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Details

Stereochemistry ABSOLUTE
Molecular Formula C63H113N11O12
Molecular Weight 1216.6378
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALISPORIVIR

SMILES

CC[C@@H]1NC(=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](NC(=O)[C@H](C(C)C)N(CC)C(=O)[C@@H](C)N(C)C1=O)C(C)C

InChI

InChIKey=OLROWHGDTNFZBH-XEMWPYQTSA-N
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

HIDE SMILES / InChI

Molecular Formula C63H113N11O12
Molecular Weight 1216.6378
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 1
Optical Activity UNSPECIFIED

Alisporivir (DEBIO-025) is a first-in-class synthetic cyclophilin inhibitor, in development with Debiopharm as an oral treatment for hepatitis C virus (HCV) infections. Alisporivir has the potential to be used for the treatment of additional diseases such as other viral infections, certain muscular dystrophies, and myocardial infarction. Alisporivir has potent anti-hepatitis C virus (HCV) activity both in vitro and in vivo. It is currently being evaluated in phase II clinical trials.

Approval Year

PubMed

PubMed

TitleDatePubMed
The non-immunosuppressive cyclosporin DEBIO-025 is a potent inhibitor of hepatitis C virus replication in vitro.
2006 Apr
DEB025 (Alisporivir) inhibits hepatitis C virus replication by preventing a cyclophilin A induced cis-trans isomerisation in domain II of NS5A.
2010 Oct 27

Sample Use Guides

Hepatitis C: Alisporivir (ALV) 600 mg twice daily (BID) with Peginterferon alfa-2a (PEG) and ribavirin (RBV) for 1 week, followed by an additional 23 or 47 weeks according to response-guided treatment duration (RGT)
Route of Administration: Oral
The 50% effective concentration for inhibition of HCV subgenomic replicon replication in Huh 5-2 cells (luciferase assay) by DEBIO-025 was 0.27 +/- 0.03 ug/mL and for CsA 2.8 +/- 0.4 ug/mL. The concentration that reduced the growth of exponentially proliferating Huh 5-2 cells by 50% was greater than 27 ug/mL for DEBIO-025 and 12 +/- 6 ug/mL for CsA, resulting in a selectivity index of approximately 900 for DEBIO-025 and 40 for CsA. DEBIO-025, at concentrations of 0.5 and 1 ug/mL, was able to clear cells from their HCV replicon within three to four passages, whereas treatment with CsA at the same concentrations for seven consecutive passages did not result in clearance of the HCV replicon.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:57:28 GMT 2023
Edited
by admin
on Sat Dec 16 17:57:28 GMT 2023
Record UNII
VBP9099AA6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALISPORIVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
DEBIO-025
Code English
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)
Common Name English
ALISPORIVIR [USAN]
Common Name English
alisporivir [INN]
Common Name English
Alisporivir [WHO-DD]
Common Name English
UNIL025
Code English
UNIL-025
Code English
(D-MEALA)3-(ETVAL)4-CSA
Common Name English
DEBIO025
Code English
DEB-025
Code English
DEB025
Code English
Code System Code Type Description
USAN
YY-92
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
SMS_ID
100000126040
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID401027752
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
INN
8900
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
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WIKIPEDIA
ALISPORIVIR
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
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NCI_THESAURUS
C169774
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
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DRUG BANK
DB12139
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
EVMPD
SUB33108
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
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PUBCHEM
11513676
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
FDA UNII
VBP9099AA6
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL1651956
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
CAS
254435-95-5
Created by admin on Sat Dec 16 17:57:29 GMT 2023 , Edited by admin on Sat Dec 16 17:57:29 GMT 2023
PRIMARY
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