nafcillin   Click here for help

GtoPdb Ligand ID: 10942

Synonyms: Ethoxynaphthamido Penicillin Sodium | Nallpen® | Unipen®
Approved drug
nafcillin is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Nafcillin is a semi-synthetic naphthalene, penicillinase resistant β-lactam antibacterial.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 121.24
Molecular weight 414.12
XLogP 3.28
No. Lipinski's rules broken 0
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Canonical SMILES CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)O)(C)C)cccc2
Isomeric SMILES CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)O)(C)C)cccc2
InChI InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1965))
IUPAC Name Click here for help
(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-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
1491 nafcillin
Synonyms Click here for help
Ethoxynaphthamido Penicillin Sodium | Nallpen® | Unipen®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nafcillin
Other databases
CAS Registry No. 147-52-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1443
DrugBank Ligand DB00607
DrugCentral Ligand 1869
GtoPdb PubChem SID 405560383
PubChem CID 8982
Search Google for chemical match using the InChIKey GPXLMGHLHQJAGZ-JTDSTZFVSA-N
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UniChem Compound Search for chemical match using the InChIKey GPXLMGHLHQJAGZ-JTDSTZFVSA-N
UniChem Connectivity Search for chemical match using the InChIKey GPXLMGHLHQJAGZ-JTDSTZFVSA-N