Molnupiravir | EIDD-2801 CAS#2349386-89-4 | COVID-19 inhibitor

MedKoo Cat#: 555745 | Name: EIDD-2801

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Molnupiravir, also known as EIDD-2801 and MK-4482, is an orally bioavailable form of a highly potent ribonucleoside analog that inhibits the replication of multiple RNA viruses including SARS-CoV-2, the causative agent of COVID-19. EIDD-2801 has been shown to improve pulmonary function, decrease body weight loss and reduce the amount of virus in the lung. In addition to activity against coronaviruses, EIDD-2801, in laboratory studies, has demonstrated activity against seasonal and bird influenza, respiratory syncytial virus, chikungunya virus, Ebola virus, Venezuelan equine encephalitis virus, and Eastern equine encephalitis virus. EIDD-2801 is a prodrug of EIDD-1931.

Chemical Structure

EIDD-2801

CAS#2349386-89-4

Theoretical Analysis

MedKoo Cat#: 555745

Name: EIDD-2801

CAS#: 2349386-89-4

Chemical Formula: C13H19N3O7

Exact Mass: 329.1223

Molecular Weight: 329.31

Elemental Analysis: C, 47.42; H, 5.82; N, 12.76; O, 34.01

Price and Availability

Size	Price	Availability
100mg	USD 150.00	Ready to ship
200mg	USD 250.00	Ready to ship
500mg	USD 400.00	Ready to ship
1g	USD 550.00	Ready to ship
5g	USD 950.00	Ready to ship
10g	USD 1,650.00	Ready to ship
20g	USD 2,950.00	Ready to ship

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Related CAS #

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Synonym

Molnupiravir; MK-4482; MK4482; MK 4482; EIDD-2801; EIDD 2801; EIDD2801; prodrug-EIDD-1931; prodrug-EIDD 1931; prodrug-EIDD1931.

IUPAC/Chemical Name

((2R,3S,4R,5R)-3,4-dihydroxy-5-((E)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl isobutyrate

InChi Key

HTNPEHXGEKVIHG-QCNRFFRDSA-N

InChi Code

InChI=1S/C13H19N3O7/c1-6(2)12(19)22-5-7-9(17)10(18)11(23-7)16-4-3-8(15-21)14-13(16)20/h3-4,6-7,9-11,17-18,21H,5H2,1-2H3,(H,14,15,20)/t7-,9-,10-,11-/m1/s1

SMILES Code

O[C@@H]([C@H]([C@H](N1C(N/C(C=C1)=N/O)=O)O2)O)[C@H]2COC(C(C)C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C20R07B22

View CoA: current batch, Lot#C20R05B01

QC Data

View QC data: current batch, Lot#C20R07B22

View QC data: current batch, Lot#C20R05B01

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Molnupiravir (EIDD-2801) is a bioavailable prodrug of the ribonucleoside analog EIDD-1931 that has broad spectrum antiviral activity against influenza virus and multiple coronaviruses, such as SARS-CoV-2, MERS-CoV, SARS-CoV.

In vitro activity:

Molnupiravir is a broad-spectrum antiviral that is an orally bioavailable prodrug of the nucleoside analogue β-D-N4-hydroxycytidine (NHC). Molnupiravir or NHC can increase G to A and C to U transition mutations in replicating coronaviruses. These increases in mutation frequencies can be linked to increases in antiviral effects. Here, the effects of the active compound NHC 5'-triphosphate (NHC-TP) against the purified severe acute respiratory syndrome coronavirus 2 RNA-dependent RNA polymerase complex were studied. The efficiency of incorporation of natural nucleotides over the efficiency of incorporation of NHC-TP into model RNA substrates followed the order GTP (12,841) > ATP (424) > UTP (171) > CTP (30), indicating that NHC-TP competes predominantly with CTP for incorporation. No significant inhibition of RNA synthesis was noted as a result of the incorporated monophosphate in the RNA primer strand. When embedded in the template strand, NHC-monophosphate supported the formation of both NHC:G and NHC:A base pairs with similar efficiencies. The extension of the NHC:G product was modestly inhibited, but higher nucleotide concentrations could overcome this blockage. In contrast, the NHC:A base pair led to the observed G to A (G:NHC:A) or C to U (C:G:NHC:A:U) mutations. Together, these biochemical data support a mechanism of action of molnupiravir that is primarily based on RNA mutagenesis mediated via the template strand. Reference: J Biol Chem. 2021 Jul; 297(1): 100770. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8110631/

In vivo activity:

The efficacy of the MK-4482 prodrug was next assessed in the Syrian hamster model, which is regarded as a preclinical model of mild disease, with animals having self-limiting pneumonia.. Given the possibility for oral dosing, the utility of MK-4482 as a treatment following high-risk exposure was inspected. Two groups of hamsters (n = 6 per group) were treated with MK-4482 (250 mg/kg) by oral gavage 12 h and 2 h before (pre-infection treatment group) or 12 h post-infection (post-infection treatment group). Lung tissue samples were collected at the peak of virus replication and disease, day 4 post-infection, for analysis. In contrast to levels of shedding, a 1-log decrease in viral RNA was detected in the lungs of pre-infection and post-infection groups, respectively, when compared to the vehicle control group (Fig. 2d). This corresponded to a 2-log decrease in infectious virus in the lungs of the MK-4482 treated groups when compared to the vehicle controls (Fig. 2e). MK-4482 was not detected in the tissue. Then compared to the vehicle, viral genomes from MK-4482 treated animals had a significant accumulation of nucleotide substitutions (Supplementary Table 2). Together, these results are consistent with the RNA mutagenesis function of MK-4482 in the reduction of infectious virus and disease in treated animals. If adequately priced for widespread global use, MK-4482 should be considered as an oral postexposure application for SARS-CoV-2. Reference: Nat Commun. 2021; 12: 2295. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8052374/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	303.67
	DMF	50.0	151.83

