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Rasagiline information


Rasagiline
Clinical data
Trade namesAzilect, Azipron, others
Other namesVP-1012, N-propargyl-1(R)-aminoindan[1]
AHFS/Drugs.comMonograph
MedlinePlusa606017
License data
  • EU EMA: by INN
  • US FDA: Rasagiline
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
  • N04BD02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)[2]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability36%
Protein binding88 – 94%
MetabolismLiver (CYP1A2-mediated)
Elimination half-life3 hours[citation needed]
ExcretionKidney and fecal
Identifiers
IUPAC name
  • (R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine
CAS Number
  • 136236-51-6 ☒N
PubChem CID
  • 3052776
IUPHAR/BPS
  • 6641
DrugBank
  • DB01367 checkY
ChemSpider
  • 2314553 checkY
UNII
  • 003N66TS6T
KEGG
  • D08469 ☒N
  • as salt: D02562 ☒N
ChEMBL
  • ChEMBL887 checkY
PDB ligand
  • RAS (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID3041112 Edit this at Wikidata
ECHA InfoCard100.301.709 Edit this at Wikidata
Chemical and physical data
FormulaC12H13N
Molar mass171.243 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C#CCN[C@H]2c1ccccc1CC2
InChI
  • InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1 checkY
  • Key:RUOKEQAAGRXIBM-GFCCVEGCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rasagiline (Azilect, Azipron) is an irreversible inhibitor of monoamine oxidase-B[3] used as a monotherapy to treat symptoms in early Parkinson's disease or as an adjunct therapy in more advanced cases.[4]

The racemic form of the drug was invented by Aspro Nicholas in the early 1970s. Moussa B.H. Youdim identified it as a potential drug for Parkinson's disease, and working with collaborators at Technion – Israel Institute of Technology in Israel and the drug company, Teva Pharmaceuticals, identified the R-isomer as the active form of the drug.[5] Teva brought it to market in partnership with Lundbeck in Europe and Eisai in the US and elsewhere. It was approved in Europe in 2005 and in the US in 2006.

Rasagiline is used to treat symptoms of Parkinson's disease both alone and in combination with other drugs. It has shown efficacy in both early and advanced Parkinsons, and appears to be especially useful in dealing with non-motor symptoms like fatigue.[6][7][8]

Rasagiline has not been tested in pregnant women and is Pregnancy Category C in the US.[8]

  1. ^ Akao Y, Maruyama W, Yi H, Shamoto-Nagai M, Youdim MB, Naoi M (June 2002). "An anti-Parkinson's disease drug, N-propargyl-1(R)-aminoindan (rasagiline), enhances expression of anti-apoptotic bcl-2 in human dopaminergic SH-SY5Y cells". Neuroscience Letters. 326 (2): 105–8. doi:10.1016/s0304-3940(02)00332-4. PMID 12057839. S2CID 29736753.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  3. ^ Oldfield V, Keating GM, Perry CM (2007). "Rasagiline: a review of its use in the management of Parkinson's disease". Drugs. 67 (12): 1725–47. doi:10.2165/00003495-200767120-00006. PMID 17683172. S2CID 195688993.
  4. ^ Gallagher DA, Schrag A (2008). "Impact of newer pharmacological treatments on quality of life in patients with Parkinson's disease". CNS Drugs. 22 (7): 563–86. doi:10.2165/00023210-200822070-00003. PMID 18547126. S2CID 29707067.
  5. ^ Lakhan SE (July 2007). "From a Parkinson's disease expert: Rasagiline and the future of therapy" (PDF). Molecular Neurodegeneration. 2 (1): 13. doi:10.1186/1750-1326-2-13. PMC 1929084. PMID 17617893.
  6. ^ Stocchi F, Fossati C, Torti M (2015). "Rasagiline for the treatment of Parkinson's disease: an update". Expert Opinion on Pharmacotherapy. 16 (14): 2231–41. doi:10.1517/14656566.2015.1086748. PMID 26364897. S2CID 6823552.
  7. ^ Poewe W, Mahlknecht P, Krismer F (September 2015). "Therapeutic advances in multiple system atrophy and progressive supranuclear palsy". Movement Disorders. 30 (11): 1528–38. doi:10.1002/mds.26334. PMID 26227071. S2CID 30312372.
  8. ^ a b Azilect Prescribing Information Label last revised May, 2014

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