Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C62H111N11O12 |
Molecular Weight | 1202.6112 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1([C@@H](C)CC)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=O)[C@]([H])([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC1=O)C(C)C
InChI
InChIKey=RPJPZDVUUKWPGT-FOIHOXPVSA-N
InChI=1S/C62H111N11O12/c1-25-28-29-40(15)52(75)51-56(79)65-43(27-3)58(81)67(18)33-47(74)71(22)50(39(14)26-2)55(78)66-48(37(10)11)61(84)68(19)44(30-34(4)5)54(77)63-41(16)53(76)64-42(17)57(80)69(20)45(31-35(6)7)59(82)70(21)46(32-36(8)9)60(83)72(23)49(38(12)13)62(85)73(51)24/h25,28,34-46,48-52,75H,26-27,29-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b28-25+/t39-,40+,41-,42+,43-,44-,45-,46-,48-,49-,50-,51-,52+/m0/s1
Molecular Formula | C62H111N11O12 |
Molecular Weight | 1202.6112 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
9-(N-methyl-L-isoleucine)-cyclosporin A (NIM-811, SDZ 811) is a cyclosporin A analog that is completely devoid of immunosuppressive capacity but exhibits potent and selective anti-human immunodeficiency virus type 1 (HIV-1) activity. NIM-811 interferes at two stages of the viral replication cycle: (i) translocation of the preintegration complex to the nucleus and (ii) production of infectious virus particles. NIM-811 induces a concentration-dependent reduction of HCV RNA in the replicon cells with an IC50 of 0.66 uM at 48 h. NIM-811 blocks the mitochondrial permeability transition induced by calcium and inorganic phosphate. NIM-811 blocks cell killing and prevents in situ mitochondrial inner membrane permeabilization and depolarization during tumor necrosis factor-α–induced apoptosis to cultured rat hepatocytes.Novartis discontinued development of SDZ 811 as an oral therapy for hepatitis C and HIV-1 infections.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of the mitochondrial permeability transition by the nonimmunosuppressive cyclosporin derivative NIM811. | 2002 Jul |
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NIM811, a cyclophilin inhibitor, exhibits potent in vitro activity against hepatitis C virus alone or in combination with alpha interferon. | 2006 Sep |
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Cyclophilin inhibitors: an emerging class of therapeutics for the treatment of chronic hepatitis C infection. | 2012 Oct 29 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00983060
BID in various doses (between 100 mg - 600 mg bid) + SOC (PEG IFN and RBV)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16940091
NIM-811 induces a concentration-dependent reduction of HCV RNA in the replicon cells with an IC50 of 0.66 uM at 48 h. Furthermore, a greater than three-log10 viral RNA reduction is achieved after treating the cells with as little as 1 uM of NIM811 for 9 days.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:59:59 GMT 2023
by
admin
on
Fri Dec 15 16:59:59 GMT 2023
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Record UNII |
96262S4I14
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Record Status |
Validated (UNII)
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Record Version |
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-
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96262S4I14
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NIM811
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