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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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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/)
Classification Click here for help
Compound class Nucleic acid
Compound subclass Antisense oligonucleotide (ASO)
Target Major intermediate early region 2 mRNA (CMV gene UL123 that encodes protein IE2)
Approved drug? Yes (FDA (1998))
Withdrawn drug? Yes
IUPAC Name Click here for help
2'-deoxy-P-thio-guanylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-2'-deoxy-P-thio-guanylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-2'-deoxy-P-thio-guanylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-P-thio-thymidylyl-(3'->5')-2'-deoxy-P-thio-guanylyl-(3'->5')-2'-deoxy-P-thio-cytidylyl-(3'->5')-2'-deoxy-guanosine
International Nonproprietary Names Click here for help
INN number INN
7509 fomivirsen
Synonyms Click here for help
ISIS 2922 | ISIS-2922 | ISIS2922 | Vitravene®
Database Links Click here for help
CAS Registry No. 144245-52-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1201688
DrugBank Ligand DB06759
GtoPdb PubChem SID 500839943
PubChem CID 71587551
Search Google for chemical match using the InChIKey YXPFHXCUIFJZDH-JCSPNYBJSA-N
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UniChem Compound Search for chemical match using the InChIKey YXPFHXCUIFJZDH-JCSPNYBJSA-N
UniChem Connectivity Search for chemical match using the InChIKey YXPFHXCUIFJZDH-JCSPNYBJSA-N