volanesorsen   Click here for help

GtoPdb Ligand ID: 8681

Synonyms: APOC-III antisense inhibitor | ISIS 304801 | ISIS-APOCIIIRx | Waylivra®
Approved drug
volanesorsen is an approved drug (EMA (2019))
Compound class: Synthetic organic
Comment: Volanesorsen is an antisense oligonucleotide (ASO) designed to reduce levels of apolipoprotein C-III (APOC3) in patients with elevated blood triglyceride levels [2]. Reducing triglycerides via APOC3 could be beneficial in patients with inherited hypertriglyceridemia (e.g. those with familial chylomicronemia syndrome, FCS) [1]. The role of APOC3 in hypertriglyceridemia and the effects APOC3 ASO use are reviewed in [3].
HELM annotation for this RNA (from PubChem) is RNA1{[MOE](A).[sp][MOE](G).[sp][MOE]([5meC]).[sp][MOE](T).[sp][MOE](T).[sp][dR]([5meC]).[sp][dR](T).[sp][dR](T).[sp][dR](G).[sp][dR](T).[sp][dR]([5meC]).[sp][dR]([5meC]).[sp][dR](A).[sp][dR](G).[sp][dR]([5meC]).[sp][MOE](T).[sp][MOE](T).[sp][MOE](T).[sp][MOE](A).[sp][MOE](T)}$$$$.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 130
Hydrogen bond donors 44
Rotatable bonds 156
Topological polar surface area 3216.79
Molecular weight 7160.03
XLogP 6.58
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES COCCO[C@@H]1[C@H](OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cnc3c2ncnc3N)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(nc2=O)N)O)n2cnc3c2nc(N)[nH]c3=O)O)n2cnc3c2ncnc3N)O)n2cc(C)c(nc2=O)N)O)n2cc(C)c(nc2=O)N)O)n2cc(C)c(=O)[nH]c2=O)O)n2cnc3c2nc(N)[nH]c3=O)O)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(nc2=O)N)O)[C@H](O[C@H]1n1cc(C)c(=O)[nH]c1=O)COP(=S)(O[C@@H]1[C@@H](COP(=S)(O[C@@H]2[C@@H](COP(=S)(O[C@@H]3[C@@H](COP(=S)(O[C@@H]4[C@@H](CO)O[C@H]([C@@H]4OCCOC)n4cnc5c4ncnc5N)O)O[C@H]([C@@H]3OCCOC)n3cnc4c3nc(N)[nH]c4=O)O)O[C@H]([C@@H]2OCCOC)n2cc(C)c(nc2=O)N)O)O[C@H]([C@@H]1OCCOC)n1cc(C)c(=O)[nH]c1=O)O
Isomeric SMILES COCCO[C@@H]1[C@H](OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H](C[C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2OP(=S)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cnc3c2ncnc3N)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)OCCOC)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(nc2=O)N)O)n2cnc3c2nc(N)[nH]c3=O)O)n2cnc3c2ncnc3N)O)n2cc(C)c(nc2=O)N)O)n2cc(C)c(nc2=O)N)O)n2cc(C)c(=O)[nH]c2=O)O)n2cnc3c2nc(N)[nH]c3=O)O)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(=O)[nH]c2=O)O)n2cc(C)c(nc2=O)N)O)[C@H](O[C@H]1n1cc(C)c(=O)[nH]c1=O)COP(=S)(O[C@@H]1[C@@H](COP(=S)(O[C@@H]2[C@@H](COP(=S)(O[C@@H]3[C@@H](COP(=S)(O[C@@H]4[C@@H](CO)O[C@H]([C@@H]4OCCOC)n4cnc5c4ncnc5N)O)O[C@H]([C@@H]3OCCOC)n3cnc4c3nc(N)[nH]c4=O)O)O[C@H]([C@@H]2OCCOC)n2cc(C)c(nc2=O)N)O)O[C@H]([C@@H]1OCCOC)n1cc(C)c(=O)[nH]c1=O)O
InChI Key IJUQCWMZCMFFJP-GQSLRNSLSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2019))
IUPAC Name Click here for help
Ade-MeOEt(-2)Ribf-sP-Gua-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-m5Cyt-dRibf-sP-dThd-sP-dThd-sP-dGuo-sP-dThd-sP-m5Cyt-dRibf-sP-m5Cyt-dRibf-sP-dAdo-sP-dGuo-sP-m5Cyt-dRibf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Ade-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf
International Nonproprietary Names Click here for help
INN number INN
10166 volanesorsen
Synonyms Click here for help
APOC-III antisense inhibitor | ISIS 304801 | ISIS-APOCIIIRx | Waylivra®
Database Links Click here for help
CAS Registry No. 915430-78-3 (source: WHO INN record)
GtoPdb PubChem SID 252166881
PubChem CID 121494123
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