mipomersen   Click here for help

GtoPdb Ligand ID: 7364

Synonyms: ISIS 301012 parent acid | isis-301012 | Kynamro®
Approved drug
mipomersen is an approved drug (FDA (2013))
Compound class: Nucleic acid
Comment: Mipomersen is a synthetic phosphorothioate antisense oligonucleotide (ASO) that is designed to block hepatic production of apolipoprotein B-100 as a mechanism to reduce levels of very low-density lipoprotein (vLDL) and LDL. It is a second generation 2′-O-methoxyethyl containing ASO that is formulated as a sodium adduct for clinical administration.
2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES COCCOC1C(SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(CC2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2SP(=O)(OCC2OC(C(C2O)OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2ncnc3N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cnc3c2ncnc3N)[O-])C(OC1n1cc(C)c(nc1=O)N)COP(=O)(SC1C(COP(=O)(SC2C(COP(=O)(SC3C(COP(=O)(SC4C(CO)OC(C4OCCOC)n4cnc5c4nc(N)[nH]c5=O)[O-])OC(C3OCCOC)n3cc(C)c(nc3=O)N)[O-])OC(C2OCCOC)n2cc(C)c(nc2=O)N)[O-])OC(C1OCCOC)n1cc(C)c(=O)[nH]c1=O)[O-]
Isomeric SMILES COCCO[C@@H]1[C@H](SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H](C[C@@H]2SP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2SP(=O)(OC[C@@H]2O[C@@H]([C@H]([C@H]2O)OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2ncnc3N)[O-])OCCOC)n2cc(C)c(nc2=O)N)[O-])OCCOC)n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cc(C)c(nc2=O)N)[O-])n2cc(C)c(=O)[nH]c2=O)[O-])n2cnc3c2nc(N)[nH]c3=O)[O-])n2cnc3c2ncnc3N)[O-])[C@H](O[C@H]1n1cc(C)c(nc1=O)N)COP(=O)(S[C@@H]1[C@@H](COP(=O)(S[C@@H]2[C@@H](COP(=O)(S[C@@H]3[C@@H](COP(=O)(S[C@@H]4[C@@H](CO)O[C@H]([C@@H]4OCCOC)n4cnc5c4nc(N)[nH]c5=O)[O-])O[C@H]([C@@H]3OCCOC)n3cc(C)c(nc3=O)N)[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 TZRFSLHOCZEXCC-HIVFKXHNSA-A

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Nucleic acid
Compound subclass Antisense oligonucleotide (ASO)
Target apolipoprotein B (APOB) 100 mRNA
Approved drug? Yes (FDA (2013))
Approved drug? Yes. FDA (2013)
International Nonproprietary Names Click here for help
INN number INN
8946 mipomersen
Synonyms Click here for help
ISIS 301012 parent acid | isis-301012 | Kynamro®
Database Links Click here for help
CAS Registry No. 1000120-98-8 (source: Scifinder)
ChEMBL Ligand CHEMBL2219536
DrugBank Ligand DB05528
GtoPdb PubChem SID 178103936
PubChem CID 71301230
Search Google for chemical match using the InChIKey TZRFSLHOCZEXCC-HIVFKXHNSA-A
Search Google for chemicals with the same backbone TZRFSLHOCZEXCC
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UniChem Compound Search for chemical match using the InChIKey TZRFSLHOCZEXCC-HIVFKXHNSA-A
UniChem Connectivity Search for chemical match using the InChIKey TZRFSLHOCZEXCC-HIVFKXHNSA-A
Wikipedia Mipomersen