Anidulafungin

Anidulafungin
Clinical data
Pronunciation/eɪˌnɪdjʊləˈfʌndʒɪn/ ay-NID-yuu-lə-FUN-jin
Trade namesEraxis, Ecalta
Other names(4R,5S)-4,5-Dihydroxy-N2-[[4''-(pentyloxy)-p-terphenyl-4-yl]carbonyl]-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline cyclic (6→1)-peptide[1]
1-[(4R,5R)-4,5-Dihydroxy-N2-[[4''-(pentyloxy)[1',1':4',1''-terphenyl]-4-yl]carbonyl]-L-ornithine]echinocandin B[2]
AHFS/Drugs.comMonograph
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability100% (intravenous use only)
Protein bindingExtensive (>99%)
MetabolismHepatic metabolism not observed, CYP system not involved
Elimination half-life27 hours; 40–50 hours (terminal)
ExcretionFeces (~30%), urine (<1%)
Identifiers
  • 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.184.856 Edit this at Wikidata
Chemical and physical data
FormulaC58H73N7O17
Molar mass1140.254 g·mol−1
3D model (JSmol)
  • CCCCCOc1ccc(cc1)c2ccc(cc2)c3ccc(cc3)C(=O)N[C@H]6C[C@@H](O)[C@@H](O)NC(=O)C4[C@@H](O)[C@@H](C)CN4C(=O)C(NC(=O)C(NC(=O)C5C[C@@H](O)CN5C(=O)C(NC6=O)[C@@H](C)O)[C@@H](O)[C@H](O)c7ccc(O)cc7)[C@@H](C)O
  • InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42?,43+,44?,45?,46?,47?,48-,49+,50+,54+/m0/s1 checkY
  • Key:JHVAMHSQVVQIOT-QZNDWXLFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Anidulafungin (INN)[1]: 42  (trade names Eraxis, Ecalta) is a semisynthetic echinocandin used as an antifungal drug. It was previously known as LY303366.[3][4][5] It may also have application in treating invasive Aspergillus infection when used in combination with voriconazole.[6] 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, an enzyme important to the synthesis of the fungal cell wall.[7]

It is on the World Health Organization's List of Essential Medicines.[8]

  1. ^ a b "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 43" (PDF). World Health Organization. 2000. Retrieved 11 November 2016.
  2. ^ "Eraxis (anidulafungin) for Injection, for Intravenous Use. Full Prescribing Information". Roerig (Division of Pfizer, Inc.), New York, NY 10017. Retrieved 11 November 2016.
  3. ^ Krause DS, Reinhardt J, Vazquez JA, Reboli A, Goldstein BP, Wible M, et al. (June 2004). "Phase 2, randomized, dose-ranging study evaluating the safety and efficacy of anidulafungin in invasive candidiasis and candidemia". Antimicrobial Agents and Chemotherapy. 48 (6): 2021–2024. doi:10.1128/AAC.48.6.2021-2024.2004. PMC 415613. PMID 15155194.
  4. ^ Pfaller MA, Boyken L, Hollis RJ, Messer SA, Tendolkar S, Diekema DJ (November 2005). "In vitro activities of anidulafungin against more than 2,500 clinical isolates of Candida spp., including 315 isolates resistant to fluconazole". Journal of Clinical Microbiology. 43 (11): 5425–5427. doi:10.1128/JCM.43.11.5425-5427.2005. PMC 1287823. PMID 16272464.
  5. ^ Pfaller MA, Diekema DJ, Boyken L, Messer SA, Tendolkar S, Hollis RJ, et al. (November 2005). "Effectiveness of anidulafungin in eradicating Candida species in invasive candidiasis". Antimicrobial Agents and Chemotherapy. 49 (11): 4795–4797. doi:10.1128/AAC.49.11.4795-4797.2005. PMC 1280139. PMID 16251335.
  6. ^ Grau S, Azanza JR, Ruiz I, Vallejo C, Mensa J, Maertens J, et al. (January 2017). "Cost-effectiveness analysis of combination antifungal therapy with voriconazole and anidulafungin versus voriconazole monotherapy for primary treatment of invasive aspergillosis in Spain". ClinicoEconomics and Outcomes Research. 9: 39–47. doi:10.2147/CEOR.S122177. PMC 5221484. PMID 28115858.
  7. ^ Zida A, Bamba S, Yacouba A, Ouedraogo-Traore R, Guiguemdé RT (March 2017). "Anti-Candida albicans natural products, sources of new antifungal drugs: A review". Journal de Mycologie Médicale. 27 (1): 1–19. doi:10.1016/j.mycmed.2016.10.002. PMID 27842800.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.