GS-441524
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GS-441524
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CAS No:
1191237-69-0
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Formula:
C12H13N5O4
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Chemical Name:
GS-441524
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Synonyms:
(2R,3R,4S,5R)-2-(4-Aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile;GS-441524;GS441524;(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile;GS-441524 solution;EVO984;EVO 984;EVO-984;GS 441524
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CAS No:
Description
GS-441524 is a nucleoside analogue that terminates the RNA chain of viral RNA-dependent RNA polymerase. GS-441524 was developed by Gilead Sciences, Inc as part of their research into human RNA virus disease such as Ebola. GS-441524 is a small molecule that exhibits potent antiviral activity against a number of RNA viruses, including the zoonotic severe acute respiratory syndrome (SARS) coronavirus ( Cho et al., 2012).
GS-441524 is a C-nucleoside analog that is (2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile substituted by a 4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl group at position 2. It is the active metabolite of remdesivir and exhibits a broad range of inhibitory activity against various RNA viruses including HCV, parainfluenza and SARS-CoV. It has a role as a drug metabolite, an antiviral agent and an anticoronaviral agent. It is a pyrrolotriazine, a nitrile, a C-nucleoside and an aromatic amine.|GS-441524 is an adenosine nucleotide analog antiviral, similar to [remdesivir]. This molecule was patented in 2009. In vitro studies of GS-441524 have determined it has a higher EC50 than remdesivir against a number of viruses, meaning GS-441524 is less potent. GS-441524 continues to be studied in the treatment of Feline Infectious Peritonitis Virus, a coronavirus that only infects cats.
Safety Information
|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P308+P313, P309+P311, P310, P312, P321, P332+P313, P333+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)
GS-441524 has been found to transport poorly into cells compared to remdesivir.
GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate.
GS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate, which is incorporated into the genome of virions, terminating its replication.
(2R,3R,4S,5R)-2-(4-Aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furancarbonitrile
GS-441524 Use and Manufacturing
GS-441524 requires intracellular phosphorylation via cellular kinases to a nucleoside monophosphate and subsequently to the active triphosphate metabolite (NTP) ( Cho et al., 2012 ; Sheahan et al., 2017; Warren et al., 2016). The active NTP analog functions as a competitor of the natural nucleoside triphosphates in viral RNA synthesis. The active form of GS-441524 has been shown to inhibit RSV RNA-dependent RNA polymerase mediated transcription by incorporating into the nascent viral transcript and causing premature termination ( Sheahan et al., 2017 ). We hypothesized that GS-441524 would be activated in feline cells, attenuate FIPV replication, have low cytotoxicity in feline cells in vitro and effectively treat cats with experimentally induced FIP.
Computed Properties
Molecular Weight:291.26
XLogP3:-1.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:291.09675391
Monoisotopic Mass:291.09675391
Topological Polar Surface Area:150
Heavy Atom Count:21
Complexity:456
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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