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1. Flumadine
2. Hydrochloride, Rimantadine
3. Remantadine
4. Riamantadine
5. Rimantadine Hydrochloride
6. Roflual
1. 13392-28-4
2. 1-(1-adamantyl)ethanamine
3. 1-rimantadine
4. 1-(adamantan-1-yl)ethan-1-amine
5. Alpha-methyl-1-adamantanemethylamine
6. Alpha-methyladamantanemethylamine
7. 1-(adamantan-1-yl)ethanamine
8. Rimantadin
9. 1-adamantan-1-yl-ethylamine
10. Rimantadine (inn)
11. 0t2ef4jqtu
12. Chembl959
13. 1-adamantanemethylamine, .alpha.-methyl-
14. .alpha.-methyladamantanemethylamine
15. 1-(tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanamine
16. Rimantadina
17. Rimantadinum
18. Rimantadine [inn]
19. Rimantadine [inn:ban]
20. Rimantadinum [inn-latin]
21. 1-(1-adamantyl)ethylamin
22. Rimantadina [inn-spanish]
23. [1-(1-adamantyl)ethyl]amine Hydrochloride
24. (r)-1-(1-adamantyl)ethylamine
25. Rimant
26. Tricyclo[3.3.1.13,7]decane-1-methanamine, Alpha-methyl-, (-)-
27. 1-(1-adamantyl)ethylamine
28. 117857-51-9
29. Hsdb 7438
30. Enamine_005755
31. Ncgc00159491-02
32. Rimant & .alpha. Ifn
33. Unii-0t2ef4jqtu
34. Rimantadine (flumadine)
35. Rimantidine & .alpha.ifn
36. 1-adamantan-1-ylethylamine
37. Brn 2715740
38. Rimantidin
39. 1-(1-adamantyl)-ethylamine
40. Rimantadin A
41. Tricyclo(3.3.1.13,7)decane-1-methanamine, Alpha-methyl-
42. Rimantadine [mi]
43. Maybridge1_002066
44. Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, Alpha-methyl-
45. 1-adamantanemethylamine, Alpha-methyl-
46. Rimantadine [hsdb]
47. Rimantadine [vandf]
48. Schembl2981
49. 1-tricyclo[3.3.1.1~3,7~]dec-1-ylethanamine
50. Oprea1_602732
51. Rimantadine [who-dd]
52. Schembl2619249
53. Chembl1201272
54. Dtxsid2023561
55. Schembl20409367
56. Chebi:94440
57. Hms1410f13
58. Hms2090l19
59. Hms3604n13
60. Hms3655j05
61. Albb-013870
62. Bcp12269
63. Hy-b0338
64. Bbl013215
65. Bdbm50216627
66. S1964
67. Stk177253
68. (alpha-methyl-1-adamantyl)methylamine
69. Akos000264537
70. Akos006238592
71. Akos016038537
72. .alpha.-methyl-1-adamantanemethylamine
73. Am84461
74. Ccg-236078
75. Db00478
76. 4-bromo-7-(trifluoromethyl)- Quinoline
77. Idi1_007990
78. (rs)-1-(1-adamantyl)ethanamine
79. Ncgc00159491-03
80. Ncgc00159491-05
81. Ncgc00159491-11
82. As-68744
83. Sbi-0206810.p001
84. Db-042207
85. Ft-0630403
86. Sw220023-1
87. C07236
88. D08483
89. Q42171
90. 1-[(3r,5s,7s)-adamantan-1-yl]ethan-1-amine
91. Ab00638368-09
92. Ab00959689-03
93. Ab01506092_02
94. Ab01506092_03
95. 392r284
96. Brd-a84282119-003-01-2
97. Z56757137
98. Tricyclo[3.3.1.13,7]decane-1-methanamine, A-methyl-
99. Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl-
100. Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, .alpha.-methyl-
101. Tricyclo[3,3,1,1(3,7)]decane-1-methanamine, .alpha.-methyl-
102. Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl- & Ifn.alpha
| Molecular Weight | 179.30 g/mol |
|---|---|
| Molecular Formula | C12H21N |
| XLogP3 | 2.6 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Exact Mass | 179.167399674 g/mol |
| Monoisotopic Mass | 179.167399674 g/mol |
| Topological Polar Surface Area | 26 Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 180 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Rimantadine is indicated for the prophylaxis of respiratory tract infections caused by influenza A virus in adults and children, and the treatment of respiratory tract infections caused by influenza A virus in adults./Included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
Prevent infection with various strains of influenza A virues
Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2110
Swine influenza (H1N1) viruses contain a unique combination of gene segments that have not been reported previously among swine or human influenza viruses in the US or elsewhere. The H1N1 viruses are resistant to amantadine and rimantadine but not to oseltamivir or zanamivir.
