U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21N8O8PS4.C2H4O2.H2O
Molecular Weight 762.752
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTAROLINE FOSAMIL ACETATE

SMILES

O.CC(O)=O.[H][C@]12SCC(SC3=NC(=CS3)C4=CC=[N+](C)C=C4)=C(N1C(=O)[C@H]2NC(=O)C(=N/OCC)\C5=NSC(NP(O)([O-])=O)=N5)C(O)=O

InChI

InChIKey=KRWPPVCZNGQQHZ-IINIBMQSSA-N
InChI=1S/C22H21N8O8PS4.C2H4O2.H2O/c1-3-38-26-13(16-25-21(43-28-16)27-39(35,36)37)17(31)24-14-18(32)30-15(20(33)34)12(9-40-19(14)30)42-22-23-11(8-41-22)10-4-6-29(2)7-5-10;1-2(3)4;/h4-8,14,19H,3,9H2,1-2H3,(H4-,24,25,27,28,31,33,34,35,36,37);1H3,(H,3,4);1H2/b26-13-;;/t14-,19-;;/m1../s1

HIDE SMILES / InChI

Description

Ceftaroline fosamil is a 5th generation cephalosporin with an in vitro spectrum of activity including Streptococcus agalactiae, penicillin- and cephalosporin-resistant S. pneumoniae, S. pyogenes, methicillin-susceptible S. aureus and methicillin-resistant S. aureus, Haemophilus influenzae, Klebsiella oxytoca, K. pneumoniae and Moraxella catarrhalis. Ceftaroline fosamil (TAK-599 or PPI-0903), the prodrug of the active metabolite, ceftaroline, was synthesized by Takeda Pharmaceutical Co., Ltd and developed by Cerexa, Inc. and Forest Laboratories, Inc. It is currently approved by the FDA for the treatment of acute bacterial skin and skin structure infections (ABSSSI) and community-acquired bacterial pneumonia (CABP) in adults. Ceftaroline fosamil is marketed under the brand name TEFLARO®, indicated in adult and pediatric patients 2 months of age and older for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible isolates of the following Gram-positive and Gram-negative microorganisms: Staphylococcus aureus (including methicillin-susceptible and ‑resistant isolates), Streptococcus pyogenes, Streptococcus agalactiae, Escherichia coli, Klebsiella pneumoniae, and Klebsiella oxytoca. TEFLARO is also indicated in adult and pediatric patients 2 months of age and older for the treatment of community-acquired bacterial pneumonia (CABP) caused by susceptible isolates of the following Gram-positive and Gram-negative microorganisms: Streptococcus pneumoniae (including cases with concurrent bacteremia), Staphylococcus aureus (methicillin-susceptible isolates only), Haemophilus influenzae, Klebsiella pneumoniae, Klebsiella oxytoca, and Escherichia coli. Ceftaroline provides in vitro bactericidal activity against methicillin-, vancomycin-, daptomycin-, and linezolid-resistant Gram-positive organisms and select Gram-negative pathogens. The pharmacodynamics of ceftaroline is similar to other β-lactam agents. Ceftaroline exhibits a favorable adverse effect profile and is generally well tolerated. The bactericidal action of ceftaroline is mediated through binding to essential penicillin-binding proteins (PBPs). Ceftaroline is bactericidal against S. aureus due to its affinity for PBP2a and against Streptococcus pneumoniae due to its affinity for PBP2x.

Originator

Approval Year

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
TEFLARO

Approved Use

Teflaro is indicated in adult and pediatric patients 2 months of age and older for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible isolates of the following Grampositive and Gram-negative microorganisms: Staphylococcus aureus (including methicillin-susceptible and -resistant isolates), Streptococcus pyogenes, Streptococcus agalactiae, Escherichia coli, Klebsiella pneumoniae, and Klebsiella oxytoca. 1.2 Community-Acquired Bacterial Pneumonia Teflaro is indicated in adult and pediatric patients 2 months of age and older for the treatment of community-acquired bacterial pneumonia (CABP) caused by susceptible isolates of the following Grampositive and Gram-negative microorganisms: Streptococcus pneumoniae (including cases with concurrent bacteremia), Staphylococcus aureus (methicillin-susceptible isolates only), Haemophilus influenzae, Klebsiella pneumoniae, Klebsiella oxytoca, and Escherichia coli.

