Identification
- Summary
Anidulafungin is an antifungal used in the treatment of several types of candida infections.
- Brand Names
- Ecalta, Eraxis
- Generic Name
- Anidulafungin
- DrugBank Accession Number
- DB00362
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Anidulafungin (DB00362)
- Weight
- Average: 1140.2369
Monoisotopic: 1139.506293945 - Chemical Formula
- C58H73N7O17
- Synonyms
- Anidulafungin
- Anidulafungina
- Anidulafungine
- Anidulafunginum
- External IDs
- LY-303366
- LY-307853
- LY-329960
- LY-333006
- LY303366
- VEC
- VER 002
- VER-002
- VER002
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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bloodstream infection ••• ••••• ••••••••••• ••••••••• Treatment of Candida infections •••••••••••• Treatment of Candidemia •••••••••••• Treatment of Esophageal candidiasis •••••••••••• ••••• Treatment of Fungal peritonitis caused by candida •••••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism A1,3-beta-glucan synthase component FKS1 inhibitorAspergillus niger (strain CBS 513.88 / FGSC A1513) - 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
- Adverse Effects
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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).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Anidulafungin. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Anidulafungin. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Anidulafungin. Phenindione The therapeutic efficacy of Phenindione can be increased when used in combination with Anidulafungin. Phenprocoumon The therapeutic efficacy of Phenprocoumon can be increased when used in combination with Anidulafungin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Ecalta (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ecalta Injection, powder, for solution 100 mg Intravenous Pfizer Europe Ma Eeig 2020-12-23 Not applicable EU 
Eraxis Powder, for solution 100 mg / vial Intravenous Pfizer Canada Ulc 2008-01-25 2013-07-19 Canada 
Eraxis Kit 50 mg/15mL Intravenous Pfizer Inc. 2007-05-15 2007-05-15 US 
Eraxis Powder, for solution 100 mg / vial Intravenous Pfizer Canada Ulc 2010-01-25 Not applicable Canada Eraxis Injection, powder, lyophilized, for solution 50 mg/15mL Intravenous Roerig 2006-02-17 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gd-anidulafungin Powder, for solution 100 mg / vial Intravenous Genmed A Division Of Pfizer Canada Ulc Not applicable Not applicable Canada
Categories
- ATC Codes
- J02AX06 — Anidulafungin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Cyclic peptides / P-terphenyls / Macrolactams / N-acyl-alpha amino acids and derivatives / Biphenyls and derivatives / Benzamides / Benzoyl derivatives / Phenoxy compounds / Phenol ethers / 1-hydroxy-2-unsubstituted benzenoids show 14 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkanolamine / Alkyl aryl ether / Alpha-amino acid or derivatives / Alpha-oligopeptide / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzamide show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- antibiotic antifungal drug, echinocandin, semisynthetic derivative, azamacrocycle, heterodetic cyclic peptide (CHEBI:55346)
- Affected organisms
- Candida albicans and other yeasts
- Aspergillis, Candida and other fungi
- Candida parapsilosis
- Coolia tropicalis
Chemical Identifiers
- UNII
- 9HLM53094I
- CAS number
- 166663-25-8
- InChI Key
- 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
- 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'-(pentyloxy)-[1,1'-biphenyl]-4-yl]benzamide
- SMILES
- [H][C@]1(NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)[C@H](C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C1=O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(OCCCCC)C=C1)[C@@H](C)O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@@H](C)O
References
- Synthesis Reference
Scott Jenkins, Gary Liversidge, Deborah Neville, "Nanoparticulate Anidulafungin Compositions and Methods for Making the Same." U.S. Patent US20090238867, issued September 24, 2009.
US20090238867- General References
- Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [Article]
- Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [Article]
- Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. doi: 10.4103/0253-7613.62396. [Article]
- Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [Article]
- Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [Article]
- Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [Article]
- Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. doi: 10.1592/phco.29.1.17. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D03211
- PubChem Compound
- 166548
- PubChem Substance
- 46505616
- ChemSpider
- 145752
- BindingDB
- 50417554
- 341018
- ChEBI
- 55346
- ChEMBL
- CHEMBL264241
- Therapeutic Targets Database
- DAP000546
- PharmGKB
- PA164742938
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Anidulafungin
- FDA label
- Download (2.25 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Aspergillosis / Candidemia 1 4 Completed Other Fungal Infections / Obesity 1 4 Completed Other Obesity, Morbid 1 4 Completed Prevention Central Nervous System Fungal Infections / Fungaemia / Fungal Infections / Lung Diseases, Fungal 1 4 Completed Treatment Candidemia 1
Pharmacoeconomics
- Manufacturers
- Vicuron pharmaceuticals inc
- Packagers
- Ben Venue Laboratories Inc.
- Pfizer Inc.
- Pharmacia Inc.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous 100 mg Injection, powder, for solution Parenteral Injection, powder, for solution Parenteral 100 MG Injection, powder, for solution Injection, powder, for solution 100 MG Injection, solution Intravenous Injection, powder, for solution 50 mg Injection, powder, for solution Intravenous; Parenteral 100 MG Powder Intravenous 100 MG Injection, powder, lyophilized, for solution Intravenous 100 mg Solution Parenteral 122.000 mg Injection, powder, lyophilized, for solution Intravenous 100 mg/30mL Injection, powder, lyophilized, for solution Intravenous 50 mg/15mL Kit Intravenous 100 mg/30mL Kit Intravenous 50 mg/15mL Powder Intravenous 100 mg/1vial Powder, for solution Intravenous 100 mg / vial Injection, powder, lyophilized, for solution Intravenous Injection, powder, lyophilized, for solution Intravenous 100 mg/vial Injection, solution, concentrate Intravenous 100 mg Injection Parenteral Solution Intravenous 100.000 mg Injection, solution Intravenous 100 mg - Prices
Unit description Cost Unit Eraxis(water dil) 100 mg vial 216.0USD vial Eraxis(water dil) 50 mg vial 108.0USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7198796 No 2007-04-03 2022-06-13 US US6384013 No 2002-05-07 2012-03-19 US CA2362481 No 2008-11-04 2020-03-02 Canada CA2091663 No 2007-10-30 2013-03-15 Canada US5965525 No 1999-10-12 2020-02-17 US US6960564 No 2005-11-01 2021-04-12 US US7709444 No 2010-05-04 2021-04-12 US
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 0.0564 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 292.29 m3·mol-1 Chemaxon Polarizability 122.78 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6513 Blood Brain Barrier - 0.9833 Caco-2 permeable - 0.7967 P-glycoprotein substrate Substrate 0.9066 P-glycoprotein inhibitor I Non-inhibitor 0.6298 P-glycoprotein inhibitor II Inhibitor 0.6296 Renal organic cation transporter Non-inhibitor 0.9085 CYP450 2C9 substrate Non-substrate 0.7737 CYP450 2D6 substrate Non-substrate 0.8428 CYP450 3A4 substrate Substrate 0.644 CYP450 1A2 substrate Non-inhibitor 0.949 CYP450 2C9 inhibitor Non-inhibitor 0.8978 CYP450 2D6 inhibitor Non-inhibitor 0.8104 CYP450 2C19 inhibitor Non-inhibitor 0.8827 CYP450 3A4 inhibitor Non-inhibitor 0.8221 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8637 Ames test Non AMES toxic 0.7638 Carcinogenicity Non-carcinogens 0.8077 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7797 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9863 hERG inhibition (predictor II) Inhibitor 0.6881
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 413.0098289 predictedDarkChem Lite v0.1.0 [M+H]+ 416.1744289 predictedDarkChem Lite v0.1.0 [M+Na]+ 413.4415289 predictedDarkChem Lite v0.1.0
Targets
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- Kind
- Protein
- Organism
- Aspergillus niger (strain CBS 513.88 / FGSC A1513)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- 1,3-beta-d-glucan synthase activity
- Specific Function
- Catalytic subunit of the 1,3-beta-glucan synthase. Synthesizes 1,3-beta-glucan, a major structural component of the cell wall. Involved in cell wall synthesis, maintenance and cell wall remodeling ...
- Gene Name
- fksA
- Uniprot ID
- A2QLK4
- Uniprot Name
- 1,3-beta-glucan synthase component FKS1
- Molecular Weight
- 216972.8 Da
References
- Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1. [Article]
- 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. [Article]
- 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. [Article]
- Ponton J: [The fungal cell wall and the mechanism of action of anidulafungin]. Rev Iberoam Micol. 2008 Jun;25(2):78-82. [Article]
- 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. doi: 10.1016/S1130-1406(09)70006-3. Epub 2009 May 7. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 18, 2024 09:15