Download Current Antiviral Drugs

Appendix II
Current Antiviral
Drugs
Note that while this table is as extensive as
was possible at the time of writing, it is not
possible to provide details of all antiviral
drugs that may be available worldwide
since approval status and/or availability
varies between countries. Some of the drugs
listed (e.g. brivudine, inosine pranobex,
rimantadine, and tromantadine) may be
available in a limited range of countries.
About the chapter opener image
Dengue Virus
(Courtesy of the Research Collaboratory
for Structural Bioinformatics Protein
Data Bank and David S. Goodsell, The
Scripps Research Institute, USA.)
Chemical name*
[(1R)-4-[2-amino-6(cyclopropylamino)
purin-9-yl]-1cyclopent-2-enyl]
methanol
2-amino-9-(2hydroxyethoxymethyl)-3,9-dihydro6H-purin-6-one
{[2-(6-amino-9H-purin9-yl)ethoxy]methyl}
phosphonic acid
Adamantan-1-amine
Tetrahydrofuran-3yl[3-[(4-aminophenyl)
sulfonyl-(2methylpropyl)
amino]-1-benzyl2-hydroxy-propyl]
aminomethanoate
Abacavir (Ziagen)
Aciclovir (Zovirax,
Zovir)
Adefovir dipivoxil
(Preveon,
Hepsera)
Amantadine
(Symmetrel)
Amprenavir
(Agenerase)
Human immunodeficiency virus
(Retroviridae)
Influenza A virus
(Orthomyxoviridae)
Protease inhibitor,
replaced by
fosamprenavir
Ion channel inhibitor,
interferes with
viral penetration
and uncoating,
may interfere with
assembly
Reverse transcriptase
inhibitor (nucleotide
analog, chain
terminator)
DNA polymerase
inhibitor (nucleoside
analog, chain
terminator)
Herpes simplex
virus, varicellazoster virus
(Herpesviridae)
Hepatitis B
virus (Hepadnaviridae)
Nucleoside analog
reverse transcriptase
inhibitor (chain
terminator)
Mode of action
Human immunodeficiency virus
(Retroviridae)
Virus target(s)
Oral
Oral
Oral
Oral, topical,
intravenous
Oral
Route of
administration
H2N
P
O
NH2
HO
HO
H2N
HN
N
H
N
N
O
Structure
O
O
N
S
O
N
N
O
N
N
N
N
NH2
OH
N
N
NH2
H
N
N
OH
O
OH
O
APPENDIX II
O
Drug name
(Trade name**)
284
Current Antiviral Drugs
5-[(E)-2-bromoethenyl]1-4S,5R)-4-hydroxy5-hydroxymethyl)
oxolan-2-yl]pyrimidine2,4-dione
[1-(4-amino-2-oxopyrimidin-1-yl)-3hydroxy-propan-2-yl]
oxymethyl-phosphonic
acid
(1R,5S,6R)-2,8dioxabicyclo[3.3.0]
oct-6-yl]N-[(2S,3R)-4[(4-aminophenyl)
sulfonyl-(2methylpropyl)amino]3-hydroxy-1-phenylbutan-2-yl]carbamate
Brivudine (Helpin,
Zerpex, Zonavir,
Zostex)
Cidofovir (Vistide)
Darunavir
(Prezista)
DNA polymerase
inhibitor (nucleotide
analog)
Cytomegalovirus
(Herpesviridae)
Protease inhibitor
DNA polymerase
inhibitor (nucleoside
analog)
Varicellazoster virus
(Herpesviridae)
Human immunodeficiency virus
(Retroviridae)
