Anidulafungin
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MedKoo CAT#: 314269

CAS#: 166663-25-8

Description: Anidulafungin, also known as LY303366, is a semisynthetic echinocandin used as an antifungal drug. Anidulafungin was approved on 2/21/2006. Anidulafungin has proven efficacy against esophageal candidiasis, but its main use will probably be in invasive Candida infection; it may 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, an enzyme important to the synthesis of the fungal cell wall. Anidulafungin inhibits glucan synthase, an enzyme important in the formation of (1→3)-β-D-glucan, a major fungal cell wall component. Glucan synthase is not present in mammalian cells, so it is an attractive target for antifungal activity.


Chemical Structure

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Anidulafungin
CAS# 166663-25-8

Theoretical Analysis

MedKoo Cat#: 314269
Name: Anidulafungin
CAS#: 166663-25-8
Chemical Formula: C58H73N7O17
Exact Mass: 1139.50629
Molecular Weight: 1140.24
Elemental Analysis: C, 61.09; H, 6.45; N, 8.60; O, 23.85

Price and Availability

Size Price Availability Quantity
200.0mg USD 1950.0 2 Weeks
500.0mg USD 2950.0 2 Weeks
1.0g USD 3950.0 2 Weeks
2.0g USD 6950.0 2 Weeks
5.0g USD 14950.0 2 Weeks
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Synonym: LY303366; LY-303366; LY 303366; Anidulafungin; VEchinocandin; Brand name: Eraxis; Ecalta.

IUPAC/Chemical Name: N-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6,20-bis((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)-4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxamide

InChi Key: JHVAMHSQVVQIOT-DJLNKZBGSA-N

InChi Code: 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

SMILES Code: CCCCCOC1=CC=C(C2=CC=C(C3=CC=C(C(N[C@@H]4C[C@@H](O)[C@@H](O)NC([C@@H]5[C@@H](O)[C@@H](C)CN5C([C@H]([C@@H](O)C)NC([C@H]([C@@H](O)[C@@H](O)C6=CC=C(O)C=C6)NC([C@@H]7C[C@@H](O)CN7C([C@H]([C@@H](O)C)NC4=O)=O)=O)=O)=O)=O)=O)C=C3)C=C2)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1140.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hinske LC, Weis F, Heyn J, Hinske P, Beiras-Fernandez A. The role of micafungin and anidulafungin in the treatment of systemic fungal infections: applications and patents for two novel echinocandins. Recent Pat Antiinfect Drug Discov. 2012 Apr;7(1):1-7. Review. PubMed PMID: 22044354.

2: George J, Reboli AC. Anidulafungin: when and how? The clinician's view. Mycoses. 2012 Jan;55(1):36-44. doi: 10.1111/j.1439-0507.2011.02052.x. Epub 2011 Jun 13. Review. PubMed PMID: 21668526.

3: Wilke M. Treatment and prophylaxis of invasive candidiasis with anidulafungin, caspofungin and micafungin and its impact on use and costs: review of the literature. Eur J Med Res. 2011 Apr 28;16(4):180-6. Review. PubMed PMID: 21486732; PubMed Central PMCID: PMC3352074.

4: Glöckner A. Treatment and prophylaxis of invasive candidiasis with anidulafungin, caspofungin and micafungin:review of the literature. Eur J Med Res. 2011 Apr 28;16(4):167-79. Review. PubMed PMID: 21486731; PubMed Central PMCID: PMC3352073.

5: Kofla G, Ruhnke M. Pharmacology and metabolism of anidulafungin, caspofungin and micafungin in the treatment of invasive candidosis: review of the literature. Eur J Med Res. 2011 Apr 28;16(4):159-66. Review. PubMed PMID: 21486730; PubMed Central PMCID: PMC3352072.

6: Tapısız A. Anidulafungin: is it a promising option in the treatment of pediatric invasive fungal infections? Expert Rev Anti Infect Ther. 2011 Mar;9(3):339-46. doi: 10.1586/eri.11.7. Review. PubMed PMID: 21417873.

7: Mayr A, Aigner M, Lass-Flörl C. Anidulafungin for the treatment of invasive candidiasis. Clin Microbiol Infect. 2011 Mar;17 Suppl 1:1-12. doi: 10.1111/j.1469-0691.2010.03448.x. Review. PubMed PMID: 21251147.

8: Kuti EL, Kuti JL. Pharmacokinetics, antifungal activity and clinical efficacy of anidulafungin in the treatment of fungal infections. Expert Opin Drug Metab Toxicol. 2010 Oct;6(10):1287-300. doi: 10.1517/17425255.2010.518143. Review. PubMed PMID: 20822479.

9: Lanternier F, Lortholary O. [Anidulafungin: a new therapeutic option in systemic candidiasis]. Med Mal Infect. 2010 Aug;40(8):440-8. doi: 10.1016/j.medmal.2009.12.002. Epub 2010 Jan 21. Review. French. PubMed PMID: 20096516.

10: Menichetti F. Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. Review. PubMed PMID: 19877741.



Additional Information

Anidulafungin was originally manufactured and submitted for FDA approval by Vicuron Pharmaceuticals. Pfizer acquired the drug upon its acquisition of Vicuron in the fall of 2005. Pfizer gained approval by the Food and Drug Administration (FDA) on February 21, 2006.