Details of the Drug

General Information of Drug (ID: DM42W1B)

Drug Name
Cefmetazole
Synonyms
CMZ; Cefmetazolo; Cefmetazolum; Cefmetazole Monosodium Salt; CS 1170; SKF 83088; U 72791; CS-1170; Cefmetazole [USAN:INN]; Cefmetazolo [INN-Spanish]; Cefmetazolum [INN-Latin]; U-72791A; Cefmetazole (USP/INN); (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, sodium salt; (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 6beta-{[(cyanomethyl)sulfanyl]acetamido}-6alpha-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Pneumonia CA40 Approved [2]
Staphylococcal pneumonia N.A. Approved [2]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 471.5
Logarithm of the Partition Coefficient (xlogp) -0.6
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
The bioavailability of drug is 100% []
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.5 mL/min/kg [4]
Elimination
80% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.50 +/- 0.14 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 212.0717 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.15% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.13 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.0942 mg/mL [3]
Chemical Identifiers
Formula
C15H17N7O5S3
IUPAC Name
(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
InChI
InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
InChIKey
SNBUBQHDYVFSQF-HIFRSBDPSA-N
Cross-matching ID
PubChem CID
42008
ChEBI ID
CHEBI:3489
CAS Number
56796-20-4
DrugBank ID
DB00274
TTD ID
D05UBX
VARIDT ID
DR00539
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein 3 (Bact mrcA) TT85JMW FTSI_ECOLI Binder [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [7]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Cefmetazole
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Kanamycin. Bacterial infection [1A00-1C4Z] [9]
Amikacin DM5PDRB Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Amikacin. Bacterial infection [1A00-1C4Z] [9]
Streptomycin DME1LQN Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Streptomycin. Bacterial infection [1A00-1C4Z] [9]
Gentamicin DMKINJO Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Gentamicin. Bacterial infection [1A00-1C4Z] [9]
Tobramycin DMUI0CH Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Tobramycin. Bacterial infection [1A00-1C4Z] [9]
Coadministration of a Drug Treating the Disease Different from Cefmetazole (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Framycetin DMF8DNE Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Framycetin. Alcoholic liver disease [DB94] [9]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Cefmetazole due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [10]
Ethanol DMDRQZU Moderate Decreased metabolism of Cefmetazole caused by Ethanol mediated inhibition of non-CYP450 enzyme. Cystitis [GC00] [11]
Ethacrynic acid DM60QMR Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Ethacrynic acid. Essential hypertension [BA00] [12]
Furosemide DMMQ8ZG Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Furosemide. Heart failure [BD10-BD1Z] [12]
Bumetanide DMRV7H0 Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Bumetanide. Heart failure [BD10-BD1Z] [12]
Probenecid DMMFWOJ Moderate Decreased elimination of Cefmetazole caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [13]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Cefmetazole due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [10]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefmetazole and Plazomicin. Urinary tract infection [GC08] [14]
⏷ Show the Full List of 9 DDI Information of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050637.
2 Cefmetazole FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Clinical relevance of antibiotic-induced endotoxin release in patients undergoing hepatic resection. World J Surg. 1999 Jan;23(1):75-9.
7 Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61.
8 Screening of antibiotics that interact with organic anion-transporting polypeptides 1B1 and 1B3 using fluorescent probes. Biol Pharm Bull. 2011;34(3):389-95.
9 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
10 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
11 Brown KR, Guglielmo BJ, Pons VG, Jacobs RA "Theophylline elixir, moxalactam, and a disulfiram reaction." Ann Intern Med 97 (1982): 621-2. [PMID: 6214982]
12 Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
13 Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]
14 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]