ceftaroline fosamil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 4169 402741-13-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • zinforo
  • ceftaroline fosamil acetate
  • ceftaroline fosamil acetate monohydrate
  • TAK 599
  • PPI-0903
  • ceftaroline fosamil
  • teflaro
Ceftaroline is a cephalosporin antibacterial drug with in vitro activity against Gram-positive and -negative bacteria. 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.
  • Molecular weight: 684.67
  • Formula: C22H21N8O8PS4
  • CLOGP: -6.89
  • LIPINSKI: 2
  • HAC: 16
  • HDO: 4
  • TPSA: 223.24
  • ALOGS: -4.48
  • ROTB: 11
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.20 g P

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 0.53 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 83.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.80 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.09 hours Lombardo F, Berellini G, Obach RS
BA (Bioavailability) 0 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,ALK,AURKA,AURKB,AURKC,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK4,CDK5,CDK9,DDR1,DYRK1B,DYRK3,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K1,MAP3K14,MAP3K2,MAP3K21,MAP3K3,MAP3K7,MAP4K1,MAPK1,MAPK10,MAPK12,MAPK7,MAPK8,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,MELK,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM1,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK10,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 79
kinase-selectivity-class AXL,CDK9,DYRK1B,EPHB4,GRK2,MAP2K6,MAPK7,PRKDC,STK33,SYK,TEK,TTK,ZAP70 13
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Oct. 29, 2010 FDA CEREXA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Off label use 61.15 59.79 52 523 1102200 89525672

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Off label use 91.62 36.61 83 731 638252 41982269
Eosinophilia 68.09 36.61 25 789 32874 42587647
Agranulocytosis 47.94 36.61 19 795 30593 42589928
Neutropenia 38.27 36.61 31 783 199400 42421121

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Off label use 92.41 40.24 92 1017 1500093 109088097
Neutropenia 89.47 40.24 52 1057 374568 110213622
Eosinophilia 81.43 40.24 28 1081 57908 110530282
Agranulocytosis 64.64 40.24 24 1085 61736 110526454
Drug ineffective 44.15 40.24 64 1045 1520476 109067714

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DI02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Other cephalosporins and penems
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
MeSH PA D000097902 beta Lactam Antibiotics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:231911 renoprotective agent
CHEBI has role CHEBI:22587 antiviral agent
CHEBI has role CHEBI:49103 drug metabolite

Related Drugs by ATC class:

J01DI Other cephalosporins and penems 5 drugs
cefiderocolceftobiprole medocarilceftolozanefaropenemprobenecid

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Pneumonia due to Escherichia coli indication 51530003
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Pneumococcal pneumonia indication 233607000
Streptococcus pyogenes infection indication 302809008
Infection due to Staphylococcus aureus indication 406602003
Pneumonia due to Staphylococcus aureus indication 441658007
Skin and Skin Structure Streptococcus Agalactiae Infection indication
Hemolytic anemia contraindication 61261009 DOID:583
Impaired renal function disorder contraindication 197663003
Pseudomembranous enterocolitis contraindication 397683000




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.48 acidic
pKa2 2.96 acidic
pKa3 7.53 acidic
pKa4 13.05 acidic
pKa5 2.0 Basic
pKa6 0.14 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
400MG/VIAL TEFLARO ABBVIE N200327 Oct. 29, 2010 RX POWDER INTRAVENOUS 8247400 Feb. 10, 2031 METHOD OF TREATING BACTERIAL INFECTIONS
600MG/VIAL TEFLARO ABBVIE N200327 Oct. 29, 2010 RX POWDER INTRAVENOUS 8247400 Feb. 10, 2031 METHOD OF TREATING BACTERIAL INFECTIONS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
4030298 VUID
N0000182256 NUI
D08884 KEGG_DRUG
229016-73-3 SECONDARY_CAS_RN
400827-55-6 SECONDARY_CAS_RN
4030297 VANDF
4030298 VANDF
4030305 VANDF
C2001525 UMLSCUI
CHEBI:70714 CHEBI
1W8 PDB_CHEM_ID
CHEMBL501122 ChEMBL_ID
CHEMBL3544973 ChEMBL_ID
D000097583 MESH_DESCRIPTOR_UI
DB06590 DRUGBANK_ID
10899 IUPHAR_LIGAND_ID
8827 INN_ID
7P6FQA5D21 UNII
9852981 PUBCHEM_CID
1040004 RXNORM
177759 MMSL
27590 MMSL
401240 MMSL
d07706 MMSL
013547 NDDF
013548 NDDF
702414006 SNOMEDCT_US
702415007 SNOMEDCT_US
714785008 SNOMEDCT_US
C2001521 UMLSCUI
CHEMBL4594371 ChEMBL_ID
189345-04-8 SECONDARY_CAS_RN
H36Z0FHR8K UNII

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Teflaro HUMAN PRESCRIPTION DRUG LABEL 1 0456-0400 POWDER, FOR SOLUTION 400 mg INTRAVENOUS NDA 28 sections
Teflaro HUMAN PRESCRIPTION DRUG LABEL 1 0456-0400 POWDER, FOR SOLUTION 400 mg INTRAVENOUS NDA 28 sections
Teflaro HUMAN PRESCRIPTION DRUG LABEL 1 0456-0600 POWDER, FOR SOLUTION 600 mg INTRAVENOUS NDA 28 sections
Teflaro HUMAN PRESCRIPTION DRUG LABEL 1 0456-0600 POWDER, FOR SOLUTION 600 mg INTRAVENOUS NDA 28 sections
Ceftaroline Fosamil HUMAN PRESCRIPTION DRUG LABEL 1 60505-6124 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 400 mg INTRAVENOUS ANDA 25 sections
Ceftaroline Fosamil HUMAN PRESCRIPTION DRUG LABEL 1 60505-6125 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 600 mg INTRAVENOUS ANDA 25 sections