CLOXACILLIN BENZATHINE

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

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

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Description

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	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Skin and soft tissue infections 33	Curative	Approved 8,429	TEGOPEN
Respiratory tract infections 85	Curative	Approved 8,429	TEGOPEN
Septic arthritis 4	Curative	Approved 8,429	TEGOPEN
Bacterial osteomyelitis 4	Curative	Approved 8,429	TEGOPEN
Infective endocarditis 5	Curative	Approved 8,429	TEGOPEN
Septicaemia 15	Curative	Approved 8,429	TEGOPEN
Urinary tract infections 205	Curative	Approved 8,429	TEGOPEN
Bacterial otitis 4	Curative	Approved 8,429	TEGOPEN
Meningitis 18	Curative	Approved 8,429	TEGOPEN

C_max

Value	Dose	Co-administered	Analyte	Population
60 μg/mL	2 g single, intravenous		CLOXACILLIN serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
310 μg × h/mL	2 g single, intravenous		CLOXACILLIN serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
43 min	2 g single, intravenous		CLOXACILLIN serum	Homo sapiens

Doses

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Dose	Population	Adverse events
12 g 1 times / day steady, intravenous Studied dose	unhealthy, 21 years n = 1	Disc. AE: Agranulocytosis...
12 g 1 times / day multiple, intravenous (median) Studied dose	unhealthy, 66 - 80 years n = 23	Disc. AE: Acute kidney injury...
9.8 g 1 times / day multiple, intravenous (mean) Studied dose	unhealthy, adult n = 54	Other AEs: Neutropenia, Rash...

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AEs

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AE	Significance	Dose	Population
Agranulocytosis	1 patient Disc. AE	12 g 1 times / day steady, intravenous Studied dose	unhealthy, 21 years n = 1
Acute kidney injury	23 patients Disc. AE	12 g 1 times / day multiple, intravenous (median) Studied dose	unhealthy, 66 - 80 years n = 23
Neutropenia	2 patients	9.8 g 1 times / day multiple, intravenous (mean) Studied dose	unhealthy, adult n = 54
Rash	4 patients	9.8 g 1 times / day multiple, intravenous (mean) Studied dose	unhealthy, adult n = 54
Fever	5 patients	9.8 g 1 times / day multiple, intravenous (mean) Studied dose	unhealthy, adult n = 54

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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 1,537 PEPT2 32

Drug as perpetrator

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Target	Modality	Activity
PEPT1 22	inhibitor 3,277	weak [Ki 3000 uM]
OAT3 644	inhibitor 3,277	yes [IC50 13 uM]
OAT4 146	inhibitor 3,277	yes [IC50 21 uM]
BSEP 403	inhibitor 3,277	yes [IC50 41.6 uM]
OAT1 603	inhibitor 3,277	yes [IC50 550 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
P-gp 1,537	substrate 3,367	likely	yes (pharmacogenomic study)
PEPT2 32	substrate 3,367	moderate [Ki 950 uM]
PEPT1 49	substrate 3,367	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Staphylococcal scalded skin syndrome.	2001 Apr	11313519
Comparison of methods for the determination of antimicrobial resistance in Staphylococcus aureus from bovine mastitis.	2001 Feb	11254096
[Successful medical treatment of spinal epidural abscess].	2001 Feb	11181217
Short-course therapy for right-side endocarditis due to Staphylococcus aureus in drug abusers: cloxacillin versus glycopeptides in combination with gentamicin.	2001 Jul 1	11389505
Interaction energies between beta-lactam antibiotics and E. coli penicillin-binding protein 5 by reversible thermal denaturation.	2001 Jun	11369864

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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).

Show entries

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

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Classification Tree

Code System

Code

PART 526 INTRAMAMMARY DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 526.464B

Beta-Lactam Antibiotic

NCI_THESAURUS

C1500

PART 526 INTRAMAMMARY DOSAGE FORM NEW ANIMAL DRUGS

CFR

21 CFR 526.464A

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Code System

Code

Type

Description

ECHA (EC/EINECS)

245-855-2

PRIMARY

DAILYMED

AC79L7PV2G

PRIMARY

MESH

C006692

PRIMARY

DRUG BANK

DBSALT001648

PRIMARY

SMS_ID

300000017672

PRIMARY

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ACTIVE MOIETY


					O6X5QGC2VB

CLOXACILLIN

SUBSTANCE RECORD


					AC79L7PV2G

CLOXACILLIN BENZATHINE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator