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Also known as: 104227-87-4, Famvir, Brl-42810, Famciclovirum, 2-(2-(2-amino-9h-purin-9-yl)ethyl)propane-1,3-diyl diacetate, Famciclovirum [inn-latin]
Molecular Formula
C14H19N5O4
Molecular Weight
321.33  g/mol
InChI Key
GGXKWVWZWMLJEH-UHFFFAOYSA-N
FDA UNII
QIC03ANI02

Famciclovir
An aminopurine derivative and prodrug of penciclovir which is a competitive inhibitor of herpes simplex 2 DNA polymerase. It is used to treat HERPES SIMPLEX VIRUS INFECTION.
Famciclovir is a Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor. The mechanism of action of famciclovir is as a DNA Polymerase Inhibitor, and DNA Polymerase Inhibitor.
1 2D Structure

Famciclovir

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate
2.1.2 InChI
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
2.1.3 InChI Key
GGXKWVWZWMLJEH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)COC(=O)C
2.2 Other Identifiers
2.2.1 UNII
QIC03ANI02
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,3-propanediol, 2-(2-(2-amino-9h-purin-9-yl)ethyl)-, Diacetate (ester)

2. 9-(4-acetoxy-3-(acetoxymethyl)but-1-yl)-2-aminopurine

3. Brl 42810

4. Brl-42810

5. Brl42810

6. Famvir

2.3.2 Depositor-Supplied Synonyms

1. 104227-87-4

2. Famvir

3. Brl-42810

4. Famciclovirum

5. 2-(2-(2-amino-9h-purin-9-yl)ethyl)propane-1,3-diyl Diacetate

6. Famciclovirum [inn-latin]

7. Brl 42810

8. [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] Acetate

9. Famciclovir (famvir)

10. 2-[(acetyloxy)methyl]-4-(2-amino-9h-purin-9-yl)butyl Acetate

11. Fcv

12. Chebi:4974

13. 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine

14. Nsc-758921

15. Qic03ani02

16. 1,3-propanediol, 2-(2-(2-amino-9h-purin-9-yl)ethyl)-, Diacetate (ester)

17. 2-(2-(2-amino-9h-purin-9-yl)ethyl)-1,3-propanediol Diacetate (ester)

18. Ncgc00095133-01

19. Famciclovir 100 Microg/ml In Acetonitrile

20. 2-(2-(2-amino-9h-purin-9-yl)ethyl)-1,3-propanediol Diacetate

21. 2-[2-(2-amino-9h-purin-9-yl)ethyl]-1,3-propanediol Diacetate

22. Dsstox_cid_3038

23. Dsstox_rid_76845

24. Dsstox_gsid_23038

25. Oravir

26. Acetic Acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl Ester

27. 2-(acetoxymethyl)-4-(2-amino-4,5-dihydro-9h-purin-9-yl)butyl Acetate

28. 2-[2-(2-amino-9h-purin-9-yl)ethyl]trimethylene Diacetate;2-[2-(2-amino-9h-purin-9-yl)ethyl]trimethylene Diacetate

29. Smr000466375

30. Famvir (tn)

31. Cas-104227-87-4

32. Sr-01000759358

33. Unii-qic03ani02

34. Famciclovir [usan:inn:ban]

35. 1,3-propanediol, 2-[2-(2-amino-9h-purin-9-yl)ethyl]-, Diacetate (ester)

36. 2-[2-(2-amino-9h-purin-9-yl)ethyl]-1,3-propanediol Diacetate (ester)

