Sulopenem etzadroxil

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

Hodoodo CAT#: H329476

CAS#: 1000296-70-7

Description: Sulopenem etzadroxil is a penem antibiotic agent. Sulopenem was more stable than imipenem against swine and human dehydropeptidase-Is. Sulopenem is one of the antibiotics that do not induce the appearance of subclones resistant to the drug.

Chemical Structure

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Sulopenem etzadroxil
CAS# 1000296-70-7
Instruction

Theoretical Analysis

Hodoodo Cat#: H329476
Name: Sulopenem etzadroxil
CAS#: 1000296-70-7
Chemical Formula: C19H27NO7S3
Exact Mass: 477.10
Molecular Weight: 477.605
Elemental Analysis: C, 47.78; H, 5.70; N, 2.93; O, 23.45; S, 20.14

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sulopenem etzadroxil; PF-03709270; PF03709270; PF 03709270; PF-3709270; PF3709270; PF 3709270.

IUPAC/Chemical Name: ((2-ethylbutanoyl)oxy)methyl (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-carboxylate

InChi Key: NBPVNGWRLGHULH-JKOUTOBWSA-N

InChi Code: InChI=1S/C19H27NO7S3/c1-4-11(5-2)17(23)26-9-27-18(24)14-19(28-12-6-7-30(25)8-12)29-16-13(10(3)21)15(22)20(14)16/h10-13,16,21H,4-9H2,1-3H3/t10-,12+,13+,16-,30?/m1/s1

SMILES Code: CCC(CC)C(=O)OCOC(=O)C1=C(S[C@H]2CC[S+]([O-])C2)S[C@@H]3[C@@H]([C@@H](C)O)C(=O)N13

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 477.61 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:
In vitro protocol:
In vivo protocol:

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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.