nafcillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 1869 147-52-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • naphthamidopenicillin
  • nafcilin
  • nallpen
  • naphcillin
  • nafcillin sodium
  • nafcillin
  • nafcillin sodium salt monohydrate
  • nafcillin sodium salt
A semi-synthetic antibiotic related to penicillin.
  • Molecular weight: 414.48
  • Formula: C21H22N2O5S
  • CLOGP: 3.53
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 95.94
  • ALOGS: -4.38
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
3 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 27 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 188.60 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.22 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.13 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 11, 1965 FDA WYETH AYERST

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01CF06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase resistant penicillins
FDA CS M0016152 Penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Staphylococcal meningitis indication 12166008
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Staphylococcal infectious disease indication 56038003
Staphylococcal endocarditis indication 73028002
Acute bacterial sinusitis indication 75498004
Infection of bone indication 111253001
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Sepsis due to Staphylococcus aureus indication 448417001
Staphylococcus Aureus Joint Infection indication
Staphylococcal Prosthetic Heart Valve Endocarditis indication
Pyrexia of unknown origin off-label use 7520000
Kidney disease contraindication 90708001 DOID:557
Infectious mononucleosis contraindication 271558008 DOID:8568
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.76 acidic

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 Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4018987 VUID
N0000178981 NUI
D00928 KEGG_DRUG
7177-50-6 SECONDARY_CAS_RN
4018987 VANDF
4019849 VANDF
C0027324 UMLSCUI
CHEBI:7447 CHEBI
NFN PDB_CHEM_ID
CHEMBL1443 ChEMBL_ID
CHEMBL1200344 ChEMBL_ID
CHEMBL1568276 ChEMBL_ID
D009254 MESH_DESCRIPTOR_UI
DB00607 DRUGBANK_ID
10942 IUPHAR_LIGAND_ID
1491 INN_ID
4CNZ27M7RV UNII
8982 PUBCHEM_CID
218589 RXNORM
2025 MMSL
3048 MMSL
5145 MMSL
d00029 MMSL
002698 NDDF
004837 NDDF
372898000 SNOMEDCT_US
55435000 SNOMEDCT_US
91169009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
NULLFCILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1017 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 23 sections
NULLFCILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1019 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3713 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3714 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3715 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3124 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3125 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3126 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 24 sections
Nafcillin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3128 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Nafcillin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-3129 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 24 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9124 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9125 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9126 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 23 sections
Nafcillin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-9224 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Nafcillin Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0781-9225 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 24 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-139 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 26 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-140 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 26 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-141 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 25 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 36000-175 INJECTION 1 g INTRAMUSCULAR ANDA 26 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 36000-176 INJECTION 2 g INTRAMUSCULAR ANDA 26 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 44567-221 POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 25 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 44567-222 POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 25 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 44567-223 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 13 sections
Nafcillin Human Prescription Drug Label 1 55150-122 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 23 sections
Nafcillin Human Prescription Drug Label 1 55150-123 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 23 sections
Nafcillin Human Prescription Drug Label 1 55150-123 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 23 sections
Nafcillin Human Prescription Drug Label 1 55150-124 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 23 sections
Nafcillin Human Prescription Drug Label 1 55150-124 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 23 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 63323-327 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 13 sections
Nafcillin HUMAN PRESCRIPTION DRUG LABEL 1 63323-328 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 13 sections