(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1010
• Molecular Formular: C17H17N3O6S2
• Molecular Mass: 423.46338
• Monoisotopic Mass: 423.05587728
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)CSc2ccncc2)C(=C(C1)COC(=O)C)C(=O)O
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)C)CSc1ccncc1
• InChI: InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
• InChIKey: UQLLWWBDSUHNEB-CZUORRHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cephapirin; CEPR
• Brand Name: Ambrocef; Cefa; Cefatrex; Cefatrexyl; Cefadyl
• Synonyms: Cefapirin; Cefapirina [INN-Spanish]; Cefapirine [INN-French]; Cefapirinum [INN-Latin]; Cefaprin sodium; Cefaprin; Cephapirin Sodium; Cephapirine; Cephapirin; (6R,7R)-3-[(Acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-3-[(Acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-[2-(4-Pyridylthio)acetamido]cephalosporanic Acid; Cephaprin

Database IDs

• CAS Number: 21593-23-7
• PubChem SID: 160964473; 46505227
• PubChem CID: 30699

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.540687
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.5915926
• LogD (pH = 7.4): -4.131089
• Log P: -2.0011034
• Molar Refractivity: 102.4307 cm^3
• Polarizability: 39.824234 Å^3
• Polar Surface Area: 125.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.18
• LOG S: -3.45
• Solubility (Water): 1.51e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1030 mg/L; DMSO; Methanol (Sparingly)
• Apperance: Beige Solid
• Melting Point: >135°C (dec.)
• Hydrophobicity(logP): -0.1

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB01139

• Drug Groups: approved
• Description: Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms. [PubChem]
• Indication: For treatment of infections caused by susceptible bacteria.
• Pharmacology: Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.
• Toxicity: Rats exposed via the oral route to cephapirin displayed low acute toxicity (LD₅₀ = 14000 mg/kg). The most common adverse reactions are hypersensitivity reactions and alterations to liver function. Evidence of white blood cell disorders and anaemia were noted in some subjects.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Major metabolite detected is desacetylcephapirin.

Toronto Research Chemicals - C261500

An antimicrobial agent.

REFERENCES

• Tan, J.S., et al.: Antimicrob. Agents Chemother., 15, 510 (1979)