Details of the Drug

General Information of Drug (ID: DMY5JEP)

Drug Name
Mezlocillin
Synonyms
Mezlin; Mezlocilina; Mezlocillinum; Mezlocillin (USAN/INN); (2S,5R,6R)-3,3-dimethyl-6-[[(2R)-2-[(3-methylsulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-6-{[(2R)-2-({[3-(methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl}amino)-2-phenylacetyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylic acid; 6beta-{(2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido}penicillanic acid
Indication
Disease Entry ICD 11 Status REF
Acute gonococcal cervicitis N.A. Approved [1]
Aspiration pneumonia N.A. Approved [1]
Bacteremia 1A73 Approved [1]
Urinary tract infection GC08 Approved [2]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01CA10: Mezlocillin
J01CA: Penicillins with extended spectrum
J01C: BETA-LACTAM ANTIBACTERIALS, PENICILLINS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 539.6
Logarithm of the Partition Coefficient (xlogp) -0.2
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 9
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 2.1 mL/min/kg [4]
Elimination
45% 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 1.3 - 4.4 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 555.97803 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.7% [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 0.09 L/kg [4]
Chemical Identifiers
Formula
C21H25N5O8S2
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-6-[[(2R)-2-[(3-methylsulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCN(C4=O)S(=O)(=O)C)C(=O)O)C
InChI
InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1
InChIKey
YPBATNHYBCGSSN-VWPFQQQWSA-N
Cross-matching ID
PubChem CID
656511
ChEBI ID
CHEMBL6919
CAS Number
51481-65-3
UNII
OH2O403D1G
DrugBank ID
DB00948
TTD ID
D00NJJ
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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 3 (Bact mrcA) TT85JMW FTSI_ECOLI 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 Mezlocillin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mycophenolic acid DMRBMAU Moderate Altered absorption of Mezlocillin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [7]
Probenecid DMMFWOJ Minor Decreased elimination of Mezlocillin caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [8]

References

1 Mezlocillin FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050549.
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 Bactericidal effect of piperacillin alone and combined. Presse Med. 1986 Dec 20;15(46):2297-302.
7 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
8 Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]