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Related CAS#:
55268-75-2 97232-97-8
1803240-98-3 229499-08-5
64544-07-6 56238-63-2
65527-51-7 555268-75-2
123458-61-7 56271-94-4

55268-75-2

55268-75-2 structure
55268-75-2 structure
  • Name: Cefuroxime
  • Chemical Name: cefuroxime
  • CAS Number: 55268-75-2
  • Molecular Formula: C16H16N4O8S
  • Molecular Weight: 424.385
  • Catalog: API Antibiotics Cephalosporin
  • Create Date: 2018-06-20 17:34:29
  • Modify Date: 2024-01-02 15:08:02
  • Cefuroxime is an orally active second-generation cephalosporin antibiotic with increased stability to β-lactamase. Cefuroxime has a broad spectrum activity against Gram-positive and Gram-negative bacteria[1].
Name cefuroxime
Synonyms EINECS 259-560-1
cefuroxim
U1troxim
Ketocef
(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefuroxime
Biocidin
cefaloxime
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)-1-oxoethyl]amino]-8-oxo-, (6R,7R)-
Cephuroxime
MFCD00864991
CXM
Biofuroksym
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-Carbamoyloxymethyl-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
EkLxirrm
Description Cefuroxime is an orally active second-generation cephalosporin antibiotic with increased stability to β-lactamase. Cefuroxime has a broad spectrum activity against Gram-positive and Gram-negative bacteria[1].
Related Catalog
In Vitro Cefuroxime is highly active against S. aureus (MIC=0.25 μg/ml), regardless of whether the strains produces a penicillinase. It is against Staphylococcus aureus methicillin susceptible; S. aureus, methicillin resistant, Streptococcus pyogenes, S. pneumoniae, S. viridans, S. faecalis, and Clostridium spp with MIC values of 0.25 μg/ml, 5.9 μg/ml, 0.125 μg/ml, 0.125 μg/ml, 0.125 μg/ml, >125.0 μg/ml, and 1.2 μg/ml, respectively[1]. Cefuroxime (10-100 μg/ml; 2-6 hours) rapidly bactericidal, its action is comparatively slow against the strains of S. aureus, but, even so, over 99% of the initial inoculum is killed by 6 h. The gram-negative organisms are killed rapidly, and in most cases over 99% of the very large inocula are killed within 2 h; the β-lactamase-producing strains are killed as quickly as non-enzyme-producing strains[1].
In Vivo Rabbits (weighing 2.0 to 2.5 kg) are challenged intravenously with S. aureus strain 630 (a penicillinase-producing strain), the median effective dose of Cefuroxime is 3 mg/kg as a result of the protection test[2].
References

[1]. Callaghan, et al. Cefuroxime, a New Cephalosporin Antibiotic: Activity in Vitro. Antimicrob Agents Chemother. 1976 Mar;9(3):511-9.

[2]. D M Ryan, et al. Cefuroxime, a New Cephalosporin Antibiotic: Activity in Vivo. Antimicrob Agents Chemother. 1976 Mar;9(3):520-5.
Density 1.8±0.1 g/cm3
Melting Point 171.5-173°C
Molecular Formula C16H16N4O8S
Molecular Weight 424.385
Exact Mass 424.068878
PSA 199.06000
LogP 0.47
Index of Refraction 1.735

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0329000
CHEMICAL NAME :
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2- furanyl(methyoxyimino)acetyl)amino)-8-oxo-, (6R-(6-alpha,7-beta(Z)))-
CAS REGISTRY NUMBER :
55268-75-2
LAST UPDATED :
199707
DATA ITEMS CITED :
19
MOLECULAR FORMULA :
C16-H16-N4-O8-S
MOLECULAR WEIGHT :
424.42
WISWESSER LINE NOTATION :
T46 ANV ES GUTJ G1OVZ HVQ CMVYUNO1&- BT5OJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
64 mg/kg/16H-I
TOXIC EFFECTS :
Behavioral - toxic psychosis
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,965,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRUGAY Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. (ADIS Press International Inc., Suite B-30, Oxford Ct. Business Center, 582 Middletown Blvd., Langhorne, PA 19047) V.1- 1971- Volume(issue)/page/year: 17,233,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
30 gm/kg/5W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - changes in lung weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),130,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 gm/kg/5W-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - normocytic anemia Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),130,1979 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
8800 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - other postnatal measures or effects
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
24 gm/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
32 gm/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
4400 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases R42/43
Safety Phrases 22-24-37-45
RIDADR NONH for all modes of transport
RTECS XI0329000
1189-71-5 structure

1189-71-5
56271-94-4 structure

56271-94-4

~92%

55268-75-2 structure

55268-75-2
Literature: Antibioticos S.p.A. Patent: US6642378 B1, 2003 ; Location in patent: Page/Page column 2-3 ;
870-30-4 structure

870-30-4
56271-94-4 structure

56271-94-4

~71%

55268-75-2 structure

55268-75-2
Literature: Antibioticos S.p.A. Patent: US6642378 B1, 2003 ; Location in patent: Page/Page column 3-4 ;
97232-97-8 structure

97232-97-8

~%

55268-75-2 structure

55268-75-2
Literature: Journal of Pharmaceutical Sciences, , vol. 83, # 4 p. 553 - 558

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