Peramivir
- CAS No.
- 330600-85-6
- Chemical Name:
- Peramivir
- Synonyms
- Bcx-1812;Rapiacta;PeraMiviv;Peramivir;Aids114230;Rwj-270201;Aids-114230;Peramivir Monomer;Peramivir(BCX-1812);Paramivir waterless
- CBNumber:
- CB41457720
- Molecular Formula:
- C15H28N4O4
- Molecular Weight:
- 328.41
- MDL Number:
- MFCD09837902
- MOL File:
- 330600-85-6.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 170 - 172°C (dec.) |
|---|---|
| Density | 1.39 |
| storage temp. | 2-8°C |
| solubility | Methanol (Slightly, Heated), Water (Slightly) |
| pka | 4.08±0.70(Predicted) |
| form | Solid |
| color | White to Off-White |
| InChIKey | XRQDFNLINLXZLB-CKIKVBCHSA-N |
| SMILES | [C@H]1(C(O)=O)C[C@@H](NC(N)=N)[C@H]([C@@H](NC(C)=O)C(CC)CC)[C@@H]1O |
| FDA UNII | 9ZS94HQO3B |
| ATC code | J05AH03 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | |||||||||
| NFPA 704 |
|
Peramivir price More Price(50)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 23765 | Peramivir ≥98% | 330600-85-6 | 1mg | $54 | 2026-04-30 | Buy |
| Cayman Chemical | 23765 | Peramivir ≥98% | 330600-85-6 | 5mg | $223 | 2026-04-30 | Buy |
| Cayman Chemical | 23765 | Peramivir ≥98% | 330600-85-6 | 10mg | $418 | 2026-04-30 | Buy |
| Cayman Chemical | 23765 | Peramivir ≥98% | 330600-85-6 | 25mg | $913 | 2026-04-30 | Buy |
| TRC | TRC-P285500-1MG | Peramivir | 330600-85-6 | 1mg | $244 | 2026-06-03 | Buy |
Peramivir Chemical Properties, Uses, Production
Description
Peramivir is a neuraminidase (NA) inhibitor that was approved in Japan in 2010 for treatment of patients with influenza. It is the only NA inhibitor available for IV use and is the first of two NA inhibitors approved in 2010, the second being the inhaled drug laninamivir octanoate . Peramivir is the only NA inhibitor approved for IV use,which gives it a unique place in influenza treatment for seriously ill patients. Peramivir was discovered using structure-based drug design and is synthesized in six steps from Boc-protected methyl (1S,4R)-4-amino-cyclopent-2-enecarboxylate, which is prepared from 2-azabicyclo[2.2.1]hept-5-en-3-one. Cycloaddition of the cyclopentene olefin with a nitrile oxide provided an intermediate fused cyclopentane-dihydroisoxazole. Hydrogenolysis and acetylation set up a fully functionalized cyclopentane with all four stereocenters established. Deprotection of the amine and acid groups was followed by installation of the guanidine moiety to provide peramivir. Like zanamivir and oseltamivir, peramivir is a potent inhibitor of influenza virus A and B NA [strain A(H1N1) IC50= 0.34 nM; strain A(H3N2) IC50= 0.60 nM; strain B IC50= 1.36 nM]. However, peramivir is less potent against oseltamivirresistant viruses that have the H275Y NA mutation. These viruses remain sensitive to zanamivir. Peramivir is active against influenza A and B viruses and has a lowenzymatic off-rate, suggesting that it could inhibitNAactivity for a prolonged period and allow lower frequency of dosing. Peramivir has proven efficacious in preclinical animal models of influenza infection.
Description
Peramivir is an inhibitor of influenza neuraminidase (IC50s = 0.09 and 11 nM for influenza A and B neuraminidases, respectively). It is selective for influenza neuraminidase over bacterial, mammalian, and other viral neuraminidases (IC50s = >300 μM). Peramivir inhibits neuraminidase activity in H1N1, H2N2, H3N2, and H6N2 influenza strains (IC50s = 0.09-1.1 nM) and reduces lysis of MDCK cells infected with influenza (EC50s = <0.01-21 nM). Pretreatment with peramivir (10-100 mg/kg) protects mice against lethal influenza infections. It also increases survival in ferrets infected intranasally with avian influenza type A H5N1 when injected intramuscularly after infection. Formulations containing peramivir have been used to treat influenza.
