1,024 μg/ml for wild-type and multidrug-resistant Acinetobacter strains. Zidebactam is a PBP2 inhibitor that show a potent β-lactam enhancer effect against A. baumannii, including a multidrug-resistant OXA-23-producing ST2 international clone." />

Zidebactam
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MedKoo CAT#: 319537

CAS#: 1436861-97-0

Description: Zidebactam, also known as WCK-5107, is a Beta lactamase inhibitor. Zidebactam is a novel Inhibitor of PBP2 Showing Potent "β-Lactam Enhancer" Activity against Pseudomonas aeruginosa, Including Multidrug-Resistant Metallo-β-Lactamase-Producing High-Risk Clones. Zidebactam demonstrated specific high-affinity binding to PBP2 of A. baumannii (0.01 μg/ml for both of the compounds). The MIC of zidebactam was >1,024 μg/ml for wild-type and multidrug-resistant Acinetobacter strains. Zidebactam is a PBP2 inhibitor that show a potent β-lactam enhancer effect against A. baumannii, including a multidrug-resistant OXA-23-producing ST2 international clone.


Chemical Structure

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Zidebactam
CAS# 1436861-97-0

Theoretical Analysis

MedKoo Cat#: 319537
Name: Zidebactam
CAS#: 1436861-97-0
Chemical Formula: C13H21N5O7S
Exact Mass: 391.12
Molecular Weight: 391.400
Elemental Analysis: C, 39.89; H, 5.41; N, 17.89; O, 28.61; S, 8.19

Price and Availability

Size Price Availability Quantity
2mg USD 150 Ready to ship
5mg USD 250 Ready to ship
10mg USD 450 Ready to ship
25mg USD 850 Ready to ship
50mg USD 1450 Ready to ship
100mg USD 2450 Ready to ship
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Synonym: WCK-5107; WCK 5107; WCK5107; Zidebactam

IUPAC/Chemical Name: (1R,2S,5R)-7-oxo-2-(2-((R)-piperidine-3-carbonyl)hydrazine-1-carbonyl)-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate

InChi Key: YCZPXRQPDCXTIO-BBBLOLIVSA-N

InChi Code: InChI=1S/C13H21N5O7S/c19-11(8-2-1-5-14-6-8)15-16-12(20)10-4-3-9-7-17(10)13(21)18(9)25-26(22,23)24/h8-10,14H,1-7H2,(H,15,19)(H,16,20)(H,22,23,24)/t8-,9-,10+/m1/s1

SMILES Code: O=C(NNC([C@@H]1CC[C@@H]2C[N@]1C(N2OS(=O)(O)=O)=O)=O)[C@@H]3CCCNC3

Appearance: White to off-white solid powder

Purity: >98% (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, not in water

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: Multidrug-resistant Acinetobacter baumannii has rapidly spread worldwide, resulting in a serious threat to hospitalized patients. Zidebactam and WCK 5153 are novel non-β-lactam bicyclo-acyl hydrazide β-lactam enhancer antibiotics being developed to target multidrug-resistant A. baumannii

Biological target: Zidebactam (WCK-5107) is a potent β-lactamase inhibitor. Zidebactam also is a penicillin-binding protein2 (PBP2) inhibitor with an IC50 of 0.26 μg/mL.
In vitro activity: Zidebactam alone exhibited variable activity (MIC50/90 0.25/>128 mg/L) when tested against WT Enterobacteriaceae. Overall, E. coli (MIC50/90 0.12/0.12 mg/L) and Enterobacter spp. (MIC50/90 0.12/0.25 mg/L) isolates exhibited low zidebactam MIC values, whereas indole-positive Proteeae (MIC50/90 >128/>128 mg/L) and Serratiamarcescens (MIC50/90 >128/>128 mg/L) showed much higher zidebactam MICs. Among WT Klebsiella spp. isolates, zidebactam MICs ranged from 0.12 to >128 mg/L (MIC50/90 0.25/>128 mg/L; Table 2) Reference: J Antimicrob Chemother. 2017 Jun 1;72(6):1696-1703. https://academic.oup.com/jac/article-lookup/doi/10.1093/jac/dkx050
In vivo activity: The peritonitis model study was performed with K. pneumoniae NCTC 13443. Cefepime at 100 mg/kg of body weight (3 doses) did not provide protection to infected mice (Table 3). The 50% effective dose (ED50) and ED90 of zidebactam or WCK 5153 in combination with 100 mg/kg of cefepime were 19.46 and 49.77 mg/kg, respectively. The efficacy of aztreonam in combination with BLEs was not evaluated in the peritonitis model, since the combination was studied in detail employing the thigh infection model. Reference: Antimicrob Agents Chemother. 2019 Apr 25;63(5):e00128-19. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/30782985/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 250.0 638.73
Water 50.0 127.75

Preparing Stock Solutions

The following data is based on the product molecular weight 391.40 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.

