CAS 166663-25-8|Eraxis|anidulafungin|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...

General Information

Structure

Molecular Formula

C₅₈H₇₃N₇O₁₇

Molecular Mass

1140.23692

Exact Mass

1139.50629391

Charge

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

InChIKey

JHVAMHSQVVQIOT-MFAJLEFUSA-N

Canonic Smiles

CCCCCOc1ccc(cc1)c1ccc(cc1)c1ccc(cc1)C(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)[C@H](O)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@H](O)C)C

Isomeric Smiles

O[C@H]1[C@H](CN2[C@@H]1C(=O)N[C@H](O)[C@H](O)C[C@H](NC(=O)c1ccc(cc1)c1ccc(cc1)c1ccc(OCCCCC)cc1)C(=O)N[C@H](C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)N[C@H](C(=O)N[C@H](C2=O)[C@H](O)C)[C@H](O)[C@@H](O)c1ccc(O)cc1)[C@H](O)C)C

Calculated Properties

JChem

Acid pKa

9.457179

H Acceptors

H Donor

LogD (pH = 5.5)

-1.4572647

LogD (pH = 7.4)

-1.4609743

Log P

-1.4572171

Molar Refractivity

292.2932

Polarizability

116.85305

Polar Surface Area

377.42

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

1.87

LOG S

-4.31

Solubility (Water)

5.64e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Anidulafunginanidulafungin

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

Brand Name

Eraxis

IUPAC Traditional name

eraxis

Names and Identifiers

Registration numbers

PubChem SID

16096370946505616

PubChem CID

166548

CAS Number

166663-25-8

Registration numbers

Properties

Physical Property

Solubility

Practically insoluble

Hydrophobicity(logP)

2.9

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00362

Drug Groups

approved; investigational

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]

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

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.

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

Biotransformation

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.

Half Life

40-50 hours

Protein Binding

84%

Elimination

Less than 1% of the administered radioactive dose was excreted in the urine. Anidulafungin is not hepatically metabolized.

Distribution

* 30 to 50 L

Clearance

* 1 L/h

References

• Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [Pubmed]

• Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [Pubmed]

• Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. [Pubmed]

• Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [Pubmed]

• Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [Pubmed]

• Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [Pubmed]

• 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]

• 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

• [Wikipedia]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. Pubmed

• 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

• Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. Pubmed

• Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. Pubmed

• 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

• Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. Pubmed

• Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. Pubmed

• Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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