Tazobactam

Identification

Summary

Tazobactam is a beta lactamase inhibitor administered with antibiotics such as piperacillin and ceftolozane to prevent their degradation, resulting in increased efficacy.

Brand Names

Zerbaxa, Zosyn

Generic Name

Tazobactam

DrugBank Accession Number

DB01606

Background

Tazobactam is an antibiotic of the beta-lactamase inhibitor class that prevents the breakdown of other antibiotics by beta-lactamase enzyme producing organisms. It is combined with Piperacillin and Ceftolozane for the treatment of a variety of bacterial infections.

Piperacillin-tazobactam was initially approved by the FDA in 1994, and ceftolozane-tazobactam was approved by the FDA in 2014^Label, providing wider antibacterial coverage for gram-negative infections. In June 2019, ceftolozane-tazobactam was approved by the FDA for treating hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia, which are significant causes of morbidity and mortality in hospitalized patients.¹⁵

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Tazobactam (DB01606)

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Weight

Average: 300.291
Monoisotopic: 300.052840204

Chemical Formula

C₁₀H₁₂N₄O₅S

Synonyms

• Tazobactam
• Tazobactamum

External IDs

• CL 298,741
• CL-298741
• YTR-830H

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Pharmacology

Indication

Tazobactam is used in combination with piperacillin or ceftolozane to broaden the spectrum of piperacillin antibacterial action, treating susceptible infections. As with any other antibiotic, tazobactam should only be used for infections that are either proven or strongly suspected to be susceptible to the tazobactam containing drug.

Tazobactam-piperacillin

When combined with piperacillin, it is used to treat a variety of infections, including those caused by aerobic and facultative gram-positive and gram-negative bacteria, in addition to gram-positive and gram-negative anaerobes. Some examples of infections treated with piperacillin-tazobactam include cellulitis, diabetic foot infections, appendicitis, and postpartum endometritis infections.¹¹ Certain gram-negative bacilli infections with beta-lactamase producing organisms cannot be treated with piperacillin-tazobactam, due to a gene mutation conferring antibiotic resistance.¹

Tazobactam-ceftolozane

Tazobactam is used in combination with ceftolozane for the treatment of infections caused by designated susceptible microorganisms in adult and pediatric patients:¹⁴

• Complicated Intra-abdominal Infections (cIAI), used in combination with metronidazole
• Complicated Urinary Tract Infections (cUTI), including pyelonephritis
• Hospital-acquired Bacterial Pneumonia and Ventilator-associated Bacterial Pneumonia (HABP/VABP)

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Complicated urinary tract infection	Combination Product in combination with: Ceftolozane (DB09050)	••••••••••••
Used in combination to treat	Nosocomial pneumonia	Combination Product in combination with: Ceftolozane (DB09050)	••••••••••••
Used in combination to treat	Pyelonephritis	Combination Product in combination with: Ceftolozane (DB09050)	••••••••••••
Used in combination to treat	Ventilator associated bacterial pneumonia	Combination Product in combination with: Ceftolozane (DB09050)	••••••••••••
Used in combination to treat	Complicated intra-abdominal bacterial infections	Regimen in combination with: Metronidazole (DB00916), Ceftolozane (DB09050)	••••••••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Tazobactam inhibits the action of bacterial beta-lactamase producing organisms, which are normally resistant to beta-lactam antibiotics. This augments the effects of antibiotics which would otherwise not be effective in treating certain infections. These antibiotics contain a beta-lactam ring in their chemical structure, which is destroyed by beta-lactam resistant organisms.⁴ When combined with other antibiotics, a variety of infections, including serious and life-threatening infections may be treated.^14,11

Mechanism of action

Tazobactam broadens the spectrum of piperacillin¹¹ and ceftolozane¹⁴ by making them effective against organisms that express beta-lactamase and would normally degrade them. This occurs through the irreversible inhibition of beta-lactamase enzymes. In addition, tazobactam may bind covalently to plasmid-mediated and chromosome-mediated beta-lactamase enzymes. Tazobactam is predominantly effective against the OHIO-1, SHV-1, and TEM groups of beta-lactamases, but may also inhibit other beta-lactamases.^8,9,10

Tazobactam shows little antibacterial activity by itself, and for this reason, is generally not administered alone.¹⁴

Target	Actions	Organism
ABeta-lactamase TEM	inhibitor	Salmonella typhi
ABeta-lactamase Ohio-1	inhibitor	Enterobacter cloacae
ABeta-lactamase SHV-1	inhibitor	Escherichia coli

Absorption

Tazobactam is coadministered with piperacillin or ceftolozane, pharmacokinetic information will be provided for these combinations.

