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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

CAS 166663-25-8
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 Weight 1140.2 g/mol
Molecular Formula C58H73N7O17
XLogP32.3
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count17
Rotatable Bond Count14
Exact Mass1139.50629389 g/mol
Monoisotopic Mass1139.50629389 g/mol
Topological Polar Surface Area377 Ų
Heavy Atom Count82
Formal Charge0
Complexity2150
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 1  
Drug NameERAXIS
Active IngredientANIDULAFUNGIN
CompanyVICURON (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.


BUILDING BLOCK

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