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Substance Name: Cefixime [USAN:USP:INN:BAN:JAN]
RN: 79350-37-1
UNII: XZ7BG04GJX
InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N

Note

  • A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.

Molecular Formula

  • C16-H15-N5-O7-S2

Molecular Weight

  • 453.4545
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent

Names and Synonyms

Name of Substance

  • Cefixime
  • Cefixime [USAN:USP:INN:BAN:JAN]
  • FK 027

MeSH Heading

  • Cefixime

Synonyms

  • (-)-Cefixim
  • (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-(carboxymethyl)oxime) trihydrate
  • (6R,7R)-7-(2-(2-Amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(Z)-(O-(carboxymethyl)oxime)trihydrate
  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, trihydrate, (6R-(6alpha,7beta(Z)))-
  • BRN 6025058
  • Cefixim
  • Cefixima
  • Cefixima [Spanish]
  • Cefixime
  • Cefiximum
  • Cefiximum [Latin]
  • Cefixoral
  • Cefspan
  • Cephoral
  • CL 284,635
  • CL 284635
  • FK 027
  • FR 17027
  • Oroken
  • Suprax
  • UNII-XZ7BG04GJX
  • Unixime

Systematic Name

  • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6R,7R)-

Registry Numbers

CAS Registry Number

  • 79350-37-1

FDA UNII

  • XZ7BG04GJX

Other Registry Number

  • 214265-67-5

System Generated Number

  • 0079350371

Molecular Formulas

Molecular Formula

  • C16-H15-N5-O7-S2

Molecular Formula Fragment

  • C16-H15-N5-O7-S2

Structure Descriptors

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)/b20-9-/t10-,14-/m1/s1

InChIKey

OKBVVJOGVLARMR-QSWIMTSFSA-N

Smiles

Nc1nc(cs1)\C(=N\OCC(=O)O)\C(=O)N[C@H]2[C@H]3SCC(=C(N3C2=O)C(=O)O)C=C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 3200mg/kg (3200mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
dog LD50 intravenous > 3200mg/kg (3200mg/kg) KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER

GASTROINTESTINAL: NAUSEA OR VOMITING
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
dog LD50 oral > 600mg/kg (600mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 intravenous 4420mg/kg (4420mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 intravenous 6990mg/kg (6990mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 0.120 (none)   EST
Atmospheric OH Rate Constant 1.36E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.