Peramivir | BCX 1812 | RWJ 270201 | CAS#330600-85-6 | Neuraminidase inhibitor

MedKoo Cat#: 314258 | Name: Peramivir

Description:

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

Peramivir, also known as BCX1812 and RWJ 270201, is an antiviral drug for the treatment of influenza. Peramivir is a neuraminidase inhibitor, acting as a transition-state analogue inhibitor of influenza neuraminidase and thereby preventing new viruses from emerging from infected cells. Peramivir was approved to treat influenza infection in adults.

Chemical Structure

Peramivir

CAS#330600-85-6 (free)

Theoretical Analysis

MedKoo Cat#: 314258

Name: Peramivir

CAS#: 330600-85-6 (free)

Chemical Formula: C15H28N4O4

Exact Mass: 328.2111

Molecular Weight: 328.41

Elemental Analysis: C, 54.86; H, 8.59; N, 17.06; O, 19.49

Price and Availability

Size	Price	Availability
100mg	USD 150.00	Ready to ship
250mg	USD 250.00	Ready to ship
500mg	USD 400.00	Ready to ship
1g	USD 650.00	2 Weeks
2g	USD 950.00	2 Weeks
5g	USD 1,650.00	2 Weeks

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Related CAS #

330600-85-6 (free) 1041434-82-5 (hydrate)

Synonym

BCX1812; BCX1812; BCX 1812; RWJ270201; RWJ 270201; RWJ270201; Peramivir. Brand name: Rapivab; Rapiacta and Peramiflu.

IUPAC/Chemical Name

(1S,2S,3R,4R)-3-((S)-1-acetamido-2-ethylbutyl)-4-guanidino-2-hydroxycyclopentanecarboxylic acid

InChi Key

XRQDFNLINLXZLB-CKIKVBCHSA-N

InChi Code

InChI=1S/C15H28N4O4/c1-4-8(5-2)12(18-7(3)20)11-10(19-15(16)17)6-9(13(11)21)14(22)23/h8-13,21H,4-6H2,1-3H3,(H,18,20)(H,22,23)(H4,16,17,19)/t9-,10+,11+,12-,13+/m0/s1

SMILES Code

O=C([C@@H]1[C@@H](O)[C@@H]([C@@H](NC(C)=O)C(CC)CC)[C@H](NC(N)=N)C1)O

Appearance

Solid powder

Purity

>95% (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

>2 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#C23B01B18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Peramivir (RWJ-270201;BCX-1812) is a highly potent, selective and orally active influenza virus neuraminidase (NA) inhibitor, with IC50 values ranging form 0.9 to 4.3 nM for nine NA subtypes.

In vitro activity:

Peramivir dose-dependently inhibited TNF-α release with the half-maximal inhibitory concentration (IC50) as 4.3 µM (Figure 1C). This study tested the cytotoxicity of peramivir in macrophages by a CCK-8 assay to eliminate the inhibitory effect on TNF-α might be achieved by cytotoxicity. Results demonstrated that no apparent toxicity was observed in the peramivir-treated macrophages at concentrations up to 40 μM (Figure 1D). Reference: Front Immunol. 2022 Feb 28;13:856327. https://pubmed.ncbi.nlm.nih.gov/35296098/

In vivo activity:

This study demonstrates the antiviral activity of peramivir in a mouse model of H7N9 avian influenza virus infection. The data show that repeated administration of peramivir at 30 mg/kg of body weight successfully eradicated the virus from the respiratory tract and extrapulmonary tissues during the acute response, prevented clinical signs of the disease, including neuropathy, and eventually protected mice against lethal H7N9 influenza virus infection. Reference: Antimicrob Agents Chemother. 2015 Dec;59(12):7255-64. https://pubmed.ncbi.nlm.nih.gov/26369969/

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 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. Zhang CX, Tu Y, Sun XC, Chen DG, Zhang WN, Zhuang CL, Wang ZB, Su L. Peramivir, an Anti-Influenza Virus Drug, Exhibits Potential Anti-Cytokine Storm Effects. Front Immunol. 2022 Feb 28;13:856327. doi: 10.3389/fimmu.2022.856327. PMID: 35296098; PMCID: PMC8918788. 2. Kobayashi M, Kodama M, Noshi T, Yoshida R, Kanazu T, Nomura N, Soda K, Isoda N, Okamatsu M, Sakoda Y, Yamano Y, Sato A, Kida H. Therapeutic efficacy of peramivir against H5N1 highly pathogenic avian influenza viruses harboring the neuraminidase H275Y mutation. Antiviral Res. 2017 Mar;139:41-48. doi: 10.1016/j.antiviral.2016.12.011. Epub 2016 Dec 22. PMID: 28012921. 3. Farooqui A, Huang L, Wu S, Cai Y, Su M, Lin P, Chen W, Fang X, Zhang L, Liu Y, Zeng T, Paquette SG, Khan A, Kelvin AA, Kelvin DJ. Assessment of Antiviral Properties of Peramivir against H7N9 Avian Influenza Virus in an Experimental Mouse Model. Antimicrob Agents Chemother. 2015 Dec;59(12):7255-64. doi: 10.1128/AAC.01885-15. Epub 2015 Sep 14. PMID: 26369969; PMCID: PMC4649212. 4. Onishi M, Kitano M, Taniguchi K, Homma T, Kobayashi M, Yoshinaga T, Naito A, Sato A. Intravenous peramivir inhibits viral replication, and leads to bacterial clearance and prevention of mortality during murine bacterial co-infection caused by influenza A(H1N1)pdm09 virus and Streptococcus pneumoniae. Antiviral Res. 2015 May;117:52-9. doi: 10.1016/j.antiviral.2015.02.012. Epub 2015 Mar 6. PMID: 25752738.

