About Authors:
Mayure.Vijay Kumar*1, Mayure.Ashok2, Athiya Mohammadi1, C.P.Meher1
Department of pharmaceutical chemistry
1Maheshwara College of Pharmacy, Chitkul (V), Isnapur “X” Road, Patancheru, Hyderabad,
2Gokaraju Rangaraju College of pharmacy, Hyderabad.
*mayurevijaykumar@gmail.com
ABSTRACT:
Viruses are the ultimate expression of parasitism:they not only take nutrition fom the host cell but also direct its metabolic machinery to synthesize new virus particle. viral chemotherapy, therefore, is difficult, as it would require interference with cellular metabolism in the host. for the treatment of viral infection numerous drugs are developed yet,also so many drugs are undergoing research for this aspect. The presented review article is deals with the various antiviral drugs having different pharmacological effects along with the adverse effect associated with it.
REFERENCE ID: PHARMATUTOR-ART-1654
INTRODUCTION:
Most viral diseases, with the exception of those caused by Human immunodeficiency virus, are self-limited illnesses that do not require specific antiviral therapy. The currently available antiviral drugs target 3 main groups of viruses: Herpes, Hepatitis and Influenza viruses. With the exception of the antisense molecule fomivirsen, all antiherpes drugs inhibit viral replication by serving as competitive substrates for viral DNA polymerase. Drugs for the treatment of Influenza inhibit the ion channel M2 protein or the enzyme neuraminidase. Combination therapy with interferon-α and Ribavirin remains the backbone treatment for chronic hepatitis C; the addiction of serine protease inhibitors improves the treatment outcome of patients infected with hepatitis C virus genotype with interferon or a combination of nucleoside (t)ide analogues. Notably, almost all the nucleos(t)ide analogues for the treatment of chronic hepatitis B possess anti-human immunodeficiency virus properties, and they inhibit replication of hepatitis B virus by serving as competitive substrates for its DNA polymerase. Some antiviral drugs possess multiple potential clinical applications, such as ribavirin for the treatment of chronic hepatitis C and respiratory syncytial virus and cidofovir for the treatment of cytomegalovirus and other DNA viruses. Drug resistance is an emerging threat to the clinical utility of antiviral drugs. The major mechanisms for drug resistance are mutations in the viral DNA polymerase gene or in genes that encode for the viral kinases required for the activation of certain drugs such as acyclovir and ganciclovir. Widespread antiviral resistance has limited the clinical utility of M2 inhibitors for the prevention and treatment of influenza infections. This article provides an overview of clinically available antiviral drugs for the primary care physician, with a special focus on pharmacology, clinical uses, and adverse effects. Antiviral drugs were invented to prevent viral infections. They are one class of antimicrobial and harmless to human body. Instead of destroying the target pathogen, antiviral drugs inhibit proteins that contribute one or several steps in viral infection. It is difficult to invent new safe and effective antivirals because the harm to host cells must be taken in to consideration and variation of viruses.
Four classes of antivirals:
1) Neuraminidase inhibitors.
2) Protease inhibitors.
3) Neutralizing antibodies.
4) Protein-based fusion inhibitors.
|
NAME OF THE DRUG |
USES |
ADVERSE EFFECTS |
REFERENCE |
|
ABACAVIR: Trade name: Ziagen IUPAC name: {(1S, 4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl] cyclopent-2-en-1-yl} methanol. Chemical formula: C14H18N6O Molecular mass: 286.332 g/mol. Bioavailability: 83% Plasma half: 1.54±0.63h Melt. Point: 165oC |
Used to treat HIV and AIDS. It is also used in combination with other antiretroviral agents.
