Alisporivir

Alisporivir
Clinical data
ATC code	None;
Identifiers
CAS Number	254435-95-5 ;
PubChem CID	11513676;
ChemSpider	9688467 ;
KEGG	D10087 ;
ChEMBL	CHEMBL1651956 ;
NIAID ChemDB	268533;
ECHA InfoCard	100.234.903
Chemical and physical data
Formula	C63H113N11O12
Molar mass	1216.64 g/mol
3D model (JSmol)	Interactive image;
	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 ; Key:OLROWHGDTNFZBH-XEMWPYQTSA-N ;
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Alisporivir (INN), or Debio 025, DEB025, (or UNIL-025) is a cyclophilin inhibitor.^[1] Its structure is reminiscent of, and synthesized from ciclosporin.

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]

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 2 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". Br. J. Pharmacol. 155 (4): 574–84. doi:10.1038/bjp.2008.285. PMC 2579666. PMID 18641676.
↑ Gallay, PA; Lin K. (15 February 2013). "Profile of alisporivir and its potential in the treatment of hepatitis C." Drug Des Devel Ther. 7: 105–115. doi:10.2147/DDDT.S30946. PMC 3578503. PMID 23440335.
↑ 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.
↑ 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.
↑ 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". Antimicrob. Agents Chemother. 53 (3): 967–76. doi:10.1128/AAC.00939-08. PMC 2650540. PMID 19104013.

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[pmid18641676-1] 1 2 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". Br. J. Pharmacol. 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 Des Devel Ther. 7: 105–115. doi:10.2147/DDDT.S30946. PMC 3578503. PMID 23440335.

[pmid18212100-3] 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.

[pmid16557546-4] 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.

[pmid19104013-5] 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". Antimicrob. Agents Chemother. 53 (3): 967–76. doi:10.1128/AAC.00939-08. PMC 2650540. PMID 19104013.

Clinical data

ATC code	None
Identifiers
CAS Number	254435-95-5^Y
PubChem CID	11513676
ChemSpider	9688467^Y
KEGG	D10087^N
ChEMBL	CHEMBL1651956^N
NIAID ChemDB	268533
ECHA InfoCard	100.234.903
Chemical and physical data
Formula	C₆₃H₁₁₃N₁₁O₁₂
Molar mass	1216.64 g/mol
3D model (JSmol)	Interactive image
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
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