Chemical Properties
White to Off-White Solid
Originator
BioCryst Pharmaceuticals Inc. (United States)
Uses
A new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza.
Uses
Peramivir is a new antiviral agent for influenza treatment; it can be used as neuraminidase inhibitor for treating human and avian influenza
Definition
Peramivir is a member of the class of guanidines that is used (as its trihydrate) for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.
brand name
Rapiacta, PeramiFlu
Synthesis
Several syntheses of this drug have been reported and the improved route disclosed in a recent patent is described in the scheme. Ring opening of commercially available (à)-2- azabicyclo[2.2.1]hept-5-en-3-one (117) with methanolic HCl followed by classical resolution with Ltartaric acid gave the (1S,4R)-methyl ester 118 in 85% yield. Protection of 118 with Boc anhydride and TEA in CH2Cl2 afforded carbamate 119 in 90% yield. Alkene 119 was then subject to nitrone dipolar cycloaddition conditions involving 2-ethyl-N-hydroxybutanimidoyl chloride 120 and triethylamine, followed by the basic workup and then treatment with methanolic HCl, ultimately resulting in dihydroisoxazole 121. Interestingly, the nitrone generated from 120 approached alkene 119 from the less hindered face and proceeded with remarkable regioselectivity to provide azacycle 121 in 76% yield for the three step sequence. Treatment of 121 with 1.5 eq. lithium aluminum hydride resulted in rupture of the N-O bond within this system, which afforded the amino alcohol 122 in 81% yield. It should be noted that neither the Boc group or the methyl ester were reduced under these reaction conditions. Then, a one-pot three step sequence involving acetylation of the amino group, removal of the Boc group, and hydrolysis of the carboxylic ester followed by guanylation with pyrazolecarboxamidine hydrochloride (123) provided peramivir (X) in 82% yield over the final four steps.
References
[1] D. YOUNG K B C Fowler. RWJ-270201 (BCX-1812): a novel neuraminidase inhibitor for influenza.[J]. Philosophical Transactions of the Royal Society B: Biological Sciences, 2001, 25 1: 1905-1913. DOI: 10.1098/rstb.2001.1004
[2] NADEZHDA E. YUN . Injectable peramivir mitigates disease and promotes survival in ferrets and mice infected with the highly virulent influenza virus, A/Vietnam/1203/04 (H5N1)[J]. Virology, 2008, 374 1: Pages 198-209. DOI: 10.1016/j.virol.2007.12.029
Peramivir Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Chembest Research Laboratories Limited | 021-20908456 | sales@BioChemBest.com | China | 5996 | 61 |
| JinYan Chemicals(ShangHai) Co.,Ltd. | 13817811078 | sales@jingyan-chemical.com | China | 9963 | 60 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| BOC Sciences | 1-631-485-4226; 16314854226 | info@bocsci.com | United States | 9920 | 65 |
| Wuhan Fortuna Chemical Co., Ltd | 027-59207852 13308628970 | buy@fortunachem.com | China | 2684 | 58 |
| Shanghai T&W Pharmaceutical Co., Ltd. | +86 21 61551611 | China | 9874 | 58 | |
| Acesys Pharmatech | 18860950986 | tangmanman@zenjipharma.com | China | 1731 | 55 |
| Moltt Biocem Co., Ltd. | +86-21-38682181 15900741819 | China | 281 | 55 |
Related articles
- Side effects of Peramivir
- Peramivir (trade name Rapivab) is an antiviral drug developed by BioCryst Pharmaceuticals for the treatment of influenza.
- Apr 11,2022
View Latest Price from Peramivir manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-07-27 | Peramivir
330600-85-6
|
$30.00-106.00 | 99.90% | 10g | TargetMol Chemicals Inc. | ||
 |
2026-06-30 | Peramivir
330600-85-6
|
1kg | 99% | 10000KGS | Shaanxi Dideu New Materials Co. Ltd | ||
 |
2025-12-24 | Peramivir
330600-85-6
|
1KG | 99.0% | 1000 tons | Shaanxi Dideu Medichem Co. Ltd |
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