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
Bacteremia 1A73 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Pneumonia CA40 Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Urinary tract infection GC08 Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01DC06: Cefonicid
J01DC: Second-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 542.6
Logarithm of the Partition Coefficient (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 [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.38 mL/min/kg [4]
Elimination
99% 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 4.5 hours [4]
Metabolism
The drug is not metabolised []
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% [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 0.14 L/kg [4]
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
CHEMBL3491
CAS Number
61270-58-4
UNII
6532B86WFG
DrugBank ID
DB01328
TTD ID
D01BQC
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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 (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] [7]

References

1 Cefonicid FDA Label
2 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
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 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 Engle JE, Drago J, Carlin B, Schoolwerth AC "Letter: Reversible acute renal failure after cephalothin." Ann Intern Med 83 (1975): 232-3. [PMID: 1147461]