CAS 79350-37-1|CAS 97164-56-2|Cefixima [Spanish]|Cefiximum [Latin]|Unixime|Cefixim|cefixime|Cefixime Anhydrous|Oroken|(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-et...

General Information

Structure

Molecular Formula

C₁₆H₁₅N₅O₇S₂

Molecular Mass

453.4496

Exact Mass

453.04128985

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

3.4486887

H Acceptors

H Donor

LogD (pH = 5.5)

-4.517875

LogD (pH = 7.4)

-7.089293

Log P

-1.5863124

Molar Refractivity

104.9118

Polarizability

39.59456

Polar Surface Area

184.51

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.25

LOG S

-3.64

Solubility (Water)

1.04e-01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Cefixima [Spanish]Cefiximum [Latin]CefiximCefixime Anhydrous(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[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 AcidCefixime E-isomer(E)-Cefixime (Cefixime EP Impurity D)Cefixime

Brand Name

UniximeOrokenCFIXCefspanCefixoralSupraxCephoral

IUPAC Traditional name

cefixime cefixim

IUPAC name

(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 (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

Names and Identifiers

Registration numbers

CAS Number

79350-37-197164-56-2

PubChem SID

160964016

PubChem CID

6321411

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-0.4

Solubility

55.11 mg/L

Product Information

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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

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]

TRC

C242820

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Rajadurai, R. et al.: Anal. Chem. Ind. J., 9, 265 (2010)

• Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC Traditional name

• IUPAC name

Registration numbers

• CAS Number

• PubChem SID

• PubChem CID

Properties

• Physical Property

• Product Information

• Safety Information

Related Proteins

Molecular Spectra

Molecule Details

• DrugBank

• TRC

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Commercial Catalog

TRC

C242820

Synonyms

Brand Name

UniximeOrokenCFIXCefspanCefixoralSupraxCephoral

IUPAC Traditional name

cefixime cefixim

IUPAC name

PubChem SID

160964016

Physical Property

Hydrophobicity(logP)

-0.4

Solubility

55.11 mg/L

Product Information

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

From Data Sources

• 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

• Rajadurai, R. et al.: Anal. Chem. Ind. J., 9, 265 (2010)

• Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010)

DrugBank

DB00671

Drug Groups

approved

Description

Indication

Pharmacology

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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

TRC

C242820

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

Molecule

ID:553