In vitro protocol:

In vivo protocol:

1. Farooqui A, Huang L, Wu S, Cai Y, Su M, Lin P, Chen W, Fang X, Zhang L, Liu Y, Zeng T, Paquette SG, Khan A, Kelvin AA, Kelvin DJ. Assessment of Antiviral Properties of Peramivir against H7N9 Avian Influenza Virus in an Experimental Mouse Model. Antimicrob Agents Chemother. 2015 Dec;59(12):7255-64. doi: 10.1128/AAC.01885-15. Epub 2015 Sep 14. PMID: 26369969; PMCID: PMC4649212. 2. Onishi M, Kitano M, Taniguchi K, Homma T, Kobayashi M, Yoshinaga T, Naito A, Sato A. Intravenous peramivir inhibits viral replication, and leads to bacterial clearance and prevention of mortality during murine bacterial co-infection caused by influenza A(H1N1)pdm09 virus and Streptococcus pneumoniae. Antiviral Res. 2015 May;117:52-9. doi: 10.1016/j.antiviral.2015.02.012. Epub 2015 Mar 6. PMID: 25752738.

1: Xu M, Cai T, Yue T, Zhang P, Huang J, Liu Q, Wang Y, Luo R, Li Z, Luo L, Ji C, Tan X, Zheng Y, Whitley R, De Clercq E, Yin Q, Li G. Comparative Effectiveness of Oseltamivir versus Peramivir for Hospitalized Children (ages 0-5 years) with Influenza Infection. Int J Infect Dis. 2023 Jan 3:S1201-9712(22)00680-4. doi: 10.1016/j.ijid.2022.12.043. Epub ahead of print. PMID: 36608788. 2: Sarukhanyan E, Shanmugam TA, Dandekar T. In Silico Studies Reveal Peramivir and Zanamivir as an Optimal Drug Treatment Even If H7N9 Avian Type Influenza Virus Acquires Further Resistance. Molecules. 2022 Sep 12;27(18):5920. doi: 10.3390/molecules27185920. PMID: 36144655; PMCID: PMC9503969. 3: Zhang CX, Tu Y, Sun XC, Chen DG, Zhang WN, Zhuang CL, Wang ZB, Su L. Peramivir, an Anti-Influenza Virus Drug, Exhibits Potential Anti-Cytokine Storm Effects. Front Immunol. 2022 Feb 28;13:856327. doi: 10.3389/fimmu.2022.856327. PMID: 35296098; PMCID: PMC8918788. 4: Mtambo SE, Ugbaja SC, Kumalo HM. Impact of the R292K Mutation on Influenza A (H7N9) Virus Resistance towards Peramivir: A Molecular Dynamics Perspective. Molecules. 2022 Mar 2;27(5):1645. doi: 10.3390/molecules27051645. PMID: 35268746; PMCID: PMC8912059. 5: Mtambo SE, Ugbaja SC, Mushebenge AG, Abubakar BH, Ntuli ML, Kumalo HM. Intermolecular Mechanism and Dynamic Investigation of Avian Influenza H7N9 Virus' Susceptibility to E119V-Substituted Peramivir-Neuraminidase Complex. Molecules. 2022 Mar 2;27(5):1640. doi: 10.3390/molecules27051640. PMID: 35268741; PMCID: PMC8911867. 6: Cies JJ, Moore WS 2nd, Marino D, Deacon J, Enache A, Chopra A. Oxygenator impact on peramivir in extra-corporeal membrane oxygenation circuits. Perfusion. 2022 Feb 28:2676591211060975. doi: 10.1177/02676591211060975. Epub ahead of print. PMID: 35225084. 7: Kato M, Saisho Y, Tanaka H, Bando T. Improvement of respiratory symptoms and health-related quality of life with peramivir in influenza patients with chronic respiratory disease: Additional outcomes of a randomized, open-label study. Influenza Other Respir Viruses. 2021 Sep;15(5):651-660. doi: 10.1111/irv.12835. Epub 2021 Mar 8. PMID: 33683019; PMCID: PMC8404055. 8: Fang YH, Hsu TH, Lin TY, Liu CH, Chou SC, Wu JY, Perng PC. Comparing intravenous peramivir with oral oseltamivir for patients with influenza: a meta- analysis of randomized controlled trials. Expert Rev Anti Infect Ther. 2021 Aug;19(8):1039-1046. doi: 10.1080/14787210.2021.1878025. Epub 2021 Mar 1. PMID: 33641583. 9: Chen HD, Wang X, Yu SL, Ding YH, Wang ML, Wang JN. Clinical Effectiveness of Intravenous Peramivir Compared With Oseltamivir in Patients With Severe Influenza A With Primary Viral Pneumonia: A Randomized Controlled Study. Open Forum Infect Dis. 2020 Nov 18;8(1):ofaa562. doi: 10.1093/ofid/ofaa562. PMID: 33447633; PMCID: PMC7793458. 