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70797-11-4 molecular structure
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(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 and InChIs

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

Cite this record

CBID:313 http://www.chembase.cn/molecule-313.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
70797-11-4
PubChem SID
160963776
PubChem CID
107654

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3837736  H Acceptors 11 
H Donor LogD (pH = 5.5) -2.3815353 
LogD (pH = 7.4) -3.7226677  Log P -0.28924468 
Molar Refractivity 166.5938 cm3 Polarizability 57.50968 Å3
Polar Surface Area 208.74 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.85  LOG S -4.08 
Solubility (Water) 5.13e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
-0.9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00430 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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