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CEFTRIAXONE

CEFTRIAXONE Structure
CAS No.
73384-59-5
Chemical Name:
CEFTRIAXONE
Synonyms
CEFTRIAZONE;Ceftriazone sodiuM;Ceftriaxone Sodium Ep Impurity A;Rocefin;Biotrakson;Rocephin(e);CEFTRIAXONE;CEFATRIAXONE;Cefatriaxone From;Antibiotic Ro-13-9904
CBNumber:
CB9114533
Molecular Formula:
C18H18N8O7S3
Molecular Weight:
554.58
MOL File:
73384-59-5.mol
Modify Date:
2024/8/1 23:06:22

CEFTRIAXONE Properties

Melting point 155 °C
Density 1.96±0.1 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
solubility DMSO (Slightly), Methanol (Slightly)
pka pKa –3.2±0.6 (Uncertain);–1.8±0.2 (Uncertain);2.57±0.50 (Uncertain);2.90±0.50 (Uncertain);8.03±0.40 (Uncertain)
form Solid
color Off-White to Pale Yellow
Stability Hygroscopic
CAS DataBase Reference 73384-59-5(CAS DataBase Reference)
EPA Substance Registry System Ceftriaxone (73384-59-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H315-H317-H334-H319-H335
Precautionary statements  P261-P285-P304+P341-P342+P311-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Hazard Codes  Xn
Risk Statements  42/43
Safety Statements  22-24-37-45
HS Code  29349990

CEFTRIAXONE Chemical Properties,Uses,Production

Description

Ceftriaxone has the same C-7 side-chain moiety as cefotaxime and ceftizoxime, but the C-3 side chain consists of a metabolically stable and activating thiotriazinedione in place of the normal acetyl group. The C-3 side chain is sufficiently acidic that at normal pH, it forms an enolic sodium salt; thus, the commercial product is a disodium salt.

Uses

Ceftriaxone is an antibacterial, a third-generation cephalosporin.

Definition

ChEBI: A cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups.

Antimicrobial activity

Most β-lactamase-producing enterobacteria are highly susceptible, as are streptococci (but not enterococci) and fastidious Gram-negative bacilli, although brucellae are less sensitive (MIC 0.25–2 mg/L). Treatment failure has been reported in tularemia. Ps. aeruginosa, mycoplasmas, mycobacteria and L. monocytogenes are resistant.

Acquired resistance

Ceftriaxone is hydrolyzed by some chromosomal enzymes, including those of Enterobacter spp. and B. fragilis. Derepression of chromosomal β-lactamase production can cause resistance in some species of Gram-negative bacilli in vitro and has been observed in patients.

Clinical Use

Uses of Ceftriaxone are similar to those of cefotaxime, the long half-life offering the advantage of once-daily administration. It is used in the treatment of acute bacterial meningitis and as an alternative to rifampicin (rifampin) in the prophylaxis of meningococcal disease.

Side effects

Reactions are those common to other cephalosporins. Mention has been made of thrombocytopenia, thrombocytosis, leukopenia, eosinophilia abdominal pain, phlebitis, rash, fever and increased values in liver function tests. Diarrhea is common and suppression of the aerobic and anaerobic fecal flora has been associated with the appearance of resistant bacteria and yeasts.
Biliary pseudolithiasis due to concretions of insoluble calcium salt has been described in adults but principally in children. The precipitates can be detected in a high proportion of patients by ultrasonography and can occasionally cause pain, but resolve on cessation of treatment. Ceftriaxone is better avoided in patients with pre-existing biliary disease, but the principal hazard appears to be misdiagnosis of gallbladder disease and unnecessary surgery.

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