Anidulafungin

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
Thumb
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

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
A1,3-beta-glucan synthase component FKS1
inhibitor
Aspergillus 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
Medicalerrors
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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).

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.
DrugInteraction
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Anidulafungin.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Anidulafungin.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Anidulafungin.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Anidulafungin.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Anidulafungin.
WarfarinThe therapeutic efficacy of Warfarin can be increased when used in combination with Anidulafungin.
Interactions
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Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Ecalta (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EcaltaInjection, powder, for solution100 mgIntravenousPfizer Europe Ma Eeig2020-12-23Not applicableEU flag
EraxisInjection, powder, lyophilized, for solution100 mg/30mLIntravenousRoerig2006-02-17Not applicableUS flag
EraxisPowder, for solution100 mg / vialIntravenousPfizer Canada Ulc2010-01-25Not applicableCanada flag
EraxisKit50 mg/15mLIntravenousPfizer Inc.2007-05-152007-05-15US flag
EraxisInjection, powder, lyophilized, for solution50 mg/15mLIntravenousRoerig2006-02-17Not applicableUS flag
EraxisKit100 mg/30mLIntravenousPfizer Inc.2007-05-152007-05-15US flag
EraxisPowder, for solution100 mg / vialIntravenousPfizer Canada Ulc2008-01-252013-07-19Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gd-anidulafunginPowder, for solution100 mg / vialIntravenousGenmed A Division Of Pfizer Canada UlcNot applicableNot applicableCanada flag

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
  1. Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [Article]
  2. Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [Article]
  3. 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]
  4. Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [Article]
  5. Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [Article]
  6. Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [Article]
  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. doi: 10.1592/phco.29.1.17. [Article]
  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. [Article]
KEGG Drug
D03211
PubChem Compound
166548
PubChem Substance
46505616
ChemSpider
145752
BindingDB
50417554
RxNav
341018
ChEBI
55346
ChEMBL
CHEMBL264241
Therapeutic Targets Database
DAP000546
PharmGKB
PA164742938
Drugs.com
Drugs.com Drug Page
Wikipedia
Anidulafungin
AHFS Codes
  • 08:14.16 — Echinocandins
FDA label
Download (2.25 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAspergillosis / Candidemia1
4CompletedOtherBMI >30 kg/m2 / Mycoses1
4CompletedOtherObesity Morbid / Obesity, Morbid1
4CompletedPreventionCentral Nervous System Fungal Infections / Fungaemia / Lung Diseases, Fungal / Mycoses1
4CompletedTreatmentCandidemia1
4CompletedTreatmentCandidemia / Candidiasis, Invasive1
4CompletedTreatmentCandidiasis1
4CompletedTreatmentInfections, Fungal / Liver Diseases1
4TerminatedTreatmentAspergillosis1
3CompletedTreatmentAspergillosis1

Pharmacoeconomics

Manufacturers
  • Vicuron pharmaceuticals inc
Packagers
  • Ben Venue Laboratories Inc.
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionParenteral
Injection, powder, for solution
Injection, solutionIntravenous
Injection, powder, for solutionIntravenous
Injection, powder, for solutionIntravenous100 mg
Injection, powder, for solutionIntravenous; Parenteral
PowderIntravenous
Injection, powder, lyophilized, for solutionIntravenous100 mg
Injection, powder, lyophilized, for solutionIntravenous100 mg/30mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/15mL
KitIntravenous100 mg/30mL
KitIntravenous50 mg/15mL
PowderIntravenous100 mg/1vial
Powder, for solutionIntravenous100 mg / vial
Injection, powder, lyophilized, for solutionIntravenous
Injection, solution, concentrateIntravenous
InjectionParenteral
Prices
Unit descriptionCostUnit
Eraxis(water dil) 100 mg vial216.0USD vial
Eraxis(water dil) 50 mg vial108.0USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7198796No2007-04-032022-06-13US flag
US6384013No2002-05-072012-03-19US flag
CA2362481No2008-11-042020-03-02Canada flag
CA2091663No2007-10-302013-03-15Canada flag
US5965525No1999-10-122020-02-17US flag
US6960564No2005-11-012021-04-12US flag
US7709444No2010-05-042021-04-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityPractically insolubleNot Available
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0564 mg/mLALOGPS
logP1.87ALOGPS
logP-1.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area377.42 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity292.29 m3·mol-1ChemAxon
Polarizability122.78 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6513
Blood Brain Barrier-0.9833
Caco-2 permeable-0.7967
P-glycoprotein substrateSubstrate0.9066
P-glycoprotein inhibitor INon-inhibitor0.6298
P-glycoprotein inhibitor IIInhibitor0.6296
Renal organic cation transporterNon-inhibitor0.9085
CYP450 2C9 substrateNon-substrate0.7737
CYP450 2D6 substrateNon-substrate0.8428
CYP450 3A4 substrateSubstrate0.644
CYP450 1A2 substrateNon-inhibitor0.949
CYP450 2C9 inhibitorNon-inhibitor0.8978
CYP450 2D6 inhibitorNon-inhibitor0.8104
CYP450 2C19 inhibitorNon-inhibitor0.8827
CYP450 3A4 inhibitorNon-inhibitor0.8221
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8637
Ames testNon AMES toxic0.7638
CarcinogenicityNon-carcinogens0.8077
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7797 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9863
hERG inhibition (predictor II)Inhibitor0.6881
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  1. 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]
  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. [Article]
  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. [Article]
  4. Ponton J: [The fungal cell wall and the mechanism of action of anidulafungin]. Rev Iberoam Micol. 2008 Jun;25(2):78-82. [Article]
  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. doi: 10.1016/S1130-1406(09)70006-3. Epub 2009 May 7. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 13, 2021 16:24