Remdesivir

Remdesivir, sold under the brand name Veklury,[1] is a broad-

spectrum antiviral medication developed by the biopharmaceutical
Remdesivir
company Gilead Sciences.[2] It is administered via injection into a
vein.[3][4] As of 2020, remdesivir is being tested as a specific
treatment for COVID-19, and has been authorized for emergency
use in the US, India,[5] Singapore,[6] and approved for use in Japan
for people with severe symptoms.[7][8][1][9] It also received
approval in the UK in May 2020, however, it was going to be
rationed due to limited supply.[10] It may shorten the time it takes
to recover from the infection.[11]

Side effects may include liver inflammation and an infusion-

related reaction with nausea, low blood pressure, and sweating.[12]
It is a prodrug that is converted in the body into GS-441524, a
ribonucleotide analog.

Earlier studies found antiviral activity against several RNA viruses

including SARS coronavirus and MERS coronavirus, but it is not
approved for any indication.[2][7] Remdesivir was originally
developed to treat hepatitis C[13] and was then tested against Ebola
virus disease and Marburg virus disease, but was ineffective for all
of these viral infections.[2] As of May 2020, remdesivir is
approved for use in Japan with an indication to treat SARS-CoV-2 Clinical data
infection.[1]
Pronunciation /rɛmˈdɛsɪvɪər/ rem-
DESS-i-veer
Trade names Veklury
Contents Other names GS-5734
Side effects AHFS/Drugs.com Professional Drug
Research Facts (https://www.
Ebola drugs.com/ppa/rem
COVID-19 desivir.html)

Access Routes of Intravenous

administration
Pharmacology ATC code None
Activation
Mechanism of action Legal status
Pharmacokinetics Legal status Investigational / Rx-
Resistance only

Interactions Identifiers
Synthesis IUPAC name
Terminology (2S)-2-{(2R,3S,4R,5R)-[5-(4-Aminopyrrolo[2,1-f]
[1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxy-tetr
Other animals
References ahydro-furan-2-ylmethoxy]phenoxy-(S)-phos

Further reading phorylamino}propionic acid 2-ethyl-butyl est

er
External links
CAS Number 1809249-37-3 (htt
p://www.commonch
Side effects emistry.org/Chemic
alDetail.aspx?ref=1
The most common adverse effects in studies of remdesivir for 809249-37-3)
COVID‑19 include respiratory failure and organ impairment,
including low albumin, low potassium, low count of red blood PubChem CID 121304016 (https://
cells, low count of platelets that help with clotting, and yellow pubchem.ncbi.nlm.
discoloration of the skin.[14] Other reported side effects include nih.gov/compound/
gastrointestinal distress, elevated transaminase levels in the blood 121304016)
(liver enzymes), and infusion site reactions.[4]
DrugBank DB14761 (https://w
Other possible side effects of remdesivir include: ww.drugbank.ca/dr
ugs/DB14761)
Infusion‐related reactions. Infusion‐related reactions
ChemSpider 58827832 (http://w
have been seen during a remdesivir infusion or around
the time remdesivir was given.[15] Signs and symptoms ww.chemspider.co
of infusion‐related reactions may include: low blood m/Chemical-Structu
pressure, nausea, vomiting, sweating, and shivering.[15] re.58827832.html)
Increases in levels of liver enzymes, seen in abnormal UNII 3QKI37EEHE (http
liver blood tests.[15] Increases in levels of liver enzymes
s://fdasis.nlm.nih.g
have been seen in people who have received remdesivir,
which may be a sign of inflammation or damage to cells ov/srs/srsdirect.js
in the liver.[15] p?regno=3QKI37E
EHE)

Research KEGG D11472 (https://ww

w.kegg.jp/entry/D11
Remdesivir was originally created and developed by Gilead 472)
Sciences in 2009, as part of the company's research and ChEBI CHEBI:145994 (htt
development program for hepatitis C.[13] It did not work against
ps://www.ebi.ac.uk/
hepatitis C as hoped,[13] but was then repurposed and studied as a
chebi/searchId.do?
potential treatment for Ebola virus disease and Marburg virus
chebiId=CHEBI:14
infections.[16] According to the Czech News Agency, this new line
of research was carried out under the direction of scientist Tomáš 5994)
Cihlář.[17] Gilead Sciences subsequently discovered that ChEMBL ChEMBL4065616
remdesivir had antiviral activity in vitro against multiple (https://www.ebi.ac.
filoviruses, pneumoviruses, paramyxoviruses, and uk/chembldb/index.
coronaviruses. [18]
php/compound/insp
Preclinical and clinical research and development was done in ect/ChEMBL40656
collaboration between Gilead Sciences and various U.S. 16)
government agencies and academic institutions.[19][20][21][22] Chemical and physical data