Launch Date

2010
Curative
Approved
8429
TEFLARO

Approved Use

Teflaro is indicated in adult and pediatric patients 2 months of age and older for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible isolates of the following Grampositive and Gram-negative microorganisms: Staphylococcus aureus (including methicillin-susceptible and -resistant isolates), Streptococcus pyogenes, Streptococcus agalactiae, Escherichia coli, Klebsiella pneumoniae, and Klebsiella oxytoca. 1.2 Community-Acquired Bacterial Pneumonia Teflaro is indicated in adult and pediatric patients 2 months of age and older for the treatment of community-acquired bacterial pneumonia (CABP) caused by susceptible isolates of the following Grampositive and Gram-negative microorganisms: Streptococcus pneumoniae (including cases with concurrent bacteremia), Staphylococcus aureus (methicillin-susceptible isolates only), Haemophilus influenzae, Klebsiella pneumoniae, Klebsiella oxytoca, and Escherichia coli.

Launch Date

2010
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
22.3 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27044549/
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFTAROLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
51.9 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27044549/
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFTAROLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27044549/
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFTAROLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27044549/
600 mg single, intravenous
dose: 600 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFTAROLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Disc. AE: Drug eruption, Cardiac failure...
AEs leading to
discontinuation/dose reduction:
Drug eruption (1%)
Cardiac failure (0.4%)
Nausea (0.4%)
Rash (0.4%)
Generalized rash (0.4%)
Rash maculo-papular (0.4%)
Urticaria (0.4%)
Abdominal infection (0.2%)
Acne (0.2%)
ALT increased (0.2%)
Application site erythema (0.2%)
Ascites (0.2%)
AST increased (0.2%)
Blood alkaline phosphatase increased (0.2%)
Cough (0.2%)
Dermatitis allergic (0.2%)
Diarrhoea (0.2%)
Drug hypersensitivity (0.2%)
Dyspnoea (0.2%)
Oedema generalized (0.2%)
Hepatic enzyme increased (0.2%)
Hyperhidrosis (0.2%)
Hypokalaemia (0.2%)
Necrotizing fasciitis (0.2%)
Osteomyelitis (0.2%)
Osteomyelitis acute (0.2%)
Palpitations (0.2%)
Pleural effusion (0.2%)
Pneumonia (0.2%)
Pyrexia (0.2%)
Rash papular (0.2%)
Rash pruritic (0.2%)
Toxic epidermal necrolysis (0.2%)
Vomiting (0.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
2000 mg single, intravenous
Highest studied dose
Dose: 2000 mg
Route: intravenous
Route: single
Dose: 2000 mg
Sources:
https://www.ema.europa.eu/en/documents/assessment-report/zinforo-epar-public-assessment-report_en.pdf
Page: p.95
unhealthy
n = 236
Health Status: unhealthy
Condition: Bacterial skin and soft tissue infections
Population Size: 236
Sources:
https://www.ema.europa.eu/en/documents/assessment-report/zinforo-epar-public-assessment-report_en.pdf
Page: p.95
Sources:
https://www.ema.europa.eu/en/documents/assessment-report/zinforo-epar-public-assessment-report_en.pdf
Page: p.95
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
n = 1300
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sex: M+F
Population Size: 1300
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Disc. AE: Hypersensitivity...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (0.3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Disc. AE: Hypersensitivity, Diarrhea, Clostridium difficile...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity (serious)
Diarrhea, Clostridium difficile
Seroconversion test
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
ALT increased 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
AST increased 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Abdominal infection 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Acne 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Application site erythema 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Ascites 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Blood alkaline phosphatase increased 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Cough 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Dermatitis allergic 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Diarrhoea 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Drug hypersensitivity 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Dyspnoea 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Hepatic enzyme increased 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Hyperhidrosis 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Hypokalaemia 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Necrotizing fasciitis 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Oedema generalized 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Osteomyelitis acute 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Osteomyelitis 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Palpitations 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Pleural effusion 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Pneumonia 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Pyrexia 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Rash papular 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Rash pruritic 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Toxic epidermal necrolysis 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Vomiting 0.2%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Cardiac failure 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Generalized rash 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Nausea 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Rash maculo-papular 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Rash 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Urticaria 0.4%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Drug eruption 1%
Disc. AE
600 mg 3 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
unhealthy, 52.6 (16.51)
n = 506
Health Status: unhealthy
Condition: Complicated bacterial skin and soft tissue infections
Age Group: 52.6 (16.51)
Sex: M+F
Population Size: 506
Sources:
https://pubmed.ncbi.nlm.nih.gov/30597021
Page: p.1089
Hypersensitivity 0.3%
Disc. AE
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
n = 1300
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sex: M+F
Population Size: 1300
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Diarrhea, Clostridium difficile Disc. AE
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Seroconversion test Disc. AE
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Hypersensitivity serious
Disc. AE
600 mg 2 times / day multiple, intravenous
Recommended
Dose: 600 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Acute bacterial skin and skin structure infections|Community-acquired bacterial pneumonia
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/200327s001lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
inhibitor
1767

