Details of the Drug

General Information of Drug (ID: DM83EBP)

Drug Name
Alisporivir
Synonyms DEB-025; Debio-025; HCV infection therapy, Debiopharm/Novartis; HIV infection therapy, Debiopharm
Indication
Disease Entry ICD 11 Status REF
Duchenne dystrophy 8C70 Phase 3 [1]
Hepatitis C virus infection 1E51.1 Phase 3 [2]
Middle East Respiratory Syndrome (MERS) 1D64 Investigative [3]
Severe acute respiratory syndrome (SARS) 1D65 Investigative [4]
Drug Type
Protein/peptide drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 1216.6
Logarithm of the Partition Coefficient (xlogp) 7.9
Rotatable Bond Count (rotbonds) 15
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C63H113N11O12
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
Canonical SMILES
CC[C@H]1C(=O)N([C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)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
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
Cross-matching ID
PubChem CID
11513676
ChEBI ID
CHEMBL1651956
CAS Number
254435-95-5
UNII
VBP9099AA6
DrugBank ID
DB12139
TTD ID
D0CE0O
INTEDE ID
DR1885
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium signal-modulating cyclophilin ligand (CAML) TTATDGJ CAMLG_HUMAN Inhibitor [5]
HUMAN cyclophilin A (CYPA) TTS41ER PPIA_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02465203) 3-year Follow-up Study to Assess the Viral Activity in Hepatitis C Patients Who Failed Feeder DEB025/Alisporivir Study.
2 ClinicalTrials.gov (NCT01500772) Alisporivir With PEG and RBV in Protease Inhibitor (PI) Treatment Failure Patients With Chronic Hepatitis C
3 Therapeutic options for the 2019 novel coronavirus (2019-nCoV). Nat Rev Drug Discov. 2020 Mar;19(3):149-150.
4 Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
5 DEB025 (Alisporivir) inhibits hepatitis C virus replication by preventing a cyclophilin A induced cis-trans isomerisation in domain II of NS5A. PLoS One. 2010 Oct 27;5(10):e13687.
6 Profile of alisporivir and its potential in the treatment of hepatitis C. Drug Des Devel Ther. 2013;7:105-15.