Recalculate based on batch purity %
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. Sader HS, Rhomberg PR, Flamm RK, Jones RN, Castanheira M. WCK 5222 (cefepime/zidebactam) antimicrobial activity tested against Gram-negative organisms producing clinically relevant β-lactamases. J Antimicrob Chemother. 2017 Jun 1;72(6):1696-1703. doi: 10.1093/jac/dkx050. PMID: 28333332. 2. Moya B, Barcelo IM, Cabot G, Torrens G, Palwe S, Joshi P, Umarkar K, Takalkar S, Periasamy H, Bhagwat S, Patel M, Bou G, Oliver A. In Vitro and In Vivo Activities of β-Lactams in Combination with the Novel β-Lactam Enhancers Zidebactam and WCK 5153 against Multidrug-Resistant Metallo-β-Lactamase-Producing Klebsiella pneumoniae. Antimicrob Agents Chemother. 2019 Apr 25;63(5):e00128-19. doi: 10.1128/AAC.00128-19. PMID: 30782985; PMCID: PMC6496095. 3. Bhagwat SS, Periasamy H, Takalkar SS, Palwe SR, Khande HN, Patel MV. The Novel β-Lactam Enhancer Zidebactam Augments the In Vivo Pharmacodynamic Activity of Cefepime in a Neutropenic Mouse Lung Acinetobacter baumannii Infection Model. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02146-18. doi: 10.1128/AAC.02146-18. PMID: 30670419; PMCID: PMC6437547.
In vitro protocol: 1. Sader HS, Rhomberg PR, Flamm RK, Jones RN, Castanheira M. WCK 5222 (cefepime/zidebactam) antimicrobial activity tested against Gram-negative organisms producing clinically relevant β-lactamases. J Antimicrob Chemother. 2017 Jun 1;72(6):1696-1703. doi: 10.1093/jac/dkx050. PMID: 28333332.
In vivo protocol: 1. Moya B, Barcelo IM, Cabot G, Torrens G, Palwe S, Joshi P, Umarkar K, Takalkar S, Periasamy H, Bhagwat S, Patel M, Bou G, Oliver A. In Vitro and In Vivo Activities of β-Lactams in Combination with the Novel β-Lactam Enhancers Zidebactam and WCK 5153 against Multidrug-Resistant Metallo-β-Lactamase-Producing Klebsiella pneumoniae. Antimicrob Agents Chemother. 2019 Apr 25;63(5):e00128-19. doi: 10.1128/AAC.00128-19. PMID: 30782985; PMCID: PMC6496095. 2. Bhagwat SS, Periasamy H, Takalkar SS, Palwe SR, Khande HN, Patel MV. The Novel β-Lactam Enhancer Zidebactam Augments the In Vivo Pharmacodynamic Activity of Cefepime in a Neutropenic Mouse Lung Acinetobacter baumannii Infection Model. Antimicrob Agents Chemother. 2019 Mar 27;63(4):e02146-18. doi: 10.1128/AAC.02146-18. PMID: 30670419; PMCID: PMC6437547.

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1: Moya B, Barcelo IM, Bhagwat S, Patel M, Bou G, Papp-Wallace KM, Bonomo RA, Oliver A. Potent β-Lactam Enhancer Activity of Zidebactam and WCK 5153 against Acinetobacter baumannii, Including Carbapenemase-Producing Clinical Isolates. Antimicrob Agents Chemother. 2017 Oct 24;61(11). pii: e01238-17. doi: 10.1128/AAC.01238-17. Print 2017 Nov. PubMed PMID: 28848013; PubMed Central PMCID: PMC5655067.

2: Sader HS, Rhomberg PR, Flamm RK, Jones RN, Castanheira M. WCK 5222 (cefepime/zidebactam) antimicrobial activity tested against Gram-negative organisms producing clinically relevant β-lactamases. J Antimicrob Chemother. 2017 Jun 1;72(6):1696-1703. doi: 10.1093/jac/dkx050. PubMed PMID: 28333332.

3: Moya B, Barcelo IM, Bhagwat S, Patel M, Bou G, Papp-Wallace KM, Bonomo RA, Oliver A. WCK 5107 (Zidebactam) and WCK 5153 Are Novel Inhibitors of PBP2 Showing Potent "β-Lactam Enhancer" Activity against Pseudomonas aeruginosa, Including Multidrug-Resistant Metallo-β-Lactamase-Producing High-Risk Clones. Antimicrob Agents Chemother. 2017 May 24;61(6). pii: e02529-16. doi: 10.1128/AAC.02529-16. Print 2017 Jun. PubMed PMID: 28289035; PubMed Central PMCID: PMC5444176.

4: Sader HS, Castanheira M, Huband M, Jones RN, Flamm RK. WCK 5222 (Cefepime-Zidebactam) Antimicrobial Activity against Clinical Isolates of Gram-Negative Bacteria Collected Worldwide in 2015. Antimicrob Agents Chemother. 2017 Apr 24;61(5). pii: e00072-17. doi: 10.1128/AAC.00072-17. Print 2017 May. PubMed PMID: 28242660; PubMed Central PMCID: PMC5404591.

5: Livermore DM, Mushtaq S, Warner M, Vickers A, Woodford N. In vitro activity of cefepime/zidebactam (WCK 5222) against Gram-negative bacteria. J Antimicrob Chemother. 2017 May 1;72(5):1373-1385. doi: 10.1093/jac/dkw593. PubMed PMID: 28158732.

Lang PA, Leissing TM, Page MGP, Schofield CJ, Brem J. Structural Investigations of the Inhibition of Escherichia coli AmpC β-Lactamase by Diazabicyclooctanes. Antimicrob Agents Chemother. 2021 Jan 20;65(2):e02073-20. doi: 10.1128/AAC.02073-20. PMID: 33199391; PMCID: PMC7849013.