ChemicalBook > CAS DataBase List > GS-441524

GS-441524

Product Name: GS-441524
CAS No.: 1191237-69-0
Chemical Name: GS-441524
Synonyms: GS-441;(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile;(2R,3R,4S,5R)-2-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile;(2R,3R,4S,5R)-2-(4-AMINOPYRROLO[2,1-F][1,2,4]TRIAZIN-7-YL)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLANE-2-;NUC;Remdesivir intermediates;GS-4;EVO984;GS441525;S-441524
CBNumber: CB04808604
Molecular Formula: C12H13N5O4
Formula Weight: 291.26
MOL File: 1191237-69-0.mol

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GS-441524 Property

Melting point:: > 233° C (dec.)
Density: 1.84±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (>25 mg/ml)
pka: 12.13±0.70(Predicted)
form: solid
color: Off-white
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChI: InChI=1/C12H13N5O4/c13-4-12(10(20)9(19)7(3-18)21-12)8-2-1-6-11(14)15-5-16-17(6)8/h1-2,5,7,9-10,18-20H,3H2,(H2,14,15,16)/t7-,9-,10-,12+/s3
InChIKey: BRDWIEOJOWJCLU-QHRJDZJMNA-N
SMILES: C([C@]1(C2=CC=C3C(=NC=NN23)N)[C@@H]([C@H](O)[C@@H](CO)O1)O)#N |&1:1,12,13,15,r|
CAS DataBase Reference: 1191237-69-0

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 30469
Product name: GS-441524
Packaging: 1mg
Price: $26
Updated: 2024/03/01

Cayman Chemical

Product number: 30469
Product name: GS-441524
Packaging: 25mg
Price: $160
Updated: 2024/03/01

Cayman Chemical

Product number: 30469
Product name: GS-441524
Packaging: 5mg
Price: $45
Updated: 2024/03/01

Cayman Chemical

Product number: 30469
Product name: GS-441524
Packaging: 10mg
Price: $77
Updated: 2024/03/01

Tocris

Product number: 7227
Product name: GS441524
Purity: ≥98%(HPLC)
Packaging: 50
Price: $545
Updated: 2021/12/16

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GS-441524 Chemical Properties,Usage,Production

Description

GS-441524 is the active prodrug of the broad-spectrum antiviral Remdesivir. GS-441524 is an adenosine nucleotide analog in viral RNA production. It is a nucleotide analog inhibitor of RNA-dependent RNA polymerases (RdRps). The compound interferes with the action of viral RNA polymerase and evades proofreading by viral exoribonuclease (ExoN), causing a decrease in viral RNA production (RNA synthesis arrest), either by terminating RNA chains or causing mutations. It inhibits MERS-CoV or SARS-CoV-infected HAE cultures (EC50=74nM and 69nM) and murine hepatitis virus (MHV) (EC50=30nM). In vivo, remdesivir (25 and 50 mg/kg) reduces lung viral titers and prevents weight loss in a mouse model of SARS-CoV infection. Remdesivir is used as a treatment for Ebola virus disease and Marburg virus infections and other single-stranded RNA viruses such as respiratory syncytial virus, Junin virus, Lassa fever virus, Nipah virus, Hendra virus and the coronaviruses (including MERS and SARS viruses). Remdesivir is effective in the control of 2019-nCoV (COVID-19) infection in vitro. It now also has been studied as a potential treatment for SARS-CoV-2 infections.

Uses

GS-441524 is originally identified as an active metabolite of Remdesivir that is an antiviral drug, a novel nucleotide analog prodrug.

Definition

ChEBI: 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.

Acquired resistance

Resistance to GS-441524 can exist at the time of diagnosis, but this is uncommon. Rather, it tends to occur during treatment and is often partial at first and necessitates a higher dosage to accommodate for it. It can become total in some cats. Resistance is the biggest problem in cats with neurological disease, especially those that present with neurological disease or develop brain infections during treatment or during a relapse after what appears to have been a successful treatment. Many cats with partial drug resistance can be treated for their disease signs but will relapse as soon as the treatment is stopped. There have been cats "treated" for FIP for over a year with no cure, but ultimately resistance becomes worse or the owner runs out of money.

Biological Activity

GS 441524 is a viral RNA-dependent RNA polymerase (RdRp) inhibitor and broad spectrum antiviral nucleotide; active metabolite of Remdesivir. Competes with natural nucleoside triphosphates, blocking viral RNA synthesis. Exhibits antiviral activity against viruses from Coronaviridae family including SARS-CoV-2 in vitro, and SARS-CoV and feline infectious peritonitis virus (FIPV) in vitro and in vivo. Inhibits SARS-CoV and MERS-CoV- infected HAE cultures (EC50 values are 0.18 and 0.86 μM, respectively) and inhibits murine hepatitis virus (MHV) (EC50 = 1.1 μM).