Piperacillin-tazobactam

Peak plasma concentrations occur immediately after the completion of intravenous infusion. Following several doses of piperacillin-tazobactam infusions every 6 hours, peak concentrations were similar to those that were measured after the initial dose.¹¹

Ceftolozane-piperacillin

AUC: 24.4-25 mcg•h/mL

Peak concentrations are reached on day 1 after the first dose and range from 18 to 18.4 mcg/mL.¹⁴

Volume of distribution

18.2 L when given with piperacillin ¹¹

13.5-18.2 L when given with ceftolozane ¹⁴

Piperacillin-tazobactam is widely distributed in body tissues and fluids. These may include but are not limited to the intestine, gallbladder, lung, female reproductive organs, and the bile. Meningeal distribution of piperacillin-tazobactam increases with inflammation, but is otherwise low.¹¹

Protein binding

Tazobactam is bout 30% bound to plasma proteins.¹¹

Metabolism

Tazobactam is mainly metabolized to M1, an inactive metabolite.¹¹ Hydrolysis occurs on the beta-lactam ring to form M1 (the inactive metabolite).^14,5

Hover over products below to view reaction partners

• Tazobactam
  • M1 metabolite, Tazobactam

Route of elimination

Tazobactam and its metabolite are mainly eliminated by the kidneys with about 80% of the administered dose eliminated as unchanged drug. The remaining drug is excreted as a single metabolite.¹¹

Half-life

Piperacillin-tazobactam

After a single dose in healthy volunteers, the plasma half-life of piperacillin and tazobactam was in the range of 0.7 to 1.2 hours.¹¹

Ceftolozane-tazobactam

0.91-1.03 hours ¹⁴

Clearance

Because tazobactam is cleared by the kidneys and is a substrate of the transporters OAT1 and OAT3, inhibitors of these transporters should be avoided to ensure efficacy.¹¹ Dosage adjustments of piperacillin-tazobactam and ceftolozane-tazobactam must be made for patients with impaired renal clearance.^14,11,12

The mean clearance rate of tazobactam was found to be 48.3-83.6 mL/min in patients admitted to the intensive care unit who were given renal replacement therapy and receiving intravenous piperacillin-tazobactam.⁶

The clearance of tazobactam is dependent on renal function, as determined by renal clearance.^Label,7

Adverse Effects

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Toxicity

Overdose

Post-marketing reports have been made of overdose cases with piperacillin/tazobactam. Nausea, vomiting, and diarrhea are frequent manifestations of an overdose. Neuromuscular excitability or seizures may also occur with high intravenous doses or renal failure. There is no specific antidote. Provide supportive measures in case of an overdose. Anticonvulsive agents may be indicated when neuromuscular excitability or seizures occur. If anaphylaxis occurs, traditional measures should be taken to manage hypersensitivity (for example, adrenaline, antihistamines, corticosteroids, and oxygen/airway maintenance).¹² Similar measures should be taken after a ceftolozane-tazobactam overdose.^Label Hemodialysis can be used to remove the drug from the circulation ^Label,11.