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
Oral
Intravenous
Oral
Oral
HO
HO
HO
O
HN
P
O
N
H
O
NH
Br
H
N
O
H
H
O
NH2
N
OH
N
N
H
O
H
N
N
OCH3
Current Antiviral Drugs
O
O
H
N
NH2
O
(S)
S
O
N
O
OH
O
HO
N
O
HO
CH3O
O
O
Methyl N-[(1S)-1[[[(2S,3S)-2-hydroxy3-[[(2S)-2- (methoxycarbonylamino)-3,3dimethyl-butanoyl]
amino]-4-phenylbutyl]-[(4-pyridin2-ylphenyl)methyl]
amino] carbamoyl]2,2-dimethyl-propyl]
carbamate
O
Atazanavir
(Reyataz)
APPENDIX II
285
Human immunodeficiency virus
(Retroviridae)
N-[2-[4-[3-(1methylethyl
amino) pyridin-2yl] piperazin-1-yl]
carbonyl-1H-indol-5-yl]
methanesulfonamide
9-[5-(hydroxymethyl)
oxolan-2-yl]-3H-purin6-one
Docosan-1-ol
8-chloro-5-(2cyclopropylethynyl)5-(trifluoromethyl)-4oxa-2-azabicyclo[4.4.0]
deca-7,9,11-trien-3-one
Delavirdine
(Rescriptor)
Didanosine
(Videx)
Docosanol
(Abreva)
Efavirenz (Sustiva,
Stocrin)
Human immunodeficiency virus
(Retroviridae)
Herpes
simplex virus
(Herpesviridae)
(and other
enveloped
viruses)
Non-nucleoside
reverse transcriptase
inhibitor
Fusion (entry)
inhibitor
Nucleoside analog
reverse transcriptase
inhibitor (competitive
and chain terminator)
Non-nucleoside
reverse transcriptase
inhibitor
Mode of action
Oral
Topical
Oral
Oral
Route of
administration
Cl
HO
HO
O
O
S
NH
Structure
F
H
N
O
O
OO
F
F
N
N
N
H
N
H
O
N
H
N
N
O
N
N
APPENDIX II
Human immunodeficiency virus
(Retroviridae)
Virus target(s)
Chemical name*
Drug name
(Trade name**)
286
Current Antiviral Drugs
4-amino-5-fluoro-1[2-(hydroxymethyl)1,3-oxathiolan-5-yl]pyrimidin-2-one
Acetyl-YTSLIHSLIEESQ
NQQEKNEQELLELDKW
ASLWNWF-amide
2-amino-9-[4-hydroxy3-(hydroxymethyl)2-methylidenecyclopentyl]-3H-purin6-one
4-[6-amino-5-bromo2-[(4-cyanophenyl)
amino] pyrimidin4-yl]oxy-3,5dimethylbenzonitrile
[2-(acetyloxymethyl)4-(2-aminopurin-9-yl)butyl]acetate
Emtricitabine
(Emtriva,
Coviracil)
Enfuvirtide
(Fuzeon)
Entecavir
(Baraclude)
Etravirine
(Intelence)
Famciclovir
(Famvir)
Herpes simplex
virus, varicellazoster virus
(Herpesviridae)
DNA polymerase
inhibitor; prodrug of
penciclovir
Non-nucleoside
reverse transcriptase
inhibitor
Reverse transcriptase
inhibitor (nucleoside
analog, multiple
inhibitory stages)
Hepatitis B virus
(Hepadnaviridae)
Human immunodeficiency virus
(Retroviridae)
Subcutaneous
Fusion inhibitor
(biomimetic peptide)
Human immunodeficiency virus
(Retroviridae)
Oral
Oral
Oral
Oral
Nucleoside analog
reverse transcriptase
inhibitor (chain
terminator)
Human immunodeficiency virus
(Retroviridae)
S
O
N
N
O
N
O
O
O
N
N
N
H
O
N
N
O
N
O
Br
NH2
NH2
HN
N
N
N
HO
N
H2N
HO
N
Structure too large to show in print. Please see http://www.
