Tazobactam | CAS#89786-04-9 | β-lactamase Inhibitor

MedKoo Cat#: 314257 | Name: Tazobactam

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tazobactam is a β-lactamase inhibitor. Tazobactam inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. It is commonly used as its sodium salt, tazobactam sodium. Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, one of the preferred antibiotic treatments for nosocomial pneumonia caused by Pseudomonas aeruginosa.[medical citation needed] Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express β-lactamase and would normally degrade piperacillin. Tazobactam is derived from the penicillin nucleus and is a penicillinic acid sulfone.

Chemical Structure

Tazobactam

CAS#89786-04-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 314257

Name: Tazobactam

CAS#: 89786-04-9 (free acid)

Chemical Formula: C10H12N4O5S

Exact Mass: 300.0528

Molecular Weight: 300.29

Elemental Analysis: C, 40.00; H, 4.03; N, 18.66; O, 26.64; S, 10.68

Price and Availability

Size	Price	Availability
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 450.00	Ready to ship
2g	USD 750.00	Ready to ship
5g	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

89786-04-9 (free acid) 89785-84-2 (sodium)

Synonym

YTR830, YTR 830, YTR-830, AC7620, AC 7620, AC-7620, DB01606, DB 01606, DB-01606, CL298741, CL 298741, CL-298741, Tazobactam

IUPAC/Chemical Name

(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

InChi Key

LPQZKKCYTLCDGQ-WEDXCCLWSA-N

InChi Code

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

SMILES Code

O=C([C@@H]([C@@](CN1N=NC=C1)(C)S([C@]2([H])C3)(=O)=O)N2C3=O)O

Appearance

White to off-white solid powder

Purity

>94% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C22B06B14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Tazobactam (CL-298741) is a potent β-lactamases inhibitor and penicillin antibiotic.

In vitro activity:

In the present work, SHV-1 and the Ser(130) --> Gly inhibitor-resistant variant of SHV-1 beta-lactamase were inactivated with tazobactam, a potent class A beta-lactamase inhibitor. Reference: J Biol Chem. 2004 May 7;279(19):19494-501. https://pubmed.ncbi.nlm.nih.gov/14757767/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	55.0	183.16
	Water	1.0	3.33

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 300.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

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. PMID: 14757767. 2. Yang Y, Janota K, Tabei K, Huang N, Siegel MM, Lin YI, Rasmussen BA, Shlaes DM. Mechanism of inhibition of the class A beta -lactamases PC1 and TEM-1 by tazobactam. Observation of reaction products by electrospray ionization mass spectrometry. J Biol Chem. 2000 Sep 1;275(35):26674-82. doi: 10.1074/jbc.M002369200. PMID: 10837472.

In vitro protocol:

In vivo protocol:

TBD

1: Zhanel GG, Chung P, Adam H, Zelenitsky S, Denisuik A, Schweizer F, LagacÃ©-Wiens PR, Rubinstein E, Gin AS, Walkty A, Hoban DJ, Lynch JP 3rd, Karlowsky JA. Ceftolozane/tazobactam: a novel cephalosporin/β-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. Review. PubMed PMID: 24352909. 2: Hong MC, Hsu DI, Bounthavong M. Ceftolozane/tazobactam: a novel antipseudomonal cephalosporin and β-lactamase-inhibitor combination. Infect Drug Resist. 2013 Nov 29;6:215-23. doi: 10.2147/IDR.S36140. Review. PubMed PMID: 24348053; PubMed Central PMCID: PMC3848746. 3: Lam WJ, Bhowmick T, Gross A, Vanschooneveld TC, Weinstein MP. Using higher doses to compensate for tubing residuals in extended-infusion piperacillin-tazobactam. Ann Pharmacother. 2013 Jun;47(6):886-91. doi: 10.1345/aph.1R721. Epub 2013 May 28. Review. PubMed PMID: 23715072. 4: Ruggero MA, Argento AC, Heavner MS, Topal JE. Molecular Adsorbent Recirculating System (MARS(Â®)) removal of piperacillin/tazobactam in a patient with acetaminophen-induced acute liver failure. Transpl Infect Dis. 2013 Apr;15(2):214-8. doi: 10.1111/tid.12031. Epub 2012 Dec 28. Review. PubMed PMID: 23279615. 5: Falagas ME, Tansarli GS, Ikawa K, Vardakas KZ. Clinical outcomes with extended or continuous versus short-term intravenous infusion of carbapenems and piperacillin/tazobactam: a systematic review and meta-analysis. Clin Infect Dis. 2013 Jan;56(2):272-82. doi: 10.1093/cid/cis857. Epub 2012 Oct 16. Review. PubMed PMID: 23074314. 6: Acosta GarcÃa H, Victoria Gil-Navarro M, Cotrina Luque J, Cisneros Herreros JM, Lepe JimÃ©nez JA, Bautista Paloma J. [Piperacillin-tazobactam in continuous or expanded perfusion vs intermittent perfusion]. Farm Hosp. 2012 Sep-Oct;36(5):424-9. doi: 10.1016/j.farma.2011.06.013. Epub 2012 Aug 4. Review. Spanish. PubMed PMID: 22871367. 7: Mah GT, Mabasa VH, Chow I, Ensom MH. Evaluating outcomes associated with alternative dosing strategies for piperacillin/tazobactam: a qualitative systematic review. Ann Pharmacother. 2012 Feb;46(2):265-75. doi: 10.1345/aph.1Q378. Epub 2012 Jan 24. Review. PubMed PMID: 22274145. 8: Kaufman SE, Donnell RW, Hickey WS. Rationale and evidence for extended infusion of piperacillin-tazobactam. Am J Health Syst Pharm. 2011 Aug 15;68(16):1521-6. doi: 10.2146/ajhp100694. Review. PubMed PMID: 21817083. 9: Hayashi Y, Roberts JA, Paterson DL, Lipman J. Pharmacokinetic evaluation of piperacillin-tazobactam. Expert Opin Drug Metab Toxicol. 2010 Aug;6(8):1017-31. doi: 10.1517/17425255.2010.506187. Review. PubMed PMID: 20636224. 10: Rotschafer JC, Ullman M. Comparative pharmacodynamics of intermittent and prolonged infusions of piperacillin/tazobactam using Monte Carlo simulation and steady-state pharmacokinetic data from hospitalized patients. Ann Pharmacother. 2009 Nov;43(11):1887-9. doi: 10.1345/aph.1M462. Epub 2009 Oct 6. Review. PubMed PMID: 19809005. 11: Uji T, Hashimoto Y. [Pharmacological properties and clinical efficacies of tazobactam/piperacillin (Zosyn 2.25, Zosyn 4.5), an injectable antibiotic combined with beta-lactamase inhibitor]. Nihon Yakurigaku Zasshi. 2009 Jun;133(6):351-8. Review. Japanese. PubMed PMID: 19521033. 12: Wolf MF, Simon A. The use of piperacillin-tazobactam in neonatal and paediatric patients. Expert Opin Drug Metab Toxicol. 2009 Jan;5(1):57-69. doi: 10.1517/17425250802614688 . Review. PubMed PMID: 19236229. 13: Peterson LR. Antibiotic policy and prescribing strategies for therapy of extended-spectrum beta-lactamase-producing Enterobacteriaceae: the role of piperacillin-tazobactam. Clin Microbiol Infect. 2008 Jan;14 Suppl 1:181-4. Review. Erratum in: Clin Microbiol Infect. 2008 May;14 Suppl 5:21-4. PubMed PMID: 18154544. 14: 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. Review. PubMed PMID: 17547502. 15: Fahim S, Jain V, Victor G, Pierscianowski T. Piperacillin-tazobactam-induced drug hypersensitivity syndrome. Cutis. 2006 Jun;77(6):353-7. Review. PubMed PMID: 16838767. 16: Fouyssac F, Salmon A, Mansuy L, Schmitt C, Bordigoni P, Chastagner P. [Treatment of febrile neutropenia episodes in children, with a piperacillin-tazobactam and netilmicin combination]. Med Mal Infect. 2005 Jun;35(6):357-62. Review. French. PubMed PMID: 15982848. 17: Kotapati S, Kuti JL, Geissler EC, Nightingale CH, Nicolau DP. The clinical and economic benefits of administering piperacillin-tazobactam by continuous infusion. Intensive Crit Care Nurs. 2005 Apr;21(2):87-93. Review. PubMed PMID: 15778072. 18: SchÃ¸nning K, Tvede M. [Piperacillin/tazobactam--Tazocin. A penicillin-based alternative to 3rd generation cephalosporins and carbapenems]. Ugeskr Laeger. 2002 May 13;164(20):2606-10. Review. Danish. PubMed PMID: 12043402. 19: Venditti M, Cassone M, Falcone M, Pavoni G, Pistella E, Paris A. [Piperacillin-tazobactam in the treatment of severe nosocomial infections]. Recenti Prog Med. 2002 Mar;93(3):200-11. Review. Italian. PubMed PMID: 11942173. 20: Young M, Plosker GL. Piperacillin/tazobactam: a pharmacoeconomic review of its use in moderate to severe bacterial infections. Pharmacoeconomics. 2001;19(11):1135-75. Review. PubMed PMID: 11735679.