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Sulopenem

Names

[ CAS No. ]:
120788-07-0

[ Name ]:
Sulopenem

[Synonym ]:
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[[(3S)-tetrahydro-3-thienyl]thio]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (R)-S-oxide
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-[[(3S)-tetrahydro-1-oxido-3-thienyl]thio]-, (5R,6S)-
(3S)-3-({(5R
(5R,6S)-6-(1(R)-Hydroxyethyl)-2-[(1(R)-oxo-3(S)-thiolanyl)thio]-2-penem-3-carboxylic acid
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-{[(3S)-1-oxidotetrahydro-3-thiophenyl]sulfanyl}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CP-70,429
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-{[(3S)-1-oxidotetrahydrothiophen-3-yl]sulfanyl}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate

Biological Activity

[Description]:

Sulopenem (CP-70429) is an orally active, parenteral penem antibiotic with broad-spectrum activities against Gram-positive and Gram-negative bacteria. Sulopenem has the potential for urinary tract infections and intra-abdominal infections treatment. Sulopenem is inactive against Pseudomonas aeruginosa and Xanthomonas maltophilia[1][2][3].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Bacterial

[Target]

MIC: 0.015-0.12 µg/mL (E. coli)[1]


[In Vitro]

Sulopenem has the potential for uncomplicated and complicated urinary tract infections and intra-abdominal infections treatment, including multidrug-resistant (MDR) infections and infections attributable to quinolone-nonsusceptible and/or extended-spectrum β-lactamase (ESBL)-producing Gram-negative bacilli[1]. Sulopenem inhibits the growth of most isolates of aerobic and anaerobic Gram-positive and Gram-negative bacteria, including methicillin-susceptible Staphylococcus aureus, Streptococcus pneumoniae (penicillin-susceptible and -resistant isolates), group A and B β-hemolytic streptococci, Listeria monocytogenes, Enterobacteriaceae, Haemophilus influenzae, and Moraxella catarrhalis but excluding P. aeruginosa and Stenotrophomonas maltophilia, at a concentration of ≤1 μg/mL[1].

[In Vivo]

The protective effects of Sulopenem in murine experimental systemic infections are superior to those of Imipenem/Cilastatin. In murine experimental mixed infection with Escherichia coli and Bacteroides fragilis, Sulopenem has lower ED50. In guinea pigs experimental lung infection with Klebsiella pneumoniae, Sulopenem is more effective than CZON or Cefotiam[3].

[References]

[1]. James A Karlowsky, et al. In Vitro Activity of Sulopenem, an Oral Penem, Against Urinary Isolates of Escherichia coli. Antimicrob Agents Chemother. 2018 Dec 21;63(1):e01832-18.

[2]. M Minamimura, et al. 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.

[3]. M Nagashima, et al. In Vitro and in Vivo Activities of Sulopenem Compared With Those of Imipenem and Cephalosporins. Jpn J Antibiot. 1996 Apr;49(4):303-23.

Chemical & Physical Properties

[ Density]:
1.74g/cm3

[ Boiling Point ]:
693.1ºC at 760mmHg

[ Molecular Formula ]:
C12H15NO5S3

[ Molecular Weight ]:
349.44600

[ Flash Point ]:
373ºC

[ Exact Mass ]:
349.01100

[ PSA ]:
164.72000

[ LogP ]:
1.21000

[ Vapour Pressure ]:
3.2E-22mmHg at 25°C

[ Index of Refraction ]:
1.768

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds