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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18ClN3O5S
Molecular Weight 435.881
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOXACILLIN

SMILES

[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=LQOLIRLGBULYKD-JKIFEVAISA-N
InChI=1S/C19H18ClN3O5S/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)/t13-,14+,17-/m1/s1

HIDE SMILES / InChI

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
[Reversible renal failure in female patients with acute interstitial nephritis caused by cloxacillin].
1992 Dec 7-14
Cloxacillin-induced acute tubulo interstitial nephritis.
1992 Oct
Spontaneous spinal epidural abscess.
2001 Dec
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
Epidermal dysplasia and Malassezia infection in two West Highland White Terrier siblings: an inherited skin disorder or reaction to severe Malassezia infection?
2001 Oct
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.
2001 Sep
Influence of failure of primary wound healing on subsequent recurrence of pilonidal sinus. combined prospective study and randomised controlled trial.
2002
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
Combined antibiotic and free radical trap treatment is effective at combating Staphylococcus-aureus-induced septic arthritis.
2002
Pathogenic agents of chronic suppurative otitis media in Ilorin, Nigeria.
2002 Apr
Patterns of isolation of common gram positive bacterial pathogens and their susceptibilities to antimicrobial agents in Jimma Hospital.
2002 Apr
Antibiogram and beta-lactamase production of Staphylococcus aureus isolates from different human clinical specimens in Edo State, Nigeria.
2002 Apr-Jun
Spinal epidural abscess in a neonate.
2002 Aug
Bilateral renal abscesses in a healthy child.
2002 Dec
Effect of proguanil interaction on bioavailability of cloxacillin.
2002 Dec
A prospective study of infections in burn patients.
2002 Feb
Efficacy of ceftriaxone and gentamicin given once a day by using human-like pharmacokinetics in treatment of experimental staphylococcal endocarditis.
2002 Feb
Prevalence of coagulase-negative staphylococci in bovine mastitis in Zimbabwe.
2002 Jun
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.
2002 May
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.
2002 May 1
The effect of an intramammary teat seal on new intramammary infections.
2002 Oct
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
[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
Staphylococcus aureus subcutaneous abscess complicating acupuncture: need for implementation of proper infection control guidelines.
2003 Apr
[Community-acquired necrotizing pneumonia associated with bacteriemia and metastatic septic foci].
2003 Apr
A severity score for complicated skin and soft tissue infections derived from phase III studies of linezolid.
2003 Apr
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.
2003 Apr 12
Risk of anaphylaxis in a hospital population in relation to the use of various drugs: an international study.
2003 Apr-May
[Drying off cows: a comparative study with two dry cow products].
2003 Aug 15
Case 1--a 65-year-old female patient presented to Kijabe Mission Hospital with a complaint of left thigh swelling.
2003 Aug 22
Folliculitis decalvans--a retrospective study in a tertiary referred centre, over five years.
2003 Feb
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.
2003 Feb
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 Feb
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.
2003 Feb
Comparison of beta-lactamases of classes A and D: 1.5-A crystallographic structure of the class D OXA-1 oxacillinase.
2003 Jan
Pattern of aerobic bacteria with their drug susceptibility of surgical inpatients.
2003 Jul
Use of antibiotic-loaded polymethyl methacrylate beads in the management of musculoskeletal sepsis--a retrospective study.
2003 Jun
Suspected chlamydial keratoconjunctivitis in British cattle.
2003 Jun 21
Lucio's phenomenon.
2003 May
Infective endocarditis and cardiac surgery in intravenous drug abusers and HIV-1 infected patients.
2003 May
Neonatal Staphylococcal scalded skin syndrome complicating ileal atresia.
2003 May
[Vesicular/pustular lesions in a patient with atopic dermatitis].
2003 May
Empyema thoracis: a 10-year comparative review of hospitalised children from south Asia.
2003 Nov
[Treatment of mastitis in general practice].
2003 Nov 6
AmpC cephalosporinase hyperproduction in Acinetobacter baumannii clinical strains.
2003 Oct
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 15:03:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:25 GMT 2023
Record UNII
O6X5QGC2VB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOXACILLIN
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
CLOXACILLIN [HSDB]
Common Name English
cloxacillin [INN]
Common Name English
CLOXACILLIN [MART.]
Common Name English
CLOXACILLIN [VANDF]
Common Name English
Cloxacillin [WHO-DD]
Common Name English
OXACILLIN SODIUM MONOHYDRATE IMPURITY E [EP IMPURITY]
Common Name English
6-(((3-(2-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
CLOXACILLIN [MI]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 556.165
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-VATC QJ51RC26
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-ATC J01CF02
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-VATC QS01AA90
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-VATC QG51AG05
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-VATC QJ51CF02
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
LIVERTOX 229
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
CFR 21 CFR 526.464
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
WHO-VATC QJ01CF02
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
Code System Code Type Description
PUBCHEM
6098
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
INN
1533
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
EVMPD
SUB06780MIG
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
SMS_ID
100000084036
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL891
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
NCI_THESAURUS
C61688
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
MESH
D003023
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
DRUG BANK
DB01147
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
CHEBI
49566
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
RXCUI
2625
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-514-7
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
FDA UNII
O6X5QGC2VB
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
WIKIPEDIA
CLOXACILLIN
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
DAILYMED
O6X5QGC2VB
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022853
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
MERCK INDEX
m3673
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
720
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
CAS
61-72-3
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
HSDB
3042
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
LACTMED
Cloxacillin
Created by admin on Fri Dec 15 15:03:26 GMT 2023 , Edited by admin on Fri Dec 15 15:03:26 GMT 2023
PRIMARY
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