(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 489
• Molecular Formular: C21H22N2O5S
• Molecular Mass: 414.47478
• Monoisotopic Mass: 414.12494281
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)c1c2c(ccc1OCC)cccc2
• Canonical 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
• InChIKey: GPXLMGHLHQJAGZ-JTDSTZFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Nafcilin-1; Nafcillin sodium for injection; Nallpen; Nallpen In Plastic Container; Naphcillin; Unipen
• Synonyms: Nafcilina [INN-Spanish]; Nafcillin Sodium; Nafcillin sodium salt; Nafcilline [INN-French]; Nafcillinum [INN-Latin]; Nafcillin

Database IDs

• CAS Number: 985-16-0
• PubChem SID: 46508100; 160963952
• PubChem CID: 8982

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3094113
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.11520102
• LogD (pH = 7.4): -1.1349657
• Log P: 2.289126
• Molar Refractivity: 108.1384 cm^3
• Polarizability: 43.10996 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -4.38
• Solubility (Water): 1.72e-02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 3.3

DETAILS

DrugBank - DB00607

• Drug Groups: approved
• Description: A semi-synthetic antibiotic related to penicillin. [PubChem]
• Indication: For the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drugs.
• Pharmacology: Nafcillin is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. The drugs in this class are highly resistant to inactivation by staphylococcal penicillinase and are active against penicillinase-producing and non penicillinase-producing strains of Staphylococcus aureus. The penicillinase- resistant penicillins are active in vitro against a variety of other bacteria.
• Toxicity: Serious toxicity is unlikely following large doses of nafcillin. Acute ingestion of large doses of nafcillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins.
• Half Life: The serum half-life of nafcillin administered by the intravenous route ranged from 33 to 61 minutes as measured in three separate studies.
• Protein Binding: 89.9 ±1.5%
• Elimination: Nafcillin is primarily eliminated by nonrenal routes, namely hepatic inactivation and excretion in the bile.
• External Links: Wikipedia; RxList; Drugs.com