Sulopenem | CAS#120788-07-0 | beta-lactamase inhibitor

MedKoo Cat#: 329475 | Name: Sulopenem

Description:

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

Sulopenem, also known as CP-70429, is a potent beta-lactamase inhibitor.Sulopenem showed potent antibacterial activity against gram-positive and gram-negative bacteria except Pseudomonas aeruginosa and Xanthomonas maltophilia. CP-70,429 was stable to various types of beta-lactamases except for the enzyme from X. maltophilia and was 16- to 128-fold more active than the other compounds against beta-lactamase-producing strains of Enterobacter cloacae and Citrobacter freundii.

Chemical Structure

Sulopenem

CAS#120788-07-0 (free base)

Theoretical Analysis

MedKoo Cat#: 329475

Name: Sulopenem

CAS#: 120788-07-0 (free base)

Chemical Formula: C12H15NO5S3

Exact Mass: 349.0112

Molecular Weight: 349.43

Elemental Analysis: C, 41.25; H, 4.33; N, 4.01; O, 22.89; S, 27.52

Price and Availability

Size	Price	Availability
5mg	USD 250.00	2 Weeks
25mg	USD 650.00	2 Weeks
100mg	USD 1,850.00	2 Weeks
200mg	USD 2,750.00	2 Weeks
500mg	USD 3,950.00	2 Weeks
1g	USD 4,950.00	2 Weeks

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Related CAS #

112294-81-2 (sodium) 120788-07-0 (free base)

Synonym

CP-70,429; CP 70,429; CP70,429; CP-70429; CP 70429; CP70429; Sulopenem;

IUPAC/Chemical Name

(5R,6S)-6-((R)-1-hydroxyethyl)-3-(((3S)-1-oxidotetrahydrothiophen-3-yl)thio)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

InChi Key

FLSUCZWOEMTFAQ-IIOOQZKLSA-N

InChi Code

InChI=1S/C12H15NO5S3/c1-5(14)7-9(15)13-8(11(16)17)12(20-10(7)13)19-6-2-3-21(18)4-6/h5-7,10,14H,2-4H2,1H3,(H,16,17)/t5-,6+,7+,10-,21?/m1/s1

SMILES Code

C[C@H]([C@@H]1[C@H]2SC(S[C@H]3CC[S+](C3)[O-])=C(C(O)=O)N2C1=O)O

Appearance

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

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

Instruction

View handling instruction

Biological target:

Sulforaphane is an inducer of Nrf2 and is also an inhibitor of histone deacetylase (HDAC) and NF-κB.

In vitro activity:

The in vitro activity of sulopenem supports its potential in the treatment of intra-abdominal and urinary tract infections. Sulopenem demonstrated potent in vitro antimicrobial activity against Enterobacterales isolates regardless of infection type, inhibiting 99.2% of isolates at ≤1 mg/L. Sulopenem maintained activity against ciprofloxacin-, nitrofurantoin- and trimethoprim/sulfamethoxazole-non-susceptible subsets (MIC50/90, 0.03-0.06/0.12-0.5 mg/L). Reference: J Antimicrob Chemother. 2023 Jun 1;78(6):1406-1414. https://pubmed.ncbi.nlm.nih.gov/37042351/

In vivo activity:

Sulopenem, an intravenous and oral penem, shows promise for treating uncomplicated and complicated urinary tract infections. It exhibits activity against fluoroquinolone-resistant, extended spectrum β-lactamases-producing, multidrug-resistant Enterobacterales. Sulopenem remains effective against various pathogens, including Gram-negative and Gram-positive microorganisms. Clinical trials have shown mixed results in comparison to other antibiotics, with potential for use in patients with resistant pathogens. Reference: Drugs. 2022 Apr;82(5):533-557. https://pubmed.ncbi.nlm.nih.gov/35294769/

