mipomersen sodium

Chemical data

Formula

C230H305N67Na19O122P19S19

Molecular weight

7595 g/mol

IUPAC name

nonadecasodium;[(2R,3R,4S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3R,4S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3R,4S,5R)-3-[[(2R,3R,4S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3R,4S,5R)-3-[[(2S,3S,4R,5S)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2S,3S,4R,5S)-3-[[(2S,3S,4R,5S)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2S,3S,4S,5S)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-hydroxy-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(6-aminopurin-9-yl)-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(2-amino-6-oxo-1H-purin-9-yl)-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyloxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyloxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyloxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphoryl]sulfanyl-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-[(2R,3R,4S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-yl]sulfanylphosphinate

SMILES

CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)([O-])S[C@H]3C[C@@H](O[C@@H]3COP(=O)([O-])S[C@H]4C[C@@H](O[C@@H]4COP(=O)([O-])S[C@H]5C[C@@H](O[C@@H]5COP(=O)([O-])S[C@H]6C[C@@H](O[C@@H]6COP(=O)([O-])S[C@H]7C[C@@H](O[C@@H]7COP(=O)([O-])S[C@H]8C[C@@H](O[C@@H]8COP(=O)([O-])S[C@H]9C[C@@H](O[C@@H]9COP(=O)([O-])S[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])S[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=C(C(=O)NC1=O)C)COP(=O)([O-])S[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])S[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])S[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=NC2=C1N=C(NC2=O)N)CO)N1C=NC2=C(N=CN=C21)N)N1C=NC2=C1N=C(NC2=O)N)N1C=C(C(=O)NC1=O)C)N1C=C(C(=NC1=O)N)C)N1C=C(C(=O)NC1=O)C)N1C=NC2=C1N=C(NC2=O)N)N1C=C(C(=NC1=O)N)C)SP(=O)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=O)NC1=O)C)SP(=O)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=NC1=O)N)C)SP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)OCCOC)SP(=O)([O-])OC[C@H]1[C@@H]([C@@H]([C@H](O1)N1C=C(C(=NC1=O)N)C)OCCOC)SP(=O)([O-])OC[C@H]1[C@@H]([C@@H]([C@H](O1)N1C=NC2=C(N=CN=C21)N)OCCOC)SP(=O)([O-])OC[C@H]1[C@@H]([C@@H]([C@H](O1)N1C=C(C(=NC1=O)N)C)OCCOC)SP(=O)([O-])OC[C@H]1[C@@H]([C@@H]([C@H](O1)N1C=C(C(=NC1=O)N)C)OCCOC)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]

InChIKey

OSGPYAHSKOGBFY-KMHHXCEHSA-A

Polar surface area

3080 Ų

H-bond donors

26

H-bond acceptors

157

Formal charge

0

via PubChem

Drug data · ChEMBL

Max clinical phase

Approved

Molecule type

Oligonucleotide

First approval

2013

Admin. routes

parenteral

Indications

familial hypercholesterolemia, Hypercholesterolemia

via ChEMBL · EBI

Wikidata facts

Subclass of

chemical compound

Has use

medication

via Wikidata · CC0