Basic information
- CAS
229016-73-3- Standard SMILES
CCO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(Sc3nc(-c4cc[n+](C)cc4)cs3)CS[C@H]12)c1nsc(NP(=O)(O)O)n1- InChIKey
ZCCUWMICIWSJIX-NQJJCJBVSA-N- Molecular formula
- C22H21N8O8PS4
- Average molar mass
- 684.7 g/mol
- Monoisotopic mass
- 684.01028026
Overview
Ceftaroline fosamil is a cephalosporin having [4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl and {(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl}amino side groups located at positions 3 and 7 respectively. The N-phospho prodrug of ceftaroline, a broad-spectrum antibiotic active against methicillin-resistant Staphylococcus aureus (MRSA). It is used for the treatment of adults with acute bacterial skin and skin structure infections. It has a role as an antimicrobial agent, an antibacterial drug and a prodrug. It is a cephalosporin, an iminium betaine, an oxime O-ether, an organic phosphoramidate, a member of thiadiazoles and a member of 1,3-thiazoles. It is functionally related to a ceftaroline.
Names & identifiers
- Preferred name
- Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner salt
- IUPAC
- (6R,7R)-7-[[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- PyridiniuM, 4-[2-[[(6R,7R)-2-carboxy-7-[[(2Z)-2-(ethoxyiMino)-2-[5-(phosphonoaMino)-1,2,4-thiadiazol-3-yl]acetyl]aMino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]thio]-4-thiazolyl]-1-Methyl-, inner salt
- Molecular formula
- C22H21N8O8PS4
- Molecular weight
- 684.67
Names & synonyms
Ceftaroline fosamil229016-73-3ceftarolina fosamiloceftarolinum fosamilumCHEBI:70718(6R,7R)-7-[[(2Z)-2-ethoxyimino-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateCeftaroline fosamil anhydrous7P6FQA5D21DTXSID60177444Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-1-oxo-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)ethyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner saltPyridinium, 4-[2-[[(6R,7R)-2-carboxy-7-[[(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]thio]-4-thiazolyl]-1-methyl-, inner salt(6R,7R)-7-({(2Z)-2-(ethoxyimino)-2-[5-(phosphonoamino)-1,2,4-thiadiazol-3-yl]acetyl}amino)-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Show more names
TAK 599 HCLPPI0903freeacidTAK-599 free acidceftoreline fosimilCeftaroline Impurity7Ceftaroline inner saltCeftaroline Fosamil Impurity 4Ceftaroline FosaMil Inner saltCeftaroline Fosamil Impurity LPyridiniuM,4-[2-[[(6R,7R)-2-carboxy-7-[[(2Z)-2-(ethoxyiMino)-2-[5-(phosphonoaMino)-1,2,4-thiadiazol-3Chemicalbook-yl]acetyl]aMino]-8-oxo-5-thia-1-azabicyclo
Pyridinium, 4-(2-(((6R,7R)-2-carboxy-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-1-methyl-, inner salt(6R,7R)-7-(((2Z)-2-(ethoxyimino)-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-3-((4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl)sulfanyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate(6R,7R)-7-(((2Z)-2-ethoxyimino-2-(5-(phosphonoamino)-1,2,4-thiadiazol-3-yl)acetyl)amino)-3-((4-(1-methylpyridin-1-ium-4-yl)-1,3-thiazol-2-yl)sulfanyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateFosamil, CeftarolineRefChem:57274DTXCID1099935J01DI02ceftaroline
Database identifiers
- CAS
229016-73-3- PubChem CID
- 9852981
- DTXSID
DTXSID60177444- ChEMBL
CHEMBL4594371、CHEMBL501122- ChEBI
CHEBI:70718
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 330 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 17
- Rotatable bonds
- 10
- Heavy atoms
- 43
- Formal charge
- 0
- Complexity
- 1,210
Experimental & physicochemical properties
Solubility>100 mg/ml
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physicochemical properties
- FDA UNII
- 7 P6FQA5D21 · 7P6FQA5D21
Safety & regulation
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Ceftaroline fosamil
vLess-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
ATC Code
J01DI02
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Bindingapproximately 20%.
Pharmacodynamics
The time that unbound plasma concentration of ceftaroline exceeds the minimum inhibitory concentration (MIC) of the infecting organism has been shown to best correlate with efficacy in a neutropenic murine thigh infection model with S. aureus and S. pneumoniae. No significant effect on QTc (corrected QT interval) interval was detected at peak plasma concentration or at any other time.
Mechanism of ActionCeftaroline fosamil is an antibacterial drug.
Biological Half-Life1.60 hours (600 mg dose).
Metabolism/MetabolitesCeftaroline fosamil is converted into bioactive ceftaroline in plasma by a phosphatase enzyme. Hydrolysis of the beta-lactam ring of ceftaroline occurs to form the microbiologically inactive, open-ring metabolite ceftaroline M-1.
FDA Pharmacological Classification
CEFTAROLINE FOSAMIL
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.
Absorption, Distribution and Excretion
primarily eliminated by the kidneys (6% in feces within 48 hours).
Median 20.3 L (18.3-21.6 L).
Applications
UsesCeftaroline Fosamil is a cephalosporin antibiotic. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and Gram-positive bacteria.
Suppliers26 total
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
Shenzhen Excellent Biotech Co., Ltd.13480692018 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
深圳卓越生物医药科技有限公司0755-26050679 18318671572 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
苏州莱惠生物技术有限公司180-1316-0973
上海立崎生物医学研究中心18014399201 · [email protected]
上海万千化工有限公司18796480002 18796480002 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
济南药研药物化学有限公司[email protected]
career henan chemical co+86-0371-86658258 · [email protected]
广州牌牌生物科技有限公司+86-13602409664 +86-17788709170 · [email protected]
南京法恩化学有限公司025-85710122 17714198479 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
南京美韬医药科技有限公司[email protected] · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]
上海亿万化工有限公司00-18662433356 18662433356 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
上海相辉医药科技有限公司13611835272 13611835272 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
Shenzhen Excellent Biomedical Technology Co.,Ltd.+86-0755-26050679 15915472436 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418684 +86-18949823763 · [email protected]
上海博拓生物科技有限公司16621358918 · [email protected]
Dideu Industries Group Limited+8617392712697 · [email protected]
Additional notes
DefinitionChEBI: A cephalosporin that is the N-phospho prodrug of ceftaroline. A broad-spectrum antibiotic, it is active against methicillin-resistant Staphylococcus aureus (MRSA). It is used for the treatment of adults with acute bacterial kin and skin structure infections.
Related reactions
2 records
Compound notes
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