Fomivirsen sodium

Category	Cytomegalovirus (CMV)
CAS	160369-77-7
Description	Fomivirsen sodium, an antisense 21 mer phosphorothioate oligonucleotide, is an antiviral drug used in cytomegalovirus retinitis (CMV) studies, including AIDS. It binds to and degrades mRNAs encoding the CMV immediate early 2 protein (required for viral replication), thereby providing biological activity for CMV retinitis by inhibiting viral proliferation.

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Product Information

Synonyms	Fomivirsen sodium
IUPAC Name	1-[4-[[3-[[5-(2-amino-6-oxo-5H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-5H-purin-9-yl)-3-[[3-[[5-(2-amino-6-oxo-5H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-[[[2-[[[5-(2-amino-6-oxo-5H-purin-9-yl)-2-[[[2-[[[5-(2-amino-6-oxo-5H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-3-yl]oxy-sulfanylphosphoryl]oxymethyl]oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxo-1,3-diazinan-1-yl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
Molecular Weight	7122.04
Molecular Formula	C204H243N63Na20O114P20S20
Canonical SMILES	CC1CN(C(=O)NC1=O)C2CC(C(O2)COP(=S)(O)OC3CC(OC3COP(=S)(O)OC4CC(OC4COP(=O)(OC5CC(OC5COP(=S)(O)OC6CC(OC6CO)N7C=NC8C7=NC(=NC8=O)N)N9C=CC(=NC9=O)N)S)N1C=NC2C1=NC(=NC2=O)N)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1C=NC2C1=NC(=NC2=O)N)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1CC(C(=O)NC1=O)C)OP(=S)(O)OCC1C(CC(O1)N1C=NC2C1=NC(=NC2=O)N)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=S)(O)OCC1C(CC(O1)N1C=NC2C1=NC(=NC2=O)N)O
InChI	InChI=1S/C204H283N63O114P20S20/c1-80-44-253(195(291)237-169(80)270)145-31-98(119(349-145)62-328-387(306,407)367-97-30-144(252-22-16-137(210)226-194(252)290)348-118(97)61-327-400(319,420)380-109-42-157(266-78-219-162-167(266)230-187(214)235-182(162)283)361-131(109)74-340-398(317,418)378-107-40-154(262-53-89(10)178(279)246-204(262)300)357-127(107)70-336-395(314,415)375-104-37-151(259-50-86(7)175(276)243-201(259)297)355-125(104)68-334-396(315,416)376-105-38-152(260-51-87(8)176(277)244-202(260)298)358-128(105)71-337-401(320,421)381-110-43-158(267-79-220-163-168(267)231-188(215)236-183(163)284)359-129(110)72-338-388(307,408)368-93-26-140(248-18-12-133(206)222-190(248)286)343-113(93)56-322-383(302,403)362-91-24-155(341-111(91)54-268)264-76-217-160-165(264)228-185(212)233-180(160)281)369-389(308,409)323-58-115-94(27-141(345-115)249-19-13-134(207)223-191(249)287)364-384(303,404)329-63-120-101(34-148(350-120)256-47-83(4)172(273)240-198(256)294)372-392(311,412)332-66-123-99(32-146(353-123)254-45-81(2)170(271)238-196(254)292)370-390(309,410)324-59-116-95(28-142(346-116)250-20-14-135(208)224-192(250)288)365-385(304,405)330-64-121-102(35-149(351-121)257-48-84(5)173(274)241-199(257)295)373-393(312,413)333-67-124-100(33-147(354-124)255-46-82(3)171(272)239-197(255)293)371-391(310,411)325-60-117-96(29-143(347-117)251-21-15-136(209)225-193(251)289)366-386(305,406)331-65-122-103(36-150(352-122)258-49-85(6)174(275)242-200(258)296)374-394(313,414)335-69-126-106(39-153(356-126)261-52-88(9)177(278)245-203(261)299)377-397(316,417)339-73-130-108(41-156(360-130)265-77-218-161-166(265)229-186(213)234-181(161)282)379-399(318,419)326-57-114-92(25-139(344-114)247-17-11-132(205)221-189(247)285)363-382(301,402)321-55-112-90(269)23-138(342-112)263-75-216-159-164(263)227-184(211)232-179(159)280/h11-22,75-131,138-163,268-269H,23-74H2,1-10H3,(H,301,402)(H,302,403)(H,303,404)(H,304,405)(H,305,406)(H,306,407)(H,307,408)(H,308,409)(H,309,410)(H,310,411)(H,311,412)(H,312,413)(H,313,414)(H,314,415)(H,315,416)(H,316,417)(H,317,418)(H,318,419)(H,319,420)(H,320,421)(H2,205,221,285)(H2,206,222,286)(H2,207,223,287)(H2,208,224,288)(H2,209,225,289)(H2,210,226,290)(H2,211,232,280)(H2,212,233,281)(H2,213,234,282)(H2,214,235,283)(H2,215,236,284)(H,237,270,291)(H,238,271,292)(H,239,272,293)(H,240,273,294)(H,241,274,295)(H,242,275,296)(H,243,276,297)(H,244,277,298)(H,245,278,299)(H,246,279,300)
Purity	≥98% (HPLC)
Solubility	In Vitro: H2O : 100 mg/mL(14.04 mM;Need ultrasonic)
Appearance	White to off-white (Solid)
Storage	-20°C, stored under nitrogen * In solvent : -80°C 6 months -20°C 1 month (stored under nitrogen)
Complexity	20200
Exact Mass	7119.2341703
In Vitro	Antisense oligonucleotide acts a complementary nucleotide to the messenger RNA of the major immediate-early region proteins of human cytomegalovirus, it disrupts the replication of the virus through an antisense mechanism. Fomivirsen is 21-mer phosphorothioate ASO with CpG motif near its 5' end, with the sequence 5'-GCG TTT GCT CTT CTT CTT GCG-3', resulting in mRNA degradation by RNase H-mediated mechanism. Fomivirsen inhibits CMV replication in human retinal pigment epithelial (RPE) cells and in human fibroblast cells (MRC-5 cells) in a dose-dependent manner. The mean IC50 are 0.03 µM for RPE cells and 0.2 µM for MRC5 cells.
Target	CMV