	Solvent	mg/mL	mM
Solubility
	DMSO	83.3	238.46

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 349.43 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. Maher JM, Huband MD, Blankers CG, Puttagunta S, Aronin SI, Castanheira M. In vitro activity of sulopenem and comparator agents against Enterobacterales and anaerobic clinical isolates collected during the SENTRY Antimicrobial Surveillance Program. J Antimicrob Chemother. 2023 Jun 1;78(6):1406-1414. doi: 10.1093/jac/dkad099. Erratum in: J Antimicrob Chemother. 2023 May 02;: PMID: 37042351; PMCID: PMC10232259. 2. Walkty AJ, Karlowsky JA, Baxter MR, Lagace-Wiens PRS, Adam HJ, Zhanel GG. In vitro activity of sulopenem against 1880 bacterial pathogens isolated from Canadian patients with urinary tract infections (CANWARD, 2014-21). J Antimicrob Chemother. 2022 Nov 28;77(12):3414-3420. doi: 10.1093/jac/dkac333. PMID: 36177825. 3. Negatu DA, Shin SJ, Kim SY, Jhun BW, Dartois V, Dick T. Oral β-lactam pairs for the treatment of Mycobacterium avium complex pulmonary disease. J Infect Dis. 2023 Dec 27:jiad591. doi: 10.1093/infdis/jiad591. Epub ahead of print. PMID: 38150401. 4. Zhanel GG, Pozdirca M, Golden AR, Lawrence CK, Zelenitsky S, Berry L, Schweizer F, Bay D, Adam H, Zhanel MA, Lagacé-Wiens P, Walkty A, Irfan N, Naber K, Lynch JP 3rd, Karlowsky JA. Sulopenem: An Intravenous and Oral Penem for the Treatment of Urinary Tract Infections Due to Multidrug-Resistant Bacteria. Drugs. 2022 Apr;82(5):533-557. doi: 10.1007/s40265-022-01688-1. Epub 2022 Mar 16. PMID: 35294769.

In vitro protocol:

In vivo protocol:

1. Negatu DA, Shin SJ, Kim SY, Jhun BW, Dartois V, Dick T. Oral β-lactam pairs for the treatment of Mycobacterium avium complex pulmonary disease. J Infect Dis. 2023 Dec 27:jiad591. doi: 10.1093/infdis/jiad591. Epub ahead of print. PMID: 38150401. 2. Zhanel GG, Pozdirca M, Golden AR, Lawrence CK, Zelenitsky S, Berry L, Schweizer F, Bay D, Adam H, Zhanel MA, Lagacé-Wiens P, Walkty A, Irfan N, Naber K, Lynch JP 3rd, Karlowsky JA. Sulopenem: An Intravenous and Oral Penem for the Treatment of Urinary Tract Infections Due to Multidrug-Resistant Bacteria. Drugs. 2022 Apr;82(5):533-557. doi: 10.1007/s40265-022-01688-1. Epub 2022 Mar 16. PMID: 35294769.

