Anidulafungin

Anidulafungin
Clinical data
Pronunciation	/eɪˌnɪdjʊləˈfʌndʒɪn/ ay-NID-yuu-lə-FUN-jin
Trade names	Eraxis, others
Other names	LY303366, (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-[(4R,5R)-4,5-Dihydroxy-N2-[[4''-(pentyloxy)[1',1':4',1''-terphenyl]-4-yl]carbonyl]-L-ornithine]echinocandin B
AHFS/Drugs.com	Monograph
License data	US DailyMed: Anidulafungin;
Routes of; administration	Intravenous
ATC code	J02AX06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% (intravenous use only)
Protein binding	Extensive (>99%)
Metabolism	Hepatic metabolism not observed, CYP system not involved
Elimination half-life	27 hours; 40–50 hours (terminal)
Excretion	Feces (~30%), urine (<1%)
Identifiers
	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;
CAS Number	166663-25-8 ;
PubChem CID	166548;
DrugBank	DB00362 ;
ChemSpider	21106258 ;
UNII	9HLM53094I;
KEGG	D03211 ;
ChEBI	CHEBI:55346 ;
ChEMBL	ChEMBL1630215 ;
CompTox Dashboard (EPA)	DTXSID50873201 ;
ECHA InfoCard	100.184.856
Chemical and physical data
Formula	C58H73N7O17
Molar mass	1140.254 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:JHVAMHSQVVQIOT-QZNDWXLFSA-N ;
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Anidulafungin (INN)^[1]^: 42 (sold under the brand name Eraxis among others, is a semisynthetic echinocandin used as an antifungal medication.^[4]^[5]^[6] It may also have application in treating invasive Aspergillus infection when used in combination with voriconazole.^[7] 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.^[8]

It is on the World Health Organization's List of Essential Medicines.^[9]

^ ^a ^b "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 43" (PDF). World Health Organization. 2000. Retrieved 11 November 2016.
^ "Eraxis (anidulafungin) for Injection, for Intravenous Use. Full Prescribing Information". Roerig (Division of Pfizer, Inc.), New York, NY 10017. Retrieved 11 November 2016.
^ https://www.tga.gov.au/resources/prescription-medicines-registrations/anidulafungin-accord-healthcare-pty-ltd
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[INN-1] "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary names: List 43" (PDF). World Health Organization. 2000. Retrieved 11 November 2016.

[PI-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] ttps://www.tga.gov.au/resources/prescription-medicines-registrations/anidulafungin-accord-healthcare-pty-ltd

[4] 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.

[5] 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.

[6] 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.

[7] 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.

[8] 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.

[WHO22nd-9] 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.

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