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]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01CF02: Cloxacillin
J01CF: Beta-lactamase resistant penicillins
J01C: BETA-LACTAM ANTIBACTERIALS, PENICILLINS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01CF02: Cloxacillin
J01CF: Beta-lactamase resistant penicillins
J01C: BETA-LACTAM ANTIBACTERIALS, PENICILLINS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
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) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
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
UNII
O6X5QGC2VB
DrugBank ID
DB01147
TTD ID
D04KTZ
VARIDT ID
DR00529
ACDINA ID
D00960
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Cloxacillin 500mg/10ml solution 500mg/10ml Solution Intravenous
Jump to Detail Pharmaceutical Formulation Page of This Drug

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.