1: Dunne MW, Aronin SI, Das AF, Akinapelli K, Breen J, Zelasky MT, Puttagunta S. A phase 3 randomized trial of sulopenem vs. ertapenem in patients with complicated intraabdominal infections. Clin Microbiol Infect. 2024 Nov 2:S1198-743X(24)00507-X. doi: 10.1016/j.cmi.2024.10.025. Epub ahead of print. PMID: 39491784. 2: Dousa KM, Shin E, Kurz SG, Plummer M, Nantongo M, Bethel CR, Taracila MA, Nguyen DC, Kreiswith BN, Daley CL, Remy KE, Holland SM, Bonomo RA. Synergistic effects of sulopenem in combination with cefuroxime or durlobactam against Mycobacterium abscessus. mBio. 2024 Jun 12;15(6):e0060924. doi: 10.1128/mbio.00609-24. Epub 2024 May 14. PMID: 38742824; PMCID: PMC11237399. 3: Negatu DA, Aragaw WW, Dartois V, Dick T. A pairwise approach to revitalize β-lactams for the treatment of TB. Antimicrob Agents Chemother. 2024 May 1:e0003424. doi: 10.1128/aac.00034-24. Epub ahead of print. PMID: 38690896. 4: Negatu DA, Shin SJ, Kim SY, Jhun BW, Dartois V, Dick T. Oral β-Lactam Pairs for the Treatment of Mycobacterium avium Complex Pulmonary Disease. J Infect Dis. 2024 Aug 16;230(2):e241-e246. doi: 10.1093/infdis/jiad591. PMID: 38150401; PMCID: PMC11326814. 5: Le Terrier C, Nordmann P, Bouvier M, Poirel L. Impact of acquired broad- spectrum β-lactamases on susceptibility to oral penems/carbapenems (tebipenem, sulopenem, and faropenem) alone or in combination with avibactam and taniborbactam β-lactamase inhibitors in Escherichia coli. Antimicrob Agents Chemother. 2023 Oct 18;67(10):e0054723. doi: 10.1128/aac.00547-23. Epub 2023 Sep 5. PMID: 37668385; PMCID: PMC10583657. 6: Correction to: Sulopenem or Ciprofloxacin for the Treatment of Uncomplicated Urinary Tract Infections in Women: A Phase 3, Randomized Trial. Clin Infect Dis. 2023 Sep 18;77(6):937. doi: 10.1093/cid/ciad216. Erratum for: Clin Infect Dis. 2023 Jan 6;76(1):66-77. doi: 10.1093/cid/ciac738. PMID: 37590314; PMCID: PMC10506771. 7: Puttagunta S, Aronin SI, DiFranco-Fisher J, Koeth L. Sulopenem Disk Development, Quality Control Range, and MIC to Disk Result Correlation for Enterobacterales Isolates. J Clin Microbiol. 2023 Jul 20;61(7):e0024623. doi: 10.1128/jcm.00246-23. Epub 2023 Jun 26. PMID: 37358462; PMCID: PMC10358168. 8: Correction to: In vitro activity of sulopenem and comparator agents against Enterobacterales and anaerobic clinical isolates collected during the SENTRY Antimicrobial Surveillance Program. J Antimicrob Chemother. 2023 Jun 1;78(6):1559. doi: 10.1093/jac/dkad140. Erratum for: J Antimicrob Chemother. 2023 Jun 1;78(6):1406-1414. doi: 10.1093/jac/dkad099. PMID: 37130004; PMCID: PMC10232260. 9: Karvouniaris M, Almyroudi MP, Abdul-Aziz MH, Blot S, Paramythiotou E, Tsigou E, Koulenti D. Novel Antimicrobial Agents for Gram-Negative Pathogens. Antibiotics (Basel). 2023 Apr 16;12(4):761. doi: 10.3390/antibiotics12040761. PMID: 37107124; PMCID: PMC10135111. 10: Maher JM, Huband MD, Blankers CG, Puttagunta S, Aronin SI, Castanheira M. In vitro activity of sulopenem and comparator agents against Enterobacterales and anaerobic clinical isolates collected during the SENTRY Antimicrobial Surveillance Program. J Antimicrob Chemother. 2023 Jun 1;78(6):1406-1414. doi: 10.1093/jac/dkad099. Erratum in: J Antimicrob Chemother. 2023 Jun 1;78(6):1559. doi: 10.1093/jac/dkad140. PMID: 37042351; PMCID: PMC10232259. 