Drug Details

General Information of the Drug (ID: DR5849)
Name
Tazobactam
Synonyms
Tazobactam; 89786-04-9; Tazobactam acid; Tazobactamum; YTR-830H; YTR 830H; UNII-SE10G96M8W; CHEMBL404; CL-298741; YTR 830; CHEBI:9421; SE10G96M8W; (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; CL 298,741; YTR 830 H; 89786-04-9 (free acid); (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; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (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; SR-01000872598; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2S,3S,5R)-; Tazobactamum [INN-Latin]; YTR830H; CCRIS 2203; YTR830; Tazobactam,(S); Tazobactam [USAN:USP:INN:BAN]; (2S,3S,5R)-3-METHYL-4,4,7-TRIOXO-3-(1H-1,2,3-TRIAZOL-1-YLMETHYL)-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4?^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Cl 298741; BRN 4787943; CL298741; Tazobactum (Free acid); Tazobactam;Tazobactan acid; EC 618-303-7; BIDD:GT0212; SCHEMBL122302; CXA201; Tazobactam (JP17/USP/INN); DTXSID8023634; GTPL10789; HMS3714G17; (2S,3S,5S)-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; BCP09757; EX-A1377; HY-B1418; ZINC3787060; BDBM50053173; MFCD00867002; s3077; AKOS015960801; AC-7620; CCG-207890; CS-4914; DB01606; DS-8301; NSC 759887; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 4,4-dioxide; A-8312; C07771; D00660; T-1445; 786T049; A843310; Q423376; Tazobactam, Antibiotic for Culture Media Use Only; SR-01000872598-1; SR-01000872598-2; 89786-04-9, 89785-84-2 (sodium salt); BRD-K14312455-001-01-6; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1-triazolylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda(6)-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-[1,2,3]triazol-1-ylmethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-[1,2,3]triazol-1-ylmethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-[1,2,3]triazol-1-ylmethyl-4lambda 6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[1,2,3]triazol-1-ylmethyl-4lambda6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; (2S,3S,5R)-3-methyl-4,4,7-tris(oxidanylidene)-3-(1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3-Methyl-4,4,7-trioxo-3-[1,2,3]triazol-1-ylmethyl-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2S-(2alpha,3beta,5alpha))-; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-methyl-7- oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, [2S- (2alpha,3beta,5alpha)]-
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 24.4-25 mgh/L
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The clearance of drug is 48.3-83.6 mL/min
Elimination
Tazobactam and its metabolite are mainly eliminated by the kidneys with about 80% of the administered dose eliminated as unchanged drug
Half-life
The concentration or amount of drug in body reduced by one-half in 0.7 - 1.2 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 66.4864 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.7%
Vd
The volume of distribution (Vd) of drug is 18.2 L
Water Solubility
The ability of drug to dissolve in water is measured as 50 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C10H12N4O5S
PubChem CID
123630
Canonical SMILES
CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
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
CAS Number
CAS 89786-04-9
ChEBI ID
CHEBI:9421
TTD Drug ID
D0QQ7D
DrugBank ID
DB01606
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Tea Polyphenols      Theaceae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
                    Experimental
                    Result(s)		 Tea polyphenols used in combination with commonly used antibiotics showed synergistic bactericidal effect against multidrug-resistant Klebsiella pneumoniae.
Target and Pathway
Target(s) Staphylococcus beta-lactamase (Stap-coc blaZ)  Molecule Info  [3]
References
Reference 1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
Reference 2 In-vitro antibacterial effect of tea polyphenols combined with common antibiotics on multidrug-resistant Klebsiella pneumoniae. Minerva Med. 2020 Dec;111(6):536-543.
Reference 3 Selection of TNF-alpha binding affibody molecules using a beta-lactamase protein fragment complementation assay. N Biotechnol. 2009 Nov 30;26(5):251-9.
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