Ceftriaxone sodium

Base Information

• Chemical Name: Ceftriaxone sodium
• CAS No.: 74578-69-1
• Molecular Formula: C18H18N8Na2O7S3
• Molecular Weight: 598.552
• Hs Code.: 3004909090
• European Community (EC) Number: 277-930-0,626-956-4
• NCI Thesaurus Code: C817
• RXCUI: 203172
• Mol file: 74578-69-1.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 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]-,disodium salt, [6R-[6a,7b(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,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]-,disodium salt, (6R,7R)- (9CI);Acantex;Cefatriaxone;Ceftriaxone disodium;Ceftriaxone disodium salt;Cephtriaxone;Ceroneed;Disodiumceftriaxone;Lendacin;Longaceph;Monocef;Oframax;Ro 13-9904;Rocephin;Sefirom;Tartriakson;X 13-9904;Ceftriaxone Sodium Hydrate;

Chemical Property of Ceftriaxone sodium

Chemical Property:

• PSA: 296.63000
• LogP: -2.03600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 576.02800271
• Heavy Atom Count: 37
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

Ceftriaxone Sodium Pharmaceutical Secondary Standard; Certified Reference Material ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)[O-].[Na+]
• Recent ClinicalTrials: Prophylactic Antibiotic Use in Transarterial Chemoembolization for Hepatocellular Carcinoma
• Recent EU Clinical Trials: An open label randomized controlled trial comparing the effect of ceftriaxone plus azithromycin versus ceftriaxone for the treatment of Neisseria gonorrhoeae on the resistome
• Description: Ceftriaxone is a cephalosporin (SEF a low spor in) antibiotic that is used to treat conditions such as lower respiratory tract infections, skin and skin structure infections, urinary tract infections, pelvic inflammatory disease, bacterial septicemia, bone and joint infections, and meningitis.
• Uses: Ceftriaxone sodium is antibacteria，an impurity of Ceftriaxone (C244995). It is an antibacterial, a third-generation cephalosporin.
• Therapeutic Function: Antibacterial
• Clinical Use: Ceftriaxone sodium is a β-lactamase–resistantcephalosporin with an extremely long serum half-life.Once-daily dosing suffices for most indications. Two factorscontribute to the prolonged duration of action ofceftriaxone: high protein binding in the plasma and slowurinary excretion. Ceftriaxone is excreted in both the bileand the urine. Its urinary excretion is not affected byprobenecid. Despite its comparatively low volume ofdistribution, it reaches the cerebrospinal fluid in concentrationsthat are effective in meningitis. Nonlinear pharmacokineticsare observed. Ceftriaxone contains a highly acidic heterocyclic systemon the 3-thiomethyl group. This unusual dioxotriazine ringsystem is believed to confer the unique pharmacokineticproperties of this agent. Ceftriaxone has been associatedwith sonographically detected “sludge,” or pseudolithiasis,in the gallbladder and common bile duct. Symptoms ofcholecystitis may occur in susceptible patients, especiallythose on prolonged or high-dose ceftriaxone therapy. Theculprit has been identified as the calcium chelate. Ceftriaxone exhibits excellent broad-spectrum antibacterialactivity against both Gram-positive and Gram-negativeorganisms. It is highly resistant to most chromosomally andplasmid-mediated β-lactamases. The activity of ceftriaxoneagainst Enterobacter, Citrobacter, Serratia, indole-positiveProteus, and Pseudomonas spp. is particularly impressive. Itis also effective in the treatment of ampicillin-resistant gonorrheaand H. influenzae infections but generally less activethan cefotaxime against Gram-positive bacteria and B.fragilis.

Technology Process of Ceftriaxone sodium

There total 10 articles about Ceftriaxone sodium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

C11H15N3O4S + C12H13N5O5S2*C5H13N3 → ceftriaxone disodium (74578-69-1)

Guidance literature:

C₁₁H₁₅N₃O₄S; C₁₂H₁₃N₅O₅S₂*C₅H₁₃N₃; With sodium acetate; In water; at -50 - -40 ℃; for 1h;

In acetone; at 20 - 25 ℃; for 1h; Solvent; Reagent/catalyst;

Reference yield: 95.5%

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + 7-aminoceftrizine (58909-56-1) → ceftriaxone disodium (74578-69-1)

Guidance literature:

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-aminoceftrizine; With triethylamine; In methanol; at -2 - 3 ℃;

With sodium 2-ethylhexanoic acid; In water; isopropyl alcohol; at 26 - 30 ℃; for 2h; Product distribution / selectivity;

Reference yield: 95.5%

ceftriaxone → (6R,7R)-7-<2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido>-3-<<(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid disodium salt (Z isomer) (74578-69-1,91109-02-3,97164-54-0)

Guidance literature:

With sodium acetate; In acetone; at 17 - 20 ℃;

upstream raw materials:

7-Aminocephalosporanic acid

7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazine-3-mercapto)methyl]-3 cephalosporin-4-carboxylic acid

2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one

ceftriaxone

Refernces

• 1、 -. "Preparation method of ceftriaxone sodium". Paragraph 0060-0061; 0065-0066-0067; 0071-0073; 0077-0078. . Retrieved 2020/08/02.
• 2、 -. "A synthesis method of Ceftriaxone sodium". Paragraph 0025-0026; 0052-0053. . Retrieved 2017/05/11.