(6R)-7-[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1,4-dihydropyridin-3-yl)formamido]acetamido]-3-{[(1-methyl-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: 313
• Molecular Formular: C25H24N8O7S2
• Molecular Mass: 612.63746
• Monoisotopic Mass: 612.12093715
• SMILES: S1[C@H]2N(C(=O)C2NC(=O)[C@H](NC(=O)c2c(=O)cc([nH]c2)C)c2ccc(O)cc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: Oc1ccc(cc1)[C@H](C(=O)NC1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)NC(=O)c1c[nH]c(cc1=O)C
• InChI: InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18?,23-/m1/s1
• InChIKey: PWAUCHMQEXVFJR-JIUDAOPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-7-[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1,4-dihydropyridin-3-yl)formamido]acetamido]-3-{[(1-methyl-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: cefpiramide
• Brand Name: Cefpiramide Sodium; Cefpiramide [USAN:INN]; Cefpiramido [INN-Spanish]; Cefpiramidum [INN-Latin]
• Synonyms: SM-1652; Cefpiramide

Database IDs

• CAS Number: 70797-11-4
• PubChem SID: 160963776
• PubChem CID: 107654

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3837736
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.3815353
• LogD (pH = 7.4): -3.7226677
• Log P: -0.28924468
• Molar Refractivity: 166.5938 cm^3
• Polarizability: 57.50968 Å^3
• Polar Surface Area: 208.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.85
• LOG S: -4.08
• Solubility (Water): 5.13e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.9

DETAILS

DrugBank - DB00430

• Drug Groups: approved
• Description: Cefpiramide is a third-generation cephalosporin antibiotic.
• Indication: For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.
• Pharmacology: Cefpiramide is a cephalosporin active against Pseudomonas aeruginosa. It has a broad spectrum of antibacterial activity. Cefpiramide works by inhibiting bacterial cell wall biosynthesis. The plasma half-lives of cefpiramide in rabbits, dogs, and rhesus monkeys were much longer than those of cefoperazone and cefazolin.
• Toxicity: Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Rapidly absorbed following intramuscular injection.
• Half Life: 4.44 hours
• References: Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M: In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. [Pubmed] ; Iakovlev VP, Vishnevskii VA, Khlebnikov EP, Khadin IM, Plavlova MV, Elagina LV, Izotova GN: [Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery] Antibiot Khimioter. 1995 Sep;40(9):30-4. [Pubmed] ; Sampi K, Hattori M: [Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study] Gan To Kagaku Ryoho. 1992 Aug;19(9):1315-20. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M: In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. Pubmed
• Iakovlev VP, Vishnevskii VA, Khlebnikov EP, Khadin IM, Plavlova MV, Elagina LV, Izotova GN: [Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery] Antibiot Khimioter. 1995 Sep;40(9):30-4. Pubmed
• Sampi K, Hattori M: [Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study] Gan To Kagaku Ryoho. 1992 Aug;19(9):1315-20. Pubmed