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Sulopenem

Sulopenem
Clinical data
ATC code
  • None
Identifiers
  • (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15NO5S3
Molar mass349.43 g·mol−1
3D model (JSmol)
  • C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)S[C@H]3CC[S@@](=O)C3)C(=O)O)O
  • 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
  • Key:FLSUCZWOEMTFAQ-PRBGKLEPSA-N

Sulopenem (CP-70,429) is a thiopenem antibiotic derivative from the penem family, which unlike most related drugs is orally active. It was developed in Japan in the 1990s, and has been approved to treat uncomplicated urinary tract infections in combination with probenecid (Brand name: Orlynvah). It has reached Phase III clinical trials on several occasions and continues to be the subject of ongoing research into potential applications, especially in the treatment of multiple drug resistant urinary tract infections.[1][2][3][4][5]

In October 2024, the US Food and Drug Administration approved sulopenem etzadroxil with probenecid combination for the treatment of urinary tract infections caused by Escherichia coli, Klebsiella pneumoniae, or Proteus mirabilis in adult women with limited alternative oral antibiotic options. The combination was developed by Iterum Therapeutics under the trade name ORLYNVAH™.[6]

See also

References

  1. ^ Minamimura M, Taniyama Y, Inoue E, Mitsuhashi S (July 1993). "In vitro antibacterial activity and beta-lactamase stability of CP-70,429 a new penem antibiotic". Antimicrobial Agents and Chemotherapy. 37 (7): 1547–1551. doi:10.1128/AAC.37.7.1547. PMC 188011. PMID 8363389.
  2. ^ Hamilton-Miller JM (November 2003). "Chemical and microbiologic aspects of penems, a distinct class of beta-lactams: focus on faropenem". Pharmacotherapy. 23 (11): 1497–1507. doi:10.1592/phco.23.14.1497.31937. PMID 14620395. S2CID 43705118.
  3. ^ Ednie LM, Appelbaum PC (May 2009). "Antianaerobic activity of sulopenem compared to six other agents". Antimicrobial Agents and Chemotherapy. 53 (5): 2163–2170. doi:10.1128/AAC.01557-08. PMC 2681565. PMID 19223615.
  4. ^ Bader MS, Loeb M, Leto D, Brooks AA (April 2020). "Treatment of urinary tract infections in the era of antimicrobial resistance and new antimicrobial agents". Postgraduate Medicine. 132 (3): 234–250. doi:10.1080/00325481.2019.1680052. PMID 31608743. S2CID 204545734.
  5. ^ Veeraraghavan B, Bakthavatchalam YD, Sahni RD (December 2021). "Oral Antibiotics in Clinical Development for Community-Acquired Urinary Tract Infections". Infectious Diseases and Therapy. 10 (4): 1815–1835. doi:10.1007/s40121-021-00509-4. PMC 8572892. PMID 34357517.
  6. ^ "Iterum Therapeutics Receives U.S. FDA Approval of ORLYNVAH™ (Oral Sulopenem) for the Treatment of Uncomplicated Urinary Tract Infections". Iterum Therapeutics plc. 2024-10-25. Retrieved 2024-10-25.
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