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Chemistry

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Also known as: Mipomersen sodium salt, Chembl502097, Dtxsid20212108
Molecular Formula
C230H305N67Na19O122P19S19
Molecular Weight
7595  g/mol
InChI Key
OSGPYAHSKOGBFY-KMHHXCEHSA-A

Mipomersen
1 2D Structure

Mipomersen

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 InChI
InChI=1S/C230H324N67O122P19S19.19Na/c1-97-55-278(217(309)256-177(97)231)141-45-131(112(400-141)70-381-422(327,328)442-136-50-146(283-66-108(12)196(302)275-228(283)320)406-118(136)76-387-427(337,338)448-140-54-150(294-93-253-154-191(294)266-214(243)270-200(154)306)409-120(140)78-389-428(339,340)446-138-52-148(292-91-250-151-186(240)246-89-248-188(151)292)407-121(138)79-390-430(343,344)450-169-124(413-204(160(169)373-37-27-363-17)286-59-101(5)181(235)260-221(286)313)83-394-435(353,354)455-174-128(417-209(165(174)378-42-32-368-22)291-68-110(14)198(304)277-230(291)322)87-396-434(351,352)453-172-126(415-207(163(172)376-40-30-366-20)289-62-104(8)184(238)263-224(289)316)85-395-433(349,350)452-171-123(412-206(162(171)375-39-29-365-19)288-61-103(7)183(237)262-223(288)315)82-393-432(347,348)449-168-111(69-298)410-211(159(168)372-36-26-362-16)296-95-254-155-192(296)267-215(244)271-201(155)307)439-420(323,324)384-74-117-137(51-147(405-117)284-67-109(13)197(303)276-229(284)321)444-425(333,334)388-77-119-139(53-149(408-119)293-92-252-153-190(293)265-213(242)269-199(153)305)447-426(335,336)386-71-113-132(46-142(401-113)279-56-98(2)178(232)257-218(279)310)440-421(325,326)383-73-115-135(49-145(403-115)282-65-107(11)195(301)274-227(282)319)443-424(331,332)385-75-116-134(48-144(404-116)281-64-106(10)194(300)273-226(281)318)441-423(329,330)382-72-114-133(47-143(402-114)280-57-99(3)179(233)258-219(280)311)445-429(341,342)392-81-129-176(167(380-44-34-370-24)212(419-129)297-96-255-156-193(297)268-216(245)272-202(156)308)457-438(359,360)398-86-127-173(164(377-41-31-367-21)208(416-127)290-63-105(9)185(239)264-225(290)317)454-436(355,356)399-88-130-175(166(379-43-33-369-23)210(418-130)295-94-251-152-187(241)247-90-249-189(152)295)456-437(357,358)397-84-125-170(161(374-38-28-364-18)205(414-125)287-60-102(6)182(236)261-222(287)314)451-431(345,346)391-80-122-157(299)158(371-35-25-361-15)203(411-122)285-58-100(4)180(234)259-220(285)312;;;;;;;;;;;;;;;;;;;/h55-68,89-96,111-150,157-176,203-212,298-299H,25-54,69-88H2,1-24H3,(H,323,324)(H,325,326)(H,327,328)(H,329,330)(H,331,332)(H,333,334)(H,335,336)(H,337,338)(H,339,340)(H,341,342)(H,343,344)(H,345,346)(H,347,348)(H,349,350)(H,351,352)(H,353,354)(H,355,356)(H,357,358)(H,359,360)(H2,231,256,309)(H2,232,257,310)(H2,233,258,311)(H2,234,259,312)(H2,235,260,313)(H2,236,261,314)(H2,237,262,315)(H2,238,263,316)(H2,239,264,317)(H2,240,246,248)(H2,241,247,249)(H,273,300,318)(H,274,301,319)(H,275,302,320)(H,276,303,321)(H,277,304,322)(H3,242,265,269,305)(H3,243,266,270,306)(H3,244,267,271,307)(H3,245,268,272,308);;;;;;;;;;;;;;;;;;;/q;19*+1/p-19/t111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122+,123-,124-,125+,126-,127+,128-,129-,130+,131+,132+,133+,134+,135+,136+,137+,138+,139+,140+,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,157+,158+,159-,160-,161+,162-,163-,164+,165-,166+,167-,168-,169-,170+,171-,172-,173+,174-,175+,176-,203+,204-,205+,206-,207-,208+,209-,210+,211-,212-;;;;;;;;;;;;;;;;;;;/m1.................../s1
2.1.3 InChI Key
OSGPYAHSKOGBFY-KMHHXCEHSA-A
2.1.4 Canonical SMILES
CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)([O-])SC3CC(OC3COP(=O)([O-])SC4CC(OC4COP(=O)([O-])SC5CC(OC5COP(=O)([O-])SC6CC(OC6COP(=O)([O-])SC7CC(OC7COP(=O)([O-])SC8CC(OC8COP(=O)([O-])SC9CC(OC9COP(=O)([O-])SC1C(OC(C1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])SC1C(OC(C1OCCOC)N1C=C(C(=O)NC1=O)C)COP(=O)([O-])SC1C(OC(C1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])SC1C(OC(C1OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)([O-])SC1C(OC(C1OCCOC)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-])OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)SP(=O)([O-])OCC1C(CC(O1)N1C=C(C(=NC1=O)N)C)SP(=O)([O-])OCC1C(C(C(O1)N1C=NC2=C1N=C(NC2=O)N)OCCOC)SP(=O)([O-])OCC1C(C(C(O1)N1C=C(C(=NC1=O)N)C)OCCOC)SP(=O)([O-])OCC1C(C(C(O1)N1C=NC2=C(N=CN=C21)N)OCCOC)SP(=O)([O-])OCC1C(C(C(O1)N1C=C(C(=NC1=O)N)C)OCCOC)SP(=O)([O-])OCC1C(C(C(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+]
2.1.5 Isomeric 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+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Isis 301012

