Peramivir
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MedKoo CAT#: 314258

CAS#: 330600-85-6 (free)

Description: 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. (http://en.wikipedia.org/wiki/Peramivir).


Chemical Structure

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Peramivir
CAS# 330600-85-6 (free)

Theoretical Analysis

MedKoo Cat#: 314258
Name: Peramivir
CAS#: 330600-85-6 (free)
Chemical Formula: C15H28N4O4
Exact Mass: 328.21106
Molecular Weight: 328.41
Elemental Analysis: C, 54.86; H, 8.59; N, 17.06; O, 19.49

Price and Availability

Size Price Availability Quantity
5.0mg USD 320.0 2 Weeks
10.0mg USD 560.0 2 Weeks
25.0mg USD 1150.0 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: >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: >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

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.

Recalculate based on batch purity %
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

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1: Peramivir (Rapivab): an IV neuraminidase inhibitor for treatment of influenza. Med Lett Drugs Ther. 2015 Feb 2;57(1461):17-9. PubMed PMID: 25629811.

2: Sato M, Ito M, Suzuki S, Sakuma H, Takeyama A, Oda S, Watanabe M, Hashimoto K, Miyazaki K, Kawasaki Y, Hosoya M. Influenza Viral Load and Peramivir Kinetics after Single Administration and Proposal of Regimens for Peramivir Administration against Resistant Variants. Antimicrob Agents Chemother. 2014 Dec 29. pii: AAC.04263-14. [Epub ahead of print] PubMed PMID: 25547357.

3: Komeda T, Ishii S, Itoh Y, Ariyasu Y, Sanekata M, Yoshikawa T, Shimada J. Post-marketing safety and effectiveness evaluation of the intravenous anti-influenza neuraminidase inhibitor peramivir (II): A pediatric drug use investigation. J Infect Chemother. 2014 Nov 26. pii: S1341-321X(14)00402-4. doi: 10.1016/j.jiac.2014.11.009. [Epub ahead of print] PubMed PMID: 25523716.

4: Hata A, Akashi-Ueda R, Takamatsu K, Matsumura T. Safety and efficacy of peramivir for influenza treatment. Drug Des Devel Ther. 2014 Oct 24;8:2017-38. doi: 10.2147/DDDT.S46654. eCollection 2014. PubMed PMID: 25368514; PubMed Central PMCID: PMC4216046.

5: Bentley ML, Hollistera AS, Hansenb AC, Smith JA, Cain JS. Peramivir pharmacokinetics in a patient receiving continuous veno-venous hemodiafiltration during the 2009 H1N1 influenza A pandemic. Int J Clin Pharmacol Ther. 2014 Dec;52(12):1105-11. doi: 10.5414/CP202161. PubMed PMID: 25345428.

6: Harada-Shirado K, Ikeda K, Furukawa M, Sukegawa M, Takahashi H, Shichishima-Nakamura A, Ohkawara H, Noji H, Kawabata K, Saito S, Ohto H, Ogawa K, Takeishi Y. Severe immune thrombocytopenia possibly elicited by the anti-influenza viral agent peramivir. Intern Med. 2014;53(20):2369-71. Epub 2014 Oct 15. PubMed PMID: 25318805.

7: Whitley R, Laughlin A, Carson S, Mitha E, Tellier G, Stich M, Elder J, Alexander WJ, Dobo S, Collis P, Sheridan WP. Single dose peramivir for the treatment of acute seasonal influenza: integrated analysis of efficacy and safety from two placebo-controlled trials. Antivir Ther. 2014 Oct 15. doi: 10.3851/IMP2874. [Epub ahead of print] PubMed PMID: 25318121.

8: Zhang D, Du A, Zhang L, Ma J, Meng L, Deng M, Xu J, Liu H. Pharmacokinetics of peramivir after single intravenous doses in healthy Chinese subjects. Xenobiotica. 2014 Sep 18:1-5. [Epub ahead of print] PubMed PMID: 25231091.

9: Komeda T, Ishii S, Itoh Y, Ariyasu Y, Sanekata M, Yoshikawa T, Shimada J. Post-marketing safety and effectiveness evaluation of the intravenous anti-influenza neuraminidase inhibitor peramivir (I): a drug use investigation. J Infect Chemother. 2014 Nov;20(11):689-95. doi: 10.1016/j.jiac.2014.07.006. Epub 2014 Aug 11. PubMed PMID: 25131292.

10: de Jong MD, Ison MG, Monto AS, Metev H, Clark C, O'Neil B, Elder J, McCullough A, Collis P, Sheridan WP. Evaluation of intravenous peramivir for treatment of influenza in hospitalized patients. Clin Infect Dis. 2014 Dec 15;59(12):e172-85. doi: 10.1093/cid/ciu632. Epub 2014 Aug 12. PubMed PMID: 25115871.

