Details of the Drug

General Information of Drug (ID: DMTX2BH)

Drug Name
Cefonicid
Synonyms
Cefonicido; Cefonicidum; Monocef; Praticef; Cefonicid Monosodium Salt; Sodium Cefonicid; Cefonicid (INN); Cefonicid [INN:BAN]; Cefonicido [INN-Spanish]; Cefonicidum [INN-Latin]; Monocef (TN); SK&F-75073; SKF-75073-2; (6R,7R)-7-[(2-hydroxy-2-phenylacetyl)amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-8-oxo-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-8-oxo-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]thio}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (7R)-7-(2-Hydroxy-2-phenylacetylamino)-6-oxo-3-{[1-(sulfomethyl)(1,2,3,4-tetraazol-5-ylthio)]methyl}-2H,7H,7aH-azetidino[2,1-b]1,3-thiazine-4-carboxylic acid; 6beta-[(2R)-2-hydroxy-2-phenylacetamido]-3-({[1-(sulfomethyl)-1H-tetrazol-5-yl]sulfanyl}methyl)ceph-3-em-4-carboxylic acid; 7-[(2-hydroxy-2-phenylacetyl)amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 542.6
Topological Polar Surface Area (xlogp) -1.9
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 13
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.38 mL/min/kg [3]
Elimination
99% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.5 hours [3]
Metabolism
The drug is not metabolised [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.77935 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.02% [3]
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 0.14 L/kg [3]
Chemical Identifiers
Formula
C18H18N6O8S3
IUPAC Name
(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)O)C(=O)O)CSC4=NN=NN4CS(=O)(=O)O
InChI
InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1
InChIKey
DYAIAHUQIPBDIP-AXAPSJFSSA-N
Cross-matching ID
PubChem CID
43594
ChEBI ID
CHEBI:3491
CAS Number
61270-58-4
DrugBank ID
DB01328
TTD ID
D01BQC

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial Penicillin binding protein (Bact PBP) TTJP4SM NOUNIPROTAC Binder [6]
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 Disease Different from Cefonicid (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefonicid and Plazomicin. Urinary tract infection [GC08] [16]

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
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 Affinity of cefonicid, a long-acting cephalosporin, for the penicillin-binding proteins of Escherichia coli K-12. J Antibiot (Tokyo). 1984 May;37(5):572-6.
7 Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
8 Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
9 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10 Activities of antibiotics against methicillin-resistant Staphylococcus aureus with particular reference to synergetic effect between ticarcillin and fosfomycin on penicillinase non-producing methicillin-resistant S. aureus. Jpn J Antibiot. 1993 Jun;46(6):421-7.
11 Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
12 Penicillin-binding protein sensitive to cephalexin in sporulation of Bacillus cereus. Microbiol Res. 1997 Sep;152(3):227-32.
13 Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
14 Relationship between penicillin-binding protein patterns and beta-lactamases in clinical isolates of Bacteroides fragilis with different susceptibility to beta-lactam antibiotics. J Med Microbiol. 2004 Mar;53(Pt 3):213-21.
15 Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.
16 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]