Alisporivir

Category	SARS-CoV
CAS	254435-95-5
Description	Alisporivir, also known as DEB-025, a non-immunosuppressive cyclosporine A derivative, is acyclophil ininhibitor molecule with potent anti-hepatitis C virus (HCV) activity. Treatment with alisporivir alone or combined with PEGylated IFNalpha2a reduced the viral load in patients with chronic HCV infection.

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Product Information

Synonyms	cyclo[Abu-N(Me)D-Ala-Xaa-Val-N(Me)Leu-Ala-D-Ala-N(Me)Leu-N(Me)Leu-N(Me)Val-N(Me)Bmt(E)]; (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; alisporivir; DEBIO-025; MeAla(3)EtVal(4)-cyclosporin; UNIL 025; UNIL-025; UNIL025
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
Molecular Weight	1216.64
Molecular Formula	C63H113N11O12
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
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
InChIKey	OLROWHGDTNFZBH-XEMWPYQTSA-N
Boiling Point	1294.2±65.0 °C at 760 Torr
Flash Point	736.5±34.3 °C
Purity	98.15%
Density	1.011±0.06 g/cm3
Solubility	DMSO
Appearance	White to off-white (Solid)
Storage	Store in a cool and dry place (or refer to the Certificate of Analysis).
Complexity	2360
Exact Mass	1215.857056
Index Of Refraction	1.467
In Vitro	Alisporivir prevents HCV protein-mediated collapse of the respiration-driven mitochondrial membrane potential. Alisporivir prevents HCV protein-mediated mitochondrial dysfunction outside the context of Apoptosis, calcium overload, production of ROS, dysfunction. In cell culture models, low-micromolar doses of alisporivir block SARS-CoV and MERS-CoV replication. Combination treatment with Alisporivir and ICN-1229 increases the anti-MERS-CoV activity in cell culture. Alisporivir pretreatment stimulates antigen presentation by hepatoma target cells, leading to enhancement of antigen-specific CD8+ T cell activation by 40%. Alisporivir induces an increase of MHC-I and beta-2 microglobulin on the surface of several cell lines.
In Vivo	Combination treatment with Alisporivir and ICN-1229 does not protect against SARS-CoV infection in a mouse model.
Target	HCV
Vapor Pressure	0.0±0.6 mmHg at 25°C
XLogP3-AA	7.9