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Chemistry

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Also known as: 13392-28-4, 1-(1-adamantyl)ethanamine, 1-rimantadine, 1-(adamantan-1-yl)ethan-1-amine, Alpha-methyl-1-adamantanemethylamine, Alpha-methyladamantanemethylamine
Molecular Formula
C12H21N
Molecular Weight
179.30  g/mol
InChI Key
UBCHPRBFMUDMNC-UHFFFAOYSA-N
FDA UNII
0T2EF4JQTU

Rimantadin
An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.
Rimantadine is an Influenza A M2 Protein Inhibitor. The mechanism of action of rimantadine is as a M2 Protein Inhibitor.
1 2D Structure

Rimantadin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(1-adamantyl)ethanamine
2.1.2 InChI
InChI=1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
2.1.3 InChI Key
UBCHPRBFMUDMNC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C12CC3CC(C1)CC(C3)C2)N
2.2 Other Identifiers
2.2.1 UNII
0T2EF4JQTU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Flumadine

2. Hydrochloride, Rimantadine

3. Remantadine

4. Riamantadine

5. Rimantadine Hydrochloride

6. Roflual

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 179.30 g/mol
Molecular Formula C12H21N
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass179.167399674 g/mol
Monoisotopic Mass179.167399674 g/mol
Topological Polar Surface Area26 Ų
Heavy Atom Count13
Formal Charge0
Complexity180
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

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


4.2 Drug Warning

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.


4.3 Drug Indication

For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RIMANTADINE
5.3.2 FDA UNII
0T2EF4JQTU
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - M2 Protein Inhibitors
5.4 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AC - Cyclic amines

J05AC02 - Rimantadine


5.5 Absorption, Distribution and Excretion

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.


5.6 Metabolism/Metabolites

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


5.7 Biological Half-Life

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


5.8 Mechanism of Action

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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API | Excipient name

Rimantadin

Synonyms

13392-28-4, 1-(1-adamantyl)ethanamine, 1-rimantadine, 1-(adamantan-1-yl)ethan-1-amine, Alpha-methyl-1-adamantanemethylamine, Alpha-methyladamantanemethylamine

Cas Number

13392-28-4

Unique Ingredient Identifier (UNII)

0T2EF4JQTU

About Rimantadin

An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.

Rimantadin Manufacturers

A Rimantadin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Rimantadin, including repackagers and relabelers. The FDA regulates Rimantadin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Rimantadin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Rimantadin Suppliers

A Rimantadin supplier is an individual or a company that provides Rimantadin active pharmaceutical ingredient (API) or Rimantadin finished formulations upon request. The Rimantadin suppliers may include Rimantadin API manufacturers, exporters, distributors and traders.

Rimantadin GMP

Rimantadin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Rimantadin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Rimantadin GMP manufacturer or Rimantadin GMP API supplier for your needs.

Rimantadin CoA

A Rimantadin CoA (Certificate of Analysis) is a formal document that attests to Rimantadin's compliance with Rimantadin specifications and serves as a tool for batch-level quality control.

Rimantadin CoA mostly includes findings from lab analyses of a specific batch. For each Rimantadin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Rimantadin may be tested according to a variety of international standards, such as European Pharmacopoeia (Rimantadin EP), Rimantadin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Rimantadin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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