CDC; Interim Guidance on Antiviral Recommendations for Patients with Confirmed or Suspected Swine Influenza A (H1N1) Virus Infection and Close Contacts; Available at https://www.cdc.gov/swineflu/recommendations.htm as of April 27, 2009-04-27. CDC; Health Advisory - Investigation and Interim Recommendations: Swine Influenza (H1N1); Available at https://www.cdc.gov/swineflu/pdf/HAN_042509.pdf as of April 27, 2009
Elderly patients, particularly those in chronic care facilities, are more likely than younger adults or children to experience adverse effects associated with rimantadine, primarily central nervous system (CNS) and gastrointestinal side effects.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2610
FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2610
Adverse CNS effects (e.g., nervousness, anxiety, impaired concentration, lightheadedness) are less common with usual dosages of rimantadine than amantadine, probably in part because of differences in the pharmacokinetics of the drugs. In a 6-week study of daily 200-mg prophylactic doses of rimantadine hydrochloride or amantadine hydrochloride in healthy adults, about 6 or 13% of patients receiving the respective drug discontinued therapy because of adverse CNS effects versus about 4% of those receiving placebo. While neuropsychiatric (e.g., delirium, marked behavioral changes) or psychomotor dysfunction has occurred in patients receiving amantadine, these effects have not been reported in patients receiving rimantadine.
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 596
For more Drug Warnings (Complete) data for RIMANTADINE (13 total), please visit the HSDB record page.
For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
FDA Label
Rimantadine, a cyclic amine, is a synthetic antiviral drug and a derivate of adamantane, like a similar drug amantadine. Rimantadine is inhibitory to the in vitro replication of influenza A virus isolates from each of the three antigenic subtypes (H1N1, H2H2 and H3N2) that have been isolated from man. Rimantadine has little or no activity against influenza B virus. Rimantadine does not appear to interfere with the immunogenicity of inactivated influenza A vaccine.
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.)
Nucleic Acid Synthesis Inhibitors
Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)
J - Antiinfectives for systemic use
J05 - Antivirals for systemic use
J05A - Direct acting antivirals
J05AC - Cyclic amines
J05AC02 - Rimantadine
Absorption
Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
Route of Elimination
Following oral administration, rimantadine is extensively metabolized in the liver with less than 25% of the dose excreted in the urine as unchanged drug.
Protein binding: Moderate (approximately 40%).
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
Distribution: VolD - Adults: 17 to 25 L/kg. Children: MEan of 289 L. Concentrations in the nasal mucus average 50% higher than those in plasma.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
Well absorbed; tablets and syrup are absorbed equally well after oral administration.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
Time to peak concentration: 1 to 4 hours.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
For more Absorption, Distribution and Excretion (Complete) data for RIMANTADINE (11 total), please visit the HSDB record page.
Following oral administration, rimantadine is extensively metabolized in the liver with less than 25% of the dose excreted in the urine as unchanged drug. Glucuronidation and hydroxylation are the major metabolic pathways.
Rimantadine hydrochloride is metabolized extensively in the liver to at least 3 hydroxylated metabolites. These have been designated as conjugated and unconjugated 3-, 4a-, and 4beta-hydroxylated metabolites. A glucuronide conjugate of rimantadine also has been identified.
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 598
Extensively metabolized in the liver; glucuronidation and hydroxylation are the major metabolic pathways.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
25 to 30 hours in young adults (22 to 44 years old). Approximately 32 hours in elderly (71 to 79 years old) and in patients with chronic liver disease. Approximately 13 to 38 hours in children (4 to 8 years old).
Young adults (22 to 44 years old): 25 to 30 hours. Older adults (71 to 79 years old) and patients with chronic liver disease: Approximately 32 hours. Children (4 to 8 years old): 13 to 38 hours.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
The mechanism of action of rimantadine is not fully understood. Rimantadine appears to exert its inhibitory effect early in the viral replicative cycle, possibly inhibiting the uncoating of the virus. The protein coded by the M2 gene of influenza A may play an important role in rimantadine susceptibility.
Rimantadine is thought to exert its inhibitory effect early in the viral replicative cycle, possibly by blocking or greatly reducing the uncoating of viral RNA within host cells. Genetic studies suggest that a single amino acid change on the transmembrane portion of the M2 protein can completely eliminate influenza A virus susceptibility to rimantadine.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2609
Rimantadine, like amantadine, inhibits viral replication by interfering with the influenza A virus M2 protein, an integral membrane protein. The M2 protein of influenza A functions as an ion channel and is important in at least 2 aspects of virus replication, disassembly of the infecting virus particle and regulation of the ionic environment of the transport pathway. By interfering with the ion channel function of the M2 protein, rimantadine inhibits 2 stages in the replicative cycle of influenza A. Early in the virus reproductive cycle, rimantadine inhibits uncoating of the virus particle, presumably by inhibiting the acid-mediated dissociation of the virion nucleic acid and proteins, which prevents nuclear transport of viral genome material. Rimantadine also prevents viral maturation in some strains of influenza A (e.g., H7 strains) by promoting pH-induced conformational changes in influenza A hemagglutinin during its intracellular transport late in the replicative cycle. Adsorption of the virus to and penetration into cells do not appear to be affected by rimantadine. In addition, rimantadine does not interfere with the synthesis of viral components (e.g., RNA-directed RNA polymerase activity).
McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 597
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