(2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-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: 368
• Molecular Formular: C19H17Cl2N3O5S
• Molecular Mass: 470.32638
• Monoisotopic Mass: 469.02659702
• SMILES: Clc1c(c2noc(c2C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)O)(C)C)C)c(Cl)ccc1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1c(Cl)cccc1Cl
• InChI: InChI=1S/C19H17Cl2N3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1
• InChIKey: YFAGHNZHGGCZAX-JKIFEVAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-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: (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-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: Dycill; Dynapen; Maclicine; Pathocil
• Synonyms: Diclossacillina [DCIT]; Dicloxacilina [INN-Spanish]; Dicloxacillin Sodium; Dicloxacilline [INN-French]; Dicloxacillinum [INN-Latin]; Dicloxacilin; Dicloxacycline; Dicloxacillin

Database IDs

• CAS Number: 3116-76-5
• PubChem SID: 46508182; 160963831
• PubChem CID: 18381

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7486086
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.1539227
• LogD (pH = 7.4): -0.3794561
• Log P: 2.9057844
• Molar Refractivity: 111.4419 cm^3
• Polarizability: 43.893353 Å^3
• Polar Surface Area: 112.74 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.19
• LOG S: -4.2
• Solubility (Water): 2.96e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3.63 mg/L
• Hydrophobicity(logP): 3.7

DETAILS

DrugBank - DB00485

• Drug Groups: approved
• Description: One of the penicillins which is resistant to penicillinase. [PubChem]
• Indication: Used to treat infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug.
• Pharmacology: Dicloxacillin is a beta-lactamase resistant penicillin similar to oxacillin. Dicloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of dicloxacillin results from the inhibition of cell wall synthesis and is mediated through dicloxacillin binding to penicillin binding proteins (PBPs). Dicloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Toxicity: Oral LD₅₀ in rat is 3579 mg/kg. Symptoms of overexposure include irritation, rash, labored breathing, hives, itching, wheezing, nausea, chills, and fever.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorption of the isoxazolyl penicillins after oral administration is rapid but incomplete: peak blood levels are achieved in 1-1.5 hours. Oral absorption of cloxacillin, dicloxacillin, oxacillin and nafcillin is delayed when the drugs are administered after meals.
• Half Life: The elimination half-life for dicloxacillin is about 0.7 hour.
• Protein Binding: Binds to serum protein, mainly albumin.
• Elimination: Dicloxacillin sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.
• External Links: Wikipedia; RxList; Drugs.com