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.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)C5=C(C)ON=C5C6=CC=CC=C6Cl)C(O)=O.[H][C@]78SC(C)(C)[C@@H](N7C(=O)[C@H]8NC(=O)C9=C(C)ON=C9C%10=CC=CC=C%10Cl)C(O)=O

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	C16H20N2
Molecular Weight	240.3434
Charge	0
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

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 233 Target ID: CHEMBL2354204 Sources: http://antimicrobe.org/new/drugpopup/Cloxacillin.pdf	Inhibitor 8297

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 8429	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 8429	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 8429	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 8429	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 8429	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 8429	TEGOPEN Approved Use Unknown Launch Date 1981
Urinary tract infections 205 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8429	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 8429	TEGOPEN Approved Use Unknown Launch Date 1981
Meningitis 18 Sources: https://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/cps-_monographs/cps-_(general_monographs-_t)/TEGOPEN.html	Curative	Approved 8429	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 n = 1 Health Status: unhealthy Condition: infective endocarditis caused by methicillin-susceptible Staphylococcus aureus Age Group: 21 years Sex: F Population Size: 1 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 (median) 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 n = 23 Health Status: unhealthy Condition: endocarditis or osteoarticular infections Age Group: 66 - 80 years Sex: M+F Population Size: 23 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 (mean) 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 n = 54 Health Status: unhealthy Condition: infective endocarditis Age Group: adult Sex: unknown Population Size: 54 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 n = 1 Health Status: unhealthy Condition: infective endocarditis caused by methicillin-susceptible Staphylococcus aureus Age Group: 21 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/28786715/
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: https://pubmed.ncbi.nlm.nih.gov/29665445/	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: https://pubmed.ncbi.nlm.nih.gov/29665445/
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: https://pubmed.ncbi.nlm.nih.gov/10090118/	unhealthy, adult n = 54 Health Status: unhealthy Condition: infective endocarditis Age Group: adult Sex: unknown Population Size: 54 Sources: https://pubmed.ncbi.nlm.nih.gov/10090118/
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: https://pubmed.ncbi.nlm.nih.gov/10090118/	unhealthy, adult n = 54 Health Status: unhealthy Condition: infective endocarditis Age Group: adult Sex: unknown Population Size: 54 Sources: https://pubmed.ncbi.nlm.nih.gov/10090118/
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: https://pubmed.ncbi.nlm.nih.gov/10090118/	unhealthy, adult n = 54 Health Status: unhealthy Condition: infective endocarditis Age Group: adult Sex: unknown Population Size: 54 Sources: https://pubmed.ncbi.nlm.nih.gov/10090118/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
PEPT1 20 OAT3 642 OAT1 599 OAT4 146 BSEP 402	PEPT1 49 P-gp 1537 PEPT2 32

Drug as perpetrator

Target	Modality	Activity
PEPT1 22	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB01147, https://pubmed.ncbi.nlm.nih.gov/15567297/	weak [Ki 3000 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/, https://dmd.aspetjournals.org/content/41/4/791	yes [IC50 13 uM]
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/	yes [IC50 21 uM]
BSEP 403	inhibitor 3277 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50022788	yes [IC50 41.6 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32100322/	yes [IC50 550 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1537	substrate 3367 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 32	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S096808961100455X	moderate [Ki 950 uM]
PEPT1 49	substrate 3367 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
[Reversible renal failure in female patients with acute interstitial nephritis caused by cloxacillin].	1992 Dec 7-14	1305739
Cloxacillin-induced acute tubulo interstitial nephritis.	1992 Oct	1421648
Evaluation of diazotized 4-amino-3,5-dinitrobenzoic acid (ADBA) as a new derivatizing reagent.	2001 Sep	14510132
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
Pathogenic agents of chronic suppurative otitis media in Ilorin, Nigeria.	2002 Apr	12625677
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
Effect of proguanil interaction on bioavailability of cloxacillin.	2002 Dec	12472986
Prevalence of coagulase-negative staphylococci in bovine mastitis in Zimbabwe.	2002 Jun	12240771
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.	2002 May	12418644
[Impact of regulatory measures in the trends of community consumption of antibiotics in Chile].	2002 Nov	12587509
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.	2002 Nov	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 Nov	12431868
The effect of an intramammary teat seal on new intramammary infections.	2002 Oct	12416803
Bullous reaction in leprosy: a rare phenomenon.	2002 Sep	12483969
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
Staphylococcus aureus subcutaneous abscess complicating acupuncture: need for implementation of proper infection control guidelines.	2003 Apr	12737199
[Relapsing Staphylococcus lugdunensis septic arthritis associated with a knee prosthesis].	2003 Apr	12681136
[Community-acquired necrotizing pneumonia associated with bacteriemia and metastatic septic foci].	2003 Apr	12681135
A severity score for complicated skin and soft tissue infections derived from phase III studies of linezolid.	2003 Apr	12657392
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.	2003 Apr 12	12723630
Risk of anaphylaxis in a hospital population in relation to the use of various drugs: an international study.	2003 Apr-May	12733472
NmcA carbapenem-hydrolyzing enzyme in Enterobacter cloacae in North America.	2003 Aug	12967501
[Drying off cows: a comparative study with two dry cow products].	2003 Aug 15	14582339
Case 1--a 65-year-old female patient presented to Kijabe Mission Hospital with a complaint of left thigh swelling.	2003 Aug 22	14600666
Folliculitis decalvans--a retrospective study in a tertiary referred centre, over five years.	2003 Feb	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 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
Comparison of beta-lactamases of classes A and D: 1.5-A crystallographic structure of the class D OXA-1 oxacillinase.	2003 Jan	12493831
Pattern of aerobic bacteria with their drug susceptibility of surgical inpatients.	2003 Jul	12894041
Use of antibiotic-loaded polymethyl methacrylate beads in the management of musculoskeletal sepsis--a retrospective study.	2003 Jun	12810976
Suspected chlamydial keratoconjunctivitis in British cattle.	2003 Jun 21	12846296
Lucio's phenomenon.	2003 May	12974445
Infective endocarditis and cardiac surgery in intravenous drug abusers and HIV-1 infected patients.	2003 May	12874891
Neonatal Staphylococcal scalded skin syndrome complicating ileal atresia.	2003 May	12847634
[Vesicular/pustular lesions in a patient with atopic dermatitis].	2003 May	12732117
Determination of organochlorine pesticides in agricultural soil with special reference to gamma-HCH degradation by Pseudomonas strains.	2003 May	12573562
Empyema thoracis: a 10-year comparative review of hospitalised children from south Asia.	2003 Nov	14612371
[Treatment of mastitis in general practice].	2003 Nov 6	14618169
AmpC cephalosporinase hyperproduction in Acinetobacter baumannii clinical strains.	2003 Oct	12951337
Large-volume sample stacking combined with separation by 2-hydroxypropyl-beta-cyclodextrin for analysis of isoxyzolylpenicillins by capillary electrophoresis.	2003 Sep	12973814

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 `Fri Dec 15 15:37:12 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:12 GMT 2023`
Record UNII	AC79L7PV2G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOXACILLIN BENZATHINE

Common Name

English

CLOXACILLIN BENZATHINE [MART.]

Common Name

English

CLOXACILLIN BENZATHINE SALT

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