A note on nephrotoxicity

Cases of life-threatening nephrotoxicity have been seen in critically ill patients receiving piperacillin-tazobactam. Alternative therapy and/or renal monitoring should be considered in critically ill patients.¹³

Carcinogenesis/Mutagenesis

Tazobactam tested negative for genotoxic effects in the Ames assay, an after in vitro chromosomal aberration and point mutation assay in the Chinese hamster, an various other assays.^Label

Use in pregnancy

Tazobactam has been found cross the placenta in rats. No data on human studies are available, however, rat studies have shown no teratogenetic effects at doses 6-14 times the equivalent maximum recommended human dose.¹¹

Use in lactation

There are no data on the presence of tazobactam in human breastmilk. No data are currently available on the effects of tazobactam on the infant, or how it affects milk production. Use clinical judgement and consider the maternal need for the drug and the benefits of breastfeeding the infant before administration during lactation.¹¹ Small concentrations of piperacillin-tazobactam have been found in the breastmilk and can lead to hypersensitivity in a breastfeeding infant. In some cases, breastfeeding may have to be discontinued temporarily.¹²

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abciximab	The risk or severity of bleeding can be increased when Tazobactam is combined with Abciximab.
Acamprosate	The excretion of Acamprosate can be decreased when combined with Tazobactam.
Acenocoumarol	The risk or severity of bleeding can be increased when Tazobactam is combined with Acenocoumarol.
Acetazolamide	The excretion of Tazobactam can be decreased when combined with Acetazolamide.
Acetylsalicylic acid	The excretion of Tazobactam can be decreased when combined with Acetylsalicylic acid.

Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tazobactam sodium	UXA545ABTT	89785-84-2	RFMIKMMOLPNEDG-QVUDESDKSA-M

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
ALBACTAM	Tazobactam (250 MG/1VIAL) + Piperacillin (2 G/1VIAL)	Injection, powder, for solution		บริษัท อาร์เอ็กซ์ จำกัด	2017-02-16	Not applicable
ALVOTAZ POWDER FOR SOLUTION FOR INJECTION/INFUSION 4.5G/VIAL	Tazobactam sodium (500 mg) + Piperacillin sodium (4 g)	Injection, powder, for solution	Intravenous	ALVOGEN SINGAPORE PTE. LTD.	2014-10-24	Not applicable
AVITAZ 2.25 G I.V. ENJEKSIYONLUK LIYOFILIZE TOZ IÇEREN FLAKON ,FLAKON, 1 ADET	Tazobactam (250 mg) + Piperacillin (2 g)	Injection, powder, lyophilized, for solution	Intravenous	AVİS İLAÇ SAN. VE TİC. A.Ş.	2020-08-14	Not applicable
AVITAZ 4.5 G I.V. ENJEKSIYONLUK LIYOFILIZE TOZ IÇEREN FLAKON ,FLAKON, 1 ADET	Tazobactam (500 mg) + Piperacillin (4 g)	Injection, powder, lyophilized, for solution	Intravenous	AVİS İLAÇ SAN. VE TİC. A.Ş.	2015-09-17	Not applicable
DBL PIPERACILLIN AND TAZOBACTAM FOR INJECTION 4.5 G	Tazobactam (500 MG/1VIAL) + Piperacillin (4 G/1VIAL)	Injection, powder, for solution		บริษัท ไฟเซอร์ พาร์ค เดวิส (ประเทศไทย) จำกัด	2017-05-23	2020-09-29

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Piperacillin, Tazobactam	Tazobactam sodium (0.375 g/20mL) + Piperacillin sodium (3 g/20mL)	Injection, powder, lyophilized, for solution	Intravenous	X-GEN Pharmaceuticals, Inc.	2017-02-14	2017-11-30
Piperacillin, Tazobactam	Tazobactam sodium (4.5 g/200mL) + Piperacillin sodium (36 g/200mL)	Injection, powder, lyophilized, for solution	Intravenous	X-GEN Pharmaceuticals, Inc.	2017-02-14	2017-10-31
Piperacillin, Tazobactam	Tazobactam sodium (0.5 g/50mL) + Piperacillin sodium (4 g/50mL)	Injection, powder, lyophilized, for solution	Intravenous	X-GEN Pharmaceuticals, Inc.	2017-02-14	2017-11-30

Categories

ATC Codes

J01CG02 — Tazobactam

• J01CG — Beta-lactamase inhibitors
• J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Amides
• Anti-Infective Agents
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Aza Compounds
• Azabicyclo Compounds
• Beta-Lactam Antibacterials
• beta-Lactamase Inhibitors
• beta-Lactams
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• Lactams
• OAT1/SLC22A6 inhibitors
• OAT1/SLC22A6 Substrates
• OAT3/SLC22A8 Inhibitors
• OAT3/SLC22A8 Substrates
• Sulfones
• Sulfur Compounds

