(6R,7R)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 799
• Molecular Formular: C20H21N7O6S2
• Molecular Mass: 519.55404
• Monoisotopic Mass: 519.09947343
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)Cc2c(CN)cccc2)C(=C(C1)CSc1n(nnn1)CC(=O)O)C(=O)O
• Canonical SMILES: NCc1ccccc1CC(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1CC(=O)O
• InChI: InChI=1S/C20H21N7O6S2/c21-6-11-4-2-1-3-10(11)5-13(28)22-15-17(31)27-16(19(32)33)12(8-34-18(15)27)9-35-20-23-24-25-26(20)7-14(29)30/h1-4,15,18H,5-9,21H2,(H,22,28)(H,29,30)(H,32,33)/t15-,18-/m1/s1
• InChIKey: SLAYUXIURFNXPG-CRAIPNDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-{2-[2-(aminomethyl)phenyl]acetamido}-3-({[1-(carboxymethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: precef
• Brand Name: Precef
• Synonyms: Ceforanido [INN-Spanish]; Ceforanidum [INN-Latin]; Ceforanide

Database IDs

• CAS Number: 60925-61-3
• PubChem SID: 46504532; 160964262
• PubChem CID: 43507

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.5509233
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -5.1402783
• LogD (pH = 7.4): -6.3588696
• Log P: -3.1718965
• Molar Refractivity: 139.8653 cm^3
• Polarizability: 48.582443 Å^3
• Polar Surface Area: 193.63 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.35
• LOG S: -3.42
• Solubility (Water): 1.97e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -3.7

DETAILS

DrugBank - DB00923

• Drug Groups: approved
• Description: Ceforanide is a second-generation parenteral cephalosporin antibiotic. It has a longer elimination half-life than any currently available cephalosporin. Its activity is very similar to that of cefamandole, a second-generation cephalosporin, except that ceforanide is less active against most gram-positive organisms. Many coliforms, including Escherichia coli, Klebsiella, Enterobacter, and Proteus, are susceptible to ceforanide, as are most strains of Salmonella, Shigella, Hemophilus, Citrobacter and Arizona species.
• Indication: For the treatment of infections caused by susceptible organisms.
• Pharmacology: Ceforanide is a semisynthetic second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins.
• Toxicity: Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: The major drug elimination route was urinary excretion with 85% of the dose being excreted unchanged in the urine within 12 hr, and no metabolites with antibiotic activity were observed in urine.
• Absorption: Rapidly absorbed following intramuscular injection.
• Half Life: 2.6 to 2.98 hours
• Protein Binding: 80.6%
• References: Crowle AJ, Sbarbaro JA, May MH: Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages. Tubercle. 1988 Mar;69(1):15-25. [Pubmed] ; Campoli-Richards DM, Lackner TE, Monk JP: Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy. Drugs. 1987 Oct;34(4):411-37. [Pubmed] ; Cone LA, Barton SM, Woodard DR: Treatment of scleroma with ceforanide. Arch Otolaryngol Head Neck Surg. 1987 Apr;113(4):374-6. [Pubmed] ; Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Crowle AJ, Sbarbaro JA, May MH: Effects of isoniazid and of ceforanide against virulent tubercle bacilli in cultured human macrophages. Tubercle. 1988 Mar;69(1):15-25. Pubmed
• Campoli-Richards DM, Lackner TE, Monk JP: Ceforanide. A review of its antibacterial activity, pharmacokinetic properties and clinical efficacy. Drugs. 1987 Oct;34(4):411-37. Pubmed
• Cone LA, Barton SM, Woodard DR: Treatment of scleroma with ceforanide. Arch Otolaryngol Head Neck Surg. 1987 Apr;113(4):374-6. Pubmed
• Barriere SL, Mills J: Ceforanide: antibacterial activity, pharmacology, and clinical efficacy. Pharmacotherapy. 1982 Nov-Dec;2(6):322-7. Pubmed