11: Kodama M, Yoshida R, Hasegawa T, Izawa M, Kitano M, Baba K, Noshi T, Seki T, Okazaki K, Tsuji M, Kanazu T, Kamimori H, Homma T, Kobayashi M, Sakoda Y, Kida H, Sato A, Yamano Y. The relationship between in vivo antiviral activity and pharmacokinetic parameters of peramivir in influenza virus infection model in mice. Antiviral Res. 2014 Sep;109:110-5. doi: 10.1016/j.antiviral.2014.06.016. Epub 2014 Jul 2. PubMed PMID: 24997412.

12: Park S, Kim JI, Lee I, Lee S, Hwang MW, Bae JY, Heo J, Kim D, Jang SI, Kim H, Cheong HJ, Song JW, Song KJ, Baek LJ, Park MS. Combination effects of peramivir and favipiravir against oseltamivir-resistant 2009 pandemic influenza A(H1N1) infection in mice. PLoS One. 2014 Jul 3;9(7):e101325. doi: 10.1371/journal.pone.0101325. eCollection 2014. PubMed PMID: 24992479; PubMed Central PMCID: PMC4081560.

13: Kitano M, Itoh Y, Ishigaki H, Nakayama M, Ishida H, Pham VL, Arikata M, Shichinohe S, Tsuchiya H, Kitagawa N, Kobayashi M, Yoshida R, Sato A, Le QM, Kawaoka Y, Ogasawara K. Efficacy of repeated intravenous administration of peramivir against highly pathogenic avian influenza A (H5N1) virus in cynomolgus macaques. Antimicrob Agents Chemother. 2014 Aug;58(8):4795-803. doi: 10.1128/AAC.02817-14. Epub 2014 Jun 9. PubMed PMID: 24913156; PubMed Central PMCID: PMC4135987.

14: Takemoto Y, Asai T, Ikezoe I, Yano T, Ichikawa M, Miyagawa S, Matsumoto J. Clinical effects of oseltamivir, zanamivir, laninamivir and peramivir on seasonal influenza infection in outpatients in Japan during the winter of 2012-2013. Chemotherapy. 2013;59(5):373-8. doi: 10.1159/000362436. Epub 2014 May 10. PubMed PMID: 24821568.

15: Leang SK, Kwok S, Sullivan SG, Maurer-Stroh S, Kelso A, Barr IG, Hurt AC. Peramivir and laninamivir susceptibility of circulating influenza A and B viruses. Influenza Other Respir Viruses. 2014 Mar;8(2):135-9. PubMed PMID: 24734292; PubMed Central PMCID: PMC4186459.

16: Yoshino Y, Seo K, Koga I, Kitazawa T, Ota Y. Clinical efficacy of peramivir in adult patients with seasonal influenza during the winter of 2012 in Japan. Clin Respir J. 2014 Mar 10. doi: 10.1111/crj.12129. [Epub ahead of print] PubMed PMID: 24612842.

17: Tran-To Su C, Ouyang X, Zheng J, Kwoh CK. Structural analysis of the novel influenza A (H7N9) viral Neuraminidase interactions with current approved neuraminidase inhibitors Oseltamivir, Zanamivir, and Peramivir in the presence of mutation R289K. BMC Bioinformatics. 2013;14 Suppl 16:S7. doi: 10.1186/1471-2105-14-S16-S7. Epub 2013 Oct 22. PubMed PMID: 24564719; PubMed Central PMCID: PMC3853198.

18: Tanaka A, Nakamura S, Seki M, Iwanaga N, Kajihara T, Kitano M, Homma T, Kurihara S, Imamura Y, Miyazaki T, Izumikawa K, Kakeya H, Yanagihara K, Kohno S. The effect of intravenous peramivir, compared with oral oseltamivir, on the outcome of post-influenza pneumococcal pneumonia in mice. Antivir Ther. 2014 Feb 12. doi: 10.3851/IMP2744. [Epub ahead of print] PubMed PMID: 24517996.

19: Takashita E, Ejima M, Itoh R, Miura M, Ohnishi A, Nishimura H, Odagiri T, Tashiro M. A community cluster of influenza A(H1N1)pdm09 virus exhibiting cross-resistance to oseltamivir and peramivir in Japan, November to December 2013. Euro Surveill. 2014 Jan 9;19(1). pii: 20666. PubMed PMID: 24434172.

20: Li X, Li Y, Wang J, Wang L, Zhong W, Ruan J, Zhang Z. Quantification of peramivir in dog plasma by liquid chromatography/tandem mass spectrometry employing precolumn derivatization. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jan 1;944:1-5. doi: 10.1016/j.jchromb.2013.10.027. Epub 2013 Nov 1. PubMed PMID: 24280376.