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/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
250.0 |
638.73 |
| Water |
50.0 |
127.75 |
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
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.
| 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.
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.
1. 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.
2. Kuo SC, Wang YC, Tan MC, Huang WC, Shiau YR, Wang HY, Lai JF, Huang IW, Lauderdale TL. In vitro activity of imipenem/relebactam, meropenem/vaborbactam, ceftazidime/avibactam, cefepime/zidebactam and other novel antibiotics against imipenem-non-susceptible Gram-negative bacilli from Taiwan. Journal of Antimicrobial Chemotherapy. 2021 Aug 1;76(8):2071-8.
3. Kaushik A, Ammerman NC, Parrish NM, Nuermberger EL. New β-lactamase inhibitors nacubactam and zidebactam improve the in vitro activity of β-lactam antibiotics against Mycobacterium abscessus complex clinical isolates. Antimicrobial agents and chemotherapy. 2019 Sep;63(9):10-128.
4. Bakthavatchalam YD, Elangovan D, Jaganathan SV, Subburaju N, Shankar A, Manokaran Y, Devi R, Baveja S, Devi S, Bhattacharya S, SM R. In vitro activity of two cefepime-based novel combinations, cefepime/taniborbactam and cefepime/zidebactam, against carbapenemase-expressing Enterobacterales collected in India. Microbiology Spectrum. 2023 Apr 13;11(2):e04925-22.
5. Kuo SC, Tan MC, Huang WC, Wu HC, Chen FJ, Liao YC, Wang HY, Shiau YR, Lauderdale TL. Susceptibility of Elizabethkingia spp. to commonly tested and novel antibiotics and concordance between broth microdilution and automated testing methods. Journal of Antimicrobial Chemotherapy. 2021 Mar 1;76(3):653-8.
6. Bakthavatchalam YD, Behera B, Shah A, Mathur P, Ray R, Fomda BA, Walia K, Veeraraghavan B. Tackling the unyielding: testing two novel approaches against NDM-producing Enterobacterales and Pseudomonas aeruginosa isolates collected in India. Microbiol Spectr. 2025 Jan 7;13(1):e0049724. doi: 10.1128/spectrum.00497-24. Epub 2024 Nov 19. PMID: 39560385; PMCID: PMC11705784.