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Penams / Triazoles / Thiazolidines / Tertiary carboxylic acid amides / Sulfones / Heteroaromatic compounds / Azetidines / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

1,2,3-triazole / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Azole / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Penam / Sulfone / Tertiary carboxylic acid amide / Thiazolidine

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

triazoles, penicillanic acids (CHEBI:9421)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

SE10G96M8W

CAS number

89786-04-9

InChI Key

LPQZKKCYTLCDGQ-WEDXCCLWSA-N

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

IUPAC Name

(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN1C=CN=N1)S2(=O)=O

References

Synthesis Reference

Georg Trickes, "Crystalline tazobactam, and its production and use." U.S. Patent US5763603, issued March, 1988.

US5763603

General References

1. Gin A, Dilay L, Karlowsky JA, Walkty A, Rubinstein E, Zhanel GG: Piperacillin-tazobactam: a beta-lactam/beta-lactamase inhibitor combination. Expert Rev Anti Infect Ther. 2007 Jun;5(3):365-83. doi: 10.1586/14787210.5.3.365. [Article]
2. Zhanel GG, Chung P, Adam H, Zelenitsky S, Denisuik A, Schweizer F, Lagace-Wiens PR, Rubinstein E, Gin AS, Walkty A, Hoban DJ, Lynch JP 3rd, Karlowsky JA: Ceftolozane/tazobactam: a novel cephalosporin/beta-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli. Drugs. 2014 Jan;74(1):31-51. doi: 10.1007/s40265-013-0168-2. [Article]
3. Wise R, Logan M, Cooper M, Andrews JM: Pharmacokinetics and tissue penetration of tazobactam administered alone and with piperacillin. Antimicrob Agents Chemother. 1991 Jun;35(6):1081-4. doi: 10.1128/aac.35.6.1081. [Article]
4. Williams JD: Beta-lactamases and beta-lactamase inhibitors. Int J Antimicrob Agents. 1999 Aug;12 Suppl 1:S3-7; discussion S26-7. [Article]
5. Derendorf H, Dalla Costa T: Pharmacokinetics of piperacillin, tazobactam and its metabolite in renal impairment. Int J Clin Pharmacol Ther. 1996 Nov;34(11):482-8. [Article]
6. Bauer SR, Salem C, Connor MJ Jr, Groszek J, Taylor ME, Wei P, Tolwani AJ, Fissell WH: Pharmacokinetics and pharmacodynamics of piperacillin-tazobactam in 42 patients treated with concomitant CRRT. Clin J Am Soc Nephrol. 2012 Mar;7(3):452-7. doi: 10.2215/CJN.10741011. Epub 2012 Jan 26. [Article]
7. Wooley M, Miller B, Krishna G, Hershberger E, Chandorkar G: Impact of renal function on the pharmacokinetics and safety of ceftolozane-tazobactam. Antimicrob Agents Chemother. 2014;58(4):2249-55. doi: 10.1128/AAC.02151-13. Epub 2014 Feb 3. [Article]
8. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [Article]
9. Schechter LM, Creely DP, Garner CD, Shortridge D, Nguyen H, Chen L, Hanson BM, Sodergren E, Weinstock GM, Dunne WM Jr, van Belkum A, Leopold SR: Extensive Gene Amplification as a Mechanism for Piperacillin-Tazobactam Resistance in Escherichia coli. MBio. 2018 Apr 24;9(2). pii: mBio.00583-18. doi: 10.1128/mBio.00583-18. [Article]
10. Pagan-Rodriguez D, Zhou X, Simmons R, Bethel CR, Hujer AM, Helfand MS, Jin Z, Guo B, Anderson VE, Ng LM, Bonomo RA: Tazobactam inactivation of SHV-1 and the inhibitor-resistant Ser130 -->Gly SHV-1 beta-lactamase: insights into the mechanism of inhibition. J Biol Chem. 2004 May 7;279(19):19494-501. doi: 10.1074/jbc.M311669200. Epub 2004 Feb 2. [Article]
11. FDA Approved Drug Products: ZOSYN (piperacillin and tazobactam) injection [Link]
12. Medsafe NZ: Tazocin [Link]
13. Pfizer medical information [Link]
14. FDA Approved Drug Products: ZERBAXA (ceftolozane and tazobactam) for injection, for intravenous use [Link]
15. FDA Approved Drug Products: ZERBAXA (ceftolozane and tazobactam) injection [Link]