|
Fatal hypersensitivity. Anaphylaxis. Stevens Johnson syndrome. Pancreatitis. Erythema multiforme. |
Mallal S,et.al1 |
|
ACICLOVIR: Trade name: Zovirax IUPAC name: 2-amino-1, 9-dihydro-9-((2-hydroxyethoxy) methyl)-6H-purin-6-one. Chemical formula: C8H11N5O3 Molecular mass: 225.21 g/mol. Bioavailability: 10-20% (oral) Half life: 2.2-20 hours. Protein binding: 9-33% |
Used for the treatment of Herpes Simplex virus infections, Varicella Zoster and Herpes Zoster |
Diarrhea. Headache. Agitation. Vertigo. Oedema. Arthralgia. Neutropenia. Anorexia. Stevens Johnson syndrome. Anaphylaxis. |
Garrison,et.al2 |
|
ACYCLOVIR: Trade name: Zovirax IUPAC name: 2-amino-1, 9-dihydro-9-((2-hydroxyethoxy) methyl)-6H-purin-6-one. Chemical formula: C8H11N5O3 Molecular mass: 225.21 g/mol. Bioavailability: 10-20% (oral) Half life: 2.2-20 hours. Protein binding: 9-33% |
Used for the treatment of Herpes Simplex virus infections , Varicella Zoster and Herpes Zoster, Gential Herpes. |
Diarrhea. Headache. Agitation. Vertigo. Oedema. Arthralgia. Neutropenia. Anorexia. Stevens Johnson syndrome. Anaphylaxis.
|
Garrison,et.al3 |
|
ADEFOVIR: Trade name: Hepsera. IUPAC name: {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl} phosphonic acid. Chemical formula: C8H12N5O4P Molecular mass: 273.186 g/mol. Bioavailability: 59% Half life: 7.5 hours |
Hepatitis B. Herpes simplex virus. It is failed in treatment of HIV. |
|
Marcellin P,et.al4 |
|
AMANTADINE: Trade name: Symmetrel IUPAC name: adamantam-1-amine Chemical formula: C10H17N Molecular mass: 151.249 g/mol. Bioavailability: well absorbed Half life: 10-14 hours. Protein binding: approx 67% |
It is used both as antiviral and antiparkinsonian drug. It is useful as a building block, allowing the insertion of an adamantly group. |
Insomnia. Agitation. Anxiety. Psychiatric symptoms. Parkinson’s disease. Stevens Johnson syndrome.
|
Maugh,et.al5 |
|
AMPRENAVIR: Trade name: Agenerase IUPAC name: (3S)-oxolan-3-yl N-[(2S, 3R)-3-hydroxy-4- [N-(2-methylpropyl) (4-aminobenzene) sulfonamido] -1-phenylbutan-2-yl]carbamate. Chemical formula: C25H35N3O6S Molecular mass: 505.628 g/mol. Half life: 7.1-10.6 hours Protein binding: 90% |
Used to treat HIV Infection. |
|
Shen,C.H,et.al6 |
|
Rintatolimod: Trade name: Ampligen IUPAC name: 5’-Inosinic acid, holopolymer, complex with 5’-cytidylic acid polymer with 5’-uridylic acid (1:1) |
It is tested as a treatment for illness including chronic fatigue syndrome and acquired immunodeficiency syndrome. |
Malaise. Leukopenia. Neutropenia. Leukocytosis. |
George,et.al7 |
|
ATAZANAVIR: Trade name: Reyataz IUPAC name: methyl N-[(1S)-1-{[(2S, 3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl) amino]-3, 3-dimethyl-N’-{[4-(pyridine-2-yl) phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate. Chemical formula: C38H52N6O7 Molecular mass: 704.856 g/mol. Bioavailability: 60-68% Half life: 6.5 hours. Protein binding: 86% |
It is an antiretroviral drug of the protease inhibitor. Used to treat HIV infection. |
Increase in bilirubin levels in Blood. It causes less interaction with glucose level. |
Croom KF,et.al8 |
|
ATRIPLA: (Fixed dosage form) Combination of Emtricitabine Nucleoside transcriptase inhibitor Tenofovir disproxil fumarate Nucleotide analogue reverse transcriptase inhibitor Efavirenz Non-nucleoside reverse transcriptase inhibitor. |
It is taken to patients with renal and hepatic insufficiency. HIV infection. Not recommended for patients with under 18 years age. |
Tiredness. Dizziness. GI distress. Skin discoloration. Hallucinations. Sleepness. Depression. |
Bristol-Myers Squibb,et.al9 |
|
BOCEPREVIR: Trade name: Victrelis. IUPAC name: (1R, 2S, 5S)-N-[(2Ξ)-4-amino-1-cyclobutyl-3, 4-dioxobutan-2-yl)]-3-{(2S)-2-[(tert-butylcarbamoyl) amino]-3, 3-dimethylbutanoyl}-6, 6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxamide. Chemical formula:C27H45N5O5 |
Used as a treatment for HepatitisC Genotype 1. |
|
Degertekin B,et.al10 |
|
CIDOFOVIR: Trade name: Vistide IUPAC name: ({[(S)-1-(4-amino-2-oxo-1, 2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl] oxy} methyl) phosphonic acid. Chemical formula: C8H14N3O6P Molecular mass: 279.187 g/mol. Bioavailability: complete Half life: 2.4-3.2 hours Protein binding: 6% |
Treatment of cytomegalovirus retinitis in patients with AIDS. Prevention of viral replication and transcription. |
Nephrotoxic. Probenecid.
