CLOXACILLIN SODIUM ANHYDROUS

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H17ClN3O5S.Na
Molecular Weight	457.863
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CLOXACILLIN SODIUM ANHYDROUS

Structure Search

SMILES

[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=SCLZRKVZRBKZCR-SLINCCQESA-M

InChI=1S/C19H18ClN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C19H17ClN3O5S
Molecular Weight	434.873
Charge	-1
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
Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://antimicrobe.org/new/drugpopup/Cloxacillin.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Skin and soft tissue infections 33 Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Respiratory tract infections 85 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Septic arthritis 4 Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Bacterial osteomyelitis 4 Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Infective endocarditis 5 Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Septicaemia 15 Sources: http://apps.who.int/medicinedocs/en/d/Js5406e/16.16.html#Js5406e.16.16	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Urinary tract infections 207 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Bacterial otitis 4 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981
Meningitis 19 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8583	TEGOPEN Approved Use Unknown Launch Date 1981

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
PEPT1 27 OAT3 747 OAT1 725 OAT4 150 BSEP 550	PEPT1 60 P-gp 2052 PEPT2 37

Drug as perpetrator

Target	Modality	Activity
PEPT1 29	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB01147, https://pubmed.ncbi.nlm.nih.gov/15567297/	weak [Ki 3000 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/, https://dmd.aspetjournals.org/content/41/4/791	yes [IC50 13 uM]
OAT4 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/	yes [IC50 21 uM]
BSEP 554	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50022788	yes [IC50 41.6 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/	yes [IC50 550 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19539100/	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). Sources: https://pubmed.ncbi.nlm.nih.gov/19539100/
PEPT2 37	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S096808961100455X	moderate [Ki 950 uM]
PEPT1 60	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18353114/	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Method development for measuring trace levels of penicillins in aqueous environmental samples.	2001	11507750
The isolation and characterization of Campylobacter jejuni subsp. jejuni from domestic geese (Anser anser).	2001 Apr	11309077
Acute bacterial arthritis caused by group C streptococci.	2001 Aug	11503138
Malignant otitis externa in an infant with selective IgA deficiency: a case report.	2001 Aug 20	11518592
[Cloxacilin and vancomycin bacterial action against oxalicin-susceptible Staphylococcus aureus].	2001 Feb	11351477
Skin and soft tissue infection.	2001 Jul	11980459
Staphylococcal scalded-skin syndrome in a very low birth weight premature infant.	2001 Jul	11433095
Interaction energies between beta-lactam antibiotics and E. coli penicillin-binding protein 5 by reversible thermal denaturation.	2001 Jun	11369864
Screening method for identification of beta-lactams in bovine urine by use of liquid chromatography and a microbial inhibition test.	2001 Mar	11277195
Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.	2001 Mar 16	11293583
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.	2001 Mar-Apr	11173810
OXA-35 is an OXA-10-related beta-lactamase from Pseudomonas aeruginosa.	2001 Nov	11679562
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.	2001 Sep	11605761
Evaluation of a systemic antibiotic treatment of toxic puerperal metritis in dairy cows.	2001 Sep	11573780
Analysis of beta-lactam antibiotics in incurred raw milk by rapid test methods and liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2001 Sep	11559105
[Effect of subinhibitory levels of selected antibiotics on susceptibility of Staphylococcus aureus strains to phagocytosis and killing by rabbit granulocytes].	2002	12650052
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.	2002	12195877
Clinical prevalence and antimicrobial susceptibility of Staphylococcus aureus and Staph. intermedius in dogs.	2002	12174038
Combined antibiotic and free radical trap treatment is effective at combating Staphylococcus-aureus-induced septic arthritis.	2002	12010570
Pathogenic agents of chronic suppurative otitis media in Ilorin, Nigeria.	2002 Apr	12625677
Biofilm bacteria: formation and comparative susceptibility to antibiotics.	2002 Apr	11989739
Antibiogram and beta-lactamase production of Staphylococcus aureus isolates from different human clinical specimens in Edo State, Nigeria.	2002 Apr-Jun	12403034
Clinical study of 44 cases of Staphylococcus aureus meningitis.	2002 Dec	12525921
Bilateral renal abscesses in a healthy child.	2002 Dec	12516914
Efficacy of ceftriaxone and gentamicin given once a day by using human-like pharmacokinetics in treatment of experimental staphylococcal endocarditis.	2002 Feb	11796345
Screening and mass spectral confirmation of beta-lactam antibiotic residues in milk using LC-MS/MS.	2002 Jan 16	11782216
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.	2002 Jul-Aug	12180684
[[Primary psoas abscess. Presentation of 3 cases].	2002 Jun	12174424
Identification and antimicrobial susceptibility of Staphylococcus chromogenes isolates from intramammary infections of dairy cows.	2002 Jun 20	12034545
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	11990019
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.	2002 May	12418644
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.	2002 May 1	11991409
[Impact of regulatory measures in the trends of community consumption of antibiotics in Chile].	2002 Nov	12587509
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	12431868
The effect of an intramammary teat seal on new intramammary infections.	2002 Oct	12416803
Community-acquired methicillin-resistant Staphylococcus aureus in institutionalized adults with developmental disabilities.	2002 Sep	12194775
Acute bacterial skin infections in pediatric medicine: current issues in presentation and treatment.	2003	14632104
Confirmatory analysis of beta-lactam antibiotics in kidney tissue by liquid chromatography/electrospray ionization selective reaction monitoring ion trap tandem mass spectrometry.	2003	12661018
[Simultaneous determination of five penicillins in muscle, liver and kidney from slaughtered animals using liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2003 Feb	12749189
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.	2003 Feb	12647952
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	12562713
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.	2003 Feb	12517396
Efficacy of intramammary tilmicosin and risk factors for cure of Staphylococcus aureus infection in the dry period.	2003 Jan	12613861
Use of antibiotic-loaded polymethyl methacrylate beads in the management of musculoskeletal sepsis--a retrospective study.	2003 Jun	12810976
Neonatal Staphylococcal scalded skin syndrome complicating ileal atresia.	2003 May	12847634
Determination of organochlorine pesticides in agricultural soil with special reference to gamma-HCH degradation by Pseudomonas strains.	2003 May	12573562
[Treatment of mastitis in general practice].	2003 Nov 6	14618169
AmpC cephalosporinase hyperproduction in Acinetobacter baumannii clinical strains.	2003 Oct	12951337

Patents

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 18:22:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:44 GMT 2025`
Record UNII	MWQ645MKMF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOXACILLIN SODIUM ANHYDROUS

Common Name

English

CLOXACILLIN SODIUM SALT ANHYDROUS [MI]

Preferred Name

English

NSC-756687

Code

English

CLOXACILLIN SODIUM, ANHYDROUS

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500