11: Dunne MW, Aronin SI, Das AF, Gupta J, Akinapelli K, Breen J, Zelasky MT, Puttagunta S. Applying Desirability of Outcome Ranking End Point to Randomized Trial of Sulopenem for the Treatment of Complicated Urinary Tract Infections. Clin Infect Dis. 2023 Jun 16;76(12):2213-2215. doi: 10.1093/cid/ciad149. PMID: 36949581; PMCID: PMC10273356. 12: Walkty AJ, Karlowsky JA, Baxter MR, Lagace-Wiens PRS, Adam HJ, Zhanel GG. In vitro activity of sulopenem against 1880 bacterial pathogens isolated from Canadian patients with urinary tract infections (CANWARD, 2014-21). J Antimicrob Chemother. 2022 Nov 28;77(12):3414-3420. doi: 10.1093/jac/dkac333. PMID: 36177825. 13: Dunne MW, Aronin SI, Das AF, Akinapelli K, Zelasky MT, Puttagunta S, Boucher HW. Sulopenem or Ciprofloxacin for the Treatment of Uncomplicated Urinary Tract Infections in Women: A Phase 3, Randomized Trial. Clin Infect Dis. 2023 Jan 6;76(1):66-77. doi: 10.1093/cid/ciac738. Erratum in: Clin Infect Dis. 2023 Sep 18;77(6):937. doi: 10.1093/cid/ciad216. PMID: 36069202; PMCID: PMC9825825. 14: Dunne MW, Aronin SI, Das AF, Akinapelli K, Breen J, Zelasky MT, Puttagunta S. Sulopenem for the Treatment of Complicated Urinary Tract Infections Including Pyelonephritis: A Phase 3, Randomized Trial. Clin Infect Dis. 2023 Jan 6;76(1):78-88. doi: 10.1093/cid/ciac704. PMID: 36068705; PMCID: PMC9825827. 15: Negatu DA, Zimmerman MD, Dartois V, Dick T. Strongly Bactericidal All-Oral β-Lactam Combinations for the Treatment of Mycobacterium abscessus Lung Disease. Antimicrob Agents Chemother. 2022 Sep 20;66(9):e0079022. doi: 10.1128/aac.00790-22. Epub 2022 Sep 1. PMID: 36047786; PMCID: PMC9487536. 16: Zhanel GG, Pozdirca M, Golden AR, Lawrence CK, Zelenitsky S, Berry L, Schweizer F, Bay D, Adam H, Zhanel MA, Lagacé-Wiens P, Walkty A, Irfan N, Naber K, Lynch JP 3rd, Karlowsky JA. Sulopenem: An Intravenous and Oral Penem for the Treatment of Urinary Tract Infections Due to Multidrug-Resistant Bacteria. Drugs. 2022 Apr;82(5):533-557. doi: 10.1007/s40265-022-01688-1. Epub 2022 Mar 16. PMID: 35294769. 17: Veeraraghavan B, Bakthavatchalam YD, Sahni RD. Oral Antibiotics in Clinical Development for Community-Acquired Urinary Tract Infections. Infect Dis Ther. 2021 Dec;10(4):1815-1835. doi: 10.1007/s40121-021-00509-4. Epub 2021 Aug 6. PMID: 34357517; PMCID: PMC8572892. 18: Chatwin CL, Hamrick JC, Trout REL, Myers CL, Cusick SM, Weiss WJ, Pulse ME, Xerri L, Burns CJ, Moeck G, Daigle DM, John K, Uehara T, Pevear DC. Microbiological Characterization of VNRX-5236, a Broad-Spectrum β-Lactamase Inhibitor for Rescue of the Orally Bioavailable Cephalosporin Ceftibuten as a Carbapenem-Sparing Agent against Strains of Enterobacterales Expressing Extended-Spectrum β-Lactamases and Serine Carbapenemases. Antimicrob Agents Chemother. 2021 Jul 16;65(8):e0055221. doi: 10.1128/AAC.00552-21. Epub 2021 Jul 16. PMID: 34001510; PMCID: PMC8284453. 19: Bader MS, Loeb M, Leto D, Brooks AA. Treatment of urinary tract infections in the era of antimicrobial resistance and new antimicrobial agents. Postgrad Med. 2020 Apr;132(3):234-250. doi: 10.1080/00325481.2019.1680052. Epub 2019 Oct 24. PMID: 31608743. 20: Haq SF, Shanbhag AP, Karthikeyan S, Hassan I, Thanukrishnan K, Ashok A, Sukumaran S, Ramaswamy S, Bharatham N, Datta S, Samant S, Katagihallimath N. A strategy to identify a ketoreductase that preferentially synthesizes pharmaceutically relevant (S)-alcohols using whole-cell biotransformation. Microb Cell Fact. 2018 Dec 3;17(1):192. doi: 10.1186/s12934-018-1036-2. PMID: 30509260; PMCID: PMC6276252.