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

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

MedKoo CAT#: 329475

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

Description: 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)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329475
Name: Sulopenem
CAS#: 120788-07-0 (free base)
Chemical Formula: C12H15NO5S3
Exact Mass: 349.01
Molecular Weight: 349.430
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	2 Weeks
25mg	USD 650	2 Weeks
100mg	USD 1850	2 Weeks
200mg	USD 2750	2 Weeks
500mg	USD 3950	2 Weeks
1g	USD 4950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	83.3	238.46

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:	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.
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.

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1: Kosowska-Shick K, Ednie LM, McGhee P, Appelbaum PC. Comparative antipneumococcal activities of sulopenem and other drugs. Antimicrob Agents Chemother. 2009 Jun;53(6):2239-47. doi: 10.1128/AAC.01531-08. PubMed PMID: 19307366; PubMed Central PMCID: PMC2687188.

2: Wujcik CE, Kadar EP. Reduction of in-source collision-induced dissociation and thermolysis of sulopenem prodrugs for quantitative liquid chromatography/electrospray ionization mass spectrometric analysis by promoting sodium adduct formation. Rapid Commun Mass Spectrom. 2008 Oct;22(20):3195-206. doi: 10.1002/rcm.3722. PubMed PMID: 18803331.

3: Ednie LM, Appelbaum PC. Antianaerobic activity of sulopenem compared to six other agents. Antimicrob Agents Chemother. 2009 May;53(5):2163-70. doi: 10.1128/AAC.01557-08. PubMed PMID: 19223615; PubMed Central PMCID: PMC2681565.

4: Yoshida T, Tateda E, Hiramatsu K, Yokota T. [In vitro antibacterial activity of a new parenteral penem, sulopenem]. Jpn J Antibiot. 1996 Apr;49(4):324-37. Japanese. PubMed PMID: 8786624.

5: Inoue E, Komoto E, Taniyama Y, Mitsuhashi S. [Antibacterial activity of sulopenem, a new parenteral penem antibiotic]. Jpn J Antibiot. 1996 Apr;49(4):338-51. Japanese. PubMed PMID: 8786625.

6: Nagashima M, Goto S, Yoshida T, Matsunaga T, Shimohira H, Ogawa M. [In vitro and in vivo activities of sulopenem compared with those of imipenem and cephalosporins]. Jpn J Antibiot. 1996 Apr;49(4):303-23. Japanese. PubMed PMID: 8786623.

7: Komoto A, Otsuki M, Nishino T. [In vitro and in vivo antibacterial activities of sulopenem, a new penem antibiotic]. Jpn J Antibiot. 1996 Apr;49(4):352-66. Japanese. Erratum in: Jpn J Antibiot 1996 May;49(5):508. PubMed PMID: 8786626.

8: Watanabe K, Kato N, Tanaka-Bandoh K, Tanaka Y, Kato H, Ueno K. [In vitro activities of sulopenem, a new parenteral penem, against anaerobes]. Jpn J Antibiot. 1996 Apr;49(4):367-76. Japanese. PubMed PMID: 8786627.

9: Noey EL, Tibrewal N, Jiménez-Osés G, Osuna S, Park J, Bond CM, Cascio D, Liang J, Zhang X, Huisman GW, Tang Y, Houk KN. Origins of stereoselectivity in evolved ketoreductases. Proc Natl Acad Sci U S A. 2015 Dec 22;112(51):E7065-72. doi: 10.1073/pnas.1507910112. PubMed PMID: 26644568; PubMed Central PMCID: PMC4697376.

10: Turner B, Murch L. Interscience Conference on Antimicrobial Agents and Chemotherapy--49th annual meeting. Part 2. 12-15 September 2009, San Francisco, CA, USA. IDrugs. 2009 Nov;12(11):670-2. PubMed PMID: 19844847.

11: Osuna S, Jiménez-Osés G, Noey EL, Houk KN. Molecular dynamics explorations of active site structure in designed and evolved enzymes. Acc Chem Res. 2015 Apr 21;48(4):1080-9. doi: 10.1021/ar500452q. PubMed PMID: 25738880.

12: Kaczmarek FM, Dib-Hajj F, Shang W, Gootz TD. High-level carbapenem resistance in a Klebsiella pneumoniae clinical isolate is due to the combination of bla(ACT-1) beta-lactamase production, porin OmpK35/36 insertional inactivation, and down-regulation of the phosphate transport porin phoe. Antimicrob Agents Chemother. 2006 Oct;50(10):3396-406. PubMed PMID: 17005822; PubMed Central PMCID: PMC1610099.

13: Hujer KM, Hamza NS, Hujer AM, Perez F, Helfand MS, Bethel CR, Thomson JM, Anderson VE, Barlow M, Rice LB, Tenover FC, Bonomo RA. Identification of a new allelic variant of the Acinetobacter baumannii cephalosporinase, ADC-7 beta-lactamase: defining a unique family of class C enzymes. Antimicrob Agents Chemother. 2005 Jul;49(7):2941-8. PubMed PMID: 15980372; PubMed Central PMCID: PMC1168656.

14: Hamilton-Miller JM. Chemical and microbiologic aspects of penems, a distinct class of beta-lactams: focus on faropenem. Pharmacotherapy. 2003 Nov;23(11):1497-507. Review. PubMed PMID: 14620395.

15: Okamoto K, Gotoh N, Nishino T. Pseudomonas aeruginosa reveals high intrinsic resistance to penem antibiotics: penem resistance mechanisms and their interplay. Antimicrob Agents Chemother. 2001 Jul;45(7):1964-71. PubMed PMID: 11408209; PubMed Central PMCID: PMC90586.

16: Minamimura M, Taniyama Y, Inoue E, Mitsuhashi S. In vitro antibacterial activity and beta-lactamase stability of CP-70,429 a new penem antibiotic. Antimicrob Agents Chemother. 1993 Jul;37(7):1547-51. PubMed PMID: 8363389; PubMed Central PMCID: PMC188011.

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