Details of the Drug

General Information of Drug (ID: DMIR5QP)

Drug Name
Azlocillin
Synonyms
Azlocilina; Azlocilline; Azlocillinum; Securopen; Bayer Brand of Azlocillin; Azlocilina [INN-Spanish]; Azlocillin Sodium (Sterile); Azlocilline [INN-French]; Azlocillinum [INN-Latin]; Bay-e 6905; Azlocillin (USAN/INN); Azlocillin [USAN:BAN:INN]; (2R,5R,6S)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2R,5S,6S)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-((R)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2S)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2S)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5S,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2r,5s,6s)-3,3-dimethyl-7-oxo-6-{[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (6R)-3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 2,2-dimethyl-6beta-[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3alpha-carboxylic acid; 3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3,3-dimethyl-7-oxo-6-{[{[(2-oxoimidazolidin-1-yl)carbonyl]amino}(phenyl)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-((R)-2-(2-Oxoimidazolidin-1-carboxamido)-2-phenylacetamido)penicillansaeure
Indication
Disease Entry ICD 11 Status REF
Aspiration pneumonia N.A. Approved [1]
Bacteremia 1A73 Approved [1]
Pseudomonas infection 1B92 Approved [2]
Urinary tract infection GC08 Approved [1]
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01CA09: Azlocillin
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): 0 Molecular Weight (mw) 461.5
Logarithm of the Partition Coefficient (xlogp) 0.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 7
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 2.5 mL/min/kg [4]
Elimination
65% 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 - 1.5 hours [4]
Metabolism
The drug is metabolized via renal and intraintestinal degradation by bowel bacteria []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 650.04999 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.65% [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 0.26 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [3]
Chemical Identifiers
Formula
C20H23N5O6S
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-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)N4CCNC4=O)C(=O)O)C
InChI
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChIKey
JTWOMNBEOCYFNV-NFFDBFGFSA-N
Cross-matching ID
PubChem CID
6479523
ChEBI ID
CHEMBL2956
CAS Number
37091-66-0
UNII
HUM6H389W0
DrugBank ID
DB01061
TTD ID
D0PA2N
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP 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 (Bact PBP) TTJP4SM NOUNIPROTAC Binder [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Azlocillin FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
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 Reactivation of peptidoglycan synthesis in ether-permeabilized Escherichia coli after inhibition by beta-lactam antibiotics. Antimicrob Agents Chemother. 1989 Dec;33(12):2101-8.