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| | Ceftriaxone sodium Basic information |
| Product Name: | Ceftriaxone sodium | | Synonyms: | CEFATRIAXONE;2,5,6-tetrahydro-2-methyl-5,6-dioxo-)(methoxyimino)acetyl)amino)-8-oxo-3-(((;4-triazin-3-yl)thio)methyl)-,sodiumsalt,hydrate(2:4:7)(6r-(6-alpha,7-2;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]-, disodium salt, [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]-, disodium salt, (6R,7R)-;[6R-[6alpha,7beta(Z)]]-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]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt;Ceftriaxone sodium;Ceferiaxone SodiuM Sterile | | CAS: | 74578-69-1 | | MF: | C18H19N8NaO7S3 | | MW: | 578.57 | | EINECS: | 277-930-0 | | Product Categories: | Pharmaceutical intermediates, pharmaceutical raw materials;Pharmaceutical intermediates;Pharma;Pharmaceutical intermediate;74578-69-1 | | Mol File: | 74578-69-1.mol |  |
| | Ceftriaxone sodium Chemical Properties |
| storage temp. | 4°C, protect from light | | solubility | Soluble in DMSO (50 mM) | | color | White to off-white | | Water Solubility | Water : ≥ 40 mg/mL (66.60 mM) | | InChIKey | CDCJSJLFRBHEHN-ZZKDXJNYNA-N | | SMILES | C(C1=C(CS[C@]2([H])[C@H](NC(=O)/C(/C3N=C(N)SC=3)=N\OC)C(=O)N12)CSC1=NC(=O)C(=O)NN1C)(=O)O.[NaH] |&1:5,7,r| | | CAS DataBase Reference | 74578-69-1(CAS DataBase Reference) |
| | Ceftriaxone sodium Usage And Synthesis |
| 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. | | Originator | Rocephin,Roche,Switz.,1982 | | Uses | Ceftriaxone sodium is antibacteria，an impurity of Ceftriaxone (C244995). It is an antibacterial, a third-generation cephalosporin. | | Brand name | Rocephin (Roche). | | Therapeutic Function | Antibacterial | | Hazard | Moderately toxic. Low toxicity by inges-
tion. Human systemic effects.
| | 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.
| | Side effects | Ceftriaxone sodium is a bactericidal agent that acts by inhibition of bacterial cell
wall synthesis. Ceftriaxone has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and
Gram-positive bacteria. | | Side effects | Common side effects of Ceftriaxone sodium include:
symptoms of a blood cell disorder;
diarrhea;
vaginal itching or discharge;
warmth, tight feeling, or a hard lump where the injection was given;
rash;
abnormal liver function tests. | | Synthesis | A solution of sodium-2-ethyl hexanoate (390 g) in acetone (2.0 Ltr) is added to the wet Ceftriaxone acid obtained in Example 2 is suspended in a mixture of acetone and water. The reaction mixture is charcoalized and filtered. To the clear filtrate is added acetone whereupon the product precipitated. The precipitated solid is filtered, washed with acetone and dried to get 515 g of Ceftriaxone sodium hemiheptahydrate. HPLC purity = Above 99.5%. | | Veterinary Drugs and Treatments | Ceftriaxone is used to treat serious infections, particularly against
susceptible Enterobacteriaceae that are not susceptible to other less
expensive agents or when aminoglycosides are not indicated (due
to their potential toxicity). Its long half life, good CNS penetration,
and activity
against Borrelia burgdorferi also has made it a potential
choice for treating Lyme’s disease. | | storage | +4°C |
| | Ceftriaxone sodium Preparation Products And Raw materials |
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