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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

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 Formula	C₂₃₀H₃₀₅N₆₇Na₁₉O₁₂₂P₁₉S₁₉
Molecular Weight	7595 g/mol
Hydrogen Bond Donor Count	26
Hydrogen Bond Acceptor Count	157
Rotatable Bond Count	156
Exact Mass	7591.7553328 g/mol
Monoisotopic Mass	7589.7486232 g/mol
Topological Polar Surface Area	3080 Å²
Heavy Atom Count	476
Formal Charge	0
Complexity	20500
Isotope Atom Count	0
Defined Atom Stereocenter Count	70
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	20

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Kynamro
PubMed Health	Mipomersen (Injection)
Drug Classes	Antihyperlipidemic
Drug Label	KYNAMRO (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 Ingredient	Mipomersen sodium
Dosage Form	Solution
Route	Subcutaneous
Strength	200mg/ml (200mg/ml)
Market Status	Prescription
Company	Genzyme

2 of 2
Drug Name	Kynamro
PubMed Health	Mipomersen (Injection)
Drug Classes	Antihyperlipidemic
Drug Label	KYNAMRO (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 Ingredient	Mipomersen sodium
Dosage Form	Solution
Route	Subcutaneous
Strength	200mg/ml (200mg/ml)
Market Status	Prescription
Company	Genzyme

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

FDF Dossiers