Details of the Drug

General Information of Drug (ID: DMUTL7O)

Drug Name

Cloxacillin

Synonyms

Chloroxacillin; Clossacillina; Cloxacilina; Cloxacilline; Cloxacillinum; MCIPC; Orbenin; Syntarpen; Tegopen; Clossacillina [DCIT]; Cloxacillin sodium; Methocillin S; BRL 1621; Cloxacilina [INN-Spanish]; Cloxacillin (INN); Cloxacillin [INN:BAN]; Cloxacilline [INN-French]; Cloxacillinum [INN-Latin]; Cloxapen (TN); Cloxapen (sodium monohydrate); Methylchlorphenylisoxazoryl-penicillin; Novo-Cloxin; Nu-Cloxi; Orbenin (TN); Tegopen (sodium monohydrate); BRL-1621 (sodium monohydrate); P-25 (sodium monohydrate); [3-(O-CHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL]PENICILLIN; (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (3-(o-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin; 6-(((3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
Staphylococcal pneumonia	N.A.	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[2]
Sinusitis	CA0A.Z	Investigative	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

435.9

Logarithm of the Partition Coefficient (xlogp)

2.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is well absorbed from the gastrointestinal tract []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Elimination: 75% of drug is excreted from urine in the unchanged form [3]
Metabolism: The drug is metabolized via the breakage of the beta-lactam ring to form an inactive penicilloic acid metabolite [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 76.39552 micromolar/kg/day [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.0139 mg/mL [3]

Chemical Identifiers

Formula: C19H18ClN3O5S
IUPAC Name: (2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI: InChI=1S/C19H18ClN3O5S/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)/t13-,14+,17-/m1/s1
InChIKey: LQOLIRLGBULYKD-JKIFEVAISA-N

Cross-matching ID

PubChem CID: 6098
ChEBI ID: CHEBI:49566
CAS Number: 61-72-3
DrugBank ID: DB01147
TTD ID: D04KTZ
VARIDT ID: DR00529
ACDINA ID: D00960

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[7]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Glyceryl monooleate	E00473	5283468	Bioadhesive material; Emollient; Emulsifying agent; Emulsion stabilizing agent; Gelling agent; Modified-release agent; Surfactant
Trihydroxystearin	E00317	25100	Emollient; Emulsifying agent; Solvent; Surfactant; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Cloxacillin 500mg/10ml solution	500mg/10ml	Solution	Intravenous

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References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 061454.
2	Cloxacillin FDA Label
3	BDDCS applied to over 900 drugs
4	Hartman NR, Mao JJ, Zhou H, Boyne MT 2nd, Wasserman AM, Taylor K, Racoosin JA, Patel V, Colatsky T: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. Regul Toxicol Pharmacol. 2014 Oct;70(1):182-8. doi: 10.1016/j.yrtph.2014.07.002. Epub 2014 Jul 8.
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Development of a receptor-based microplate assay for the detection of beta-lactam antibiotics in different food matrices. Anal Chim Acta. 2007 Mar 14;586(1-2):296-303.
7	Potential cholestatic activity of various therapeutic agents assessed by bile canalicular membrane vesicles isolated from rats and humans. Drug Metab Pharmacokinet. 2003;18(1):16-22.
8	Pro-inflammatory cytokines enhance dilatation of bile canaliculi caused by cholestatic antibiotics. Toxicol In Vitro. 2019 Aug;58:51-59. doi: 10.1016/j.tiv.2019.03.015. Epub 2019 Mar 12.