|
Becker MN,et.al11 |
|
DARUNAVIR: Trade name: Prezista. IUPAC name: [(1R, 5S, 6R)-2, 8-dioxabicyclo [3.2.0] oct-6-yl] N-[(2S, 3R)-4-[(4-aminophenyl) sulfonyl-(2-methylpropyl) amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate. Chemical formula: C27H37N307S Molecular mass: 547.665 g/mol. Bioavailability: Half life: 15 hours Protein binding: 95% |
It is a protease inhibitor class. It is an OARAC recommended treatment option for treatment option for treatment of naïve and treatment –experienced adults and adolescents. |
|
Rodger D MacArthura ,et.al12 |
|
DIDANOSINE: Trade name: Videx. IUPAC name: 9-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purin-6(9H)-one. Chemical formula: C10H12N4O3 Molecular mass: 236.227 g/mol. Bioavailability: 30-54% Half life: 1.5 hours Protein binding: <5% |
It is a reverse transcriptase inhibitor, effective against HIV and used in combination with other antiretroviral drug therapy. |
Neuropathy. Pancreatitis. Retinal changes. Black box warning. Optic neuritis. Abdominal pain. Diarrhea. |
Moyle GJ,et.al13 |
|
DOCOSANOL: Trade name: Behenyl alcohol. IUPAC name: Docosan-1-ol[1] Chemical formula: C22H46O Molecular mass: 326.6 g/mol. |
It is used traditionally as an Emollient, emulsifier, and thickner in cosmetics, |
Skin irritation. Headache. Swelling. Acne. Burning. Redness. Acute diarrhea. Soreness. |
Liverstrong.com,et.al14 |
|
EFAVIRENZ: Trade name: Sustiva IUPAC name: (4S)-6-chloro-4-(2-cyclopropylethnyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one. Chemical formula: C14H9clF3NO2 Molecular mass: 315.675 g/mol. Half life: 40-55 hours. Protein binding: 99.5-99.75% |
It is used as part of highly active antiretroviral therapy (HARRT) for the treatment of HIV type 1. |
Neurologic, psychiatric effects. Insomnia. Nightmares. Depression. Psychosis. Cause birth defects. False positive results in some urine tests for marijuana. |
Hasse,B;et.al15 |
|
EMTRICITABINE: Trade name: Emtriva IUPAC name: 4-amino-5-fluoro-1-[(2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one Chemical formula: C8H10FN3O3S Molecular mass: 247.248 g/mol. Bioavailability: 93% Half life: 10 hours Protein binding: <4% |
It is a nucleoside reverse transcriptase inhibitor for the treatment of HIV infection in adults and children. |
Diarrhea. Headache. Nausea. Rash. Hyperpigmentation. Hepatotoxicity. Lactic acidosis. |
Leaf,et.al16 |
|
FAMCICLOVIR: Trade name: Famvir IUPAC name: 2-[{acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butylacetate Chemical formula: C14H19N5O4 Molecular mass: 321.332 g/mol. Bioavailability: 75-77% Half life: 2-2.3 hours Protein binding: 20-25%
|
Used in various Herpes virus infections. |
Mild to extreme stomach upset, headaches, mild fever. |
Luber AD,et.al17 |
|
FOSAMPRENAVIR: Trade name: Lexiva IUPAC name: {[(2S,3S)-1-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid. Chemical formula: C25H36N3O9PS Molecular mass: 585.608 g/mol. Bioavailability: Unknown Half life: 7.7hours Protein binding: 90% |
It is a pro drug of the protease inhibitor and antiretroviral drug amprenavir.
