Alisporivir

Alisporivir (INN), or Debio 025, DEB025, (or UNIL-025) is a cyclophilin inhibitor.[1] Its structure is reminiscent of, and synthesized from ciclosporin.

Alisporivir
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
ECHA InfoCard100.234.903
Chemical and physical data
FormulaC63H113N11O12
Molar mass1216.662 g·mol−1
3D model (JSmol)
SMILES
  • O=C1N[C@H](C(=O)N(C)[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N(C)[C@H](C(=O)N(C)[C@H](C(=O)N(C)[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N(C)[C@@H](C(=O)N(CC)[C@H]1C(C)C)C)CC)[C@H](O)[C@H](C)C/C=C/C)C)C(C)C)CC(C)C)CC(C)C)C)C)CC(C)C)C(C)C
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 Y
  • Key:OLROWHGDTNFZBH-XEMWPYQTSA-N Y
 NY (what is this?)  (verify)

It inhibits cyclophilin A.[2] Alisporivir is not immunosuppressive.[3]

It is being researched for potential use in the treatment of hepatitis C.[4][5] It has also been investigated for Duchenne muscular dystrophy[1] and may have therapeutic potential in Alzheimer's disease.[6]

Alisporivir is under development by Debiopharm for Japan and by Novartis for the rest of the world (licence granted by Debiopharm) since February 2010.

References

  1. Reutenauer J, Dorchies OM, Patthey-Vuadens O, Vuagniaux G, Ruegg UT (October 2008). "Investigation of Debio 025, a cyclophilin inhibitor, in the dystrophic mdx mouse, a model for Duchenne muscular dystrophy". British Journal of Pharmacology. 155 (4): 574–84. doi:10.1038/bjp.2008.285. PMC 2579666. PMID 18641676.
  2. Gallay, PA; Lin K. (15 February 2013). "Profile of alisporivir and its potential in the treatment of hepatitis C." Drug Design, Development and Therapy. 7: 105–115. doi:10.2147/DDDT.S30946. PMC 3578503. PMID 23440335.
  3. Ptak RG, Gallay PA, Jochmans D, et al. (April 2008). "Inhibition of human immunodeficiency virus type 1 replication in human cells by Debio-025, a novel cyclophilin binding agent". Antimicrob. Agents Chemother. 52 (4): 1302–17. doi:10.1128/AAC.01324-07. PMC 2292519. PMID 18212100.
  4. Paeshuyse J, Kaul A, De Clercq E, et al. (April 2006). "The non-immunosuppressive cyclosporin DEBIO-025 is a potent inhibitor of hepatitis C virus replication in vitro". Hepatology. 43 (4): 761–70. doi:10.1002/hep.21102. PMID 16557546. S2CID 45825453.
  5. Coelmont L, Kaptein S, Paeshuyse J, et al. (December 2008). "Debio 025, a cyclophilin binding molecule, is highly efficient in clearing HCV replicon containing cells, alone or when combined with Specifically Targeted Antiviral Therapy for HCV (STAT-C) inhibitors". Antimicrobial Agents and Chemotherapy. 53 (3): 967–76. doi:10.1128/AAC.00939-08. PMC 2650540. PMID 19104013.
  6. "USC study reveals potential new treatment target for Alzheimer's disease | Keck School of Medicine of USC". Retrieved 2021-06-16.
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