inducer
389
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111

CYP1A1
110

CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2C8
911

CYP2C19
1478

CYP2E1
882
CYP2A6
543

CYP
270

CYP1A1
349

CYP1A2
1054

CYP2B6
664

CYP2C8
693

CYP2C19
991

CYP2E1
667
CYP
76

CYP1A2
701

CYP2B6
547

CYP2C8
168

CYP2C19
293

CYP3A4/5
124
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 no
CYP
147
 no
CYP1A2
1692
 no
CYP1A2
1692
 no
CEFTAROLINE
4
CYP2B6
1001
 no
CYP2B6
1001
 no
CEFTAROLINE
4
CYP2C19
1553
 no
CYP2C19
1553
 no
CEFTAROLINE
4
CYP2C8
965
 no
CYP2C8
965
 no
CEFTAROLINE
4
CYP2C9
1819
 no
CYP2C9
1819
 no
CEFTAROLINE
4
CYP3A4/5
335
 no
CYP3A4/5
335
 no
CEFTAROLINE
4
CYP1A1
218
 unlikely
CYP1A1
218
 unlikely
CEFTAROLINE
4
CYP1A2
1692
 unlikely
CYP1A2
1692
 unlikely
CEFTAROLINE
4
CYP2A6
739
 unlikely
CYP2A6
739
 unlikely
CEFTAROLINE
4
CYP2B6
1001
 unlikely
CYP2B6
1001
 unlikely
CEFTAROLINE
4
CYP2C19
1553
 unlikely
CYP2C19
1553
 unlikely
CEFTAROLINE
4
CYP2C8
965
 unlikely
CYP2C8
965
 unlikely
CEFTAROLINE
4
CYP2C9
1819
 unlikely
CYP2C9
1819
 unlikely
CEFTAROLINE
4
CYP2D6
1891
 unlikely
CYP2D6
1891
 unlikely
CEFTAROLINE
4
CYP2E1
970
 unlikely
CYP2E1
970
 unlikely
CEFTAROLINE
4
CYP3A4
1925
 unlikely
CYP3A4
1925
 unlikely
CEFTAROLINE
4
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 unlikely
CYP
270
 unlikely
CEFTAROLINE
4
CYP1A1
349
 unlikely
CYP1A1
349
 unlikely
CEFTAROLINE
4
CYP1A2
1054
 unlikely
CYP1A2
1054
 unlikely
CEFTAROLINE
4
CYP2A6
543
 unlikely
CYP2A6
543
 unlikely
CEFTAROLINE
4
CYP2B6
664
 unlikely
CYP2B6
664
 unlikely
CEFTAROLINE
4
CYP2C19
991
 unlikely
CYP2C19
991
 unlikely
CEFTAROLINE
4
CYP2C8
693
 unlikely
CYP2C8
693
 unlikely
CEFTAROLINE
4
CYP2D6
1217
 unlikely
CYP2D6
1217
 unlikely
CEFTAROLINE
4
CYP2E1
667
 unlikely
CYP2E1
667
 unlikely
CEFTAROLINE
4
CYP3A4
1737
 unlikely
CYP3A4
1737
 unlikely
CEFTAROLINE
4
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
CEFTAROLINE
4
Sourcing

Sourcing

Vendor/AggregatorIDURL
BioSynth
C-2481
MuseChem
R036256
ZINC
ZINC000003989269
http://zinc15.docking.org/substances/ZINC000003989269
ZINC
ZINC001849823524
http://zinc15.docking.org/substances/ZINC001849823524
ZINC
ZINC001849823525
http://zinc15.docking.org/substances/ZINC001849823525
ZINC
ZINC001849823526
http://zinc15.docking.org/substances/ZINC001849823526
ZINC
ZINC001849823527
http://zinc15.docking.org/substances/ZINC001849823527
PubMed