2. Isis-301012

3. Isis301012

4. Kynamro

5. Mipomersen

2.2.2 Depositor-Supplied Synonyms

1. Mipomersen Sodium Salt

2. Chembl502097

3. Dtxsid20212108

2.3 Create Date
2010-01-26
3 Chemical and Physical Properties
Molecular Weight 7595 g/mol
Molecular Formula C230H305N67Na19O122P19S19
Hydrogen Bond Donor Count26
Hydrogen Bond Acceptor Count157
Rotatable Bond Count156
Exact Mass7591.7553328 g/mol
Monoisotopic Mass7589.7486232 g/mol
Topological Polar Surface Area3080 Ų
Heavy Atom Count476
Formal Charge0
Complexity20500
Isotope Atom Count0
Defined Atom Stereocenter Count70
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count20
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameKynamro
PubMed HealthMipomersen (Injection)
Drug ClassesAntihyperlipidemic
Drug LabelKYNAMRO (mipomersen sodium) Injection is a sterile, preservative-free, clear, colorless to slightly yellow, aqueous solution for subcutaneous injection. KYNAMRO is supplied in single-use, 2 mL, clear glass vials or single-use, 1 mL, clear glass pre...
Active IngredientMipomersen sodium
Dosage FormSolution
RouteSubcutaneous
Strength200mg/ml (200mg/ml)
Market StatusPrescription
CompanyGenzyme

2 of 2  
Drug NameKynamro
PubMed HealthMipomersen (Injection)
Drug ClassesAntihyperlipidemic
Drug LabelKYNAMRO (mipomersen sodium) Injection is a sterile, preservative-free, clear, colorless to slightly yellow, aqueous solution for subcutaneous injection. KYNAMRO is supplied in single-use, 2 mL, clear glass vials or single-use, 1 mL, clear glass pre...
Active IngredientMipomersen sodium
Dosage FormSolution
RouteSubcutaneous
Strength200mg/ml (200mg/ml)
Market StatusPrescription
CompanyGenzyme

4.2 Drug Indication

treatment of cholesterol and hypercholesterolaemia,


Treatment of heterozygous and homozygous familial hypercholesterolaemia


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anticholesteremic Agents

Substances used to lower plasma cholesterol levels. (See all compounds classified as Anticholesteremic Agents.)


Oligodeoxyribonucleotides, Antisense

Short fragments of DNA that are used to alter the function of target RNAs or DNAs to which they hybridize. (See all compounds classified as Oligodeoxyribonucleotides, Antisense.)


5.2 ATC Code

C10AX11


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