cloxacillin   Click here for help

GtoPdb Ligand ID: 11126

Synonyms: BRL-1621 | BRL1621 | chloroxacillin | Methocillin S | Syntarpen® | Tegopen®
Approved drug PDB Ligand
cloxacillin is an approved drug (FDA (1971))
Compound class: Synthetic organic
Comment: Cloxacillin is a semisynthetic beta-lactamase resistant penicillin antibiotic [1-2]. It has less potent antibacterial activity than benzylpenicillin.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 138.04
Molecular weight 435.07
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl
Isomeric SMILES OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1Cl
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
InChI Key LQOLIRLGBULYKD-JKIFEVAISA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1971))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
1533 cloxacillin
Synonyms Click here for help
BRL-1621 | BRL1621 | chloroxacillin | Methocillin S | Syntarpen® | Tegopen®
Database Links Click here for help
CAS Registry No. 61-72-3 (source: ChemIDplus)
ChEMBL Ligand CHEMBL891
DrugCentral Ligand 720
GtoPdb PubChem SID 434122186
PubChem CID 6098
RCSB PDB Ligand CXN
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