Ceftaroline fosamil

Base Information

• Chemical Name: Ceftaroline fosamil
• CAS No.: 229016-73-3
• Molecular Formula: C₂₂H₂₁N₈O₈PS₄
• Molecular Weight: 684.695
• European Community (EC) Number: 685-338-2,805-487-0
• DSSTox Substance ID: DTXSID60177444
• Wikipedia: Ceftaroline_fosamil
• NCI Thesaurus Code: C81034
• RXCUI: 1040004
• Metabolomics Workbench ID: 65215
• ChEMBL ID: CHEMBL501122
• Mol file: 229016-73-3.mol

Synonyms:ceftaroline fosamil;PPI-0903;PPI0903;TAK-599;TAK599;Teflaro

Chemical Property of Ceftaroline fosamil

Chemical Property:

• PSA: 344.02000
• LogP: 1.41980
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 10
• Exact Mass: 684.01028135
• Heavy Atom Count: 43
• Complexity: 1210

Purity/Quality:

99% ^*data from raw suppliers

CeftarolineFosamilInnersalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCON=C(C1=NSC(=N1)NP(=O)(O)O)C(=O)NC2C3N(C2=O)C(=C(CS3)SC4=NC(=CS4)C5=CC=[N+](C=C5)C)C(=O)[O-]
• Isomeric SMILES: CCO/N=C(/C1=NSC(=N1)NP(=O)(O)O)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)SC4=NC(=CS4)C5=CC=[N+](C=C5)C)C(=O)[O-]
• Recent ClinicalTrials: Randomized, Embedded, Multifactorial Adaptive Platform Trial for Community- Acquired Pneumonia
• Recent EU Clinical Trials: A Multicenter, Open-Label, Evaluator-Blinded, Randomized Study to Evaluate the Safety and Tolerability of Single-Dose IV Oritavancin Versus Standard of Care for the Treatment of Pediatric Subjects with Acute Bacterial Skin And Skin Structure Infections
• Uses: Ceftaroline Fosamil is a cephalosporin antibiotic. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and Gram-positive bacteria.

Technology Process of Ceftaroline fosamil

There total 13 articles about Ceftaroline fosamil 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: 77.0%

2-[[5-(dichlorophosphinyl)amino]-1,2,4-thiadiazole-3-yl]-2(Z)-ethoxyiminoacetyl chloride (90211-01-1) + 7β-amino-3-[4-(1-methyl-4-pyridinio)-1,3-thiazol-2-yl]thio-3-cephem-4-carboxylate dihydrochloride → ceftaroline (229016-73-3)

Guidance literature:

With sodium acetate; In water; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00126-3

Reference yield: 70.0%

C22H20N8O5S4 → ceftaroline fosamil (229016-73-3)

Guidance literature:

With tert-butyl methyl ether; phosphorus pentachloride; at -5 ℃; for 2h;

Reference yield: 68.0%

4-(2-{[(6R,7R)-2-carboxylato-7-[(2Z)-2-(ethoxyimino)-2-[5-(phosphonatoamino)-1,2,4-thiadiazol-3-yl]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]sulfanyl}-1,3-thiazol-4-yl)-1-methylpyridin-1-ium acetic acid → ceftaroline (229016-73-3)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 23h; Reagent/catalyst; Time;

upstream raw materials:

2-[[5-(dichlorophosphinyl)amino]-1,2,4-thiadiazole-3-yl]-2(Z)-ethoxyiminoacetyl chloride

benzhydryl (6R,7R)-7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

[4-(4-pyridyl)-1,3-thiazol-2-yl]thiol

4-(2-{[(6R,7R)-2-[(diphenylmethoxy)carbonyl]-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]sulfanyl}-1,3-thiazol-4-yl)pyridine

Refernces

• 1、 -. "NOVEL PROCESS FOR PREPARING CEFTAROLINE FOSAMIL". . . Retrieved 2014/05/07.
• 2、 Ishikawa, Tomoyasu,Matsunaga, Nobuyuki,Tawada, Hiroyuki,Kuroda, Noritaka,Nakayama, Yutaka,Ishibashi, Yukio,Tomimoto, Mitsumi,Ikeda, Yukihiro,Tagawa, Yoshihiko,Iizawa, Yuji,Okonogi, Kenji,Hashiguchi, Shohei,Miyake, Akio. "TAK-599, a novel N-phosphono type prodrug of anti-MRSA cephalosporin T-91825: Synthesis, physicochemical and pharmacological properties". . p. 2427 - 2437. Retrieved 2007/10/03.