During the mid-2010s, the Mintz Levin law firm prosecuted Formula C27H35N6O8P
various patent applications for remdesivir on behalf of Gilead Molar mass 602.585 g·mol−1
Sciences before the United States Patent and Trademark Office 3D model
(USPTO). The USPTO granted two patents on remdesivir to Interactive image (h
(JSmol)
Gilead Sciences on April 9, 2019: one for filoviruses,[23] and one ttps://chemapps.sto
which covered both arenaviruses and coronaviruses.[24] laf.edu/jmol/jmol.ph
p?model=CCC%28
COC%28%3DO%2
Ebola
9%5BC%40%40
In October 2015, the United States Army Medical Research H%5D%28NP%2
Institute of Infectious Diseases (USAMRIID) announced 8%3DO%29%28Oc
preclinical results that remdesivir had blocked the Ebola virus in 1ccccc1%29OC%5
Rhesus monkeys. Travis Warren, who has been a USAMRIID BC%40H%5D1O%
principal investigator since 2007, said that the "work is a result of 5BC%40%40%5
the continuing collaboration between USAMRIID and Gilead D%28%5BC%40%
Sciences".[25] The "initial screening" of the "Gilead Sciences 40H%5D%28%5B
compound library to find molecules with promising antiviral C%40%40H%5D1
activity" was performed by scientists at the Centers for Disease O%29O%29%28
Control and Prevention (CDC).[25] As a result of this work, it was
C%23N%29c1ccc2
recommended that remdesivir "should be further developed as a
n1ncnc2N%29C%2
potential treatment."[16][25]
9CC)
Remdesivir was rapidly pushed through clinical trials due to the SMILES
West African Ebola virus epidemic of 2013–2016, eventually being CCC(COC(=O)[C@@H](NP(=O)(Oc1ccccc1)OC
used in people with the disease. Preliminary results were [C@H]1O[C@@]([C@@H]([C@@H]1O)O)(C
#N)c1ccc2n1ncnc2N)C)CC
promising; it was used in the emergency setting during the Kivu
Ebola epidemic that started in 2018, along with further clinical InChI
trials, until August 2019, when Congolese health officials InChI=1S/C27H35N6O8P/c1-4-18(5-2)13-38-26
(36)17(3)32-42(37,41-19-9-7-6-8-10-19)39-1
announced that it was significantly less effective than monoclonal 4-21-23(34)24(35)27(15-28,40-21)22-12-11-2
antibody treatments such as mAb114 and REGN-EB3. The trials, 0-25(29)30-16-31-33(20)22/h6-12,16-18,21,2
however, established its safety profile.[26] 3-24,34-35H,4-5,13-14H2,1-3H3,(H,32,37)(H
2,29,30,31)/t17-,21+,23+,24+,27-,42-/m0/s1
Key:RWWYLEGWBNMMLJ-YSOARWBDSA-N

COVID-19

As of April 2020, remdesivir was viewed as the most promising treatment for COVID-19,[11] and was
included among four treatments under evaluation in the international Solidarity trial[27][28] and European
Discovery trial.[29] The FDA stated on 1 May 2020, that it is "reasonable to believe" that known and
potential benefits of remdesivir outweigh its known and potential risks, in some specific populations
hospitalized with severe COVID‑19.[7] As of May 2020, there was no good evidence that remdesivir
reduced mortality in people with COVID-19.[30]

In January 2020, Gilead Sciences began laboratory testing of remdesivir against SARS-CoV-2, stating that
remdesivir had been shown to be active against severe acute respiratory syndrome (SARS) and Middle East
respiratory syndrome (MERS) in animal models.[31][32][33] On 21 January 2020, the Wuhan Institute of
Virology applied for a Chinese "use patent", for treating COVID‑19.[34]

In a trial in China over February-March 2020, remdesivir was not effective in reducing the time for
improvement from COVID‑19 or deaths, and caused various adverse effects, requiring the investigators to
terminate the trial.[14]