|
Skin rash. Diabetes. Increased bleeding in haemophiliacs. Kidney stones. |
Eron J Jr,et.al18 |
|
FOSCARNET: Trade name: Foscavir. IUPAC name: Phosphonoformic acid Chemical formula: CH3O5P Molecular mass: 126.005 g/mol. Bioavailability: NA Half life: 3.3-6.8 hours Protein binding: 14-17%
|
Used to treat Herpes viruses, including drug-resistant cytomegalovirus and herpes simplex virus type 1 and 2 |
Nephrotoxicity. Gential ulceration. Electrolyte disturbance.
|
Canestri A,et.al19 |
|
GANCICLOVIR: Trade name: Cytovene IUPAC name: 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-3H-purin-6-one. Chemical formula: C9H13N5O4 Molecular mass: 255.23 g/mol. Bioavailability: 5% (oral) Half life: 2.5-5 hours Protein binding: |
Used to prevent cytomegalovirus infection. CMV pneumonitis in bone marrow transplant recipients. |
Haematological effects. Granulocytopenia. Neutropenia. Anaemia. Thrombocytopenia. Dyspepsia. Phlebitis. |
Rossi S,et.al20 |
|
IBACITABINE: IUPAC name: 4-amino-1-[(2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl) oxolan-2-yl]-5-iodopyrimidin-2-one. Chemical formula: C9H12IN3O4 Molecular mass: 353.11375 g/mol. |
It is used as an antiviral drug. |
|
Ann Dermatol Venereol,et.al21 |
|
IMUNOVIR: (Inosine pranobex). IUPAC name: 9-[(2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl) oxolan-2-yl]-3H-purin-6-one: 4-acetamidobenzoic acid: 1-(dimethylamino) propan-2-ol. Chemical formula: C52H78N10O17 Molecular mass: 1115.23 g/mol. |
Act as a powerful immunostimulant. Treat measles complication subacute sclerosing panencephalitis in conjunction with intrathecalinterferon therapy. |
No effects on viral particles itself. |
Campoli-Richards DM,et.al22 |
|
IDOXURIDINE: IUPAC name: 1-[(2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl) oxolan-2-yl]-5-iodo-1, 2, 3, 4-tetrahydropyrimidine-2, 4-dione. Chemical formula: C9H11IN2O5 Molecular mass: 354.099 g/mol. |
It is an anti-herpes virus antiviral drug. Used topically due to cardiotoxicity. Used for treatment of herpes simplex keratitis. |
Photophobia. Corneal clouding. Blurred vision. Eye irritation. |
Seth A,et.al23 |
|
IMIQUIMOD: Trade name: Aldara IUPAC name: 3-(2-methylpropyl)-3,5,8-triazatricyclo[7.4.0.02,6] trideca-1(9), 2(6),4,7,10,12-hexaen-7-amine. Chemical formula: C14H16N4 Molecular mass: 240.304 g/mol. Half life: 30 hours.
