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61-72-3 molecular structure
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(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

ChemBase ID: 1018
Molecular Formular: C19H18ClN3O5S
Molecular Mass: 435.88132
Monoisotopic Mass: 435.06556937
SMILES and InChIs

SMILES:
Clc1c(c2noc(c2C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)O)(C)C)C)cccc1
Canonical 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
InChIKey:
LQOLIRLGBULYKD-JKIFEVAISA-N

Cite this record

CBID:1018 http://www.chembase.cn/molecule-1018.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
IUPAC Traditional name
cloxacillin
(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Brand Name
Cloxapen
Novo-Cloxin
Nu-Cloxi
Synonyms
Cloxacillin Sodium
Cloxacillin
CAS Number
61-72-3
PubChem SID
160964481
46507109
PubChem CID
6098
CHEBI ID
49566
ATC CODE
J01CF02
QJ51CF02
QS01AA90
CHEMBL
891
Chemspider ID
5873
DrugBank ID
DB01147
KEGG ID
D07733
Unique Ingredient Identifier
O6X5QGC2VB
Wikipedia Title
Cloxacillin

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.7497845  H Acceptors
H Donor LogD (pH = 5.5) 0.55099535 
LogD (pH = 7.4) -0.9830029  Log P 2.3017397 
Molar Refractivity 106.6371 cm3 Polarizability 41.93821 Å3
Polar Surface Area 112.74 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.61  LOG S -3.91 
Solubility (Water) 5.32e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
13.9 mg/L expand Show data source
Hydrophobicity(logP)
3 expand Show data source
Admin Routes
Oral, IM expand Show data source
Bioavailability
37 to 90% expand Show data source
Excretion
Renal and biliary expand Show data source
Half Life
30 minutes to 1 hour expand Show data source
Protein Bound
95% expand Show data source
Pregnancy Category
B (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01147 external link
Item Information
Drug Groups approved
Description A semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]
Indication Used to treat infections caused by penicillinase-producing staphylococci, including pneumococci, group A beta-hemolytic streptococci, and penicillin G-sensitive and penicillin G-resistant staphylococci.
Pharmacology Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is for use against staphylococci that produce beta-lactamase.
Toxicity Oral LD50 in rat and mouse is 5000 mg/kg. Intravenous LD50 in rat is 1660 mg/kg. Symptoms of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, and swelling of face, lips, tongue, or throat.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Well absorbed from the gastrointestinal tract.
Protein Binding 95%
External Links
Wikipedia
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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