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

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 556 92665-29-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefprozil
  • cefprozile
  • cephprozyl
  • cefprozil hydrate
  • Molecular weight: 389.43
  • Formula: C18H19N3O5S
  • CLOGP: -1.87
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 4
  • TPSA: 132.96
  • ALOGS: -3.42
  • ROTB: 5
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.06 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 73 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 42.88 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.21 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.59 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -1.726 Moderate 0.78
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.809 Moderate 0.78
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.533 10^-6 cm/s Moderate 0.78
dh-clint Dog hepatocyte intrinsic clearance 1.758 uL/min/10^6 cells Moderate 0.78
dppb Dog plasma protein binding (% unbound) 60.440 % Moderate 0.78
fcs-ppb Fetal calf serum protein binding (% unbound) 40.500 % Moderate 0.78
herg hERG pIC50 4.638 pIC50 Moderate 0.78
hh-clint Human hepatocyte intrinsic clearance 2.518 uL/min/10^6 cells Moderate 0.78
hlm-clint Human liver microsomal intrinsic clearance 4.266 uL/min/mg protein Moderate 0.78
hppb Human plasma protein binding (% unbound) 42.910 % Moderate 0.78
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,ERBB2,GRK2,GRK3,GSK3B,ITK,JAK2,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,NTRK2,PDK1,PDK2,PIK3CA,PIK3CB,PIM2,PRKDC,SIK2,STK33,SYK,TEK,TGFBR1,TTK 40
kinase-selectivity-class ACVR2B,AXL,BRAF,CDK4,CDK9,DYRK1B,EIF2AK3,EPHB4,GRK2,JAK2,MAP2K6,MAP3K14,MAPK7,PRKDC,STK33,SYK,TEK,TGFBR1,TTK 19
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.820 Moderate 0.78
mh-clint Mouse hepatocyte intrinsic clearance 4.102 Moderate 0.78
mppb Mouse plasma protein binding (% unbound) 60.710 Moderate 0.78
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.524 Moderate 0.78
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 40.390 % Moderate 0.78
rh-clint Rat hepatocyte intrinsic clearance 1.854 uL/min/10^6 cells Moderate 0.78
rh-fuinc Rat hepatocyte fraction unbound in incubation 85.450 % Moderate 0.78
rppb Rat plasma protein binding (% unbound) 31.470 % Moderate 0.78
solubility-dd Solubility at pH 7.4 in DMSO 933.254 uM Moderate 0.78

Approvals:

DateAgencyCompanyOrphan
Dec. 23, 1991 FDA

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
Mouth breathing 98.39 29.38 13 1311 157 90626966
Drug hypersensitivity 67.86 29.38 55 1269 463554 90163569
Snoring 49.05 29.38 12 1312 5114 90622009
Choking 47.53 29.38 14 1310 12019 90615104
Sputum discoloured 44.17 29.38 15 1309 20376 90606747
Rhinitis allergic 34.98 29.38 12 1312 16773 90610350
Urticaria 33.19 29.38 31 1293 312703 90314420
Product availability issue 30.93 29.38 9 1315 7395 90619728
Tubulointerstitial nephritis and uveitis syndrome 30.70 29.38 5 1319 267 90626856

FDA Adverse Event Reporting System (Male)

None

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
Drug hypersensitivity 74.75 24.24 62 1850 454028 110133359
Mouth breathing 73.04 24.24 11 1901 296 110587091
Sputum discoloured 51.34 24.24 19 1893 27926 110559461
Urticaria 41.15 24.24 38 1874 318819 110268568
Clostridium difficile colitis 39.88 24.24 18 1894 43760 110543627
Oropharyngeal pain 36.71 24.24 25 1887 135251 110452136
Snoring 34.60 24.24 10 1902 6774 110580613
Choking 30.43 24.24 11 1901 15099 110572288
Idiopathic urticaria 29.49 24.24 5 1907 288 110587099
Product availability issue 28.86 24.24 9 1903 7881 110579506
Tubulointerstitial nephritis and uveitis syndrome 27.86 24.24 5 1907 401 110586986
Cough 26.42 24.24 36 1876 461605 110125782
Rhinitis allergic 25.08 24.24 10 1902 17912 110569475
Heart rate increased 24.26 24.24 20 1892 143814 110443573

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DC10 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Second-generation cephalosporins
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
CHEBI has role CHEBI:36047 antibacterial drug
MeSH PA D000097902 beta Lactam Antibiotics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents

Related Drugs by ATC class:

J01DC Second-generation cephalosporins 13 drugs
cefaclorcefamandolecefbuperazonecefmetazolecefminoxcefonicidceforanidecefotetancefotiamcefoxitincefuroximeflomoxef show all 13 →

