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+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(C)ON=C3C4=CC=CC=C4Cl)C([O-])=O

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 Na
Molecular Weight 22.9898
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

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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60 μg/mL
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
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
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:
unhealthy, 21 years
n = 1
Health Status: unhealthy
Condition: infective endocarditis caused by methicillin-susceptible Staphylococcus aureus
Age Group: 21 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Agranulocytosis...
AEs leading to
discontinuation/dose reduction:
Agranulocytosis (1 patient)
Sources:
12 g 1 times / day multiple, intravenous (median)
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 12 g, 1 times / day
Sources:
unhealthy, 66 - 80 years
n = 23
Health Status: unhealthy
Condition: endocarditis or osteoarticular infections
Age Group: 66 - 80 years
Sex: M+F
Population Size: 23
Sources:
Disc. AE: Acute kidney injury...
AEs leading to
discontinuation/dose reduction:
Acute kidney injury (23 patients)
Sources:
9.8 g 1 times / day multiple, intravenous (mean)
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
unhealthy, adult
n = 54
Health Status: unhealthy
Condition: infective endocarditis
Age Group: adult
Sex: unknown
Population Size: 54
Sources:
Other AEs: Neutropenia, Rash...
Other AEs:
Neutropenia (2 patients)
Rash (4 patients)
Fever (5 patients)
Sources:
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:
unhealthy, 21 years
n = 1
Health Status: unhealthy
Condition: infective endocarditis caused by methicillin-susceptible Staphylococcus aureus
Age Group: 21 years
Sex: F
Population Size: 1
Sources:
Acute kidney injury 23 patients
Disc. AE
12 g 1 times / day multiple, intravenous (median)
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 12 g, 1 times / day
Sources:
unhealthy, 66 - 80 years
n = 23
Health Status: unhealthy
Condition: endocarditis or osteoarticular infections
Age Group: 66 - 80 years
Sex: M+F
Population Size: 23
Sources:
Neutropenia 2 patients
9.8 g 1 times / day multiple, intravenous (mean)
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
unhealthy, adult
n = 54
Health Status: unhealthy
Condition: infective endocarditis
Age Group: adult
Sex: unknown
Population Size: 54
Sources:
Rash 4 patients
9.8 g 1 times / day multiple, intravenous (mean)
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
unhealthy, adult
n = 54
Health Status: unhealthy
Condition: infective endocarditis
Age Group: adult
Sex: unknown
Population Size: 54
Sources:
Fever 5 patients
9.8 g 1 times / day multiple, intravenous (mean)
Studied dose
Dose: 9.8 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 9.8 g, 1 times / day
Sources:
unhealthy, adult
n = 54
Health Status: unhealthy
Condition: infective endocarditis
Age Group: adult
Sex: unknown
Population Size: 54
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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).
moderate [Ki 950 uM]
yes
PubMed

PubMed

TitleDatePubMed
Method development for measuring trace levels of penicillins in aqueous environmental samples.
2001
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2001 Apr 1
[Cloxacilin and vancomycin bacterial action against oxalicin-susceptible Staphylococcus aureus].
2001 Feb
Skin and soft tissue infection.
2001 Jul
Staphylococcal scalded-skin syndrome in a very low birth weight premature infant.
2001 Jul
Severe ciprofloxacin-induced acute hepatitis.
2001 Jun
Effect of localised antibiotic infusions applied to the teat-canal and teat sinus at drying-off on mastitis in the dry-period and at calving.
2001 Nov
Detection limits of beta-lactam antibiotics in ewe milk by penzym enzymatic test.
2001 Nov
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.
2001 Sep
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.
2001 Sep
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
Biofilm bacteria: formation and comparative susceptibility to antibiotics.
2002 Apr
Spinal epidural abscess in a neonate.
2002 Aug
Effect of proguanil interaction on bioavailability of cloxacillin.
2002 Dec
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Parallux beta-lactam: a capillary-based fluorescent immunoassay for the determination of penicillin-G, ampicillin, amoxicillin, cloxacillin, cephapirin, and ceftiofur in bovine milk.
2002 Mar-Apr
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.
2002 May 1
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 Nov
Bullous reaction in leprosy: a rare phenomenon.
2002 Sep
Acute bacterial skin infections in pediatric medicine: current issues in presentation and treatment.
2003
Dicloxacillin: a higher risk than cloxacillin for infusion phlebitis.
2003
Confirmatory analysis of beta-lactam antibiotics in kidney tissue by liquid chromatography/electrospray ionization selective reaction monitoring ion trap tandem mass spectrometry.
2003
Folliculitis decalvans--a retrospective study in a tertiary referred centre, over five years.
2003 Feb
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.
2003 Feb
Pattern of aerobic bacteria with their drug susceptibility of surgical inpatients.
2003 Jul
Suspected chlamydial keratoconjunctivitis in British cattle.
2003 Jun 21
[Treatment of mastitis in general practice].
2003 Nov 6
Large-volume sample stacking combined with separation by 2-hydroxypropyl-beta-cyclodextrin for analysis of isoxyzolylpenicillins by capillary electrophoresis.
2003 Sep
Patents

Sample Use Guides

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
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 Fri Dec 15 15:25:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:17 GMT 2023
Record UNII
65LCB00B4Y
Record Status Validated (UNII)
Record Version
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Name Type Language
CLOXACILLIN SODIUM
EP   GREEN BOOK   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official 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 HYDRATE
JAN  
Common 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 Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
CFR 21 CFR 526.464C
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL891
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CLOXACILLIN SODIUM
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
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 Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
NCI_THESAURUS
C47460
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
MERCK INDEX
m3673
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY Merck Index
CAS
7081-44-9
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1142005
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
PUBCHEM
23675743
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EVMPD
SUB13400MIG
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID60110018
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
RXCUI
9864
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT000249
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EVMPD
SUB21388
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
FDA UNII
65LCB00B4Y
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
CHEBI
34978
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY