Anidulafungin
 |
|
|---|---|
| Systematic (IUPAC) name | |
| N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)- 6-[(1S,2R)-1,2-dihydroxy- 2-(4-hydroxyphenyl)ethyl]- 11,20,21,25-tetrahydroxy- 3,15-bis[(1R)-1-hydroxyethyl]- 26-methyl- 2,5,8,14,17,23-hexaoxo- 1,4,7,13,16,22-hexaazatricyclo [22.3.0.09,13] heptacosan-18-yl]- 4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide | |
| Clinical data | |
| Trade names | Eraxis |
| AHFS/Drugs.com | monograph |
| Pregnancy cat. | ? |
| Legal status | ? |
| Pharmacokinetic data | |
| Protein binding | 84 % |
| Half-life | 40-50 hours |
| Identifiers | |
| CAS number | 166663-25-8  |
| ATC code | J02AX06 |
| PubChem | CID 166548 |
| DrugBank | APRD01301 |
| ChemSpider | 21106258 |
| UNII | 9HLM53094I |
| KEGG | D03211  |
| ChEMBL | CHEMBL1201126 |
| Chemical data | |
| Formula | C58H73N7O17 |
| Mol. mass | 1140.24 g/mol |
| SMILES | eMolecules & PubChem |
|
|
 (what is this?) (verify) |
|
Anidulafungin or Eraxis (Ecalta in Europe) is a semisynthetic echinocandin used as an antifungal drug . Anidulafungin was originally manufactured and submitted for FDA approval by Vicuron Pharmaceuticals.[1] Pfizer acquired the drug upon its acquisition of Vicuron in the fall of 2005.[2] Pfizer gained approval by the Food and Drug Administration (FDA) on February 21, 2006;[3] it was previously known as LY303366. There is preliminary evidence it has a similar safety profile to caspofungin. It has proven efficacy against oesophageal candidiasis, but its main use will probably be in invasive Candida infection; it will probably also have application in treating invasive Aspergillus infection. It is a member of the class of antifungal drugs known as the echinocandins; its mechanism of action is by inhibition of (1→3)β-D-glucan synthase, which is an important component of the fungal cell wall.
[edit] Pharmacodynamics and pharmacokinetics
Anidulafungin significantly differs from other antifungals in that it undergoes chemical degradation to inactive forms at body pH and temperature. Because it does not rely on enzymatic degradation or hepatic or renal excretion, the drug is safe to use in patients with any degree of hepatic or renal impairment.[4]
Distribution: 30-50 L
Protein binding: 84%
There is no evidence anidulafungin is metabolized by the liver. Research has shown this specific drug undergoes slow chemical hydrolysis to an open-ring peptide which lacks antifungal activity. The half life of the drug is 27 hours. Thirty percent is excreted in the feces (10% as unchanged drug). Less than 1% is excreted in the urine.[5][6][7]
[edit] Mechanism of action
Anidulafungin inhibits glucan synthase, an enzyme important in the formation of β (1,3)-D-glucan, a major fungal cell wall component. Glucan synthase is not present in mammalian cells and therefore is an attractive target for antifungal activity.[8]
[edit] References
- ^ PRNewswire. Vicuron Pharmaceuticals Files New Drug Application (NDA) for Anidulafungin for Treatment of Invasive Candidiasis/Candidemia 08-18-2005.
- ^ PRNewswire. Vicuron Pharmaceuticals Stockholders Approve Merger With Pfizer 08-15-2005
- ^ "FDA Approves New Treatment for Fungal Infections". FDA News Release. Food and Drug Administration. 2006-02-21. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2006/ucm108602.htm. Retrieved 2009-08-01.
- ^ "Eraxis at RxList". 2009-06-24. http://www.rxlist.com/eraxis-drug.htm#cp. Retrieved 2009-08-01.
- ^ Trissel LA and Ogundele AB, “Compatibility of Anidulafungin With Other Drugs During Simulated Y-Site Administration,”Am J Health-Sys Pharm, 2005, 62:834-7.
- ^ Vazquez JA, “Anidulafungin: A New Echinocandin With a Novel Profile,” Clin Ther, 2005, 27(6):657-73.
- ^ Walsh TJ, Anaissie EJ, Denning DW, et al, “Treatment of Aspergillosis: Clinical Practice Guidelines of the Infectious Diseases Society of America,” Clin Infect Dis, 2008, 46(3):327-60
- ^ Denning DW. Echinocandins and pneumocandins- a new antifungal class with a novel mode of action. J Antimicrob Chemother 1997;40:611-614.
- Krause DS, Reinhardt J, Vazquez JA, Reboli A, Goldstein BP, Wible M, Henkel T (2004). "Phase 2, randomized, dose-ranging study evaluating the safety and efficacy of anidulafungin in invasive candidiasis and candidemia". Antimicrob Agents Chemother 48 (6): 2021–4. doi:10.1128/AAC.48.6.2021-2024.2004. PMC 415613. PMID 15155194. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=415613.
- Pfaller MA, Boyken L, Hollis RJ, Messer SA, Tendolkar S, Diekema DJ (2005). "In Vitro Activities of Anidulafungin against More than 2,500 Clinical Isolates of Candida spp., Including 315 Isolates Resistant to Fluconazole". J Clin Microbiol 43 (11): 5425–7. doi:10.1128/JCM.43.11.5425-5427.2005. PMC 1287823. PMID 16272464. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1287823.
- Pfaller MA, Diekema DJ, Boyken L, Messer SA, Tendolkar S, Hollis RJ, Goldstein BP (2005). "Effectiveness of anidulafungin in eradicating Candida species in invasive candidiasis". Antimicrob Agents Chemother 49 (11): 4795–7. doi:10.1128/AAC.49.11.4795-4797.2005. PMC 1280139. PMID 16251335. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1280139.
