Ceftriaxone

Names

[ Name ]:
Ceftriaxone

[Synonym ]:
Ceftriazone
Biotrakson
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)-1-oxoethyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-, (6R,7R)-
Rocefin
(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-3-{[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftriaxone
(6R,7R)-7-{(E)-[(2Z)-1-Hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)-1-oxoethyl]amino]-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thio]methyl]-8-oxo-, (6R,7R)-
Ro 13-9904/001
ceftriaxonum [INN_la]
ceftriaxome
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftriaxone [USAN:JAN]
Antibiotic Ro-13-9904
Cefatriaxone
(6R,7R)-7-[[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
MFCD00865013
EINECS 277-405-6
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Rocephin
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(1E,2Z)-2-(2,3-dihydro-2-imino-4-thiazolyl)-1-hydroxy-2-(methoxyimino)ethylidene]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-, (6R,7R)-

Biological Activity

[Description]:

Ceftriaxone is an antibiotic useful for the treatment of a number of bacterial infections.Target: AntibacterialCeftriaxone inhibits bacterial cell wall synthesis by means of binding to the penicillin-binding proteins (PBPs). Inhibition of PBPs would in turn inhibit the transpeptidation step in peptidoglycan synthesis which is required for bacterial cell walls. Like other cephalosporins, ceftriaxone is bacteriocidal and exhibits time-dependent killing. Ceftriaxone, one of the beta-lactam antibiotics, is a stimulator of EAAT2 expression with neuroprotective effects in both in vitro and in vivo models based in part on its ability to inhibit neuronal cell death by glutamate excitotoxicity. Based on this consideration and its lack of toxicity, ceftriaxone has potential to manipulate glutamate transmission and ameliorate neurotoxicity [1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Lee, S.G., et al., Mechanism of ceftriaxone induction of excitatory amino acid transporter-2 expression and glutamate uptake in primary human astrocytes. J Biol Chem, 2008. 283(19): p. 13116-23.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Melting Point ]:
155 °C

[ Molecular Formula ]:
C₁₈H₁₈N₈O₇S₃

[ Molecular Weight ]:
554.580

[ Exact Mass ]:
554.046082

[ PSA ]:
293.80000

[ LogP ]:
-0.77

[ Index of Refraction ]:
1.889

[ Storage condition ]:
2-8℃

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R42/43

[ Safety Phrases ]:
24/25

[ WGK Germany ]:
3

[ HS Code ]:
3003201700

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 3003201700