 125 mg of Tegopen four times a day.
Route of Administration: Oral
In Vitro Use Guide
The MIC of the cloxacillin for 5 MRSA (methicillin-resistant S.Aureus) strains were more than 32 (ug/ml), for 1 MRSA strain was more than 128(ug/ml) and for another 4 MRSA strains were above was more than 128 (ug/ml).
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:05 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:05 GMT 2025
Record UNII
65LCB00B4Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOXACILLIN SODIUM
EP   GREEN BOOK   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
CLOXACILLIN SODIUM HYDRATE
JAN  
Preferred Name English
EKVACILLIN
Brand Name English
SODIUM CLOXACILLIN MONOHYDRATE
Common Name English
P-25
Code English
CLOXAPEN
Brand Name English
METHOCILLIN-S
Brand Name English
Cloxacillin sodium [WHO-DD]
Common Name English
CLOXACILLIN SODIUM HYDRATE [JAN]
Common Name English
CLOXACILLIN SODIUM SALT MONOHYDRATE [MI]
Common Name English
Monosodium (2S,5R,6R)-6-[3-(O-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrate
Common Name English
CLOXACILLIN SODIUM [WHO-IP]
Common Name English
CLOXACILLIN SODIUM [USP MONOGRAPH]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, SODIUM SALT, HYDRATE (1:1:1), (2S,5R,6R)-
Systematic Name English
CLOXACILLIN SODIUM [USP IMPURITY]
Common Name English
CLOXACILLIN (AS SODIUM)
Common Name English
CLOXACILLIN SODIUM SALT MONOHYDRATE
MI  
Common Name English
CLOXACILLIN SODIUM [USP-RS]
Common Name English
TEGOPEN
Brand Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOSODIUM SALT, MONOHYDRATE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
CLOXACILLIN SODIUM [EP MONOGRAPH]
Common Name English
LATOCILLIN
Brand Name English
BRL-1621
Code English
CLOXYPEN
Brand Name English
CLOXACILLIN SODIUM [GREEN BOOK]
Common Name English
CLOXACILLIN SODIUM [ORANGE BOOK]
Common Name English
ORBENIN
Brand Name English
CLOXACILLIN SODIUM [USAN]
Common Name English
CLOXACILLIN SODIUM [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
CFR 21 CFR 526.464C
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL891
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CLOXACILLIN SODIUM
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY Description: A white, crystalline powder; odourless.Solubility: Soluble in 2.5 parts of water and in 30 parts of ethanol (~750 g/l) TS.Category: Antibiotic.Storage: Cloxacillin sodium should be kept in a tightly closed container, protected from light.Labelling: The designation sterile Cloxacillin sodium indicates that the substance complies with the additional requirements forsterile Cloxacillin sodium and may be used for parenteral administration or for other sterile applications.
WIKIPEDIA
Cloxacillin Sodium
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
NCI_THESAURUS
C47460
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
MERCK INDEX
m3673
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY Merck Index
CAS
7081-44-9
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
RS_ITEM_NUM
1142005
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
PUBCHEM
23675743
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
EVMPD
SUB13400MIG
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID60110018
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
RXCUI
9864
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY RxNorm
DRUG BANK
DBSALT000249
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
EVMPD
SUB21388
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
FDA UNII
65LCB00B4Y
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
CHEBI
34978
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
Related Record Type Details
Structure of CLOXACILLIN SODIUM ANHYDROUS
ANHYDROUS->SOLVATE
Structure of CLOXACILLIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CLOXACILLIN PENILLOIC ACID
IMPURITY -> PARENT
Structure of 3-(2-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid
IMPURITY -> PARENT
Structure of CLOXACILLIN PENICILLOIC ACID
IMPURITY -> PARENT
Structure of 6-Aminopenicillanic acid
IMPURITY -> PARENT
Related Record Type Details
Structure of CLOXACILLIN
ACTIVE MOIETY
NIH
NCATS
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