On 18 March 2020, the World Health Organization (WHO) announced the launch of a trial that would
include one group treated with remdesivir.[27][35] Other clinical trials are underway or
planned.[36][37][38][39][40][41][42][43][44][45][46]
Preliminary data from an international multi-center, placebo controlled double-blind randomized controlled
trial carried out by the U.S. National Institutes of Health, suggests that remdesivir is effective in reducing
the recovery time from 15 to 11 days in people hospitalized with COVID‑19.[47][48] On 29 April 2020,
based on results of the ACTT trial,[46] the National Institute of Allergy and Infectious Diseases (NIAID)
announced that remdesivir was better than a placebo in reducing time to recovery for people hospitalized
with advanced COVID‑19 and lung involvement.[48] The study appeared on The New England Journal of
Medicine website almost a month later on 22 May 2020, and despite generally positive results, the study
concluded that "given high mortality despite the use of remdesivir, it is clear that treatment with an antiviral
drug alone is not likely to be sufficient."[47][49] A previous Chinese study published in The Lancet did not
show significant benefits or drawbacks of using remdesivir, concluding that further research is required to
understand the effectiveness of the drug.[14] John David Norrie of the Clinical Trials Unit of the University
of Edinburgh Medical School criticised that article as underpowered due to a lack of significant results as
well as the fact that the study was ended prematurely.[50] Based on the results of its study, the NIH stopped
the ACTT trial and provided remdesivir to participants assigned to received placebo.[51]

In April 2020, the European Medicines Agency (EMA) started a 'rolling review' of data on the use of
remdesivir in COVID‑19.[52] It completed the review in May 2020.[53]

In May 2020, a number of companies in India and Pakistan have been given the right to make the
medication.[54]

In June 2020, the Committee for Medicinal Products for Human Use (CHMP) of the EMA started
evaluating remdesivir for a conditional marketing authorization after receiving an application from Gilead
Sciences.[55][56]

A small trial of remdesivir in rhesus macaque monkeys with COVID‑19 infections reported that early
treatment with remdesivir reduced damage and disease progression, but not viral shedding.[57]

On 25 June 2020, the Committee for Medicinal Products for Human Use (CHMP) of the European
Medicines Agency (EMA) recommended granting a conditional marketing authorization for remdesivir, for
the treatment of COVID-19 in adults and adolescents from 12 years of age with pneumonia who require
supplemental oxygen.[58][59][60] The brand name will be Veklury.[58][59]

Access
In January 2020, Gilead began working on restarting remdesivir production in glass-lined steel chemical
reactors at its manufacturing plant in Edmonton, Alberta.[61] On 2 February 2020, the company flew its
entire stock of remdesivir, 100 kilograms in powder form (left over from Ebola research), to its filling plant
in La Verne, California to start filling vials.[61] The Edmonton plant finished its first new batch of
remdesivir in April 2020.[61] Around the same time, fresh raw materials began to arrive from contract
manufacturers reactivated by Gilead in January.[61]

On 17 March 2020, the drug was provisionally approved for use for COVID‑19 patients in a serious
condition as a result of the outbreak in the Czech Republic.[62] On 20 March 2020, United States President
Donald Trump announced that remdesivir was available for "compassionate use" for people with
COVID‑19; FDA Commissioner Stephen Hahn confirmed the statement at the same press conference.[63] It
was later revealed that Gilead had been providing remdesivir in response to compassionate use requests
since 25 January.[13] On 23 March 2020, Gilead voluntarily suspended access for compassionate use
(excepting cases of critically ill children and pregnant women), for reasons related to supply, citing the need
to continue to provide the agent for testing in clinical trials.[11][64]
In April 2020, the European Medicines Agency (EMA) provided recommendations on compassionate use of
remdesivir for COVID‑19 in the EU.[65]

As of 11 April 2020, access in Canada was only to those who will be involved in a clinical trial.[66]

On 1 May 2020, the U.S. Food and Drug Administration granted Gilead emergency use authorization (EUA)
for remdesivir to be distributed and used by licensed health care providers to treat adults and children
hospitalized with severe COVID‐19.[8][15] Severe COVID‐19 is defined as patients with an oxygen
saturation (SpO2) ≤ 94% on room air or requiring supplemental oxygen or requiring mechanical ventilation
or requiring extracorporeal membrane oxygenation (ECMO), a heart–lung bypass machine.[67][15][68][69]
Distribution of remdesivir under the EUA will be controlled by the U.S. government for use consistent with
the terms and conditions of the EUA.[15] Gilead will supply remdesivir to authorized distributors, or directly
to a U.S. government agency, who will distribute to hospitals and other healthcare facilities as directed by
the U.S. Government, in collaboration with state and local government authorities, as needed.[15]

On 7 May 2020, Japan's Ministry of Health, Labour and Welfare approved the drug for use in Japan, in a
fast-tracked process based on the U.S. emergency authorization.[1][9]