10: Twabela A, Okamatsu M, Matsuno K, Isoda N, Sakoda Y. Evaluation of Baloxavir Marboxil and Peramivir for the Treatment of High Pathogenicity Avian Influenza in Chickens. Viruses. 2020 Dec 8;12(12):1407. doi: 10.3390/v12121407. PMID: 33302389; PMCID: PMC7762593. 11: Hsieh YH, Dugas AF, LoVecchio F, McBryde B, Ricketts EP, Saliba-Shaw K, Rothman RE. Intravenous peramivir vs oral oseltamivir in high-risk emergency department patients with influenza: Results from a pilot randomized controlled study. Influenza Other Respir Viruses. 2021 Jan;15(1):121-131. doi: 10.1111/irv.12794. Epub 2020 Oct 2. PMID: 33006445; PMCID: PMC7767951. 12: Ding H, Wu S, Dai X, Gao Y, Niu Y, Fang N, Song Y, Zhang M, Wang X, Chen T, Zhang G, Wu J, Li Y, Han J. Pharmacokinetic behavior of peramivir in the plasma and lungs of rats after trans-nasal aerosol inhalation and intravenous injection. Biomed Pharmacother. 2020 Sep;129:110464. doi: 10.1016/j.biopha.2020.110464. Epub 2020 Jul 11. PMID: 32768954. 13: Kato M, Saisho Y, Tanaka H, Bando T. Effect of peramivir on respiratory symptom improvement in patients with influenza virus infection and pre-existing chronic respiratory disease: Findings of a randomized, open-label study. Influenza Other Respir Viruses. 2021 Jan;15(1):132-141. doi: 10.1111/irv.12788. Epub 2020 Jul 17. PMID: 32677375; PMCID: PMC7767948. 14: Harada N, Shibata W, Koh H, Takashita E, Fujisaki S, Okamura H, Nanno S, Yamada K, Nakamae H, Hino M, Kakeya H. Successful treatment with baloxavir marboxil of a patient with peramivir-resistant influenza A/H3N2 with a dual E119D/R292K substitution after allogeneic hematopoietic cell transplantation: a case report. BMC Infect Dis. 2020 Jul 6;20(1):478. doi: 10.1186/s12879-020-05205-1. PMID: 32631240; PMCID: PMC7339380. 15: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Peramivir. 2020 Jun 22. PMID: 31643183. 16: Lee JS, Lee MS, Park Y, Lee J, Joo EJ, Eom JS. Clinical Effectiveness of Intravenous Peramivir versus Oseltamivir for the Treatment of Influenza in Hospitalized Patients. Infect Drug Resist. 2020 May 19;13:1479-1484. doi: 10.2147/IDR.S247421. PMID: 32547116; PMCID: PMC7245436. 17: Takashita E, Yasui Y, Nagata S, Morita H, Fujisaki S, Miura H, Shirakura M, Kishida N, Nakamura K, Kuwahara T, Sugawara H, Sato A, Akimoto M, Kaido T, Watanabe S, Hasegawa H; Influenza Virus Surveillance Group of Japan. Detection of a Peramivir-Resistant Influenza B/Yamagata-Lineage Virus Imported from Indonesia in Aichi, Japan, March 2019. Jpn J Infect Dis. 2020 Sep 24;73(5):386-390. doi: 10.7883/yoken.JJID.2020.084. Epub 2020 May 29. PMID: 32475875. 18: Yoshimura Y, Sasaki H, Horiuchi H, Miyata N, Kawakami C, Usuku S, Tachikawa N. Early combination treatment with baloxavir and peramivir for hospitalized adults with influenza A in Yokohama, Japan. Eur J Clin Microbiol Infect Dis. 2020 Sep;39(9):1637-1640. doi: 10.1007/s10096-020-03888-7. Epub 2020 Apr 14. PMID: 32291543. 19: Chen JY, Wei SK, Lai CC, Weng TS, Wang HH. A Meta-Analysis Comparing the Efficacy and Safety of Peramivir with Other Neuraminidase Inhibitors for Influenza Treatment. Medicina (Kaunas). 2020 Feb 5;56(2):63. doi: 10.3390/medicina56020063. PMID: 32033501; PMCID: PMC7073584. 20: Witcher R, Tracy J, Santos L, Chopra A. Outcomes and Adverse Effects With Peramivir for the Treatment of Influenza H1N1 in Critically Ill Pediatric Patients. J Pediatr Pharmacol Ther. 2019 Nov-Dec;24(6):497-503. doi: 10.5863/1551-6776-24.6.497. PMID: 31719811; PMCID: PMC6836703.