(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 553
• Molecular Formular: C16H15N5O7S2
• Molecular Mass: 453.4496
• Monoisotopic Mass: 453.04128985
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OCC(=O)O)/c2nc(sc2)N)C(=C(C1)C=C)C(=O)O
• Canonical SMILES: Nc1nc(cs1)/C(=N\OCC(=O)O)/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
• InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/t10-,14-/m1/s1
• InChIKey: OKBVVJOGVLARMR-QMTHXVAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefixim; cefixime
• Brand Name: CFIX; Cefixoral; Cefspan; Cephoral; Oroken; Suprax; Unixime
• Synonyms: (6R,7R)-7-[[(2E)-2-(2-Amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; Cefixime E-isomer; [6R-[6α,7β(E)]]-7-[[(2-Amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (E)-Cefixime (Cefixime EP Impurity D); Cefixima [Spanish]; Cefixime Anhydrous; Cefiximum [Latin]; Cefixim; Cefixime

Database IDs

• CAS Number: 79350-37-1; 97164-56-2
• PubChem SID: 160964016
• PubChem CID: 6321411

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4486887
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -4.517875
• LogD (pH = 7.4): -7.089293
• Log P: -1.5863124
• Molar Refractivity: 104.9118 cm^3
• Polarizability: 39.59456 Å^3
• Polar Surface Area: 184.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.25
• LOG S: -3.64
• Solubility (Water): 1.04e-01 g/l

PROPERTIES

Physical Property

• Solubility: 55.11 mg/L
• Hydrophobicity(logP): -0.4

DETAILS

DrugBank - DB00671

• Drug Groups: approved
• Description: Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.
• Indication: For use in the treatment of the following infections when caused by susceptible strains of the designated microorganisms: (1) uncomplicated urinary tract infections caused by Escherichia coli and Proteus mirabilis, (2) otitis media caused by Haemophilus influenzae (beta-lactamase positive and negative strains), Moraxella catarrhalis (most of which are beta-lactamase positive), and S. pyogenes, (3) pharyngitis and tonsillitis caused by S. pyogenes, (4) acute bronchitis and acute exacerbations of chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae (beta-lactamase positive and negative strains), and (5) uncomplicated gonorrhea (cervical/urethral) caused by Neisseria gonorrhoeae (penicillinase- and non-penicillinase-producing strains).
• Pharmacology: Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.
• Toxicity: Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Approximately 50% of the absorbed dose is excreted unchanged in the urine in 24 hours.
• Absorption: About 40%-50% absorbed orally whether administered with or without food, however, time to maximal absorption is increased approximately 0.8 hours when administered with food.
• Half Life: 3-4 hours (may range up to 9 hours). In severe renal impairment (5 to 20 mL/min creatinine clearance), the half-life increased to an average of 11.5 hours.
• Protein Binding: 65% (concentration independent)
• References: McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. [Pubmed] ; Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - C242820

(E)-Cefixime is an isomeric impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

REFERENCES

• McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. Pubmed
• Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. Pubmed
• Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010)
• Rajadurai, R. et al.: Anal. Chem. Ind. J., 9, 265 (2010)