garlandscience.com/viruses
HO
F
NH2
APPENDIX II
Current Antiviral Drugs
287
Chemical name*
(21 base antisense
phosphorothioate
oligonucleotide)
Drug name
(Trade name**)
Fomivirsen
(Vitravene)
Cytomegalovirus
(Herpesviridae)
Virus target(s)
Inhibits expression
of the IE genes of
cytomegalovirus
(mechanism disputed)
Mode of action
Intravitreal
Route of
administration
H2N
O
H2N
O
O
H2N
H2N
O
N
H
N
N
H
N
H
N
N
N
H
N
H
N
N
N
O
N
O
N
O
N
O
N
O
N
O
N
O
N
O
N
O
N
O
O
O
O
O
O
O
O
O
O
O
O
O
S
S
S
S
S
S
S
S
HO
S
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
O P
O
OH
S
HO
P O
HO
HO
P O
O P
O
OH
S
O
O
O
O
O
O
O
O
O P
O
OH
S
S
HO
O
O
O
N
N
N
N
N
N
O
N
O
N
O
N
O
N
O
N
N
N
O
H2N
H2N
N
N
H2N
H2N
O
O
O
O
O
O
O
O
N
H2N
N
NH
N
NH
H
N
H
N
N
H
N
H
N
O
O
O
NH2
O
O
O
O
O
O
O
N
NH
H
N
N
NH
N
NH
APPENDIX II
O
H 2N
Structure
288
Current Antiviral Drugs
[(2R,3S)-1-[(4aminophenyl)
sulfonyl-(2methylpropyl)amino]3-{[(3S)-oxolan-]3-yl
oxycarbonylamino}4-phenyl-butan-2-yl]
oxyphosphonic acid
Trisodium phosphonoformate hexahydrate
2-amino-9-(1,3dihydroxypropan-2yloxymethyl)-3H-purin6-one propoxymethyl)
guanine
1-[(2R,4S,5R)4-hydroxy-5(hydroxymethyl)
oxolan-2-yl]-5-iodopyrimidine-2,4-dione
1-isobutyl-1H-imidazo
[4,5-c]quinolin-4-amine
Fosamprenavir
(Lexiva)
Foscarnet
(Foscavir)
Ganciclovir
(Cymevene,
Cytovene,
Vitrasert)
Idoxuridine
(Herplex
Liquifilm, Stoxil)
Imiquimod
(Aldara)
Papillomaviruses
(Papovaviridae)
Indirect action;
stimulation of the
innate immune
system via Toll-like
receptors
Incorporated into
DNA, disrupts
transcription
and translation
(nucleoside analog)
DNA polymerase
inhibitor (competitive,
nucleoside analog,
chain terminator
only after multiple
incorporation)
Cytomegalovirus
(Herpesviridae)
Herpes
simplex virus
(Herpesviridae)
Intravenous
DNA polymerase
inhibitor
(noncompetitive,
at pyrophosphate
binding site)
Herpes
simplex virus,
other human
herpesviruses
(Herpesviridae)
Topical
Ophthalmic
Oral,
intravenous,
intravitreal
Oral
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
(prodrug of and
replacement for
amprenavir)
N
HO
H2N
HO
O
H2N
N
N
O
Ii
OH
O
NH2
N
H
N
P OH
O
OH
O
N
N
S
N
O
O
N
O
NH
O
HO
O
P
N
H
O
OH
OH
HO
O
O
O
APPENDIX II
Current Antiviral Drugs
289
Chemical name*
1-[2-hydroxy-4-[(2hydroxy-2,3-dihydro1H-inden-1-yl)
carbamoyl]-5-phenylpentyl]-4-(pyridin3-ylmethyl)-N-tertbutyl-piperazine-2carboxamide
9-[(2R,3R,4S,5R)3,4-dihydroxy-5(hydroxylmethyl)
oxolan-2-yl]-3H-purin6-one (inosine) plus
acetamidobenzoic acid
and dimethylaminoisopropanol
(Antiviral protein)
L-2¢,3¢-dideoxy-3¢thiacytidine
Drug name
(Trade name**)
Indinavir
(Crixivan)
Inosine pranobex
(Imunovir,
isoprinosine)
Interferon
