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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:9421
CAS Number: 89786-04-9
UNII: SE10G96M8W
DrugBank ID: DB01606
TTD ID: D0QQ7D
INTEDE ID: DR2453

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.