fomivirsen   Click here for help

GtoPdb Ligand ID: 13533

Synonyms: ISIS 2922 | ISIS-2922 | ISIS2922 | Vitravene®
Approved drug
fomivirsen is an approved drug (FDA (1998))
Compound class: Nucleic acid
Comment: Fomivirsen (ISIS2922) is a 21 mer antisense oligonucleotide with nuclease-resistant phosphorothioate linkages. It was designed to treat retinitis caused by cytomegalovirus (CMV) infection in immunocompromised patients with AIDS. Formulated as a sodium adduct for clinical use.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 177
Hydrogen bond donors 48
Rotatable bonds 122
Topological polar surface area 3107.73
Molecular weight 6682.43
XLogP -5.47
No. Lipinski's rules broken 4

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/)

SMILES / InChI / InChIKey
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Canonical SMILES CC1=CN([C@H]2C[C@@H]([C@@H](COP(=S)(O)O[C@H]3C[C@H](N4C=CC(=NC4=O)N)O[C@@H]3COP(=S)(O)O[C@H]5C[C@H](N6C=NC7=C6N=C(N)NC7=O)O[C@@H]5COP(=S)(O)O[C@H]8C[C@H](N9C=C(C)C(=O)NC9=O)O[C@@H]8COP(=S)(O)O[C@H]%10C[C@H](N%11C=C(C)C(=O)NC%11=O)O[C@@H]%10COP(=S)(O)O[C@H]%12C[C@H](N%13C=C(C)C(=O)NC%13=O)O[C@@H]%12COP(=S)(O)O[C@H]%14C[C@H](N%15C=NC%16=C%15N=C(N)NC%16=O)O[C@@H]%14COP(=S)(O)O[C@H]%17C[C@H](N%18C=CC(=NC%18=O)N)O[C@@H]%17COP(=S)(O)O[C@H]%19C[C@H](N%20C=NC%21=C%20N=C(N)NC%21=O)O[C@@H]%19CO)O2)OP(=S)(O)OC[C@@H]%22[C@H](C[C@H](N%23C=CC(=NC%23=O)N)O%22)OP(=S)(O)OC[C@@H]%24[C@H](C[C@H](N%25C=C(C)C(=O)NC%25=O)O%24)OP(=S)(O)OC[C@@H]%26[C@H](C[C@H](N%27C=C(C)C(=O)NC%27=O)O%26)OP(=S)(O)OC[C@@H]%28[C@H](C[C@H](N%29C=CC(=NC%29=O)N)O%28)OP(=S)(O)OC[C@@H]%30[C@H](C[C@H](N%31C=C(C)C(=O)NC%31=O)O%30)OP(=S)(O)OC[C@@H]%32[C@H](C[C@H](N%33C=C(C)C(=O)NC%33=O)O%32)OP(=S)(O)OC[C@@H]%34[C@H](C[C@H](N%35C=CC(=NC%35=O)N)O%34)OP(=S)(O)OC[C@@H]%36[C@H](C[C@H](N%37C=C(C)C(=O)NC%37=O)O%36)OP(=S)(O)OC[C@@H]%38[C@H](C[C@H](N%39C=C(C)C(=O)NC%39=O)O%38)OP(=S)(O)OC[C@@H]%40[C@H](C[C@H](N%41C=NC%42=C%41N=C(N)NC%42=O)O%40)OP(=S)(O)OC[C@@H]%43[C@H](C[C@H](N%44C=CC(=NC%44=O)N)O%43)OP(=S)(O)OC[C@@H]%45[C@H](C[C@H](N%46C=NC%47=C%46N=C(N)NC%47=O)O%45)O)C(=O)NC1=O
Isomeric SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=S)(O)O[C@H]3C[C@@H](O[C@@H]3COP(=S)(O)O[C@H]4C[C@@H](O[C@@H]4COP(=S)(O)O[C@H]5C[C@@H](O[C@@H]5COP(=S)(O)O[C@H]6C[C@@H](O[C@@H]6COP(=S)(O)O[C@H]7C[C@@H](O[C@@H]7COP(=S)(O)O[C@H]8C[C@@H](O[C@@H]8COP(=S)(O)O[C@H]9C[C@@H](O[C@@H]9COP(=S)(O)O[C@H]%10C[C@@H](O[C@@H]%10CO)N%11C=NC%12=C%11N=C(NC%12=O)N)N%13C=CC(=NC%13=O)N)N%14C=NC%15=C%14N=C(NC%15=O)N)N%16C=C(C(=O)NC%16=O)C)N%17C=C(C(=O)NC%17=O)C)N%18C=C(C(=O)NC%18=O)C)N%19C=NC%20=C%19N=C(NC%20=O)N)N%21C=CC(=NC%21=O)N)OP(=S)(O)OC[C@@H]%22[C@H](C[C@@H](O%22)N%23C=CC(=NC%23=O)N)OP(=S)(O)OC[C@@H]%24[C@H](C[C@@H](O%24)N%25C=C(C(=O)NC%25=O)C)OP(=S)(O)OC[C@@H]%26[C@H](C[C@@H](O%26)N%27C=C(C(=O)NC%27=O)C)OP(=S)(O)OC[C@@H]%28[C@H](C[C@@H](O%28)N%29C=CC(=NC%29=O)N)OP(=S)(O)OC[C@@H]%30[C@H](C[C@@H](O%30)N%31C=C(C(=O)NC%31=O)C)OP(=S)(O)OC[C@@H]%32[C@H](C[C@@H](O%32)N%33C=C(C(=O)NC%33=O)C)OP(=S)(O)OC[C@@H]%34[C@H](C[C@@H](O%34)N%35C=CC(=NC%35=O)N)OP(=S)(O)OC[C@@H]%36[C@H](C[C@@H](O%36)N%37C=C(C(=O)NC%37=O)C)OP(=S)(O)OC[C@@H]%38[C@H](C[C@@H](O%38)N%39C=C(C(=O)NC%39=O)C)OP(=S)(O)OC[C@@H]%40[C@H](C[C@@H](O%40)N%41C=NC%42=C%41N=C(NC%42=O)N)OP(=S)(O)OC[C@@H]%43[C@H](C[C@@H](O%43)N%44C=CC(=NC%44=O)N)OP(=S)(O)OC[C@@H]%45[C@H](C[C@@H](O%45)N%46C=NC%47=C%46N=C(NC%47=O)N)O
InChI InChI=1S/C204H263N63O114P20S20/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/h11-22,44-53,75-79,90-131,138-158,268-269H,23-43,54-74H2,1-10H3,(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)(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)(H3,211,227,232,280)(H3,212,228,233,281)(H3,213,229,234,282)(H3,214,230,235,283)(H3,215,231,236,284)/t90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111+,112+,113+,114+,115+,116+,117+,118+,119+,120+,121+,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148+,149+,150+,151+,152+,153+,154+,155+,156+,157+,158+,382?,383?,384?,385?,386?,387?,388?,389?,390?,391?,392?,393?,394?,395?,396?,397?,398?,399?,400?,401?/m0/s1
InChI Key YXPFHXCUIFJZDH-JCSPNYBJSA-N

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/)

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Summary of Clinical Use Click here for help
Having been approved as the first antisense antiviral drug by the FDA in 1988, fomivirsen was withdrawn from the market in the early-mid-2000s when the need for drugs to treat CMV in HIV patients was drastically reduced by the introduction of highly active antiretroviral therapy (HAART).
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