Alisporivir

Synopsis, Chemistry

DEVELOPMENTS

1 Drug(s) in Development

1 Drug(s) in Development

DIGITAL CONTENT

4 News

4 News

Product Search

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

Other Certificates

Other Suppliers

API REF. PRICE (USD / KG)

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: Debio-025, 254435-95-5, Debio 025, Unil 025, Unil-025, Deb-025

Molecular Formula

C₆₃H₁₁₃N₁₁O₁₂

Molecular Weight

1216.6 g/mol

InChI Key

OLROWHGDTNFZBH-XEMWPYQTSA-N

FDA UNII

VBP9099AA6

Alisporivir is a non-immunosuppressive analogue of cyclosporine A and an inhibitor of cyclophilins, with potential antiviral activity. Upon oral administration, alisporivir targets and inhibits human host cyclophilins, thereby inhibiting hepatitis C virus (HCV) replication in hepatocytes. Alisporivir may also inhibit the replication of various coronaviruses. In addition, it may inhibit mitochondrial cyclophilin-D, which regulates mitochondrial permeability transition pore (mPTP) opening. This may prevent cell death and tissue damage.

1 2D Structure

Alisporivir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,6S,9S,12R,15S,18S,21S,24S,27R,30S,33S)-25,30-diethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,27,28-nonamethyl-6,9,18-tris(2-methylpropyl)-3,21,24-tri(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone

2.1.2 InChI

InChI=1S/C63H113N11O12/c1-26-29-30-40(16)52(75)51-56(79)66-44(27-2)59(82)68(20)43(19)58(81)74(28-3)49(38(12)13)55(78)67-48(37(10)11)62(85)69(21)45(31-34(4)5)54(77)64-41(17)53(76)65-42(18)57(80)70(22)46(32-35(6)7)60(83)71(23)47(33-36(8)9)61(84)72(24)50(39(14)15)63(86)73(51)25/h26,29,34-52,75H,27-28,30-33H2,1-25H3,(H,64,77)(H,65,76)(H,66,79)(H,67,78)/b29-26+/t40-,41+,42-,43-,44+,45+,46+,47+,48+,49+,50+,51+,52-/m1/s1

2.1.3 InChI Key

OLROWHGDTNFZBH-XEMWPYQTSA-N

2.1.4 Canonical SMILES

CCC1C(=O)N(C(C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)C(C)C)CC)C)C

2.1.5 Isomeric SMILES

CC[C@H]1C(=O)N([C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)C(C)C)CC)C)C

2.2 Other Identifiers

2.2.1 UNII

VBP9099AA6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Debio-025

2. Meala(3)etval(4)-cyclosporin

3. Unil 025

4. Unil-025

5. Unil025

2.3.2 Depositor-Supplied Synonyms

1. Debio-025

2. 254435-95-5

3. Debio 025

4. Unil 025

5. Unil-025

6. Deb-025

7. Deb025

8. (d-meala)3-(etval)4-csa

9. Vbp9099aa6

10. Chembl1651956

11. Deb 025

12. Alisporivir (usan)

13. Alisporivir [usan]

14. (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-25,30-diethyl-33-((1r,2r,e)-1-hydroxy-2-methylhex-4-en-1-yl)-6,9,18-triisobutyl-3,21,24-triisopropyl-1,4,7,10,12,15,19,27,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

15. Cyclo(l-alanyl-d-alanyl-n-methyl-l-leucyl-n-methyl-l-leucyl-n-methyl-l-valyl-(2s,3r,4r,6e)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-(2s)-2-aminobutanoyl-n-methyl-d-alanyl-n-ethyl-l-valyl-l-valyl-n-methyl-l-leucyl)

16. Alisporivir [inn]

17. Alisporivir [usan:inn]

18. Unii-vbp9099aa6

19. Unil025

20. Meala(3)etval(4)-cyclosporin

21. Alisporivir [who-dd]

22. Debio-025;deb-025

23. Schembl6850787

24. Chebi:149837

25. Dtxsid401027752

26. Bdbm50339127

27. De-025

28. Cs-7501

29. Db12139

30. Hy-12559

31. D10087

32. Q4727236

33. (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-25,30-diethyl-33-((1r,2r)-1-hydroxy-2-methylhex-4-enyl)-6,9,18-triisobutyl-3,21,24-triisopropyl-1,4,7,10,12,15,19,27,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

34. (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-25,30-diethyl-33-((1r,2r,e)-1-hydroxy-2-methylhex-4-enyl)-6,9,18-triisobutyl-3,21,24-triisopropyl-1,4,7,10,12,15,19,27,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone

35. (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-25,30-diethyl-33-[(1r,2r,4e)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,27,28-nonamethyl-6,9,18-tris(2-methylpropyl)-3,21,24-tris(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone

36. (3s,6s,9s,12r,15s,18s,21s,24s,27r,30s,33s)-25,30-diethyl-33-[(e,1r,2r)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,27,28-nonamethyl-6,9,18-tris(2-methylpropyl)-3,21,24-tri(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₆₃H₁₁₃N₁₁O₁₂
Molecular Weight	1216.6 g/mol
XLogP3	7.9
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	15
Exact Mass	1215.85701808 g/mol
Monoisotopic Mass	1215.85701808 g/mol
Topological Polar Surface Area	279 Å²
Heavy Atom Count	86
Formal Charge	0
Complexity	2360
Isotope Atom Count	0
Defined Atom Stereocenter Count	13
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1