Pharmacokinetics

GS-441524 is a nucleoside analogue that terminates the RNA chain of viral RNA-dependent RNA polymerase. It 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-5734 is a phosphoramidate prodrug of GS-441524 that has been previously shown to inhibit the replication of several taxonomically diverse RNA viruses such as Middle East respiratory syndrome virus, Ebola virus, Lassa fever virus, Junin virus and respiratory syncytial virus, while having low cytotoxicity in a wide-range of cell lines ( Sheahan et al., 2017 ). GS-5734 has also been shown to protect rhesus monkeys from experimental Ebola virus infection ( Warren et al., 2016 ).

Side effects

GS-441524 treatment is amazingly free of systemic side effects. It can cause minor kidney damage in some cats, but this does not progress to overt renal disease. Systemic drug reactions of the vasculitis type have been seen in a few cats and can be confused with injection site reactions. However, these drug reactions are at non-injection sites and are often self-limiting or respond well to a short-term low dose of steroids. The major side-effect of GS treatment is pain at the injection sites, which varies from cat to cat and according to the injection prowess of the person doing the treatment (usually the owner). Injection site sores are a problem with some owners and usually occur when the injection site is not moved around the body (stay away from between the shoulders) and not given into the muscle and nerve layers below the subcutis. I recommend selecting sites starting an inch behind the shoulder blades, down the back to 1-2 inches before the tailhead, and one third to one-half of the way down the chest and abdomen. Many people use gabapentin before injections to help ease the pain. Injection site sores are cleared of surrounding hair and gently cleaned 4 or more times a day with sterile cotton balls soaked in 1:5 dilution of household hydrogen peroxide. They usually do not require any more sophisticated treatment and heal within 2 weeks or so.

storage

Store at -20°C

Preparation and handling

GS-441524 is supplied as a solid. A stock solution may be made by dissolving the GS-441524 in the solvent of choice, which should be purged with an inert gas. It is soluble in organic solvents such as DMSO and dimethyl formamide. The solubility of GS-441524 in these solvents is approximately 10 mg/ml.
GS-441524 is sparingly soluble in aqueous buffers. For maximum solubility in aqueous buffers, It should first be dissolved in DMSO and then diluted with the aqueous buffer of choice. It has a solubility of approximately 0.16 mg/ml in a 1:5 solution of DMSO:PBS (pH 7.2) using this method. We do not recommend storing the aqueous solution for more than one day.

Mode of action

GS-441524 undergoes intracellular phosphorylation by cellular kinases, first to a nucleoside monophosphate and then to an active triphosphate metabolite (NTP)( Cho et al., 2012; Sheahan et al., 2017; Warren et al., 2016). This active NTP analog competes with natural nucleoside triphosphates to inhibit viral RNA synthesis. Specifically, the active form of GS-441524 inhibits RNA-dependent RNA polymerase-mediated transcription by terminating nascent viral transcript prematurely. We hypothesized that, once activated in feline cells, GS-441524 would attenuate FIPV replication with minimal cytotoxicity in vitro and effectively treat cats with experimentally induced FIP.

References

1) Remdesivir and GS-441524 Retain Antiviral Activity against Delta, Omicron, and Other Emergent SARS-CoV-2 Variants DOI:10.1128/aac.00222-22
2) Therapeutic efficacy of the small molecule GS-5734 against Ebola virus in rhesus monkeys: T.K. Warren, et al.; Nature 531, 381 (2016) DOI:10.1038/nature17180
3) Late Ebola virus relapse causing meningoencephalitis: a case report: M. Jacobs, et al.; Lancet 388, 498 (2016) DOI:10.1016/S0140-6736(16)30386-5
4) Broad-spectrum antiviral GS-5734 inhibits both epidemic and zoonotic coronaviruses: T.P. Sheahan, et al.; Sci. Transl. Med. 9, eaal3653 (2017) DOI:10.1126/scitranslmed.aal3653
5) Discovery and Synthesis of a Phosphoramidate Prodrug of a Pyrrolo[2,1-f][triazin-4- amino] Adenine C-Nucleoside (GS-5734) for the Treatment of Ebola and Emerging Viruses; D. Siegel, et al.; J. Med. Chem. 60, 1648 (2017) DOI:10.1021/acs.jmedchem.6b01594
6) Coronavirus Susceptibility to the Antiviral Remdesivir (GS-5734) Is Mediated by the Viral Polymerase and the Proofreading Exoribonuclease: M.L. Agostini, et al.; mBio 9, e00221 (2018) DOI: 10.1128/mBio.00221-18
7) Mechanism of Inhibition of Ebola Virus RNA-Dependent RNA Polymerase by Remdesivir: E.P. Tchesnokov, et al.; Viruses 11, E326 (2019) DOI:10.3390/v11040326
8) Remdesivir (GS-5734) protects African green monkeys from Nipah virus challenge: M.K. Lo, et al.; Sci. Transl. Med. 11, eaau9242 (2019) DOI:10.1126/scitranslmed.aau9242
9) Broad spectrum antiviral remdesivir inhibits human endemic and zoonotic deltacoronaviruses with a highly divergent RNA dependent RNA polymerase: A.J. Brown, et al.; Antiviral Res. 169, 104541 (2019) DOI:10.1016/j.antiviral.2019.104541
10) Prophylactic and therapeutic remdesivir (GS-5734) treatment in the rhesus macaque model of MERS-CoV infection: R. de Wit, et al.; PNAS (Epub ahead of print) (2020) DOI:10.1073/pnas.1922083117
11) Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro: M. Wang, et al.; Cell Res. 30, 269 (2020) DOI:10.1038/s41422-020-0282-0
12) The nucleoside analog GS-441524 strongly inhibits feline infectious peritonitis (FIP) virus in tissue culture and experimental cat infection studies DOI: 10.1016/j.vetmic.2018.04.026