alfa (IntronA,
Roferon-A,
Viraferon;
pegylated
as Pegasys,
PegIntron,
ViraferonPeg)
Lamivudine
(Epivir)
Human immunodeficiency virus
(Retroviridae),
Hepatitis B virus
(Hepadnaviridae)
Hepatitis B virus
(Hepadnaviridae),
Hepatitis C virus
(Flaviviridae),
Papillomaviruses
(Papovaviridae),
Human
herpesvirus 8
(Herpesviridae)
Nucleoside analog
reverse transcriptase
inhibitor (chain
terminator)
Stimulation of cellmediated immunity
and induction of
cellular antiviral
state
Oral
Injection
(inhaled)
Oral
Indirect action;
stimulation of
immune system
(T cells)
N
H
HO
O
N
OH
O
NH
N
N
OH
N
OH
OH N
OH
O
O
HO
O
S
O
N
N
NH2
N
N
O
(Pegylated recombinant protein)
O
HO
HN
Structure
H
N
APPENDIX II
Herpes
simplex virus
(Herpesviridae),
Papillomaviruses
(Papovaviridae)
Oral
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
Route of
administration
Mode of action
Virus target(s)
290
Current Antiviral Drugs
(4S,5R,6R)-5acetamido-4carbamimidamido-6[(1R,2R)-3-hydroxy-2methoxypropyl]-5,6dihydro-4H-pyran-2carboxylic acid
(2S)-N-[(2S,4S,5S)-5-{[2(2,6-dimethylphenoxy)
acetyl]amino}-4hydroxy-1,6-diphenylhexan-2-yl]-3-methyl2-(2-oxo-1,3-diazinan1-yl)butanamide
4,4-difluoro-N-{(1S)-3[3-(3-isopropyl-5methyl-4H-1,2,4-triazol4-yl)-8-azabicyclo[3.2.1]
oct-8-yl]-1-phenylpropyl}
cyclohexanecarboxamide
Laninamivir
Lopinavir (with
ritonavir as
Kaletra)
Maraviroc
(Selzentry)
Human immunodeficiency virus
(Retroviridae)
Human immunodeficiency virus
(Retroviridae)
Influenza A and
B (Orthomyxoviridae)
Oral
Oral
Protease inhibitor
Chemokine receptor
antagonist (CCR5)
Inhaled
Neuraminidase
inhibitor
NH
NH
O
NH
F F
O
H2N
NH
H
O H
O
N
O
HN
O
O
H
N
H
H
O
N
O
HN
O
OH
OH
OH
N
N
N
APPENDIX II
Current Antiviral Drugs
291
Chemical name*
2-[2-hydroxy3-(3-hydroxybenzoyl)amino4-phenylsulfanylbutyl]-N-tertyl1,2,3,4,4a,5,6,7,8,8ahydroisoquinoline-3oxamide
1-cyclopropyl-5,11dihydro-4-methyl-6Hdipyrido [3,2-b:2¢,3¢-e]
[1,4] diazepin-6-one
(3R,4R,5S)-4acetylamino-5-amino3-(1-ethylpropoxy)1-cyclohexene-1carboxylic acid ethyl
ester
(Monoclonal antibody)
2-amino-9-[4-hydroxy3-(hydroxymethyl)
butyl]-3H-purin-6-one
Drug name
(Trade name**)
Nelfinavir
(Viracept)
Nevirapine
(Viramune)
Oseltamivir
(Tamiflu)
Palivizumab
(Synagis)
Penciclovir
(Denavir, Fenistil)
Non-nucleoside
reverse transcriptase
inhibitor
Human immunodeficiency virus
(Retroviridae)
Herpes
simplex virus
(Herpesviridae)
Respiratory
syncytial virus
(Paramyxoviridae)
DNA polymerase
inhibitor (nucleoside
analog)
Uptake inhibitor
(neutralizing antibody)
Neuraminidase
inhibitor
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
Oral
Injection
Oral
Oral
Oral
Route of
administration
H2N
HN
O
N
