CLOXACILLIN BENZATHINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C19H18ClN3O5S.C16H20N2
Molecular Weight	1112.106
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.CC3=C(C(=O)N[C@H]4[C@H]5SC(C)(C)[C@@H](N5C4=O)C(O)=O)C(=NO3)C6=C(Cl)C=CC=C6.CC7=C(C(=O)N[C@H]8[C@H]9SC(C)(C)[C@@H](N9C8=O)C(O)=O)C(=NO7)C%10=C(Cl)C=CC=C%10

InChI

InChIKey=COCFKSXGORCFOW-VZHMHXRYSA-N

InChI=1S/2C19H18ClN3O5S.C16H20N2/c2*1-8-11(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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27);1-10,17-18H,11-14H2/t2*13-,14+,17-;/m11./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

Molecular Formula	C16H20N2
Molecular Weight	240.3434
Charge	0
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
[Treatment of mastitis in general practice].	2003-11-06	14618169
Empyema thoracis: a 10-year comparative review of hospitalised children from south Asia.	2003-11	14612371
AmpC cephalosporinase hyperproduction in Acinetobacter baumannii clinical strains.	2003-10	12951337
Large-volume sample stacking combined with separation by 2-hydroxypropyl-beta-cyclodextrin for analysis of isoxyzolylpenicillins by capillary electrophoresis.	2003-09	12973814
Case 1--a 65-year-old female patient presented to Kijabe Mission Hospital with a complaint of left thigh swelling.	2003-08-22	14600666
[Drying off cows: a comparative study with two dry cow products].	2003-08-15	14582339
NmcA carbapenem-hydrolyzing enzyme in Enterobacter cloacae in North America.	2003-08	12967501
Pattern of aerobic bacteria with their drug susceptibility of surgical inpatients.	2003-07	12894041
Suspected chlamydial keratoconjunctivitis in British cattle.	2003-06-21	12846296
Use of antibiotic-loaded polymethyl methacrylate beads in the management of musculoskeletal sepsis--a retrospective study.	2003-06	12810976
Risk of anaphylaxis in a hospital population in relation to the use of various drugs: an international study.	2003-05-08	12733472
Lucio's phenomenon.	2003-05	12974445
Infective endocarditis and cardiac surgery in intravenous drug abusers and HIV-1 infected patients.	2003-05	12874891
Neonatal Staphylococcal scalded skin syndrome complicating ileal atresia.	2003-05	12847634
[Vesicular/pustular lesions in a patient with atopic dermatitis].	2003-05	12732117
Determination of organochlorine pesticides in agricultural soil with special reference to gamma-HCH degradation by Pseudomonas strains.	2003-05	12573562
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.	2003-04-12	12723630
Staphylococcus aureus subcutaneous abscess complicating acupuncture: need for implementation of proper infection control guidelines.	2003-04	12737199
[Relapsing Staphylococcus lugdunensis septic arthritis associated with a knee prosthesis].	2003-04	12681136
[Community-acquired necrotizing pneumonia associated with bacteriemia and metastatic septic foci].	2003-04	12681135
A severity score for complicated skin and soft tissue infections derived from phase III studies of linezolid.	2003-04	12657392
Folliculitis decalvans--a retrospective study in a tertiary referred centre, over five years.	2003-02	14503782
[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	12749189
Detection limits of antimicrobials in ewe milk by delvotest photometric measurements.	2003-02	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.	2003-02	12562713
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.	2003-02	12517396
Efficacy of intramammary tilmicosin and risk factors for cure of Staphylococcus aureus infection in the dry period.	2003-01	12613861
Comparison of beta-lactamases of classes A and D: 1.5-A crystallographic structure of the class D OXA-1 oxacillinase.	2003-01	12493831
Acute bacterial skin infections in pediatric medicine: current issues in presentation and treatment.	2003	14632104
Dicloxacillin: a higher risk than cloxacillin for infusion phlebitis.	2003	12953952
[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	12908409
Field trials on the prophylaxis of intramammary infections in pregnant heifers.	2003	12817782
Confirmatory analysis of beta-lactam antibiotics in kidney tissue by liquid chromatography/electrospray ionization selective reaction monitoring ion trap tandem mass spectrometry.	2003	12661018
Clinical study of 44 cases of Staphylococcus aureus meningitis.	2002-12	12525921
Bilateral renal abscesses in a healthy child.	2002-12	12516914
Effect of proguanil interaction on bioavailability of cloxacillin.	2002-12	12472986
[Impact of regulatory measures in the trends of community consumption of antibiotics in Chile].	2002-11	12587509
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.	2002-11	12489715
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	12431868
Antibiogram and beta-lactamase production of Staphylococcus aureus isolates from different human clinical specimens in Edo State, Nigeria.	2002-10-31	12403034
The effect of an intramammary teat seal on new intramammary infections.	2002-10	12416803
Bullous reaction in leprosy: a rare phenomenon.	2002-09	12483969
Prevalence of coagulase-negative staphylococci in bovine mastitis in Zimbabwe.	2002-06	12240771
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.	2002-05	12418644
Pathogenic agents of chronic suppurative otitis media in Ilorin, Nigeria.	2002-04	12625677
Influence of failure of primary wound healing on subsequent recurrence of pilonidal sinus. combined prospective study and randomised controlled trial.	2002	12699097
[Effect of subinhibitory levels of selected antibiotics on susceptibility of Staphylococcus aureus strains to phagocytosis and killing by rabbit granulocytes].	2002	12650052
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.	2001-09	14510132
[Reversible renal failure in female patients with acute interstitial nephritis caused by cloxacillin].	1992-12-07	1305739
Cloxacillin-induced acute tubulo interstitial nephritis.	1992-10	1421648

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 18:03:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:13 GMT 2025`
Record UNII	AC79L7PV2G
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CLOXACILLIN BENZATHINE SALT

Preferred Name

English

CLOXACILLIN BENZATHINE

Common Name

English

CLOXACILLIN BENZATHINE [MART.]

Common Name

English

CLOXACILLIN BENZATHINE [GREEN BOOK]

Common Name

English

(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-CARBOXYLIC ACID COMPOUND WITH N,N'-DIBENZYLETHYLENEDIAMINE (2:1)

Common Name

English

CLOXACILLIN BENZATHINE [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-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)

Common Name

English

CLOXACILLIN BENZATHINE SALT [MI]

Common Name

English

CLOXACILLIN BENZATHINE [USP-RS]

Common Name

English

BENZATHINE CLOXACILLIN

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 526.464B