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Overview of C58H73N7O17

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(4R,5R)-4,5-Dihydroxy-N(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
PharmaCompass
  • Chemistry
(4R,5R)-4,5-Dihydroxy-N(2)-[[41)-peptide' class="img-responsive">
Also known as: 1)-peptide'>Eraxis, 166663-25-8, Ecalta, V-echinocandin, Anidulafungina, Anidulafungine
Molecular Formula
C58H73N7O17
Molecular Weight
1140.254  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. The chemical classification of anidulafungin is Lipopeptides.
1 2D Structure

(4R,5R)-4,5-Dihydroxy-N(2)-[[41)-peptide' src='https://www.pharmacompass.com/image/drug/IN166548.png'>

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
~{N}-[(3~{S},6~{S},9~{S},11~{R},15~{S},18~{S},20~{R},21~{R},24~{S},25~{S},26~{S})-6-[(1~{S},2~{S})-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1~{R})-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.0^{9,13}]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 Depositor-Supplied Synonyms

1. Eraxis

2. 166663-25-8

3. Ecalta

4. V-echinocandin

5. Anidulafungina

6. Anidulafungine

7. Anidulafunginum

8. Anidulafungin [usan:inn]

9. Unii-9hlm53094i

10. Ly303366

11. Anidulafungin (ly303366)

12. Chebi:55346

13. Ver-002

14. 9hlm53094i

15. (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

16. Ly-303366

17. Eraxis (tn)

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

19. Anidulafungin [usan:inn:ban]

20. C58h73n7o17

21. Ecalta (tn)

22. Ac1l4yai

23. D0f9by

24. Schembl38292

25. Chembl264241

26. Molport-006-167-527

27. Bdbm50417554

28. S4286

29. Akos030526640

30. An-5571

31. Db00362

32. Ncgc00386349-01

33. At-36943

34. Ls-63738

35. Sw222238-1

36. Z-3192

37. 663a258

38. J-010304

39. (4r,5r)-4,5-dihydroxy-n(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

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

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

42. 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((r)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxo

43. N-[(3s,6s,9s,11r,15s,18s,20r,21r,24s,25s,26s)-6-[(1s,2r)-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[22.3.0.09,13]heptacosan-18-yl]- 4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide

44. 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

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

46. 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

47. Tetracosahydro-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 1140.254 g/mol
Molecular Formula C58H73N7O17
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count17
Rotatable Bond Count14
Exact Mass1139.506 g/mol
Monoisotopic Mass1139.506 g/mol
Topological Polar Surface Area377 A^2
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 adult patients.


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.


Anidulafungin is a cyclic lipopeptide echinocandin derivative with antifungal activity. Anidulafungin inhibits 1,3 beta-D-glucan synthase, an enzyme involved in fungal cell wall synthesis, resulting in cell lysis and death. This agent is active against Candida species and Aspergillus. (NCI04)


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.


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety

ANIDULAFUNGIN


5.3.2 FDA UNII

9HLM53094I


5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC]

Echinocandin Antifungal


Chemical/Ingredient structural concept [Chemical/Ingredient]

Lipopeptides


5.4 ATC Code

Anatomical main group: J - General antiinfectives for systemic use
Therapeutic subgroup: J02 - Antimycotics for systemic use
Pharmacological subgroup: J02A - Antimycotics for systemic use
Chemical subgroup: J02AX - Other antimycotics for systemic use
Chemical substance: J02AX06 - anidulafungin


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

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.


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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