37. Hsdb 8121

38. Famciclovir,(s)

39. Brl42810

40. Famciclovir, Bio-x

41. Mfcd00866964

42. 1,3-diyl Diacetate

43. Spectrum_000466

44. Famciclovir [mi]

45. Spectrum2_001101

46. Spectrum3_001675

47. Spectrum4_000611

48. Spectrum5_001548

49. Famciclovir [inn]

50. Famciclovir [jan]

51. Famciclovir [usan]

52. Chembl880

53. Famciclovir [vandf]

54. Schembl2949

55. Famciclovir [mart.]

56. Bspbio_003489

57. Famciclovir [usp-rs]

58. Famciclovir [who-dd]

59. Kbiogr_001162

60. Kbioss_000946

61. Mls000759505

62. Mls001424115

63. Mls006011896

64. Famciclovir (jan/usp/inn)

65. Spectrum1505201

66. Spbio_001202

67. Dtxsid0023038

68. Famciclovir, >=98% (hplc)

69. Gtpl11629

70. Kbio2_000946

71. Kbio2_003514

72. Kbio2_006082

73. Kbio3_002709

74. [2-(acetoxymethyl)-4-(2-aminopurin-9-yl)butyl] Acetate

75. Famciclovir [orange Book]

76. Hms1922l09

77. Hms2051g22

78. Hms2090g10

79. Hms2093k12

80. Hms2232h09

81. Hms3262o08

82. Hms3370d14

83. Hms3393g22

84. Hms3656a04

85. Hms3715f03

86. Pharmakon1600-01505201

87. Famciclovir [usp Monograph]

88. Albb-027262

89. Bcp21312

90. Diacetyl 6-deoxy-9-(4-hydroxy-3-hydroxymethyl-but-1-yl)guanine

91. Zinc1530635

92. Tox21_111442

93. Tox21_500793

94. Ak-120

95. Bdbm50248001

96. Ccg-39277

97. Nsc758921

98. S2467

99. Stk623204

100. 2-(2-(2-amino-9h-purin-9-yl)ethyl)-1,3-propanediol Diacetate Ester

101. Akos005556609

102. Tox21_111442_1

103. Ab07547

104. Ac-8066

105. Cs-1357

106. Db00426

107. Ks-5020

108. Nc00156

109. Nsc 758921

110. Ncgc00095133-02

111. Ncgc00095133-03

112. Ncgc00095133-04

113. Ncgc00095133-06

114. Ncgc00095133-15

115. Ncgc00261478-01

116. Bf164441

117. Hy-17426

118. Sbi-0206743.p001

119. Db-014809

120. F0842

121. Ft-0602549

122. Ft-0668461

123. Sw197536-3

124. A19583

125. D00317

126. 2-(2-(2-amino-9h-purin-9-yl)ethyl)propane-

127. Ab00639952-06

128. Ab00639952-08

129. Ab00639952_09

130. Ab00639952_10

131. 227f874

132. Q420186

133. Brl-42810;brl42810;brl 42810;famciclovirum

134. J-001134

135. Sr-01000759358-4

136. Sr-01000759358-5

137. 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-aminopurine

138. Brd-k45033733-001-02-3

139. Brd-k45033733-001-05-6

140. 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9h Purine

141. [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)-butyl] Acetate

142. 2-(2-(2-amino-9h-purin-9-yl)ethyl)-propane-1,3-diyl Diacetate

143. Famciclovir, United States Pharmacopeia (usp) Reference Standard

144. Famciclovir, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 321.33 g/mol
Molecular Formula C14H19N5O4
XLogP30
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass321.14370410 g/mol
Monoisotopic Mass321.14370410 g/mol
Topological Polar Surface Area122 Ų
Heavy Atom Count23
Formal Charge0
Complexity404
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameFamciclovir
PubMed HealthFamciclovir (By mouth)
Drug ClassesAntiviral
Drug LabelFamciclovir tablets contains famciclovir, an orally administered prodrug of the antiviral agent penciclovir. Chemically, famciclovir is known as 2-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate. It is a synthetic acyclic guanine derivativ...
Active IngredientFamciclovir
Dosage FormTablet
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyHetero Labs Ltd V; Teva Pharms; Macleods Pharms; Apotex; Aurobindo Pharma; Cipla; Mylan; Roxane

2 of 4  
Drug NameFamvir
PubMed HealthFamciclovir (By mouth)
Drug ClassesAntiviral
Drug LabelThe active ingredient in FAMVIR tablets is famciclovir, an orally administered prodrug of the antiviral agent penciclovir. Chemically, famciclovir is known as 2-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate. Its molecular formula is C14H...
Active IngredientFamciclovir
Dosage FormTablet
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyNovartis

3 of 4  
Drug NameFamciclovir
PubMed HealthFamciclovir (By mouth)
Drug ClassesAntiviral
Drug LabelFamciclovir tablets contains famciclovir, an orally administered prodrug of the antiviral agent penciclovir. Chemically, famciclovir is known as 2-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate. It is a synthetic acyclic guanine derivativ...
Active IngredientFamciclovir
Dosage FormTablet
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyHetero Labs Ltd V; Teva Pharms; Macleods Pharms; Apotex; Aurobindo Pharma; Cipla; Mylan; Roxane