External Links

Human Metabolome Database

HMDB0015544

KEGG Drug

D00660

KEGG Compound

C07771

PubChem Compound

123630

PubChem Substance

46508088

ChemSpider

110216

BindingDB

50053173

RxNav

37617

ChEBI

9421

ChEMBL

CHEMBL404

ZINC

ZINC000003787060

Therapeutic Targets Database

DAP000926

PharmGKB

PA164764504

Wikipedia

Tazobactam

MSDS

Download (25.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Health Services Research	Bacterial Infections	1
4	Completed	Other	Cystic Fibrosis (CF) / Cystic Fibrosis Pulmonary Exacerbation / Pseudomonas Aeruginosa Infection	1
4	Completed	Prevention	Bacterial Infections	1
4	Completed	Treatment	Appendicitis	2
4	Completed	Treatment	Appendicitis / Complicated Appendicitis / Perforated Appendicitis / Ruptured Appendicitis	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Apotex Inc.
• Baxter International Inc.
• Cardinal Health
• Wyeth Pharmaceuticals

Dosage Forms

Form	Route	Strength
Injection, powder, for solution	Intramuscular
Solution	Intravenous
Powder, for solution	Intravenous
Injection, powder, for solution	Intravenous
Injection, powder, for solution	Intravenous; Parenteral
Injection, powder, lyophilized, for solution	Intravenous
Injection, powder, lyophilized, for solution	Intravenous; Parenteral
Powder	Not applicable
Injection, powder, for solution	Intravenous	4000 mg
Injection, powder, for solution	Parenteral
Injection, powder, for solution	Intravenous	4 g
Solution	Parenteral
Injection, powder, for solution
Injection, powder, lyophilized, for solution
Powder
Solution	Intravenous	500.000 mg
Solution	Intravenous	4.170 g
Injection, solution, concentrate	Intravenous
Injection, powder, for solution	Intravenous	1000 mg
Injection, solution	Intravenous

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6900184	No	2005-05-31	2023-04-14
US8133883	No	2012-03-13	2023-04-14
US7915229	No	2011-03-29	2023-04-14
US6207661	No	2001-03-27	2019-02-22
US7129232	No	2006-10-31	2024-10-21
US8685957	No	2014-04-01	2032-09-27
US8968753	No	2015-03-03	2034-03-14
US8476425	No	2013-07-02	2032-09-27
US8906898	No	2014-12-09	2034-05-28
US9320740	No	2016-04-26	2034-03-14
US9872906	No	2018-01-23	2034-03-14
US10125149	No	2018-11-13	2035-08-14
US9724353	No	2017-08-08	2032-09-07
US10028963	No	2018-07-24	2032-09-07
US10376496	No	2019-08-13	2034-09-09
US10420841	No	2019-09-24	2034-03-14
US10933053	No	2021-03-02	2034-09-09
US11278622	No	2014-03-14	2034-03-14

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	140-147	https://www.caymanchem.com/msdss/17185m.pdf
boiling point (°C)	77	https://www.chemicalbook.com/ChemicalProductProperty_US_CB3181854.aspx
water solubility	50 mg/mL	https://www.chemicalbook.com/ChemicalProductProperty_US_CB3181854.aspx
pKa	2.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	9.59 mg/mL	ALOGPS
logP	-1.8	ALOGPS
logP	-1.4	Chemaxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.86	Chemaxon
pKa (Strongest Basic)	0.75	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	122.46 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	74.82 m3·mol-1	Chemaxon
Polarizability	26.22 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.6161
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.6156
P-glycoprotein substrate	Non-substrate	0.5351
P-glycoprotein inhibitor I	Non-inhibitor	0.8574
P-glycoprotein inhibitor II	Non-inhibitor	0.9917
Renal organic cation transporter	Non-inhibitor	0.8432
CYP450 2C9 substrate	Non-substrate	0.6516
CYP450 2D6 substrate	Non-substrate	0.812
CYP450 3A4 substrate	Substrate	0.5249
CYP450 1A2 substrate	Non-inhibitor	0.7993
CYP450 2C9 inhibitor	Non-inhibitor	0.7373
CYP450 2D6 inhibitor	Non-inhibitor	0.8832
CYP450 2C19 inhibitor	Non-inhibitor	0.7143
CYP450 3A4 inhibitor	Non-inhibitor	0.8596
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.978
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.6302
Biodegradation	Ready biodegradable	0.9593
Rat acute toxicity	1.8100 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9939
hERG inhibition (predictor II)	Non-inhibitor	0.8552

