cefapirin ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 575 21593-23-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefapirin sodium
  • cefapirin
  • cefaprin
  • cephapirin
  • cephapirine
  • cephaprin
  • cephapirin sodium
  • cephapirin benzathine
Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms.
  • Molecular weight: 423.46
  • Formula: C17H17N3O6S2
  • CLOGP: -0.29
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 2
  • TPSA: 125.90
  • ALOGS: -3.45
  • ROTB: 8

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
4 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 48 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 236.14 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.13 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.55 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 12, 1974 FDA APOTHECON

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DB08 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
First-generation cephalosporins
CHEBI has role CHEBI:36047 antibacterial drugs
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

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

DiseaseRelationSNOMED_IDDOID
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005 DOID:0040085
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Streptococcal septicemia indication 29577008
Pneumonia due to Streptococcus indication 34020007
Lower respiratory tract infection indication 50417007
Klebsiella cystitis indication 60867007
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Staphylococcal endocarditis indication 73028002
Infection of bone indication 111253001
Staphylococcal septicemia indication 111821004
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Pneumonia indication 233604007 DOID:552
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Bacterial endocarditis indication 301183007
Streptococcus pyogenes infection indication 302809008
Infectious disorder of joint indication 363162000
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Skin and Skin Structure Proteus Infection indication
Streptococcus Osteomyelitis indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Streptococcal Endocarditis indication
Proteus Mirabilis Osteomyelitis indication
Prevention of Perioperative Infection indication
Staphylococcus Aureus Urinary Tract Infection indication
Klebsiella Pneumoniae Osteomyelitis indication




๐Ÿถ Veterinary Drug Use

SpeciesUseRelation
Cattle Mastitis caused by Streptococcus dysgalactiae Indication
Cattle Mastitis caused by Staphylococcus aureus Indication

๐Ÿถ Veterinary products

ProductApplicantIngredients
ToDAY Boehringer lngelheim Animal Health USA Inc. 1
ToMORROW Boehringer lngelheim Animal Health USA Inc. 1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.39 acidic
pKa2 5.58 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
Mu-type opioid receptor GPCR IC50 5.34 WOMBAT-PK
D(2) dopamine receptor GPCR IC50 4.66 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor IC50 6.21 WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 5.31 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR IC50 5.48 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR IC50 4.82 WOMBAT-PK
D(3) dopamine receptor GPCR IC50 4.59 WOMBAT-PK
Histamine H2 receptor GPCR IC50 5.24 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR IC50 4.68 WOMBAT-PK
Cannabinoid receptor 1 GPCR IC50 4.07 WOMBAT-PK
D(4) dopamine receptor GPCR IC50 5.01 WOMBAT-PK
Kappa-type opioid receptor GPCR IC50 5.29 WOMBAT-PK
Delta-type opioid receptor GPCR IC50 5.06 WOMBAT-PK
Substance-P receptor GPCR IC50 4.89 WOMBAT-PK
Nischarin Membrane receptor IC50 4.85 WOMBAT-PK
Interstitial collagenase Enzyme IC50 4.43 WOMBAT-PK
Substance-K receptor GPCR IC50 4.85 WOMBAT-PK
Cytochrome P450 3A5 Enzyme IC50 5.11 WOMBAT-PK
Somatostatin receptor type 4 GPCR IC50 5.17 WOMBAT-PK
Cytochrome P450 2D6 Enzyme IC50 4.84 WOMBAT-PK
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4018153 VUID
N0000179299 NUI
D00908 KEGG_DRUG
24356-60-3 SECONDARY_CAS_RN
1294563 RXNORM
4018153 VANDF
4019670 VANDF
C0007737 UMLSCUI
CHEBI:554446 CHEBI
CHEMBL1599 ChEMBL_ID
DB01139 DRUGBANK_ID
97468-37-6 SECONDARY_CAS_RN
30699 PUBCHEM_CID
4396 MMSL
d00187 MMSL
002721 NDDF
004842 NDDF
370337008 SNOMEDCT_US
6873003 SNOMEDCT_US
87303007 SNOMEDCT_US
96043002 SNOMEDCT_US
D002514 MESH_DESCRIPTOR_UI
CHEMBL1201043 ChEMBL_ID
CHEMBL3989837 ChEMBL_ID
2871 INN_ID
89B59H32VN UNII

Pharmaceutical products:

None