Compound ID | 1935

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Nafcillin

Synonym(s): WY-3277

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP); PBP inhibitor
Target Pathogen: Active against Gram-positive bacteria, especially staphylococci including penicillinase producing strains
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA); parenteral application; contains naphthalen scaffold
Year first mentioned: 1961
Highest development stage: Approved by FDA in 1970
Development status: Approved
Chemical structure(s):
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Molecular weight: 414.48
Iso. SMILES: CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI Key: GPXLMGHLHQJAGZ-JTDSTZFVSA-N
Can. SMILES: CCOC1=C(C2=C(C=CC=C2)C=C1)C(=O)N[C@@H]3C(=O)N4[C@@H](C(=O)O)C(C)(C)S[C@H]34
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/8982
Guide to Pharmacology: nafcillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/32376001/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4958157/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5980628/

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