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Identification
Name Anidulafungin
Accession Number DB00362 (APRD01301)
Type small molecule
Groups approved
Description

Anidulafungin or Eraxis is an anti-fungal drug manufactured by Pfizer that gained approval by the Food and Drug Administration (FDA) in February 21, 2006; it was previously known as LY303366. There is preliminary evidence that it has a similar safety profile to caspofungin. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Eraxis
Brand mixtures Not Available
Categories
  • Antibiotics, Antifungal
CAS number 166663-25-8
Weight Average: 1140.2369
Monoisotopic: 1139.506293945
Chemical Formula C58H73N7O17
InChI Key InChIKey=JHVAMHSQVVQIOT-MFAJLEFUSA-N
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
Plain Text
IUPAC Name
N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-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[22.3.0.0^{9,13}]heptacosan-18-yl]-4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide
SMILES
[H][C@@]12C[C@@H](O)CN1C(=O)[C@@]([H])(NC(=O)[C@H](C[C@@H](O)[C@@H](O)NC(=O)[C@]1([H])[C@@H](O)[C@@H](C)CN1C(=O)[C@@]([H])(NC(=O)[C@@]([H])(NC2=O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@@H](C)O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(OCCCCC)C=C1)[C@@H](C)O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Echinocandins
  • Lactams
Substructures
  • Echinocandins
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Amino Ketones
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Aminals and Derivatives
  • Biphenyl and Derivatives
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • Lactams
  • Benzoyl Derivatives
  • Tyrosols
  • Phenyl Esters
  • Benzamides
Pharmacology
Indication For use in the treatment of the following fungal infections: Candidemia and other forms of Candida infections (intra-abdominal abscess, and peritonitis), Aspergillus infections, and esophageal candidiasis. Also considered an alternative treatment for oropharyngeal canaidiasis.
Pharmacodynamics Anidulafungin is a semi-synthetic lipopeptide synthesized from a fermentation product of Aspergillus nidulans. Anidulafungin is an echinocandin, a class of antifungal drugs that inhibits the synthesis of 1,3-β-D-glucan, an essential component of fungal cell walls. Anidulafungin is active in vitro against many Candida, as well as some Aspergillus. Like other echinocandins, anidulafungin is not active against Cryptococcus neoformans, Trichosporon, Fusarium, or zygomycetes.
Mechanism of action Anidulafungin is a semi-synthetic echinocandin with antifungal activity. Anidulafungin inhibits glucan synthase, an enzyme present in fungal, but not mammalian cells. This results in inhibition of the formation of 1,3-β-D-glucan, an essential component of the fungal cell wall, ultimately leading to osmotic instability and cell death.
Absorption Not Available
Volume of distribution
  • 30 to 50 L
Protein binding 84%
Metabolism Hepatic metabolism of anidulafungin has not been observed. Anidulafungin is not a clinically relevant substrate, inducer, or inhibitor of cytochrome P450 (CYP450) isoenzymes. Anidulafungin undergoes slow chemical degradation at physiologic temperature and pH to a ring-opened peptide that lacks antifungal activity.
Route of elimination Less than 1% of the administered radioactive dose was excreted in the urine. Anidulafungin is not hepatically metabolized.
Half life 40-50 hours
Clearance
  • 1 L/h
Toxicity During clinical trials a single 400 mg dose of anidulafungin was inadvertently administered as a loading dose. No clinical adverse events were reported. The maximum non-lethal dose of anidulafungin in rats was 50 mg/kg, a dose which is equivalent to 10 times the recommended daily dose for esophageal candidiasis (50mg/day).
Affected organisms
  • Aspergillis, Candida and other fungi
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Vicuron pharmaceuticals inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Eraxis(water dil) 100 mg vial 216.0 USD vial
Eraxis(water dil) 50 mg vial 108.0 USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 7198796 2002-06-13 2022-06-13
United States 6384013 1995-03-19 2012-03-19
Canada 2362481 2008-11-04 2020-03-02
Canada 2091663 2007-10-30 2013-03-15
Properties
State solid
Experimental Properties
Property Value Source
water solubility Practically insoluble Not Available
logP 2.9 Not Available
Predicted Properties
Property Value Source
water solubility 5.64e-02 g/l ALOGPS
logP 1.87 ALOGPS
logP -1.5 ChemAxon
logS -4.3 ALOGPS
pKa (strongest acidic) 9.46 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 17 ChemAxon
hydrogen donor count 14 ChemAxon
polar surface area 377.42 ChemAxon
rotatable bond count 14 ChemAxon
refractivity 292.29 ChemAxon
polarizability 122.38 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. Pubmed
  2. Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. Pubmed
  3. Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. Pubmed
  4. Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. Pubmed
  5. Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. Pubmed
  6. Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. Pubmed
  7. Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. Pubmed
  8. Morace G, Borghi E, Iatta R, Montagna MT: Anidulafungin, a new echinocandin: in vitro activity. Drugs. 2009;69 Suppl 1:91-4. doi: 10.2165/11315560-000000000-00000. Pubmed
External Links
Resource Link
KEGG Drug D03211 Link_out
PubChem Compound 166548 Link_out
PubChem Substance 46505616 Link_out
ChemSpider 145752 Link_out
ChEBI 55346 Link_out
ChEMBL 55346 Link_out
Therapeutic Targets Database DAP000546 Link_out
PharmGKB PA164742938 Link_out
Drugs.com http://www.drugs.com/cdi/anidulafungin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Anidulafungin Link_out
ATC Codes
  • J02AX06
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (2.25 MB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. 1,3-beta-glucan synthase component FKS1

Pharmacological action: yes
Actions: inhibitor
UniProt ID: A2QLK4 Link_out
Gene: fksA
SNPs: SNPJam Report Link_out

References:
  1. Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. Pubmed
  2. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. Pubmed
  3. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. Pubmed
  4. Ponton J: [The fungal cell wall and the mechanism of action of anidulafungin]. Rev Iberoam Micol. 2008 Jun;25(2):78-82. Pubmed
  5. Quindos G, Eraso E, Javier Carrillo-Munoz A, Canton E, Peman J: [In vitro antifungal activity of micafungin]. Rev Iberoam Micol. 2009 Mar 31;26(1):35-41. Epub 2009 May 7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19