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

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Haemophilus Influenzae Acute Otitis Media indication 19021002
Infection of skin AND/OR subcutaneous tissue indication 19824006
Bronchitis indication 32398004 DOID:6132
Streptococcal tonsillitis indication 41582007
Upper respiratory infection indication 54150009
Acute bacterial sinusitis indication 75498004
Tonsillitis indication 90176007 DOID:10456
Acute Moraxella catarrhalis bronchitis indication 195722003
Acute bacterial bronchitis indication 233598009
Streptococcus pyogenes infection indication 302809008
Infective otitis media indication 312218008
Infection due to Staphylococcus aureus indication 406602003
Acute exacerbation of chronic bronchitis indication 425748003
Moraxella Catarrhalis Acute Otitis Media indication 703469002
Pneumococcal Acute Otitis Media indication
Streptococcus Pneumoniae Bronchitis indication
Haemophilus Influenzae Chronic Bronchitis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Moraxella Catarrhalis Chronic Bronchitis indication
Haemophilus Influenzae Bronchitis indication
Pyrexia of unknown origin off-label use 7520000
Acute nephropathy contraindication 58574008
Factor II deficiency contraindication 73975000
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 2.7 acidic
pKa2 9.72 acidic
pKa3 7.63 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4020058 VUID
N0000148083 NUI
D00261 KEGG_DRUG
121123-17-9 SECONDARY_CAS_RN
19552 RXNORM
C0053882 UMLSCUI
CHEBI:3506 CHEBI
CHEMBL5314373 ChEMBL_ID
CHEMBL3301800 ChEMBL_ID
DB01150 DRUGBANK_ID
D000097670 MESH_DESCRIPTOR_UI
62977 PUBCHEM_CID
12219 IUPHAR_LIGAND_ID
4W0459ZA4V UNII
4382 MMSL
73619 MMSL
d00073 MMSL
003623 NDDF
387538005 SNOMEDCT_US
96054007 SNOMEDCT_US
4020058 VANDF
4W0459ZA4V INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefprozil HUMAN PRESCRIPTION DRUG LABEL 1 0093-1077 TABLET, FILM COATED 250 mg ORAL ANDA 25 sections
Cefprozil HUMAN PRESCRIPTION DRUG LABEL 1 0093-1078 TABLET, FILM COATED 500 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 16714-396 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 16714-397 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 16714-398 TABLET, FILM COATED 250 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 16714-399 TABLET, FILM COATED 500 mg ORAL ANDA 25 sections
Cefprozil HUMAN PRESCRIPTION DRUG LABEL 1 50090-1188 TABLET, FILM COATED 500 mg ORAL ANDA 26 sections
Cefprozil Human Prescription Drug Label 1 50090-1710 TABLET, FILM COATED 500 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 50090-1739 TABLET, FILM COATED 500 mg ORAL ANDA 24 sections
Cefprozil Human Prescription Drug Label 1 50090-3226 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 25 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 52959-300 TABLET 500 mg ORAL ANDA 14 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 53217-031 TABLET 500 mg ORAL ANDA 14 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 54868-5756 TABLET 500 mg ORAL ANDA 14 sections
Cefprozil HUMAN PRESCRIPTION DRUG LABEL 1 54868-5757 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 14 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 55648-712 TABLET, FILM COATED 250 mg ORAL ANDA 20 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 55648-713 TABLET, FILM COATED 500 mg ORAL ANDA 20 sections
Cefprozil Human Prescription Drug Label 1 57237-034 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 57237-035 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 57237-036 TABLET, FILM COATED 250 mg ORAL ANDA 24 sections
Cefprozil Human Prescription Drug Label 1 57237-037 TABLET, FILM COATED 500 mg ORAL ANDA 24 sections
Cefprozil Human Prescription Drug Label 1 65862-068 TABLET, FILM COATED 250 mg ORAL ANDA 24 sections
Cefprozil Human Prescription Drug Label 1 65862-069 TABLET, FILM COATED 500 mg ORAL ANDA 24 sections
Cefprozil Human Prescription Drug Label 1 65862-099 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 25 sections
Cefprozil Human Prescription Drug Label 1 65862-100 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 25 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 67296-0590 TABLET 500 mg ORAL ANDA 24 sections
Cefprozil HUMAN PRESCRIPTION DRUG LABEL 1 67296-1180 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Cefprozil Human Prescription Drug Label 1 67877-243 TABLET, FILM COATED 500 mg ORAL ANDA 23 sections
Cefprozil Human Prescription Drug Label 1 67877-244 TABLET, FILM COATED 250 mg ORAL ANDA 23 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 68180-273 POWDER, FOR SUSPENSION 250 mg ORAL ANDA 23 sections
CEFPROZIL HUMAN PRESCRIPTION DRUG LABEL 1 68180-401 POWDER, FOR SUSPENSION 125 mg ORAL ANDA 24 sections