GS-441524 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from GS-441524 manufacturers

Wuhan Haorong Biotechnology Co.,Ltd

Product: GS-441524 1191237-69-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500
Release date: 2025-11-27

Shaanxi Dideu New Materials Co. Ltd

Product: GS-441524 1191237-69-0
Price: US $0.00-0.00/KG
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Release date: 2025-11-26

Jinan Hong Kongda Chemical Co.,LTD

Product: GS-441524 1191237-69-0
Price: US $4000.00/kg
Min. Order: 1kg
Purity: 99.9%
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Release date: 2025-08-20

1191237-69-0, GS-441524Related Search:

Imiquimod Elafibranor(GFT505) N-Eicosanoyl Serotonin NOTUMib-1 4-Nitrophenol 2,3,5-Tri-O-benzyl-D-ribonolactone (S)-2-ethylbutyl 2-aminopropanoate hydrochloride 7-Iodopyrrolo[2,1-f][1,2,4]triazin-4-amine Phenyl dichlorophosphate (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol

(2R,3R,4S,5R)-2-(4-AMINOPYRROLO[2,1-F][1,2,4]TRIAZIN-7-YL)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLANE-2-

(2R,3R,4S,5R)-2-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile

2-C-(4-AMINOPYRROLO[2,1-F][1,2,4]TRIAZIN-7-YL)-2,5-ANHYDRO-3,4-O-(1-METHYLETHYLIDENE)-D-ALTRONONITRI

(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

D-Altrononitrile, 2-C-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-

2-C-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-D-Altrononitrile

GS441525

(2R,3R,4S,5R)-2-(4-AMINOPYRROLO[2,1-F][1,2,4]TRIAZIN-7-YL)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)TETRAHYDRO

GS-441524(EVO984)

GS-441

NUC

Remdesivir Impurity 6

S-441524

(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)

GS-4

Remdesivir impurity3

(2R,3R,4S,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

GS 441524(acid)

GS-441524(GS441524)

2-ethylbutyl ((R)-(4-nitrophenoxy)(phenoxy)phosphoryl)-L-alaninate

Remdesivir Triol Nitrile Impurity

Remdesivir intermediates

Radcivir intermediate n-3)

GS441524 Remdesivir metabolite

GS-441524

Remdesivir-011

EVO984

Remdesivir Related Compound 6 (GS-441524)

Remdesivir Related Compound 6

(2R,3R,4S,5R)-2-(4-aminopyrrolo[1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile

(2R,3R,4S,5R)-2-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-3

FIPV Nutrient Solution for R&D use only Liquid GS441524

(2 r, 3 r, 4 s, 5 r) - 2 - (4 - amino pyrrole and 4-trichlorobenzene [1] [2, 1 - F] triazine - 7 - base) - 2 hydroxy - 5-3, 4 - (hydroxymethyl) tetrahydrofuran - 2 - methyl acrylic

remdesivir power

GS-441524 USP/EP/BP

Remdesivir metabolite(GS-441524)

Remdesivir Intermediate（GS-441524）

Supply High Quality GS-441524

Remdesivir main compound 69-0

Remdesivi Intetmediate GS

(2R,3R,4S,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3...

[13C5]-GS 441524

Remdesivir Impurity 22/GS-441524/Remdesivir Triol Nitrile Impurity

(2R,3R,4R,5R)-2-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane-2-carbonitrile

GS-441524/2-C-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-D-altrononitrile

FIP FIPV

(2R，3R，4S，5R)-2-(4-aminopyrrolo[1，2-f][1，2，4]triazin-7-yl)-3，4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile(GS-441524)

200-001-8

13C5]-Remdesivir active metabolite

Redesivir Impurity 2

GS-441524, 10 mM in DMSO

GS-441524 2-C-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,5-anhydro-D-ribofuranosyl cyanide

GS-441524 ，S6814

1191237-69-0

1354832-36-1

191237-69-0

API