H
N
N
HO
N
O
S
H
N
O
O
N
H
O
O
N
N
NH2
NH
N
OH
OH
(Humanized monoclonal antibody)
O
N
O
H
H
Structure
OH
APPENDIX II
Influenza A and
B (Orthomyxoviridae)
Mode of action
Virus target(s)
292
Current Antiviral Drugs
Human immunodeficiency virus
(Retroviridae)
Respiratory
syncytial virus
(Paramyxoviridae), Lassa
fever virus
(Arenaviridae),
yellow fever
virus, hepatitis
C virus
(Flaviviridae) (in
combination
with interferon
alfa), other
viruses inhibited
in vitro
N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy1-methyl-6-oxo-1,
6-dihydro-pyrimidin2-yl)propan-2-yl)5-methyl-1,3,4oxadiazole-2carboxamide
1-b-Dribofuranosyl-1,2,4
triazole 3-carboxamide
1-(1-adamantyl)
ethanamine
Raltegravir
(Isentress)
Ribavirin
(Copegus,
Rebetol,
Ribasphere,
Vilona, Virazole,
and generics)
Rimantadine
(Flumadine)
Influenza A
(Orthomyxoviridae)
Influenza A and
B (Orthomyxoviridae)
(1S,2S,3S,4R)-3[(1S)-1-acetamido2-ethyl-butyl]-4(diaminomethylideneamino)-2hydroxy-cyclopentane1-carboxylic acid
Peramivir
Oral
Oral, inhaled
Several proposed,
none certain
(ribonucleoside
analog)
As amantadine
Oral
Intravenous
Integrase inhibitor
Neuraminidase
inhibitor
H3C
HO
H 3C
HN
O
O
N
N
H
OH
N
NH2
HN
H H
N
H
N
N
N
O
O H C CH
3
3
H
N
N
OH
OH
H3C
O
OH
O
NH2
N
O
O
OH
H
N
F
APPENDIX II
Current Antiviral Drugs
293
1-[5-(hydroxymethyl)2,5-dihydrofuran2-yl]-5-methyl-1Hpyrimidine-2,4-dione
Stavudine (Zerit)
Human immunodeficiency virus
(Retroviridae)
Human immunodeficiency virus
(Retroviridae)
N-[1-benzyl-2hydroxy-3-[3-(tertbutylcarbamoyl)1,2,3,4,4a,5,6,7,8,8adecahydroisoquinolin2-yl]-propyl]2-quinolin-2ylcarbonylaminobutanediamide
Saquinavir
(Fortovase,
Invirase)
Nucleoside analog
reverse transcriptase
inhibitor (chain
terminator)
Oral
Oral
Oral
Route of
administration
HO
O
S
HN
O
H3C
O
HN
H2N
N
Structure
HN
N
N
O
N
O
NH
O
O
OH
H
N
OH H
N
NH
O
O
O
N
H3C N
S
O
APPENDIX II
Protease inhibitor
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
1,3-thiazol-5ylmethyl[3-hydroxy-5[3-methyl-2-[methyl[(2-propan-2-yl-1,3thiazol- 4-yl)methyl]
carbamoyl]aminobutanoyl]amino-1,6diphenyl-hexan-2-yl]
aminoformate
Ritonavir (Norvir)
Mode of action
Virus target(s)
Chemical name*
Drug name
(Trade name**)
294
Current Antiviral Drugs
Herpes
simplex virus
(Herpesviridae)
Herpes
simplex virus
(Herpesviridae)
1-[4-hydroxy-5(hydroxymethyl)
oxolan-2-yl]-5(trifluoromethyl)
pyrimidine-2,4-dione
N-1-adamantyl-N[2-(dimethylamino)
ethoxy] acetamide
Trifluorothymidine
(trifluridine,
Viroptic)
Tromantadine
(Viru-Merz)
Alters glycosylation,
disrupts virus entry
and uncoating
Incorporated into DNA,
disrupts transcription
and translation
(nucleoside analog)
Protease inhibitor
