Details of the Drug

General Information of Drug (ID: DM3XNUI)

Drug Name
Tazobactam
Synonyms
TAZ; CL298741; YTR830H; CL-298741; Piprataz (TN); YTR-830H; Tazobactam (JAN/USAN/INN); (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4; (2S,3S,5R)-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
Indication
Disease Entry ICD 11 Status REF
Appendicitis DB10 Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Peritonitis N.A. Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Pelvic inflammatory disease GA05 Investigative [1]
Therapeutic Class
Antiinfective Agents
Affected Organisms
Humans and other mammals
ATC Code
J01CG02: Tazobactam
J01CG: Beta-lactamase inhibitors
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) 300.29
Logarithm of the Partition Coefficient (xlogp) -2
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 24.4-25 mgh/L [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Clearance
The clearance of drug is 48.3-83.6 mL/min [3]
Elimination
Tazobactam and its metabolite are mainly eliminated by the kidneys with about 80% of the administered dose eliminated as unchanged drug [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.7 - 1.2 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 66.4864 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.7% [6]
Vd
The volume of distribution (Vd) of drug is 18.2 L [3]
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL [4]
Chemical Identifiers
Formula
C10H12N4O5S
IUPAC Name
(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES
C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
InChI
InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1
InChIKey
LPQZKKCYTLCDGQ-WEDXCCLWSA-N
Cross-matching ID
PubChem CID
123630
ChEBI ID
CHEMBL404
CAS Number
89786-04-9
UNII
SE10G96M8W
DrugBank ID
DB01606
TTD ID
D0QQ7D
INTEDE ID
DR2453
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Staphylococcus Beta-lactamase (Stap-coc blaZ) TTHI19T BLAC_STAAU Inhibitor [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEYIEO5 AMPC_SERMA Substrate [8]
Beta-lactamase (blaB) DEEZ5CV BLO1_KLEOX Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Tazobactam 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 FDA Approved Drug Products: ZOSYN (piperacillin and tazobactam) injection
4 BDDCS applied to over 900 drugs
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 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Selection of TNF-alpha binding affibody molecules using a beta-lactamase protein fragment complementation assay. N Biotechnol. 2009 Nov 30;26(5):251-9.
8 Determination of the antibiotic resistance rates of Serratia marcescens isolates obtained from various clinical specimens. Niger J Clin Pract. 2019 Jan;22(1):125-130.
9 Characterization of piperacillin/tazobactam-resistant klebsiella oxytoca recovered from a nosocomial outbreak. PLoS One. 2015 Nov 5;10(11):e0142366.