Gs-441524
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Grundinformationen
- CAS
1191237-69-0- Standard-SMILES
N#C[C@@]1(c2ccc3c(N)ncnn23)O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
BRDWIEOJOWJCLU-LTGWCKQJSA-N- Summenformel
- C12H13N5O4
- Durchschnittliche Molmasse
- 291,26 g/mol
- Monoisotopische Masse
- 291,09675391
Überblick
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 an anticoronaviral agent, an antiviral agent and a drug metabolite. It is a nitrile, an aromatic amine, a C-nucleoside and a pyrrolotriazine.
Namen und Bezeichner
- Bevorzugter Name
- Gs-441524
- IUPAC
- (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile
- Englischer Name
- GS 441524
- Summenformel
- C12H13N5O4
- Molmasse
- 291.26
Namen und Synonyme
1191237-69-0GS-441524GS441524GS 441524EVO984EVO-9841BQK176DT62-C-(4-Aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-D-altrononitrile13C3 GS-441524CHEBI:1472812-C-(4-AMINOPYRROLO[2,1-F][1,2,4]TRIAZIN-7-YL)-2,5-ANHYDRO-D-ALTRONONITRILED-Altrononitrile, 2-C-(4-aminopyrrolo(2,1-f)(1,2,4)triazin-7-yl)-2,5-anhydro-
Weitere Namen anzeigen
GS-441(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-NUCRemdesivir intermediates200-001-8(2R,3R,4S,5R)-2-(4-aminopyrrolo[1,2-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrileGS-4
GS-82884013C3-GS-441524RefChem:144485GS-441285(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrileRemdesivir Impurity 5reacted formMFCD32666994
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -1,4
- Polarare Oberfläche (TPSA)
- 150 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 456
Physikochemische Eigenschaften
- Schmelzpunkt
- 233 ° · > 233° C (dec.)
- Dichte
- 1.84 · 1.84±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Soluble in DMSO (>25 mg/ml)
- pka
- 12.13 · 12.13±0.70(Predicted)
- Aggregatzustand
- solid
- Farbe
- Off-white
- Stabilität
- 1 year · 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 Datenbank
- 1191237 · 1191237-69-0
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.
Danger
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P302+P352, P304+P340, P305+P354+P338, P308+P316, P317, P318, P319, P321, P332+P317, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationREACH registered substance: (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carbonitrile (EC: 857-885-9)
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
Mechanism of ActionGS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate, which is incorporated into the genome of virions, terminating its replication.
Metabolism/MetabolitesGS-441524 is phosphorylated 3 times to form the active nucleoside triphosphate.
MeSH Pharmacological Classification
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.
Absorption, Distribution and ExcretionGS-441524 has been found to transport poorly into cells compared to remdesivir.
Anwendungen
BeschreibungGS-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.
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