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 329.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gordon CJ, Tchesnokov EP, Schinazi RF, Götte M. Molnupiravir promotes SARS-CoV-2 mutagenesis via the RNA template. J Biol Chem. 2021 May 11;297(1):100770. doi: 10.1016/j.jbc.2021.100770. Epub ahead of print. PMID: 33989635; PMCID: PMC8110631. 2. Rosenke K, Hansen F, Schwarz B, Feldmann F, Haddock E, Rosenke R, Barbian K, Meade-White K, Okumura A, Leventhal S, Hawman DW, Ricotta E, Bosio CM, Martens C, Saturday G, Feldmann H, Jarvis MA. Orally delivered MK-4482 inhibits SARSCoV-2 replication in the Syrian hamster model. Nat Commun. 2021 Apr 16;12(1):2295. doi: 10.1038/s41467-021-22580-8. PMID: 33863887; PMCID: PMC8052374. 3. Cox RM, Wolf JD, Plemper RK. Therapeutic MK-4482/EIDD-2801 Blocks SARS-CoV-2 Transmission in Ferrets. Res Sq [Preprint]. 2020 Oct 12:rs.3.rs-89433. doi: 10.21203/rs.3.rs-89433/v1. Update in: Nat Microbiol. 2020 Dec 3;: PMID: 33052328; PMCID: PMC7553152.

In vitro protocol:

In vivo protocol:

1. Cox RM, Wolf JD, Plemper RK. Therapeutic MK-4482/EIDD-2801 Blocks SARS-CoV-2 Transmission in Ferrets. Res Sq [Preprint]. 2020 Oct 12:rs.3.rs-89433. doi: 10.21203/rs.3.rs-89433/v1. Update in: Nat Microbiol. 2020 Dec 3;: PMID: 33052328; PMCID: PMC7553152. 2. Rosenke K, Hansen F, Schwarz B, Feldmann F, Haddock E, Rosenke R, Barbian K, Meade-White K, Okumura A, Leventhal S, Hawman DW, Ricotta E, Bosio CM, Martens C, Saturday G, Feldmann H, Jarvis MA. Orally delivered MK-4482 inhibits SARSCoV-2 replication in the Syrian hamster model. Nat Commun. 2021 Apr 16;12(1):2295. doi: 10.1038/s41467-021-22580-8. PMID: 33863887; PMCID: PMC8052374.

1: Sheahan TP, Sims AC, Zhou S, Graham RL, Pruijssers AJ, Agostini ML, Leist SR, Schäfer A, Dinnon KH 3rd, Stevens LJ, Chappell JD, Lu X, Hughes TM, George AS, Hill CS, Montgomery SA, Brown AJ, Bluemling GR, Natchus MG, Saindane M, Kolykhalov AA, Painter G, Harcourt J, Tamin A, Thornburg NJ, Swanstrom R, Denison MR, Baric RS. An orally bioavailable broad-spectrum antiviral inhibits SARS-CoV-2 in human airway epithelial cell cultures and multiple coronaviruses in mice. Sci Transl Med. 2020 Apr 6:eabb5883. doi: 10.1126/scitranslmed.abb5883. Epub ahead of print. PMID: 32253226. 2: Hampton T. New Flu Antiviral Candidate May Thwart Drug Resistance. JAMA. 2020 Jan 7;323(1):17. doi: 10.1001/jama.2019.20225. PMID: 31910262. 3: Toots M, Yoon JJ, Hart M, Natchus MG, Painter GR, Plemper RK. Quantitative efficacy paradigms of the influenza clinical drug candidate EIDD-2801 in the ferret model. Transl Res. 2020 Apr;218:16-28. doi: 10.1016/j.trsl.2019.12.002. Epub 2019 Dec 25. PMID: 31945316. 4: Toots M, Yoon JJ, Cox RM, Hart M, Sticher ZM, Makhsous N, Plesker R, Barrena AH, Reddy PG, Mitchell DG, Shean RC, Bluemling GR, Kolykhalov AA, Greninger AL, Natchus MG, Painter GR, Plemper RK. Characterization of orally efficacious influenza drug with high resistance barrier in ferrets and human airway epithelia. Sci Transl Med. 2019 Oct 23;11(515):eaax5866. doi: 10.1126/scitranslmed.aax5866. PMID: 31645453; PMCID: PMC6848974. 5: Beigel JH, Nam HH, Adams PL, Krafft A, Ince WL, El-Kamary SS, Sims AC. Advances in respiratory virus therapeutics - A meeting report from the 6th isirv Antiviral Group conference. Antiviral Res. 2019 Jul;167:45-67. doi: 10.1016/j.antiviral.2019.04.006. Epub 2019 Apr 8. PMID: 30974127; PMCID: PMC7132446.