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Molnupiravir

Molnupiravir structure

CAS No:
2349386-89-4
Formula:
C13H19N3O7
Chemical Name:
Molnupiravir
Synonyms:
((2R,3S,4R,5R)-3,4-dihydroxy-5-((E)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate;EIDD-2801(EIDD 2801);EIDD-2801;Tube994;Molnupiravir(MK-4482);Uridine, 4-oxime, 5'-(2-methylpropanoate);β-D-N4 hydroxycytidine-5'-isopropyl ester;MolnupiravirEIDD-2801(API)
Categories:
Organic Chemistry > Amides

Description

EIDD-2801 is the isopropylester prodrug of [N4-hydroxycytidine]. With improved oral bioavailability in non human primates, it is hydrolyzed in vivo, and distributes into tissues where it becomes the active 5’-triphosphate form. The active drug incorporates into the genome of RNA viruses, leading to an accumulation of mutations known as viral error catastrophe. Recent studies have shown EIDD-2801 inhibits replication of human and bat coronaviruses, including SARS-CoV-2, in mice and human airway epithelial cells. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine.|Molnupiravir is an orally bioavailable prodrug of EIDD-1931, the synthetic ribonucleoside derivative N4-hydroxycytidine and ribonucleoside analog, with potential antiviral activity against a variety of RNA viruses. Upon oral administration, molnupiravir, being a prodrug, is metabolized into its active form EIDD-1931 and converted into its triphosphate (TP) form. The TP form of EIDD-1931 is incorporated into RNA and inhibits the action of viral RNA-dependent RNA polymerase. This results in the termination of RNA transcription and decreases viral RNA production, and viral RNA replication.

Molnupiravir was originally developed as antiviral therapy for influenza. However, this antiviral has also shown activity against various other viruses, including SARS-CoV-2. The drug co-developed by Emory University, Ridgeback Biotherapeutics, and Merck is a promising oral treatment for COVID-19. The international nonproprietary name of the drug was inspired by that of Thor's hammer, Mjölnir. The idea is that the drug will strike down the virus like a mighty blow from the god of thunder.In 2019, the National Institute of Allergy and Infectious Diseases (NIAID) approved moving molnupiravir into Phase I clinical trials for influenza.In 2020, a study found that it is orally active against SARS-CoV-2 in ferrets. DRIVE then licensed molnupiravir for human clinical studies to Miami-based company Ridgeback Biotherapeutics, which later partnered with Merck & Co. to develop the drug further.

Molnupiravir is a nucleoside analogue that is N(4)-hydroxycytidine in which the 5'-hydroxy group is replaced by a (2-methylpropanoyl)oxy group. It is the prodrug of the active antiviral ribonucleoside analog N(4)-hydroxycytidine (EIDD-1931), has activity against a number of RNA viruses including SARS-CoV-2, MERS-CoV, and seasonal and pandemic influenza viruses. It is currently in phase III trials for the treatment of patients with COVID-19. It has a role as a prodrug, an anticoronaviral agent and an antiviral drug. It is a nucleoside analogue, an isopropyl ester and a ketoxime. It derives from a N(4)-hydroxycytidine.www.ebi.ac.uk

Molnupiravir Basic Attributes

Molecular Weight：

329.31

Exact Mass：

329.12229995

EC Number：

604-604-1

UNII：

YA84KI1VEW

NCI Thesaurus Code：

C172633

Color/Form：

White to Off-White

Characteristics

Melting Point：

156 - 159°C

Critical Temperature & Pressure：

-20°C, Inert atmosphere

Safety Information

wgk germany：

WGK 3

GHS Classification：

|Danger|H372 (97.22%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P314, and P501|Aggregated GHS information provided by 36 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

Drug Indication：

[N4-hydroxycytidine] and its prodrug EIDD-2801 is being studied for its activity against a number of viral infections including influenza, MERS-CoV, and SARS-CoV-2.|Treatment of Coronavirus disease 2019 (COVID-19)

Absorption：

EIDD-2801 is orally bioavailable in non-human primates.

Metabolism/Metabolites：

EIDD-2801 is hydrolyzed to [N4-hydroxycytidine], which distributes into tissues. Once inside cells, N4-hydroxycytidine is phosphorylated to the 5'-triphosphate form.

Mechanism of Action：

EIDD-2801 is hydrolyzed _in vivo_ to N4-hydroxycytidine, which is phosphorylated in tissue to the active 5’-triphosphate form, and incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations, known as viral error catastrophe. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine.

MeSH Entry Terms：

EIDD-2801

Molnupiravir Use and Manufacturing

Uses

EIDD 2801 is an orally bioavailable broad-spectrum antiviral that inhibits SARS-CoV-2 and other multiple endemic, epidemic and bat coronavirus and has the potential for seasonal and pandemic influenza treatment. An isopropylester prodrug of the ribonucleoside analog of EIDD-1931 that exhibits anti-influenza virus and coronaviruses activities.

Use Classification：

Human Drugs -> EU pediatric investigation plans

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