Gilead stated they were donating 1.5 million vials for emergency use[68] and estimated, as of April 2020,
they had enough remdesivir for 140,000 treatment courses and expect to have 500,000 courses by October
2020, and one million courses by the end of 2020.[70][71]

The initial distribution of the drug in the U.S. was tripped up by seemingly capricious decision-making and
finger-pointing, resulting in over a week of confusion and frustration among health care providers and
patients alike.[72][73][74] On 9 May 2020, the U.S. Department of Health and Human Services (HHS)
explained in a statement that it would be distributing remdesivir vials to state health departments, then
would allow each department to redistribute vials to hospitals in their respective states based upon each
department's insight into "community-level needs."[75] HHS also clarified that only 607,000 vials of Gilead's
promised donation of 1.5 million vials would be going to American patients.[75] However, HHS did not
explain why several states with some of the highest caseloads had been omitted from the first two
distribution rounds, including California, Florida, and Pennsylvania.[75] In May 2020, Gilead indicated they
would increase the number of doses donated to the U.S. from 607,000 to around 940,000.[76][74] Some of
the initial distribution was sent to the wrong hospitals, to hospitals with no intensive care units, and to
facilities without the needed refrigeration to store it.[74]

On 11 May 2020, the Committee for Medicinal Products for Human Use (CHMP) of the EMA
recommended expanding the compassionate use of remdesivir to those not on mechanical ventilation.[77] In
addition to those undergoing invasive mechanical ventilation, the compassionate use recommendations
cover the treatment of hospitalized individuals requiring supplemental oxygen, non-invasive ventilation,
high-flow oxygen devices or ECMO (extracorporeal membrane oxygenation).[77] The updated
recommendations were based on preliminary results from the NIAID-ACTT study,[46] which suggested a
beneficial effect of remdesivir in the treatment of hospitalized individuals with severe COVID-19.[77][48] In
addition, a treatment duration of five days was introduced alongside the longer ten-day course, based on
preliminary results from another study (GS-US-540-5773) suggesting that for those not requiring
mechanical ventilation or ECMO, the treatment course may be shortened from ten to five days without any
loss of efficacy.[77] Individuals who receive a five-day treatment course but do not show clinical
improvement will be eligible to continue receiving remdesivir for an additional five days.[77]

On 12 May 2020, Gilead announced that it had granted non-exclusive voluntary licenses to five generic drug
companies to manufacture remdesivir for distribution to 127 countries.[78] The agreements were structured
so that the licensees can set their own prices and will not have to pay royalties to Gilead until the WHO
declares an end to the COVID-19 emergency or another medicine or vaccine is approved for COVID-19,
whichever comes first.[78]

Pharmacology

Activation

Remdesivir is a ProTide
(Prodrug of nucleoTide)
that is able to diffuse
into cells where it is
converted to GS-441524
mono-phosphate via the
actions of esterases and a
phosphoamidase; this in
turn is further
phosphorylated to its
active metabolite
triphosphate by
nucleoside-phosphate
kinases.[80][81]

Activation of remdesivir into its active triphosphate metabolite[79]

Mechanism of
action

As an adenosine nucleoside triphosphate analog, the active metabolite of remdesivir interferes with the
action of viral RNA-dependent RNA polymerase and evades proofreading by viral exoribonuclease (ExoN),
causing a decrease in viral RNA production.[2][82] In some viruses such as the respiratory syncytial virus it
causes the RNA-dependent RNA polymerases to pause, but its predominant effect (as in Ebola) is to induce
an irreversible chain termination. Unlike with many other chain terminators, this is not mediated by
preventing addition of the immediately subsequent nucleotide, but is instead delayed, occurring after five
additional bases have been added to the growing RNA chain.[83] For the RNA-Dependent RNA Polymerase
of MERS-CoV, SARS-CoV-1, and SARS-CoV-2 arrest of RNA synthesis occurs after incorporation of three
additional nucleotides.[84][81] Hence, remdesivir is classified as a direct-acting antiviral agent that works as
a delayed chain terminator.[79][81]

Pharmacokinetics

In non-human primates, the plasma half-life of the prodrug is 20 minutes, with the main metabolite being
the nucleoside, GS-441524. Two hours post injection, the main metabolite GS-441524 is present at
micromolar concentrations, whilst intact Remdesivir is no longer detectable. Because of this rapid
extracellular conversion to the nucleoside GS-441524, some researchers have questioned whether the active
nucleotide triphosphate is truly derived from Remdesivir pro-drug removal or whether it occurs by GS-
441524 phosphorylation. The activated nucleotide triphosphate form has sustained intracellular levels in
PBMC and presumably in other cells as well.[79]

