BCX4430

BCX4430
Legal status

Legal status	Investigational New Drug
Identifiers
IUPAC name (2S,3S,4R,5R)-2-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
CAS Number	222631-44-9^Y
PubChem (CID)	69211190
ChemSpider	8620968
UNII	OLF97F86A7^Y
Chemical and physical data
Formula	C₁₁H₁₅N₅O₃
Molar mass	265.268
3D model (Jmol)	Interactive image
SMILES O[C@H]3[C@H](c2c1ncnc(N)c1nc2)N[C@H](CO)[C@H]3O
InChI InChI=1S/C11H15N5O3/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15)/t5-,7+,9-,10+/m1/s1 Key:AMFDITJFBUXZQN-KUBHLMPHSA-N

BCX4430 (Immucillin-A) is an antiviral drug, an adenosine analog^[1] (a type of nucleoside analog).^[2] It is developed by BioCryst Pharmaceuticals with funding from NIAID, originally intended as a treatment for Hepatitis C, but subsequently developed as a potential treatment for deadly filovirus infections such as Ebola virus disease and Marburg virus disease. It also shows broad-spectrum antiviral effectiveness against a range of other RNA virus families, including bunyaviruses, arenaviruses, paramyxoviruses, coronaviruses and flaviviruses. BCX4430 has been demonstrated to protect against both Ebola and Marburg viruses in both rodents and monkeys, even when administered up to 48 hours after infection,^[1] and development for use in humans is being fast-tracked due to concerns about the lack of treatment options for the 2013-2016 Ebola virus epidemic in West Africa.^[3] BCX4430 also showed efficacy against Zika virus in a mouse model, though there are no plans for human trials at this stage.^[4]

References

1 2 Warren, T. K.; Wells, J.; Panchal, R. G.; Stuthman, K. S.; Garza, N. L.; Van Tongeren, S. A.; Dong, L.; Retterer, C. J.; Eaton, B. P.; Pegoraro, G.; Honnold, S.; Bantia, S.; Kotian, P.; Chen, X.; Taubenheim, B. R.; Welch, L. S.; Minning, D. M.; Babu, Y. S.; Sheridan, W. P.; Bavari, S. (2014). "Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430". Nature. 508 (7496): 402. doi:10.1038/nature13027. PMID 24590073.
↑ Kamat SS, Burgos ES, Raushel FM. Potent inhibition of the C-P lyase nucleosidase PhnI by Immucillin-A triphosphate. Biochemistry. 2013 Oct 22;52(42):7366-8. DOI 10.1021/bi4013287 PMID 24111876
↑ BioWar Lab Helping To Develop Treatment For Ebola. Paul Rodgers, Forbes Magazine. 8 April 2014
↑ Julander JG, Siddharthan V, Evans J, Taylor R, Tolbert K, Apuli C, Stewart J, Collins P, Gebre M, Neilson S, Van Wettere A, Lee YM, Sheridan WP, Morrey JD, Babu YS. Efficacy of the broad-spectrum antiviral compound BCX4430 against Zika virus in cell culture and in a mouse model. Antiviral Res. 2016 Nov 9. pii: S0166-3542(16)30665-9. doi: 10.1016/j.antiviral.2016.11.003. PMID 27838352

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir Faldaprevir^‡ Grazoprevir Paritaprevir Simeprevir Telaprevir

NS5A inhibitors (–asvir)	Daclatasvir Elbasvir Ledipasvir MK-3682 MK-8408 Odalasvir^† Ombitasvir Ravidasvir^† Samatasvir^† Velpatasvir

NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Dasabuvir Deleobuvir^§ Filibuvir^§ Setrobuvir^§ Sofosbuvir Radalbuvir^†

Combination drugs	Elbasvir/grazoprevir Ledipasvir/sofosbuvir Ombitasvir/paritaprevir/ritonavir Sofosbuvir/daclatasvir Velpatasvir/sofosbuvir

Anti-influenza agents

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^#

Multiple/unknown	BCX4430^† Favipiravir GS-5734^† Mericitabine^† MK-608^§ NITD008^§ Moroxydine Ribavirin^#/Taribavirin^† Triazavirin

Ebolavirus

Species	Bundibugyo ebolavirus (BDBV) Reston ebolavirus (RESTV) Sudan ebolavirus (SUDV) Taï Forest ebolavirus (TAFV) Zaire ebolavirus (EBOV)

Outbreaks	List of Ebola outbreaks 1976 Sudan outbreak 1976 Zaire outbreak 2013−2016 West African Ebola virus epidemic Timeline Responses United Nations Ebola Response Fund Operation United Assistance in Guinea in Liberia in Mali in Sierra Leone in Spain in the United States in the United Kingdom Ouse to Ouse Tock Womey Massacre 2014 DR Congo outbreak

Drug candidates	BCX4430 Brincidofovir DZNep Favipiravir FGI-103 FGI-104 FGI-106 JK-05 Lamivudine Triazavirin ZMapp Vaccines cAd3-ZEBOV VSV-EBOV

Failed drug candidates	TKM-Ebola

Notable people	William Close Peter Piot Notable patients Ameyo Adadevoh Kent Brantly Pauline Cafferkey Thomas Eric Duncan Sheik Umar Khan Matthew Lukwiya Patrick Sawyer

In popular culture	The Hot Zone (1995 book) Outbreak (1995 film) Ebola Syndrome (1996 film) Executive Orders (1996 novel) 93 Days (2016 film)

Miscellaneous	Ebola virus disease Ebola River

Marburgvirus

Species	Marburg marburgvirus MARV RAVV

Drug candidates	BCX4430 FGI-103 FGI-106

In popular culture	The Hot Zone (1995 book)

Miscellaneous	Marburg virus disease Marburg

"Cuevavirus"
(proposed inclusion)

Species	"Lloviu cuevavirus" (LLOV)

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