Peramivir

Peramivir

Clinical data
Trade names	Rapivab
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Intravenous
ATC code	None
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	100% (IV)
Biological half-life	7.7 to 20.8 hours (in patients with normal renal function)
Excretion	Kidney
Identifiers
IUPAC name (1S,2S,3R,4R)-3-[(1S)-1-(Acetylamino)-2-ethylbutyl]-4-(carbamimidoylamino)-2-hydroxycyclopentanecarboxylic acid
CAS Number	330600-85-6 Y trihydrate: 1041434-82-5 Y
PubChem CID	151164
ChemSpider	135903 N
UNII	9ZS94HQO3B trihydrate: QW7Y7ZR15U Y
ChEBI	CHEBI:85202 N
ChEMBL	CHEMBL332608 Y
Chemical and physical data
Formula	C15H28N4O4
Molar mass	328.40722 g/mol
3D model (Jmol)	Interactive image
SMILES CCC(CC)[C@@H]([C@H]1[C@@H](C[C@@H]([C@H]1O)C(=O)O)NC(=N)N)NC(=O)C
InChI 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 N Key:XRQDFNLINLXZLB-CKIKVBCHSA-N N
NY (what is this?)

Peramivir (trade name Rapivab) is an antiviral drug developed by BioCryst Pharmaceuticals 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. It is approved for intravenous administration.

In October 2009, the U.S. Food and Drug Administration (FDA) issued an emergency use authorization (EUA) for the use of peramivir based on safety data from phase I, phase II, and limited phase III trial data. The emergency use authorization for peramivir expired in June 2010. On 19 December 2014, the FDA approved peramivir to treat influenza infection in adults.

Peramivir has also been approved in Japan and South Korea and is available in Japan as Rapiacta and in South Korea as Peramiflu. As of 2015, it is the only intravenous option for treating swine flu.

An intramuscular (IM) peramivir phase II study for seasonal influenza in 2008–2009 found no effect for the primary endpoint of improvement in the median time to alleviation of symptoms in subjects with confirmed, acute, uncomplicated influenza infection versus placebo.

In October 2009, it was reported that the experimental antiviral drug peramivir had been "life-saving" effective in intravenous treating 8 serious cases of swine flu. On October 23, the U.S. Food and Drug Administration (FDA) issued an Emergency Use Authorization for peramivir, allowing the use of the drug in intravenous form for hospitalized patients only in cases where the other available methods of treatment are ineffective or unavailable; for instance, if oseltamivir resistance develops and a person is unable to take zanamivir via the inhaled route. The U.S. government (department of Health and Human Services) gave BioCryst Pharmaceuticals more than $77 million to finish the Phase III clinical development of peramivir. In 2009 the department of Health and Human Services had already given about $180 million to the program. Biocryst also donated 1200 courses of treatment to the US department of Health and Human Services. The Emergency Use Authorization expired on June 23, 2010. In 2011 a phase III trial found the median durations of influenza symptoms were the same with 1 intravenous injection of peramivir against 5 days of oral oseltamivir for people with seasonal influenza virus infection.