Human immunodeficiency virus
(Retroviridae)
[R-(R*,R*)]-N-[3-[1-[5,6dihydro-4-hydroxy-2oxo-6- (2-phenylethyl)6-propyl-2H-pyran-3-yl]
propyl]phenyl]-5(trifluoromethyl)-2pyridinesulfonamide
Tipranavir
(Aptivus)
Nucleotide analog
reverse transcriptase
inhibitor (chain
terminator)
Human immunodeficiency virus
(Retroviridae)
({[(2R)-1-(6-amino-9Hpurin-9-yl)propan2-yl]oxy}methyl)
phosphonic acid
Tenofovir
(as tenofovir
disoproxil
fumarate, Viread)
Topical
Ophthalmic
Oral
Oral
O
HO
O
HN
F
F
N
N
O
F
F
O
O
N
HO O
HO P
O
F
O
OH
F
S
H
N
H3C
O
N
HO
N
N
O
N
NH
NH22
O
N
APPENDIX II
Current Antiviral Drugs
295
Chemical name*
2-[(2-amino-6-oxo3,9-dihydropurin-9-yl)
methoxy]ethyl-2amino-3-methylbutanoate
2-[(2-amino-6-oxo3,6-dihydro-9Hpurin-9-yl)methoxy]3-hydroxypropyl
(2S)-2-amino-3methylbutanoate
2-(6-aminopurin-9yl)-5-(hydroxymethyl)
oxolane-3,4-diol
hydrate
Drug name
(Trade name**)
Valaciclovir
(Valtrex)
Valganciclovir
(Valcyte)
Vidarabine,
adenosine
arabinoside
(Ara-A, Vira-A)
DNA synthesis
inhibitor
(unknown method,
ribonucleoside
analog)
DNA polymerase
inhibitor (competitive;
prodrug of ganciclovir)
Cytomegalovirus
(Herpesviridae)
Intravenous,
ophthalmic
Oral
Oral
Route of
administration
HO
H2N
H2N
N
O
H
N
N
OH
HN
O
Structure
OH
N
NH2
O
N
N
N
N
O
O
N
O
H
H2N
HO
CH3
O
H3C
N
N
O
O
O
O
CH3
NH2
CH3
APPENDIX II
Herpes simplex
virus, varicellazoster virus
(Herpesviridae).
Other viruses in
vitro
DNA polymerase
inhibitor (chain
terminator; prodrug of
acyclovir)
Mode of action
Herpes simplex
virus, varicellazoster virus
(Herpesviridae)
Virus target(s)
296
Current Antiviral Drugs
5-acetamido-4guanidino-6-(1,2,3trihydroxypropyl)-5,6dihydro-4H-pyran-2carboxylic acid
1-[(2R,4S,5S)-4-azido5-(hydroxymethyl)
oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Zanamivir
(Relenza)
Zidovudine
(Retrovir, Retrovis)
Nucleoside analog
reverse transcriptase
inhibitor (chain
terminator)
Oral
Inhaled
Neuraminidase
inhibitor
Influenza A and
B (Orthomyxoviridae)
Human immunodeficiency virus
(Retroviridae)
Oral
Nucleoside analog
reverse transcriptase
inhibitor (competitive
and chain terminator)
Human immunodeficiency virus
(Retroviridae)
O
N–- N+ N
O
HN
N
O
N
O
NH
NH2
O
H
OH
O HN
HO H
N
HO
HO
HO
N
NH2
COOH
O
** Trade names used here are trademarks (™) or registered trademarks (®).
* The formal IUPAC naming system is used here for reasons of standardization, rather than the simpler and possibly more informative names that are sometimes used elsewhere
(for example, in Figures 6.5 and 6.9).
4-amino-1-[(2R,5S)5-(hydroxymethyl)
oxolan-2-y1]-1,2dihydropyrimidin-2one
Zalcitabine (Hivid)
APPENDIX II
Current Antiviral Drugs
297