remdesivir

Also known as GS-5734, 2-ethylbutyl (2S)-2-({[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl}amino)propanoate, Veklury

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Key facts

Drug.N: 6
Drug.image: Remdesivir.svg
Drug.image_class: skin-invert-image
Drug.image2: Remdesivir-from-xtal-Mercury-3D-ball-and-stick-with-bond-orders.png
Drug.image_class2: bg-transparent
Drug.tradename: Veklury
Drug.MedlinePlus: a620033
Drug.DailyMedID: Remdesivir
Drug.pregnancy_AU: B2
Drug.routes_of_administration: Intravenous
Drug.class: Antiviral
Drug.ATC_prefix: J05
Drug.ATC_suffix: AB16
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only

via Wikipedia infobox

Chemical data

Formula: C27H35N6O8P
Molecular weight: 602.6 g/mol
IUPAC name: 2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
SMILES: CCC(CC)COC(=O)[C@H](C)N[P@](=O)(OC[C@@H]1[C@H]([C@H]([C@](O1)(C#N)C2=CC=C3N2N=CN=C3N)O)O)OC4=CC=CC=C4
InChIKey: RWWYLEGWBNMMLJ-YSOARWBDSA-N
XLogP: 1.9
Polar surface area: 204 Å²
H-bond donors: 4
H-bond acceptors: 13
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 602.2253987099999
Has use: medication

Show 12 more facts

Commons category: Remdesivir
canonical SMILES: Nc3ncnn2c3ccc2C(C#N)(C1O)OC(C1O)CO[P](=O)(NC(C)C(=O)OCC(CC)CC)Oc4ccccc4
isomeric SMILES: CCC(CC)COC(=O)[C@H](C)N[P@](=O)(OC[C@@H]1[C@H]([C@H]([C@](O1)(C#N)C2=CC=C3N2N=CN=C3N)O)O)OC4=CC=CC=C4
chemical formula: C₂₇H₃₅N₆O₈P
route of administration: intravenous infusion and defusion
on focus list of Wikimedia project: WikiProject COVID-19
side effect: hepatotoxicity
subject has role: antiviral drug
medical condition treated: Ebola hemorrhagic fever
studied by: medicine
described at URL: github.com/croningp/ChemputerAntiviralXDL/tree/master/Remdesivir
legal status (medicine): boxed warning

Sources (10)

via Wikidata · CC0

~33 min read

Encyclopedic overview

34 sections

Contents

Medical uses
Side effects
Pharmacology
Activation
Mechanism of action
Pharmacokinetics
Resistance
Interactions
Synthesis
''In vitro'' experiments
Manufacturing
Society and culture
Legal status
Australia
Canada
Czech Republic
European Union
Iran
Japan
Mexico
Singapore
United States
Economics
Names
Research
Ebola
COVID-19
Hospitalized patients
Nonhospitalized outpatients
Remdesivir/baricitinib
Remdesivir/interferon beta-1a
Veterinary uses
References
External links

{{Infobox drug | image = Remdesivir.svg | image_class = skin-invert-image | width = | alt = | caption = | image2 = Remdesivir-from-xtal-Mercury-3D-ball-and-stick-with-bond-orders.png | image_class2 = bg-transparent | width2 = | alt2 = | pronounce = | tradename = Veklury | Drugs.com = | MedlinePlus = a620033 | DailyMedID = Remdesivir | pregnancy_AU = B2 | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intravenous | class = Antiviral | ATC_prefix = J05 | ATC_suffix = AB16 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status = Schedule H | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion = | CAS_number = 1809249-37-3 | CAS_supplemental = | PubChem = 121304016 | IUPHAR_ligand = | DrugBank = DB14761 | ChemSpiderID = 58827832 | UNII = 3QKI37EEHE | KEGG = D11472 | ChEBI = 145994 | ChEMBL = 4065616 | NIAID_ChemDB = | PDB_ligand = | synonyms = GS-5734, RDV

| IUPAC_name = (2S)-2-{(2R,3S,4R,5R)-[5-(4-Aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]phenoxy-(S)-phosphorylamino}propionic acid 2-ethyl-butyl ester | C = 27 | H = 35 | N = 6 | O = 8 | P = 1 | SMILES = CCC(COC(=O)[C@@H](NP(=O)(Oc1ccccc1)OC[C@H]1O[C@@]([C@@H]([C@@H]1O)O)(C#N)c1ccc2n1ncnc2N)C)CC | StdInChI = 1S/C27H35N6O8P/c1-4-18(5-2)13-38-26(36)17(3)32-42(37,41-19-9-7-6-8-10-19)39-14-21-23(34)24(35)27(15-28,40-21)22-12-11-20-25(29)30-16-31-33(20)22/h6-12,16-18,21,23-24,34-35H,4-5,13-14H2,1-3H3,(H,32,37)(H2,29,30,31)/t17-,21+,23+,24+,27-,42-/m0/s1 | StdInChI_comment = | StdInChIKey = RWWYLEGWBNMMLJ-YSOARWBDSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }} Remdesivir, sold under the brand name Veklury, is a broad-spectrum antiviral medication developed by the biopharmaceutical company Gilead Sciences. It is administered via injection into a vein. During the COVID19 pandemic, remdesivir was approved or authorized for emergency use to treat COVID19 in numerous countries.

Excerpted from Wikipedia’s “remdesivir” article, available under the CC BY-SA 4.0 licence.