(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1225
• Molecular Formular: C15H17N5O6S2
• Molecular Mass: 427.45538
• Monoisotopic Mass: 427.06202529
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N\OC)/c2nc(sc2)N)C(=C(C1)COC)C(=O)O
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)COC
• InChI: InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
• InChIKey: WYUSVOMTXWRGEK-HBWVYFAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefpodoxime
• Brand Name: Vantin; Banan; Doxef
• Synonyms: (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cefpodoxime; R 3763; Cefpodoxime Acid; Cefpodoxime proxetil; CPDX-PR; RU 51807; Cefpodoxime

Database IDs

• CAS Number: 80210-62-4; 82619-04-3
• PubChem SID: 46504897; 160964685
• PubChem CID: 6335986

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.217438
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -2.7401698
• LogD (pH = 7.4): -3.9569473
• Log P: -1.6657981
• Molar Refractivity: 100.708 cm^3
• Polarizability: 38.09914 Å^3
• Polar Surface Area: 156.44 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.05
• LOG S: -3.36
• Solubility (Water): 1.85e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow to Beige Solid
• Melting Point: 200-202°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB01416

• Drug Groups: approved
• Description: Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. Cefpodoxime proxetil is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime.
• Indication: For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.
• Pharmacology: Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Cefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.
• Half Life: 2.09 to 2.84 hours
• Protein Binding: 22 to 33% in serum and from 21 to 29% in plasma.
• Elimination: Over the recommended dosing range (100 to 400 mg), approximately 29 to 33% of the administered cefpodoxime dose was excreted unchanged in the urine in 12 hours.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C243850

A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial.

REFERENCES

• Fujimoto, K., et al.: J. Antibiot., 40, 370 (1987)
• Utsui, Y., et al.: Antimicrob. Agents Chemother., 31, 1085 (1987)