1-(adamantan-1-yl)ethan-1-amine

• ChemBase ID: 361
• Molecular Formular: C12H21N
• Molecular Mass: 179.30184
• Monoisotopic Mass: 179.16739968
• SMILES: NC(C12CC3CC(C1)CC(C2)C3)C
• Canonical SMILES: CC(C12CC3CC(C2)CC(C1)C3)N
• 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
• InChIKey: UBCHPRBFMUDMNC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(adamantan-1-yl)ethan-1-amine
• IUPAC Traditional name: rimantadine
• Brand Name: Flumadine
• Synonyms: Rimantadine Hydrochloride; Rimantadine; Rimantadine (Flumadine)

Database IDs

• CAS Number: 13392-28-4
• PubChem SID: 160963824; 46505973
• PubChem CID: 5071

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.8055685
• LogD (pH = 7.4): -0.34652156
• Log P: 2.2170057
• Molar Refractivity: 54.5221 cm^3
• Polarizability: 22.19729 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.28
• LOG S: -4.29
• Solubility (Water): 9.15e-03 g/l

PROPERTIES

Physical Property

• Solubility: Hydrochloride salt freely soluble (50 mg/ml at 20°C)
• Hydrophobicity(logP): 3.6

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00478

• Drug Groups: approved
• Description: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza. [PubChem]
• Indication: For the prophylaxis and treatment of illness caused by various strains of influenza A virus in adults.
• 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.
• Toxicity: Oral LD₅₀ in rats is 640 mg/kg. Overdoses of a related rug, amantadine, have been reported with adverse reactions consisting of agitation, hallucinations, cardiac arrhythmia and death.
• Affected Organisms: Human Influenza A Virus
• Biotransformation: 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.
• Absorption: Well absorbed, with the tablet and syrup formulations being equally absorbed after oral administration.
• 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).
• Protein Binding: Approximately 40% over typical plasma concentrations.
• 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.
• External Links: Wikipedia; RxList; Drugs.com