4 of 4  
Drug NameFamvir
PubMed HealthFamciclovir (By mouth)
Drug ClassesAntiviral
Drug LabelThe active ingredient in FAMVIR tablets is famciclovir, an orally administered prodrug of the antiviral agent penciclovir. Chemically, famciclovir is known as 2-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate. Its molecular formula is C14H...
Active IngredientFamciclovir
Dosage FormTablet
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyNovartis

4.2 Therapeutic Uses

Antiviral Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2013)


Oral famciclovir is used for the treatment of acute, localized herpes zoster (shingles, zoster). /Included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 812


Oral famciclovir is used for the treatment of recurrent mucocutaneous herpes simplex virus (HSV) infections (HSV-1 and HSV-2) in HIV-infected adults. /Included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 813


Famciclovir has been used for the management of chronic hepatitis B virus (HBV) infection in a limited number of patients. /NOT included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 813


For more Therapeutic Uses (Complete) data for Famciclovir (12 total), please visit the HSDB record page.


4.3 Drug Warning

/These/ adverse events have been reported during post-approval use of Famvir. Because these events are reported voluntarily from a population of uncertain size, it is not always possible to reliably estimate their frequency or establish a causal relationship to drug exposure: Blood and lymphatic system disorders: Thrombocytopenia. Hepatobiliary disorders: Abnormal liver function tests, cholestatic jaundice. Nervous system disorders: Dizziness, somnolence. Psychiatric disorders: Confusion (including delirium, disorientation, and confusional state occurring predominantly in the elderly), hallucinations. Skin and subcutaneous tissue disorders: Urticaria, erythema multiforme, Stevens-Johnson syndrome, toxic epidermal necrolysis, angioedema (e.g. face, eyelid, periorbital, and pharyngeal edema).

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


The manufacturer recommends that the dosage interval of famciclovir be adjusted carefully in patients with impaired renal function to prevent drug accumulation while maintaining adequate plasma concentrations of penciclovir, the active metabolite of famciclovir.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 815


Increased serum concentrations of ALT (SGPT) occurred in 1.4-2.4% of patients receiving famciclovir in clinical trials for herpes zoster or genital herpes. Increased serum concentrations of alkaline phosphatase, total bilirubin, and albumin each occurred rarely in patients receiving the drug in clinical trials for herpes zoster or genital herpes.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 814


The most frequent adverse GI effect of famciclovir is nausea which occurred in approximately 13% of patients receiving the drug (versus in 11.6% in placebo recipients) in a large, controlled clinical trial for herpes zoster. Nausea resulted in discontinuance of famciclovir in less than 1% of patients in clinical trials for herpes zoster or genital herpes. Diarrhea was reported in approximately 8% of patients (5% of placebo recipients) and vomiting in approximately 5% of patients (3.4% of placebo recipients) in a large, controlled clinical trial for herpes zoster. Vomiting only rarely resulted in discontinuance of famciclovir in clinical trials for herpes zoster or genital herpes. Constipation, anorexia, abdominal pain, flatulence, and dyspepsia have occurred in patients receiving famciclovir in clinical trials for herpes zoster. Acute necroticohemorrhagic pancreatitis resulting in death has been reported following famciclovir administration for severe hepatitis B virus infection in a kidney graft recipient who was receiving cyclosporine concomitantly; a causal relationship to famciclovir was not established. Nausea, diarrhea, vomiting, or abdominal pain has been reported in 11, 7, 5, or 3%, respectively, of HIV-infected patients receiving famciclovir in clinical studies.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 814


For more Drug Warnings (Complete) data for Famciclovir (12 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of acute herpes zoster (shingles). Also for the treatment or suppression of recurrent genital herpes in immunocompetent patients and treatment of recurrent mucocutaneous herpes simplex infections in HIV infected patients.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Famciclovir is a prodrug that undergoes rapid biotransformation to the active antiviral compound penciclovir. Penciclovir is an anti-viral drug which has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). Therefore, herpes viral DNA synthesis and replication are selectively inhibited.


5.2 MeSH Pharmacological Classification

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)


Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FAMCICLOVIR
5.3.2 FDA UNII
QIC03ANI02
5.3.3 Pharmacological Classes
Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor [EPC]; Nucleoside Analog [EXT]; DNA Polymerase Inhibitors [MoA]
5.4 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors

J05AB09 - Famciclovir


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AD - Antivirals

S01AD07 - Famciclovir


5.5 Absorption, Distribution and Excretion

Absorption

77 %


Route of Elimination

Active tubular secretion contributes to the renal elimination of penciclovir.


