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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17ClN3O5S.Na.H2O
Molecular Weight 475.878
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOXACILLIN SODIUM

SMILES

O.[Na+].[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=KCUWTKOTPIUBRI-VICXVTCVSA-M
InChI=1S/C19H18ClN3O5S.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1

HIDE SMILES / InChI
Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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

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

CNS Penetrant
2554
Sources: www.ncbi.nlm.nih.gov/pubmed/25582344
Curator's Comment: Cloxacillin does not significantly cross the blood brain barrier.

Originator

Approval Year

1965
171
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Curative
Approved
8429
TEGOPEN

Approved Use

Unknown

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
PEPT1
20

OAT3
642

OAT1
599

OAT4
146

BSEP
402
PEPT1
49

P-gp
1537

PEPT2
32
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
PEPT1
22
 weak [Ki 3000 uM]
OAT3
644
 yes [IC50 13 uM]
OAT4
146
 yes [IC50 21 uM]
BSEP
403
 yes [IC50 41.6 uM]
OAT1
603
 yes [IC50 550 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 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).
PEPT2
32
 moderate [Ki 950 uM]
PEPT1
49
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Spontaneous spinal epidural abscess.
2001 Dec
Skin and soft tissue infection.
2001 Jul
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
Short-term (48 hours) versus long-term (7 days) antibiotic prophylaxis for permanent pacemaker implantation.
2001 Nov-Dec
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
Clinical prevalence and antimicrobial susceptibility of Staphylococcus aureus and Staph. intermedius in dogs.
2002
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.
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
Screening and mass spectral confirmation of beta-lactam antibiotic residues in milk using LC-MS/MS.
2002 Jan 16
Prevalence of coagulase-negative staphylococci in bovine mastitis in Zimbabwe.
2002 Jun
Infective endocarditis in intravenous drug abusers and HIV-1 infected patients.
2002 Jun
Intravenous cyclosporine-rifampin interaction in a pediatric bone marrow transplant recipient.
2002 Mar
Antibiotic associated diarrhoea: a controlled study comparing plain antibiotic with those containing protected lactobacilli.
2002 May
[Impact of regulatory measures in the trends of community consumption of antibiotics in Chile].
2002 Nov
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.
2002 Nov
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
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
[Relapsing Staphylococcus lugdunensis septic arthritis associated with a knee prosthesis].
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
Comparison of two protocols for the treatment of retained fetal membranes in dairy cattle.
2003 Feb
Efficacy of intramammary tilmicosin and risk factors for cure of Staphylococcus aureus infection in the dry period.
2003 Jan
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
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

Patents

20010007157
7
JP2003507080A
4
JP2003515526A
462

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 15:25:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:17 GMT 2023
Record UNII
65LCB00B4Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOXACILLIN SODIUM
EP   GREEN BOOK   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
EKVACILLIN
Brand Name English
SODIUM CLOXACILLIN MONOHYDRATE
Common Name English
P-25
Code English
CLOXAPEN
Brand Name English
METHOCILLIN-S
Brand Name English
Cloxacillin sodium [WHO-DD]
Common Name English
CLOXACILLIN SODIUM HYDRATE [JAN]
Common Name English
CLOXACILLIN SODIUM SALT MONOHYDRATE [MI]
Common Name English
Monosodium (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-carboxylate monohydrate
Common Name English
CLOXACILLIN SODIUM [WHO-IP]
Common Name English
CLOXACILLIN SODIUM [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-, SODIUM SALT, HYDRATE (1:1:1), (2S,5R,6R)-
Systematic Name English
CLOXACILLIN SODIUM HYDRATE
JAN  
Common Name English
CLOXACILLIN SODIUM [USP IMPURITY]
Common Name English
CLOXACILLIN (AS SODIUM)
Common Name English
CLOXACILLIN SODIUM SALT MONOHYDRATE
MI  
Common Name English
CLOXACILLIN SODIUM [USP-RS]
Common Name English
TEGOPEN
Brand 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-, MONOSODIUM SALT, MONOHYDRATE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
CLOXACILLIN SODIUM [EP MONOGRAPH]
Common Name English
LATOCILLIN
Brand Name English
BRL-1621
Code English
CLOXYPEN
Brand Name English
CLOXACILLIN SODIUM [GREEN BOOK]
Common Name English
CLOXACILLIN SODIUM [ORANGE BOOK]
Common Name English
ORBENIN
Brand Name English
CLOXACILLIN SODIUM [USAN]
Common Name English
CLOXACILLIN SODIUM [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
CFR 21 CFR 526.464C
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL891
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CLOXACILLIN SODIUM
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY Description: A white, crystalline powder; odourless.Solubility: Soluble in 2.5 parts of water and in 30 parts of ethanol (~750 g/l) TS.Category: Antibiotic.Storage: Cloxacillin sodium should be kept in a tightly closed container, protected from light.Labelling: The designation sterile Cloxacillin sodium indicates that the substance complies with the additional requirements forsterile Cloxacillin sodium and may be used for parenteral administration or for other sterile applications.
WIKIPEDIA
Cloxacillin Sodium
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
NCI_THESAURUS
C47460
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
MERCK INDEX
m3673
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY Merck Index
CAS
7081-44-9
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1142005
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
PUBCHEM
23675743
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EVMPD
SUB13400MIG
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID60110018
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
RXCUI
9864
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT000249
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
EVMPD
SUB21388
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
FDA UNII
65LCB00B4Y
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
CHEBI
34978
Created by admin on Fri Dec 15 15:25:17 GMT 2023 , Edited by admin on Fri Dec 15 15:25:17 GMT 2023
PRIMARY
Related Record Type Details
Structure of CLOXACILLIN SODIUM ANHYDROUS
ANHYDROUS->SOLVATE
Structure of CLOXACILLIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CLOXACILLIN PENILLOIC ACID
IMPURITY -> PARENT
Structure of 3-(2-CHLOROPHENYL)-5-METHYL-1,2-OXAZOLE-4-CARBOXYLIC ACID
IMPURITY -> PARENT
Structure of CLOXACILLIN PENICILLOIC ACID
IMPURITY -> PARENT
Structure of 6-AMINOPENICILLANIC ACID
IMPURITY -> PARENT
Related Record Type Details
Structure of CLOXACILLIN
ACTIVE MOIETY
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