Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00596)
Name
Rimantadine
Synonyms    Click to Show/Hide the Synonyms of This API
rimantadine; 13392-28-4; 1-(1-Adamantyl)ethanamine; 1-(Adamantan-1-yl)ethanamine; 1-Rimantadine; 1-(adamantan-1-yl)ethan-1-amine; alpha-Methyl-1-adamantanemethylamine; alpha-Methyladamantanemethylamine; RIMANTADIN; 1-Adamantan-1-yl-ethylamine; CHEMBL959; 1-Adamantanemethylamine, .alpha.-methyl-; .alpha.-Methyladamantanemethylamine; 1-(1-adamantyl)-ethylamine; 1-(tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanamine; Rimantadina; Rimantadinum; [1-(1-adamantyl)ethyl]amine hydrochloride; Rimantadine [INN:BAN]; Rimantadinum [INN-Latin]; 1-(1-Adamantyl)ethylamin; Rimantadina [INN-Spanish]; Tricyclo[3.3.1.13,7]decane-1-methanamine, a-methyl-; (R)-1-(1-Adamantyl)ethylamine; Rimant; 1-(1-adamantyl)ethylamine; (1S)-1-(adamantan-1-yl)ethan-1-amine; Rimantadine (INN); HSDB 7438; Enamine_005755; NCGC00159491-02; Rimant & .alpha. IFN; Rimantadine (Flumadine); Rimantidine & .alpha.IFN; 1-Adamantan-1-ylethylamine; BRN 2715740; rimantidin; Rimantadin A; 887336-05-2; 1-adamantanylethylamine; Tricyclo(3.3.1.13,7)decane-1-methanamine, alpha-methyl-; Maybridge1_002066; Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, alpha-methyl-; 1-ADAMANTANEMETHYLAMINE, alpha-METHYL-; SCHEMBL2981; 1-tricyclo[3.3.1.1~3,7~]dec-1-ylethanamine; Oprea1_602732; SCHEMBL2619249; CHEMBL1201272; DTXSID2023561; SCHEMBL20409367; CHEBI:94440; HMS1410F13; HMS2090L19; HMS3604N13; HMS3655J05; ALBB-013870; BCP12269; HY-B0338; ANW-72018; BBL013215; BDBM50216627; STK177253; (alpha-methyl-1-adamantyl)methylamine; AKOS000264537; AKOS006238592; AKOS016038537; .alpha.-Methyl-1-adamantanemethylamine; AM84461; CCG-236078; DB00478; MCULE-9027470290; 4-Bromo-7-(trifluoromethyl)- quinoline; IDI1_007990; NCGC00159491-03; NCGC00159491-05; AS-68744; SBI-0206810.P001; AB0012750; DB-042207; FT-0630403; ST45025920; SW220023-1; C07236; D08483; Q42171; 1-[(3R,5S,7s)-adamantan-1-yl]ethan-1-amine; AB00638368-09; AB00959689-03; AB01506092_02; AB01506092_03; 392R284; BRD-A84282119-003-01-2; Z56757137; Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl-; Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, .alpha.-methyl-; Tricyclo[3,3,1,1(3,7)]decane-1-methanamine, .alpha.-methyl-; Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl- & IFN.alpha
Clinical Status
Approved
Disease Indication Influenza virus infection ICD-11: 1E30 [1]
PubChem CID
5071
Formula
C12H21N
Canonical SMILES
CC(C12CC3CC(C1)CC(C3)C2)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5071"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 179.3 Topological Polar Surface Area 26
XlogP 2.6 Complexity 180
Heavy Atom Count 13 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Full List of Drug Formulations (DFMs) Containing This API
          Rimantadine 100 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycol; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Caraco Pharma; H. J. Harkins Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c yellow no. 6; Magnesium stearate; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Bryant Ranch Prepack; Carilion Materials Management; Impax Generics; Stat Rx USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Rimantadine Hydrochloride 100mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Hypromelloses; Magnesium Stearate; Cellulose; Microcrystalline; Sodium Starch Glycolate Type A Potato; Fd&C Yellow No. 6; Polyethylene Glycol
                   Dosage Form Tablet
                   Company Amneal Pharmaceuticals Of New York
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
References
1 FDA label for approved rimantadine from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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