Resistance
Mutations in the mouse hepatitis virus RNA replicase that cause partial resistance to remdesivir were
identified in 2018. These mutations make the viruses less effective in nature, and the researchers believe
they will likely not persist where the drug is not being used.[85]

Interactions
Remdesivir is at least partially metabolized by the cytochrome P450 enzymes CYP2C8, CYP2D6, and
CYP3A4.[86][87] Blood plasma concentrations of remdesivir are expected to decrease if it is administered
together with cytochrome P450 inducers such as rifampicin, carbamazepine, phenobarbital, phenytoin,
primidone, and St John's wort.[88]

On 15 June 2020, the FDA updated the fact sheets for the emergency use authorization of remdesivir to
warn that using chloroquine or hydroxychloroquine with remdesivir may reduce the antiviral activity of
remdesivir.[89] Coadministration of remdesivir and chloroquine phosphate or hydroxychloroquine sulfate is
not recommended based on in vitro data demonstrating an antagonistic effect of chloroquine on the
intracellular metabolic activation and antiviral activity of remdesivir.[87]

Synthesis
Remdesivir can be synthesized in multiple steps
from ribose derivatives. The figure to the right is
one of the synthesis routes of remdesivir invented
by Chun and coauthors from Gilead
Sciences. [90][91] In this method, intermediate a is
firstly prepared from L-alanine and phenyl
phosphorodichloridate in presence of triethylamine
and dichloromethane; triple benzyl-protected ribose
is oxidized by dimethyl sulfoxide with acetic
anhydride and give the lactone intermediate b;
pyrrolo[2,1-f] [1,2,4]triazin-4-amine is brominated,
and the amine group is protected by excess
trimethylsilyl chloride. n-Butyllithium undergoes a
halogen-lithium exchange reaction with the
bromide at −78 °C (−108 °F) to yield the
intermediate c. The intermediate b is then added to
a solution containing intermediate c dropwise.
After quenching the reaction in a weakly acidic
aqueous solution, a mixture of 1: 1 anomers was
obtained. It was then reacted with an excess of Synthesis of remdesivir in structural formulae
trimethylsilyl cyanide in dichloromethane at
−78 °C (−108 °F) for 10 minutes. Trimethylsilyl
triflate was added and reacts for one additional hour, and the mixture was quenched in an aqueous sodium
hydrogen carbonate. A nitrile intermediate was obtained. The protective group, benzyl, was then removed
with boron trichloride in dichloromethane at −20 °C (−4 °F). The excess of boron trichloride was quenched
in a mixture of potassium carbonate and methanol. A benzyl-free intermediate was obtained. The isomers
were then separated via reversed-phase HPLC. The optically pure compound and intermediate a are reacted
with trimethyl phosphate and methylimidazole to obtain a diastereomer mixture of remdesivir. In the end,
optically pure remdesivir can be obtained through chiral resolution methods.
Remdesivir requires "70 raw materials, reagents, and catalysts" to make, and approximately "25 chemical
steps."[61] Some of the ingredients are extremely dangerous to humans, especially trimethylsilyl cyanide.[61]
The original end-to-end manufacturing process required 9 to 12 months to go from raw materials at contract
manufacturers to finished product, but after restarting production in January, Gilead Sciences was able to
find ways to reduce the production time to six months.[61]

Terminology
Remdesivir is the international nonproprietary name (INN)[92] while the development code name was GS-
5734.[93]

Other animals
GS-441524 was shown in 2019 to have promise for treating feline infectious peritonitis caused by a
coronavirus.[94] It has not been evaluated or approved by the Food and Drug Administration (FDA) for the
treatment of feline coronavirus or feline infectious peritonitis but has been available since 2019 through
websites and social media as an unregulated black market substance as confirmed by the UC Davis School
of Veterinary Medicine.[95]

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Further reading
Kolata G (1 May 2020). "How Remdesivir, New Hope for Covid-19 Patients, Was Resurrected"
(https://www.nytimes.com/2020/05/01/health/coronavirus-remdesivir.html). The New York
Times.
"Remdesivir Clinical Data" (https://www.remdesivir.com/us/clinical-data/). Gilead Sciences, Inc.

External links
"Remdesivir" (https://druginfo.nlm.nih.gov/drugportal/name/remdesivir). Drug Information
Portal. U.S. National Library of Medicine.
"Gilead Sciences Update On The Company's Ongoing Response To COVID-19" (https://www.g
ilead.com/purpose/advancing-global-health/covid-19). Gilead Sciences, Inc.
 Classification D

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