PubMed

TitleDatePubMed
Ceftaroline fosamil, a cephalosporin derivative for the potential treatment of MRSA infection.
2008 Feb
Ceftaroline: a cephalosporin with expanded Gram-positive activity.
2009 Feb
Ceftaroline: a new cephalosporin with activity against resistant gram-positive pathogens.
2010 Apr
Pharmacodynamics of ceftaroline against Staphylococcus aureus studied in an in vitro pharmacokinetic model of infection.
2013 Jun
Patents

Patents

200327-001
4
EP2753620A1
4
US9481698
4

Sample Use Guides

In Vivo Use Guide
Adult patients > 18 years of age: 600 mg every 12 hours by IV infusion administered over 5 to 60 min (2.1)  Pediatric patients from 2 years to < 18 years of age weighing ≤ 33 kg: 12 mg/kg every 8 hours by IV infusion administered over 5 to 60 min. Pediatric patients from 2 years to < 18 years of age weighing > 33 kg: 400 mg every 8 hours or 600 mg every 12 hours by IV infusion administered over 5 to 60 min. (2.2)  Pediatric patients from 2 months to < 2 years of age: 8 mg/kg every 8 hours by IV infusion administered over 5 to 60 min (2.2)  Dosage adjustment is required in adult patients with creatinine clearance (CrCl) < 50 mL/min and in End-stage Renal Disease (ESRD) including hemodialysis (2.3)
Route of Administration: Intravenous
In Vitro Use Guide
Ceftaroline was very active overall against 799 S. pneumoniae (MIC(50/90,) ≤ 0.008/0.12 ug/mL) and inhibited 100.0% of all isolates at a MIC ≤ 0.5 ug/mL. Ceftaroline was very potent against penicillin-resistant (CLSI oral penicillin V breakpoints) and -intermediate S. pneumoniae (MIC(50/90), 0.12/0.25 and 0.03/0.12 ug/mL, respectively), but potency was lower than observed against penicillin-susceptible isolates (MIC(50/90), ≤ 0.008/≤ 0.008 ug/mL). Ceftaroline was also very active (MIC(50/90), ≤ 0.008/0.015 ug/mL) against 515 Haemophilus influenzae, including β-lactamase-producing strains (MIC(50/90), 0.015/0.06 ug/mL). Ceftaroline also demonstrated good activity against 205 Moraxella catarrhalis isolates (MIC(50/90), 0.06/0.12 ug/mL).
Name Type Language
CEFTAROLINE FOSAMIL ACETATE
MART.   USAN  
USAN  
Official Name English
PYRIDINIUM, 4-(2-(((6R,7R)-2-CARBOXY-7-(((2Z)-(ETHOXYIMINO)(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, MONOACETATE, MONOHYDRATE
Common Name English
CEFTAROLINE FOSAMIL ACETATE [MART.]
Common Name English
PPI-0903 MONOACETATE MONOHYDRATE
Common Name English
CEFTAROINE [VANDF]
Common Name English
CEFTAROLINE FOSAMIL MONOACETATE MONOHYDRATE [MI]
Common Name English
CEFTAROLINE FOSAMIL ACETATE [USAN]
Common Name English
(6R,7R)-7-(((2Z)-(ETHOXYIMINO)(5-(PHOSPHONOAMINO)-1,2,4-THIADIAZOL-3- YL)ACETYL)AMINO)-3-((4-(1-METHYLPYRIDINIUM-4-YL)THIAZOL-2-YL)SULFANYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-2-CARBOXYLATE MONOACETATE MONOHYDRATE
Common Name English
CEFTAROLINE FOSAMIL MONOACETATE MONOHYDRATE
MI  
Common Name English
TAK-599 MONOACETATE MONOHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
Code System Code Type Description
FDA UNII
P9VXV1408Y
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID10193134
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
RXCUI
1743286
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL501122
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
CAS
1210978-33-8
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
SUPERSEDED
SMS_ID
100000155873
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
CAS
1134503-56-2
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
SUPERSEDED
NCI_THESAURUS
C96703
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
CAS
400827-55-6
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
EVMPD
SUB129872
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
DRUG BANK
DBSALT001808
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
MERCK INDEX
m3217
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
PUBCHEM
16007393
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
PRIMARY
CAS
1442644-01-0
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
SUPERSEDED
CAS
866021-48-9
Created by admin on Fri Dec 15 16:26:25 GMT 2023 , Edited by admin on Fri Dec 15 16:26:25 GMT 2023
SUPERSEDED
NIH
NCATS
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