CAS 70797-11-4|Cefpiramide|(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-aza...

General Information

Structure

Molecular Formula

C₂₅H₂₄N₈O₇S₂

Molecular Mass

612.63746

Exact Mass

612.12093715

Charge

0

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

Canonic 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

Isomeric 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

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

Polarizability

57.50968

Polar Surface Area

208.74

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

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

CefpiramideSM-1652

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

Cefpiramido [INN-Spanish]Cefpiramide [USAN:INN]Cefpiramide SodiumCefpiramidum [INN-Latin]

Names and Identifiers

Registration numbers

CAS Number

70797-11-4

PubChem CID

107654

PubChem SID

160963776

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-0.9

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:313