|
Acts as an immune response modifier. Used in skin cancers, Bowen’s disease, squamous cell carcinoma, malignant melanomas, actinic keratosis ,etc. |
Headaches. Back pain. Muscle aches. Tiredness. Flu-. Swollen lymph nodes. Diarrhea. Fungal infections. |
Van Egmond S,et.al24 |
|
INDINAVIR: Trade name: Crixivan IUPAC name: (2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridine-3-ylmethyl)piperazine-2-carboxamide. Chemical formula: C36H47N504 Molecular mass: 613.79 g/mol. Half life: 1.8(±0.4) hours. Protein binding: 60% |
It is a protease inhibitor used as a component of highly active antiretroviral therapy to treat HIV infection and AIDS. |
Kidney stones. Kidney failure. Hyperlipidemia. Reduced creatinine clearance. Atherosclerotic disease. |
Shankar SS,et.al25 |
|
INOSINE Trade name: IUPAC name: 9-[(2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-(hydroxymethyl) oxolan-2-yl]-6, 9-dihydro-3H-purin-6-one. Chemical formula: C10H12N4O5 Molecular mass: 268.23 g/mol. |
It is used in the treatment of a variety of autoimmune diseases including Wegener’s granulomatosis. |
Spinal cord injury. Produces uric acid ingestion. Peroxynitrite scavenger. |
Takeda,et.al26 |
|
LAMIVUDINE: Trade name: Zeffix IUPAC name: 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one. Chemical formula: C8H11N3O3S Molecular mass: 229.26 g/mol. Bioavailability: 86% Half life: 5-7 hours Protein binding: <36% |
It is used in treatment of HIV. Chronic Hepatitis. Improves the Seroconversion of e-antigen positive hepatitis B and also improves staging of the liver. |
Allergic reactions. Hives. Difficult breathing. Swelling of face, tongue, or throat. |
Koziel MJ,et.al27 |
|
LOPINAVIR: Trade name: Kaletra IUPAC name: (2S)-N-[(2S, 4S, 5S)-5-[2-(2,6-dimethylphenoxy) acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1, 3-diazinan-1-yl) butanamide. Chemical formula: C37H48N4O5 Molecular mass: 628.810 g/mol. Bioavailability: Unknown Half life: 5-6 hours Protein binding: 98-99% |
It is an antiretroviral of the protease inhibitor class. It is used as a fixed-dose combination with another protease inhibitor |
Side effects have only be evaluated in the drug combination Lopinavir/Ritonavir. |
Capparelli E,et.al28 |
|
MARAVIROC: Trade name: Selzentry IUPAC name: 4,4-difluoro-N-{(1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1] oct-8-yl]-1-phenylpropyl}cyclohexanecarboxamide. Chemical formula: C29H41F2N5O Molecular mass: 513.666 g/mol. Bioavailability: 23% Half life: 16h |
It is an antiretroviral drug in the CCRS receptor antagonist class under in the treatment of HIV infection. It is also appered to reduce graft-versus-host disease in patients treated with allogeneic bone marrow transplantation for leukemia, in phase ½ study. |
Allergic reactions. Hives. Difficult breathing. Swelling of face, tongue, or throat. |
Abel S,et.al29 |
|
MOROXYDINE: Trade name: moroxidine IUPAC name: N-(Diaminomethylidene) morpholine-4-carboximidamide. Chemical formula: C6H13N5O Molecular mass: 171.20 g/mol. |
It is an antiviral drug used for the treatment of influenza . It has potential applications against a number of RNA and DNA viruses. |
Headache. Disturbed sleep. Blurred vision. Constipation. Tiredness. |
Sheppard, S.et.al30 |
|
METHISAZONE: Trade name: metisazone IUPAC name: [(1-methyl-2-oxoindol-3-ylidene)amino] thiourea. Chemical formula: C10H10N4OS Molecular mass: 234.28 g/mol. |
Used to treat smallpox |
It is effective for prophylaxis. 11-66% of vomiting is reported. |
Weiss MM, et.al31 |
|
NEVIRAPINE: Trade name: Viramune. IUPAC name: 11-cyclopropyl-4-methyl-5,11-dihydro-6H-dipyridol[3,2-b:2’,3’-e][1,4]diazepin-6-one Chemical formula: C15H14N4O Molecular mass: 266.888 g/mol. Bioavailability: 93%±9% Half life: 45h |
It is a non nucleoside reverse transcriptase inhibitor used to treat HIV-1 infection and AIDS. Used as an initial antiretroviral therapy. |
Stevens-johnson syndrome. Toxic epidermal necrolysis. Hypersensitivity
|
Patel SS,et.al32 |
CONCLUSION:
Like antibiotics, specific antivirals are used for specific viruses. Antiviral drugs are one class of antimicrobials, a larger group which also includes antibiotics, anti-fungal and anti-parasitic drugs. They are relatively harmless to the host, and therefore can be used to treat infections. The antiviral chemotherapy aims at selective inhibition of viral encoded or virus induced enzyme by an agent that does not specifically affect the enzymes normally involved in similar biochemical process of the host cell.
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