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cloxacillin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, 6-aminopenicillanic acid derivatives	720	61-72-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cloxacillin Methocillin S cloxacillin sodium cloxacillin sodium salt cloxacillin benzathine	A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN. Molecular weight: 435.88 Formula: C19H18ClN3O5S CLOGP: 2.56 LIPINSKI: 0 HAC: 8 HDO: 2 TPSA: 112.74 ALOGS: -3.91 ROTB: 4 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cloxacillin
Methocillin S
cloxacillin sodium
cloxacillin sodium salt
cloxacillin benzathine

A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.

Molecular weight: 435.88
Formula: C19H18ClN3O5S
CLOGP: 2.56
LIPINSKI: 0
HAC: 8
HDO: 2
TPSA: 112.74
ALOGS: -3.91
ROTB: 4

Status: OFM

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
2	g	O
2	g	P

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	76.40 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	75 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	40 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Sept. 17, 1974	FDA	GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Acute kidney injury	121.58	33.28	66	952	263349	63224655
Pemphigoid	57.94	33.28	15	1003	7329	63480675
Allergy to metals	57.50	33.28	10	1008	725	63487279
Iodine allergy	56.60	33.28	10	1008	794	63487210
Tubulointerstitial nephritis	51.04	33.28	17	1001	19886	63468118
Rubber sensitivity	45.98	33.28	10	1008	2321	63485683
Drug reaction with eosinophilia and systemic symptoms	42.24	33.28	17	1001	33819	63454185
Vascular purpura	38.63	33.28	8	1010	1470	63486534

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	218.74	40.09	76	1662	32936	34922257
Acute kidney injury	131.96	40.09	113	1625	304875	34650318
Hepatocellular injury	70.41	40.09	30	1708	22181	34933012
Cholestasis	58.66	40.09	28	1710	26920	34928273
Agranulocytosis	55.67	40.09	26	1712	23795	34931398
Toxic epidermal necrolysis	45.59	40.09	22	1716	21624	34933569
Nephritis allergic	44.96	40.09	9	1729	444	34954749
Eosinophilia	44.46	40.09	23	1715	26199	34928994
Thrombocytopenia	44.01	40.09	46	1692	156201	34798992
Rash maculo-papular	42.69	40.09	23	1715	28428	34926765

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	254.75	31.23	92	2651	64152	79677493
Acute kidney injury	235.19	31.23	170	2573	519234	79222411
Agranulocytosis	88.62	31.23	39	2704	44991	79696654
Tubulointerstitial nephritis	84.68	31.23	36	2707	38199	79703446
Cholestasis	83.17	31.23	39	2704	52070	79689575
Rash maculo-papular	68.57	31.23	35	2708	56043	79685602
Hepatocellular injury	67.94	31.23	33	2710	47560	79694085
Nephritis allergic	55.95	31.23	11	2732	719	79740926
Eosinophilia	54.54	31.23	28	2715	45317	79696328
Thrombocytopenia	46.21	31.23	51	2692	265208	79476437

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J01CF02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE BETA-LACTAM ANTIBACTERIALS, PENICILLINS Beta-lactamase resistant penicillins
CHEBI has role	CHEBI:33282	bactericides
CHEBI has role	CHEBI:36047	antibacterial drugs
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Staphylococcal meningitis	indication	12166008
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Staphylococcal pneumonia	indication	22754005
Sinusitis	indication	36971009
Lower respiratory tract infection	indication	50417007
Acute bacterial sinusitis	indication	75498004
Staphylococcal septicemia	indication	111821004
Pharyngitis	indication	405737000	DOID:2275
Infection due to Staphylococcus aureus	indication	406602003
Continuation Therapy for Chronic Osteomyelitis	indication

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🐶 Veterinary Drug Use

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Species	Use	Relation
Cattle	Mastitis caused by Staphylococcus aureus	Indication
Cattle	Mastitis caused by Streptococcus agalactiae	Indication

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🐶 Veterinary products

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Product	Applicant	Ingredients
Dariclox	Intervet Inc.	1
Dry-Clox Intramammary Infusion	Boehringer lngelheim Animal Health USA Inc.	1
Orbenin DC	Intervet Inc.	1

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.76	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Penicillin-binding protein	Enzyme	P72355_STAAU Q53707_STAAU Q53725_STAAU Q53729_STAAU Q9XDB3_STAAU	INHIBITOR			CHEMBL	CHEMBL
Beta-lactamase TEM	Enzyme	BLAT_ECOLX		Ki	4.89	CHEMBL
Beta-lactamase	Enzyme	A4ZYU9_ECOLX		IC50	7.59	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_CLOPE				WOMBAT-PK
Beta-lactamase	Enzyme	Q48435_KLEPN		IC50	8.40	CHEMBL
Beta-lactamase TEM	Enzyme	BLAT_SALTI		Ki	4.89	WOMBAT-PK
Efflux transporter; SugE	Transporter	Q3S5C3_SALNE		IC50	8.40	CHEMBL

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External reference:

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ID	Source
CXN	PDB_CHEM_ID
002691	NDDF
004835	NDDF
004855	NDDF
1043213	RXNORM
11126	IUPHAR_LIGAND_ID
1533	INN_ID
16492006	SNOMEDCT_US
23736-58-5	SECONDARY_CAS_RN
373276005	SNOMEDCT_US

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Pharmaceutical products:

None