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-05ox-9600000000-54f1ff15fea55805a4c4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0019000000-b5244af74391e1422763
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00ks-0970000000-493773c07878257c06e1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-1298000000-3450e9c3aec28507bfd8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052b-1970000000-c4c32fc0e55386de14c1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0btc-9710000000-330e1c3c71a23d458dd0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4l-9720000000-0bfdb1aa569f24d87615
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	164.8246835	predicted	DarkChem Lite v0.1.0
[M-H]-	167.5384835	predicted	DarkChem Lite v0.1.0
[M-H]-	159.8968	predicted	DeepCCS 1.0 (2019)
[M+H]+	164.8376835	predicted	DarkChem Lite v0.1.0
[M+H]+	168.2743835	predicted	DarkChem Lite v0.1.0
[M+H]+	162.2548	predicted	DeepCCS 1.0 (2019)
[M+Na]+	165.0294835	predicted	DarkChem Lite v0.1.0
[M+Na]+	169.03535	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase TEM

Kind

Protein

Organism

Salmonella typhi

Pharmacological action

Yes

Actions

Inhibitor

General Function

Beta-lactamase activity

Specific Function

TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalos...

Gene Name

bla

Uniprot ID

P62594

Uniprot Name

Beta-lactamase TEM

Molecular Weight

31514.865 Da

References

1. Yang Y, Rasmussen BA, Shlaes DM: Class A beta-lactamases--enzyme-inhibitor interactions and resistance. Pharmacol Ther. 1999 Aug;83(2):141-51. [Article]
2. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [Article]
3. Schechter LM, Creely DP, Garner CD, Shortridge D, Nguyen H, Chen L, Hanson BM, Sodergren E, Weinstock GM, Dunne WM Jr, van Belkum A, Leopold SR: Extensive Gene Amplification as a Mechanism for Piperacillin-Tazobactam Resistance in Escherichia coli. MBio. 2018 Apr 24;9(2). pii: mBio.00583-18. doi: 10.1128/mBio.00583-18. [Article]

Details2. Beta-lactamase Ohio-1

Kind

Protein

Organism

Enterobacter cloacae

Pharmacological action

Yes

Actions

Inhibitor

General Function

Not Available

Specific Function

Beta-lactamase activity

Gene Name

Not Available

Uniprot ID

P18251

Uniprot Name

Beta-lactamase Ohio-1

Molecular Weight

31353.795 Da

References

1. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [Article]

Details3. Beta-lactamase SHV-1

Kind

Protein

Organism

Escherichia coli

Pharmacological action

Yes

Actions

Inhibitor

General Function

Beta-lactamase activity

Specific Function

Not Available

Gene Name

bla

Uniprot ID

P0AD63

Uniprot Name

Beta-lactamase SHV-1

Molecular Weight

31223.635 Da

References

1. Pagan-Rodriguez D, Zhou X, Simmons R, Bethel CR, Hujer AM, Helfand MS, Jin Z, Guo B, Anderson VE, Ng LM, Bonomo RA: Tazobactam inactivation of SHV-1 and the inhibitor-resistant Ser130 -->Gly SHV-1 beta-lactamase: insights into the mechanism of inhibition. J Biol Chem. 2004 May 7;279(19):19494-501. doi: 10.1074/jbc.M311669200. Epub 2004 Feb 2. [Article]
2. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [Article]

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Drug created at June 13, 2005 13:24 / Updated at September 15, 2022 03:13