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

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 1744 61-32-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • meticillin sodium
  • staphcillin
  • meticillin
  • metacillin
  • methicillin
  • methycillin
  • methicillin sodium
One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.
  • Molecular weight: 380.42
  • Formula: C17H20N2O6S
  • CLOGP: 1.90
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 105.17
  • ALOGS: -3.09
  • ROTB: 5
  • 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) 4 Bocci G, Oprea TI, Benet LZ
S (Water solubility) 0.31 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 88 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 16.43 µM/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) 0.32 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.43 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.64 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -1.676 Moderate 0.66
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.186 Moderate 0.66
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.420 10^-6 cm/s Moderate 0.66
dh-clint Dog hepatocyte intrinsic clearance 2.438 uL/min/10^6 cells Moderate 0.66
dppb Dog plasma protein binding (% unbound) 73.360 % Moderate 0.66
fcs-ppb Fetal calf serum protein binding (% unbound) 62.560 % Moderate 0.66
herg hERG pIC50 4.075 pIC50 Moderate 0.66
hh-clint Human hepatocyte intrinsic clearance 1.130 uL/min/10^6 cells Moderate 0.66
hlm-clint Human liver microsomal intrinsic clearance 3.069 uL/min/mg protein Moderate 0.66
hppb Human plasma protein binding (% unbound) 76.060 % Moderate 0.66
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK2,JAK3,KDR,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKDC,SIK2,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 51
kinase-selectivity-class ACVR2B,AXL,BRAF,CDK9,GRK2,MAP2K6,TEK 7
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.504 Moderate 0.66
mh-clint Mouse hepatocyte intrinsic clearance 4.236 Moderate 0.66
mppb Mouse plasma protein binding (% unbound) 73.540 Moderate 0.66
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.297 Moderate 0.66
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 66.360 % Moderate 0.66
rh-clint Rat hepatocyte intrinsic clearance 1.419 uL/min/10^6 cells Moderate 0.66
rh-fuinc Rat hepatocyte fraction unbound in incubation 89.530 % Moderate 0.66
rppb Rat plasma protein binding (% unbound) 69.120 % Moderate 0.66
solubility-dd Solubility at pH 7.4 in DMSO 885.116 uM Moderate 0.66

Approvals:

DateAgencyCompanyOrphan
None 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 J01CF03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase resistant penicillins
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:36047 antibacterial drug

Related Drugs by ATC class:

J01CF Beta-lactamase resistant penicillins 5 drugs
cloxacillindicloxacillinfloxacillinnafcillinoxacillin

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

DiseaseRelationSNOMED_IDDOID
Bacterial septicemia indication 10001005 DOID:0040085
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Sinusitis indication 36971009
Staphylococcal meningitis off-label use 12166008
Cholangitis off-label use 82403002 DOID:9446
Bacterial endocarditis off-label use 301183007
Kidney disease contraindication 90708001 DOID:557
Infectious mononucleosis contraindication 271558008 DOID:8568
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 2.76 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
Beta-lactam-inducible penicillin-binding protein Enzyme WOMBAT-PK
NH(3)-dependent NAD(+) synthetase Enzyme IC50 5.50 WOMBAT-PK

External reference:

IDSource
4018148 VUID
N0000179727 NUI
D02196 KEGG_DRUG
4018148 VANDF
4019826 VANDF
CHEBI:6827 CHEBI
MII PDB_CHEM_ID
CHEMBL575 ChEMBL_ID
CHEMBL3181832 ChEMBL_ID
7246-14-2 SECONDARY_CAS_RN
DB01603 DRUGBANK_ID
2181306 RXNORM
1694 MMSL
5072 MMSL
d00107 MMSL
002689 NDDF
004833 NDDF
373515001 SNOMEDCT_US
61862008 SNOMEDCT_US
64888007 SNOMEDCT_US
C0025643 UMLSCUI
D008712 MESH_DESCRIPTOR_UI
6087 PUBCHEM_CID
12264 IUPHAR_LIGAND_ID
1103 INN_ID
Q91FH1328A UNII

Pharmaceutical products:

None