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Ceftriaxone

Ceftriaxone structure

CAS No:
73384-59-5
Formula:
C18H18N8O7S3
Chemical Name:
Ceftriaxone
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-,[6R-[6α,7β(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-,(6R,7R)-;(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Ceftriaxone;Biotrakson;Rocefin;Rocephalin;Rophex;Epicephin;380149-23-5
Categories:
Active Pharmaceutical Ingredients > Antibiotics

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

Ceftriaxone Basic Attributes

Molecular Weight：

554.58

Exact Mass：

554.58

EC Number：

277-405-6

DSSTox ID：

DTXSID0022773

HScode：

29349990

Characteristics

PSA：

293.80000

XLogP3：

-0.77

Density：

2.0±0.1 g/cm3

Melting Point：

155 °C

Refractive Index：

1.889

Safety Information

wgk germany：

hazard class code：

42/43

safety instructions：

22-24-37-45

Marks：

GHS Classification：

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Ceftriaxone Use and Manufacturing

Methods of Manufacturing

Method 1: Using methylhydrazine hydrochloride as raw material, reacting with potassium thiocyanate to obtain methylthiosemicarbazide, and then ringing with dimethyl oxalate to obtain triazine ring. It is then condensed with 7-ACA to make 7-amino cephalosporin (referred to as 7-ACT), and then condensed with the aminothioxime side chain that protects the amino group with chloroacetyl chloride, and finally removes the protective group to obtain ceftriax. The route is difficult to operate when protecting and deprotecting the base, the yield and quality of the product are not easy to control, and industrial production is difficult. Method 2: Mild conditions, high yields, all above 80%, capable of industrial production. Using 7-ACA as the raw material, it is first condensed with triazine to synthesize 7-ACT, and then condensed with aminothioxime active ester (phosphorus-containing active ester or mercapto heterocyclic active ester) to form cephalosporin. When using phosphorus-containing active esters, you must first protect the carboxyl and hydroxyl groups on the 7-√ ketine with mono-trimethylacetamide or dimethylmethylurea and other silylating reagents, and the operation is cumbersome. In addition, its condensation products It is cephalosporin and must undergo salt formation reaction to become cephalosporin disodium salt. When using a mercapto-heterocyclic active ester, it is not necessary to protect the carboxyl group in advance, and the condensation product forms a salt in one step, which is more convenient and advanced. The side chain triazine ring derivative can be used with hydrazine hydrate and benzaldehyde, the resulting Schiff's base reacts with dimethyl sulfate to form N-methylhydrazine sulfate, and reacts with potassium thiocyanate to form N-methyl-N- Thiosemicarbazone, cyclized with dimethyl oxalate, and finally acidified to obtain the desired triazine ring derivative.

Uses

Possible carcinogen. Packaged under nitrogen

Computed Properties

Molecular Weight:554.6
XLogP3:-1.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:8
Exact Mass:554.04605846
Monoisotopic Mass:554.04605846
Topological Polar Surface Area:288
Heavy Atom Count:36
Complexity:1110
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzaldehyde

Chlorine dioxide

Dimethyl oxalate

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