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CAS 166663-25-8

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Also known as: Eraxis, 166663-25-8, Ecalta, V-echinocandin, Ver-002, Ly303366

Molecular Formula

C₅₈H₇₃N₇O₁₇

Molecular Weight

1140.2 g/mol

InChI Key

JHVAMHSQVVQIOT-MFAJLEFUSA-N

FDA UNII

9HLM53094I

Echinocandin antifungal agent that is used in the treatment of CANDIDEMIA and CANDIDIASIS.

Anidulafungin is an Echinocandin Antifungal.

1 2D Structure

CAS 166663-25-8

2 Identification

2.1 Computed Descriptors

2.1.1 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-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide

2.1.2 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

2.1.3 InChI Key

JHVAMHSQVVQIOT-MFAJLEFUSA-N

2.1.4 Canonical SMILES

CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)NC4CC(C(NC(=O)C5C(C(CN5C(=O)C(NC(=O)C(NC(=O)C6CC(CN6C(=O)C(NC4=O)C(C)O)O)C(C(C7=CC=C(C=C7)O)O)O)C(C)O)C)O)O)O

2.1.5 Isomeric SMILES

CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)N[C@H]4C[C@H]([C@H](NC(=O)[C@@H]5[C@H]([C@H](CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)O)[C@@H]([C@H](C7=CC=C(C=C7)O)O)O)[C@@H](C)O)C)O)O)O

2.2 Other Identifiers

2.2.1 UNII

9HLM53094I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-((4r,5r)-4,5-dihydroxy-n2-((4''-(pentyloxy)(1,1':4',1''-terphenyl)-4-yl)carbonyl)-l-ornithine)-echinocandin B

2. Eraxis

3. Ly 303366

4. Ly-303366

5. Ly303366

2.3.2 Depositor-Supplied Synonyms

1. Eraxis

2. 166663-25-8

3. Ecalta

4. V-echinocandin

5. Ver-002

6. Ly303366

7. Ly-303366

8. Anidulafungin (ly303366)

9. Ver002

10. Chebi:55346

11. 9hlm53094i

12. D70013

13. D-70013

14. 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-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide

15. Anidulafungin [usan]

16. Anidulafungina

17. Anidulafungine

18. Anidulafunginum

19. Unii-9hlm53094i

20. Anidulafungin [usan:inn:ban]

21. Anidulafungin [mi]

22. Anidulafungin [inn]

23. Schembl38292

24. Anidulafungin [vandf]

25. (4r,5r)-4,5-dihydroxy-n(sup 2)-((4'-(pentyloxy)-p-terphenyl-4-yl)carbonyl)-l-ornithyl-l-threonyl-trans-4-hydroxy-l-prolyl-(s)-4-hydroxy-4-(p-hydroxyphenyl)-l-threonyl-l-threonyl-(3s,4s)-3-hydroxy-4-methyl-l-proline Cyclic (6-1)-peptide

26. Anidulafungin [mart.]

27. Anidulafungin [who-dd]

28. Chembl264241

29. Anidulafungin [ema Epar]

30. Anidulafungin [orange Book]

31. Bdbm50417554

32. Mfcd00917070

33. S4286

34. Ccg-270647

35. Cs-1824

36. Db00362

37. Ncgc00386349-01

38. Hy-13553

39. Sw222238-1

40. A13436

41. 663a258

42. J-010304

43. Q4764531

44. (4r,5r)-4,5-dihydroxy-n(sup 2)-((4''-(pentyloxy)-p-terphenyl-4-yl)carbonyl)-l-ornithyl-l-threonyl-trans-4-hydroxy-l-prolyl-(s)-4-hydroxy-4-(p-hydroxyphenyl)-l-threonyl-l-threonyl-(3s,4s)-3-hydroxy-4-methyl-l-proline Cyclic (6->1)-peptide

45. Echinocandin B, 1-((4r,5r)-4,5-dihydroxy-n(sup 2)-((4''-(pentyloxy)(1,1':4',1''-terphenyl)-4-yl)carbonyl)-l-ornithine)-

46. Echinocandin B, 1-((4r,5r)-4,5-dihydroxy-n2-((4''-(pentyloxy)(1,1':4',1''-terphenyl)-4-yl)carbonyl)-l-ornithine)

47. 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

48. N-[[(1s,2s)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-tetrahydroxy-bis[(1r)-1-hydroxyethyl]-methyl-hexaoxo-[?]yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide

49. 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[(1r)-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

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₅₈H₇₃N₇O₁₇
Molecular Weight	1140.2 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	14
Exact Mass	1139.50629389 g/mol
Monoisotopic Mass	1139.50629389 g/mol
Topological Polar Surface Area	377 Å²
Heavy Atom Count	82
Formal Charge	0
Complexity	2150
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	ERAXIS
Active Ingredient	ANIDULAFUNGIN
Company	VICURON (Application Number: N021632. Patents: 5965525, 6960564, 7709444)

4.2 Drug 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.

FDA Label

Treatment of invasive candidiasis in adults and paediatric patients aged 1 month to < 18 years.

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ANIDULAFUNGIN

5.3.2 FDA UNII

9HLM53094I

5.3.3 Pharmacological Classes

Lipopeptides [CS]; Echinocandin Antifungal [EPC]

5.4 ATC Code

J02AX06

J - Antiinfectives for systemic use

J02 - Antimycotics for systemic use

J02A - Antimycotics for systemic use

J02AX - Other antimycotics for systemic use

J02AX06 - Anidulafungin

5.5 Absorption, Distribution and Excretion

Route of Elimination

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

Volume of Distribution

30 to 50 L

Clearance

1 L/h

5.6 Metabolism/Metabolites

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.

5.7 Biological Half-Life

40-50 hours

5.8 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.

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