Volume of Distribution

1.080.17 L/kg [healthy male subjects following a single intravenous dose of penciclovir at 400 mg administered as a 1-hour intravenous infusion]


Clearance

36.6 +/- 6.3 L/hr [healthy male]

0.48 +/- 0.09 L/hr/kg [healthy male]


Following oral administration of famciclovir to lactating rats, penciclovir was distributed into breast milk at concentrations higher than those observed in plasma.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 815


Not known whether penciclovir crosses the placenta or is distributed into human milk.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 815


Following oral single-dose administration of 500 mg famciclovir to seven patients with herpes zoster, the AUC (mean + or - SD), Cmax, and tmax were 12.1+ or - 1.7 ug hr/mL, 4.0 + or - 0.7 ug/mL, and 0.7 + or - 0.2 hours, respectively. The AUC of penciclovir was approximately 35% greater in patients with herpes zoster as compared to healthy volunteers. Some of this difference may be due to differences in renal function between the two groups.

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


Renal clearance of penciclovir following the oral administration of a single 500 mg dose of famciclovir to 109 healthy male volunteers was 27.7+ or - 7.6 L/hr. Active tubular secretion contributes to the renal elimination of penciclovir.

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


For more Absorption, Distribution and Excretion (Complete) data for Famciclovir (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic


Famciclovir is deacetylated and oxidized to penciclovir. Penciclovir is phosphorylated to penciclovir triphosphate (the active metabolite) in cells infected with HSV-1, HSV-2, or VZV. The inactive metabolite 6-deoxy penciclovir is converted to penciclovir by aldehyde oxidase. Famciclovir not metabolized by CYP enzymes.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 815


Following oral administration, famciclovir is deacetylated and oxidized to form penciclovir. Metabolites that are inactive include 6-deoxy penciclovir, monoacetylated penciclovir, and 6-deoxy monoacetylated penciclovir (5%, <0.5% and <0.5% of the dose in the urine, respectively). Little or no famciclovir is detected in plasma or urine. An in vitro study using human liver microsomes demonstrated that cytochrome P450 does not play an important role in famciclovir metabolism. The conversion of 6-deoxy penciclovir to penciclovir is catalyzed by aldehyde oxidase.

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


5.7 Biological Half-Life

10 hours


Elimination half-life of penciclovir after oral administration of famciclovir 1.6-3 hours. Intracellular half-life of penciclovir triphosphate in cells infected with herpes simplex virus (HSV)-1 or HSV-2 is 10 and 20 hours, respectively; intracellular half-life in varicella zoster virus (VZV)-infected cells is 7-14 hours.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 815


The plasma elimination half-life of penciclovir was 2.0 + or - 0.3 hours after intravenous administration of penciclovir to 48 healthy male volunteers and 2.3 + or - 0.4 hours after oral administration of 500 mg famciclovir to 124 healthy male volunteers. The half-life in 17 patients with herpes zoster was 2.8 + or - 1.0 hours and 2.7 + or - 1.0 hours after single and repeated doses, respectively.

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


5.8 Mechanism of Action

Famciclovir undergoes rapid biotransformation to the active antiviral compound penciclovir, which has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). In cells infected with HSV-1, HSV-2 or VZV, viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted to penciclovir triphosphate by cellular kinases. In vitro studies demonstrate that penciclovir triphosphate inhibits HSV-2 DNA polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited.


Famciclovir is a prodrug of penciclovir, which has demonstrated inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). In cells infected with HSV-1, HSV-2 or VZV, the viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted by cellular kinases to the active form penciclovir triphosphate. Biochemical studies demonstrate that penciclovir triphosphate inhibits HSV-2 DNA polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited. Penciclovir triphosphate has an intracellular half-life of 10 hours in HSV-1-, 20 hours in HSV-2- and 7 hours in VZV-infected cells grown in culture. However, the clinical significance of the intracellular half-life is unknown.

US Natl Inst Health; DailyMed. Current Medication Information for FAMVIR (famciclovir) tablet, film coated (February 2012). Available from, as of March 16, 2013: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3c6194c0-ba69-4b16-b882-caf736a02348


API Reference Price

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20-Jan-2021
26-Aug-2024
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DOSAGE - TABLET;ORAL - 125MG **Federal Regist...DOSAGE - TABLET;ORAL - 125MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20363

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DOSAGE - TABLET;ORAL - 250MG **Federal Regist...DOSAGE - TABLET;ORAL - 250MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20363

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DOSAGE - TABLET;ORAL - 500MG **Federal Regist...DOSAGE - TABLET;ORAL - 500MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20363

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