7-[[(2Z)-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

Base Information

• Chemical Name: 7-[[(2Z)-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
• CAS No.: 73384-59-5
• Molecular Formula: C18H18N8O7S3
• Molecular Weight: 554.588
• Hs Code.: 29349990
• European Community (EC) Number: 277-405-6
• Wikipedia: Ceftriaxone
• Mol file: 73384-59-5.mol

Synonyms:73384-59-5;SCHEMBL14896587;AKOS015960562;AC-11710

Chemical Property of 7-[[(2Z)-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

Chemical Property:

• Melting Point: 155 °C
• Refractive Index: 1.889
• 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)
• PSA: 293.80000
• Density: 1.96 g/cm³
• LogP: -0.70130
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 554.04605846
• Heavy Atom Count: 36
• Complexity: 1110

Purity/Quality:

99% ^*data from raw suppliers

Ceftriaxone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-24-37-45

MSDS Files:

SDS file from LookChem

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
• Isomeric SMILES: CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C(C(C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
• Recent EU Clinical Trials: 3-day intravenous antibiotic treatment versus 3-day intravenous followed by 7-day oral antibiotic treatment for acute pyelonephritis in children 1 month to 3 years old: a non-inferiority open randomized multicentric clinical trial
• 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: Possible carcinogen. Packaged under nitrogen This drug has a broad spectrum of antimicrobial action that includes the majority of the clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, anaerobic, and blue-pus bacillus. It is resistant with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. It is used for peritonitis, sepsis, meningitis, cholangitis, empyema of the gall bladder, pneumonia, lung abscesses, pyelonephritis, infections of the bones, joints, skin, soft tissues, abdominal and gynecological infections, and for infected wounds and burns. The main synonym of this drug is rocefin. Ceftriaxone is an antibacterial, a third-generation cephalosporin.
• Therapeutic Function: Antibacterial
• 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.

Technology Process of 7-[[(2Z)-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

There total 20 articles about 7-[[(2Z)-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 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: 95.7%

C18H14N5O9PS2 + 7-aminoceftrizine (58909-56-1) → ceftriaxone (73384-59-5,92143-31-2)

Guidance literature:

With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine; In ethanol; dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1515/hc-2014-0048

Reference yield: 93.4%

C14H24N3O5PS2 + 7-aminoceftrizine (58909-56-1) → ceftriaxone (73384-59-5,92143-31-2)

Guidance literature:

With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine; In ethanol; dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1515/hc-2014-0048

Reference yield: 93.3%

C18H14N5O10PS + 7-aminoceftrizine (58909-56-1) → ceftriaxone (73384-59-5,92143-31-2)

Guidance literature:

With ethylenediaminetetraacetic acid; sulphurous acid; sodium hydrogensulfite; triethylamine; In ethanol; dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1515/hc-2014-0048

upstream raw materials:

7-[4-bromo-2(Z)-methoxyimino-3-oxobutyramido]-3-[[2,5-(dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl]-3-cephem-4-carboxylic acid

thiourea

C₁₇H₁₇ClN₆O₈S₂

(6R,7R)-7-[2-[2-(2-chloroacetamido)-4-thiazolyl]-2-syn-methoxy-iminoacetamido]-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

Downstream raw materials:

ceftriaxone disodium

Desacetylcefotaxime

Refernces

• 1、 -. "IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS". Page/Page column 11-12. . Retrieved 2008/06/13.
• 2、 -. "IMPROVED PROCESS FOR THE MANUFACTURE OF CEFTRIAXONE SODIUM". Page/Page column 8. . Retrieved 2010/02/14.