Synonym
WCK-4234; WCK 4234; WCK4234; WCK-4234 sodium; WCK-4234 (Na);
IUPAC/Chemical Name
sodium (2S,5R)-2-cyano-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate
InChi Key
RYJWKSOILDDAHI-RIHPBJNCSA-M
InChi Code
InChI=1S/C7H9N3O5S.Na/c8-3-5-1-2-6-4-9(5)7(11)10(6)15-16(12,13)14;/h5-6H,1-2,4H2,(H,12,13,14);/q;+1/p-1/t5-,6+;/m0./s1
SMILES Code
O=S(ON1[C@]2([H])CC[C@@H](C#N)N(C2)C1=O)([O-])=O.[Na+]
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
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
Limited treatment options exist to combat infections caused by multidrug-resistant (MDR) Gram negative bacteria possessing broad-spectrum β-lactamases.
Biological target:
WCK-4234 is a potent β-lactamase inhibitor.
In vitro activity:
From the contemporary collection, this study found (i) that all Enterobacteriaceae were susceptible to meropenem plus WCK 4234, (ii) that susceptibility rates for Acinetobacter baumannii were 56.5% for meropenem alone, 82.6% with 4 μg/ml WCK 4234, and 95.7% with 8 μg/ml WCK 4234, and (iii) that WCK 4234 had a modest effect on susceptibility of Pseudomonas aeruginosa.
Reference: Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01666-19. https://pubmed.ncbi.nlm.nih.gov/31611363/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
269.21
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. Iregui A, Khan Z, Landman D, Quale J. Activity of Meropenem with a Novel Broader-Spectrum β-Lactamase Inhibitor, WCK 4234, against Gram-Negative Pathogens Endemic to New York City. Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01666-19. doi: 10.1128/AAC.01666-19. PMID: 31611363; PMCID: PMC7187611.
2. Papp-Wallace KM, Nguyen NQ, Jacobs MR, Bethel CR, Barnes MD, Kumar V, Bajaksouzian S, Rudin SD, Rather PN, Bhavsar S, Ravikumar T, Deshpande PK, Patil V, Yeole R, Bhagwat SS, Patel MV, van den Akker F, Bonomo RA. Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234. J Med Chem. 2018 May 10;61(9):4067-4086. doi: 10.1021/acs.jmedchem.8b00091. Epub 2018 Apr 20. PMID: 29627985; PMCID: PMC6131718.
In vitro protocol:
1. Iregui A, Khan Z, Landman D, Quale J. Activity of Meropenem with a Novel Broader-Spectrum β-Lactamase Inhibitor, WCK 4234, against Gram-Negative Pathogens Endemic to New York City. Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01666-19. doi: 10.1128/AAC.01666-19. PMID: 31611363; PMCID: PMC7187611.
2. Papp-Wallace KM, Nguyen NQ, Jacobs MR, Bethel CR, Barnes MD, Kumar V, Bajaksouzian S, Rudin SD, Rather PN, Bhavsar S, Ravikumar T, Deshpande PK, Patil V, Yeole R, Bhagwat SS, Patel MV, van den Akker F, Bonomo RA. Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234. J Med Chem. 2018 May 10;61(9):4067-4086. doi: 10.1021/acs.jmedchem.8b00091. Epub 2018 Apr 20. PMID: 29627985; PMCID: PMC6131718.
1: Patil K, Pathan A, Naik S, Zope V, Chavan R, Yeole R. Simultaneous determination of novel β-lactamase inhibitor WCK 4234 and Meropenem in dog plasma by LC-MS/MS and its application to preclinical pharmacokinetic study. Biomed Chromatogr. 2022 Jul;36(7):e5377. doi: 10.1002/bmc.5377. Epub 2022 Apr 13. PMID: 35347720.
2: Iregui A, Khan Z, Landman D, Quale J. Activity of Meropenem with a Novel Broader-Spectrum β-Lactamase Inhibitor, WCK 4234, against Gram-Negative Pathogens Endemic to New York City. Antimicrob Agents Chemother. 2019 Dec 20;64(1):e01666-19. doi: 10.1128/AAC.01666-19. PMID: 31611363; PMCID: PMC7187611.
3: Papp-Wallace KM, Nguyen NQ, Jacobs MR, Bethel CR, Barnes MD, Kumar V, Bajaksouzian S, Rudin SD, Rather PN, Bhavsar S, Ravikumar T, Deshpande PK, Patil V, Yeole R, Bhagwat SS, Patel MV, van den Akker F, Bonomo RA. Strategic Approaches to Overcome Resistance against Gram-Negative Pathogens Using β-Lactamase Inhibitors and β-Lactam Enhancers: Activity of Three Novel Diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234. J Med Chem. 2018 May 10;61(9):4067-4086. doi: 10.1021/acs.jmedchem.8b00091. Epub 2018 Apr 20. PMID: 29627985; PMCID: PMC6131718.
4: Mushtaq S, Vickers A, Woodford N, Livermore DM. WCK 4234, a novel diazabicyclooctane potentiating carbapenems against Enterobacteriaceae, Pseudomonas and Acinetobacter with class A, C and D β-lactamases. J Antimicrob Chemother. 2017 Jun 1;72(6):1688-1695. doi: 10.1093/jac/dkx035. PMID: 28333319.
