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Rasagiline mesylate(CAS No. 161735-79-1)

Rasagiline mesylate C12H13N.CH4O3S (cas 161735-79-1) Molecular Structure

161735-79-1 Structure

Identification and Related Records

【Name】
Rasagiline mesylate
【Iupac name】
methanesulfonic acid; (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
【CAS Registry number】
161735-79-1
【Synonyms】
R-(+)-Rasagiline mesylate
methanesulfonic acid
(1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
Rasagiline methanesulfonate
1H-Inden-1-amine, 2,3-dihydro-N-2-propynyl-, (R)-, methanesulfonate
(R)-N-2-Propynyl-1-indanamine methanesulfonate
(R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine methanesulfonate
【Molecular Formula】
C12H13N.CH4O3S (Products with the same molecular formula)
【Molecular Weight】
267.34
【Inchi】
InChI=1/C12H13N.CH4O3S/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12;1-5(2,3)4/h1,3-6,12-13H,7-9H2;1H3,(H,2,3,4)/t12-;/m1./s1
【Canonical SMILES】
CS(=O)(=O)O.C#CCNC1CCC2=CC=CC=C12
【Isomers smiles】
CS(=O)(=O)O.C#CCN[C@@H]1CCC2=CC=CC=C12
【MOL File】
161735-79-1.mol

Chemical and Physical Properties

【Appearance】
White powder
【Density】
1.05 g/cm3
【Melting Point】
155-158°C
【Boiling Point】
305.5 °C at 760 mmHg
【Vapour】
0.000816mmHg at 25°C
【Flash Point】
146.8 °C
【Solubilities】
In water, 3,700 mg/L at 25 deg C (est)
【Computed Properties】
Molecular Weight:267.34398 [g/mol]
Molecular Formula:C13H17NO3S
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:2
Exact Mass:267.092914
MonoIsotopic Mass:267.092914
Topological Polar Surface Area:74.8
Heavy Atom Count:18
Formal Charge:0
Complexity:305
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Formulations/Preparations】
Oral: Tablets: 0.5 mg (of rasagiline) Azilect (Teva Neuroscience); 1 mg (of rasagiline) Azilect (Teva Neuroscience). /Rasagiline mesylate/
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl rasagline mesylate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Rasagline mesylate/
【Specification】

? Rasagiline Mesylate , its CAS NO. is 161735-79-1, the synonyms are?(r)-n-2-Propynyl-1-indanamine methanesulfonate ; (1R)-2,3-Dihydro-N-2-propyn-1-yl-1H-inden-1-amine Mesylate ; (R)-N-2-Propynyl-1-indanamine Mesylate ; Agilect ; Azilect ; TVP-101 ; Rasagiline nesylate?.

【Octanol/Water Partition Coefficient】
log Kow = 2.6 (amine) (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: M.B.H. Youdim et al., EP 436492; eidem. US 5457133 (1991, 1995 both to Teva).
【Usage】

A selective irreversible MAO-B inhibitor. Antiparkinsonian

Biomedical Effects and Toxicity

【Pharmacological Action】
- A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)
- Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
【Therapeutic Uses】
Rasagiline is used as initial monotherapy or as adjunctive therapy to levodopa for the symptomatic treatment of idiopathic parkinsonian syndrome.
Azilect (rasagiline mesylate) is indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease as initial monotherapy and as adjunct therapy to levodopa. The effectiveness of Azilect was demonstrated in patients with early Parkinson's disease who were receiving Azilect as monotherapy and who were not receiving any concomitant dopaminergic therapy. The effectiveness of Azilect as adjunct therapy was demonstrated in patients with Parkinson's disease who were treated with levodopa.
【Biomedical Effects and Toxicity】
After oral administration of (14)C-labeled rasagiline, elimination occurred primarily via urine and secondarily via feces (62% of total dose in urine and 7% of total dose in feces over 7 days), with a total calculated recovery of 84% of the dose over a period of 38 days. Less than 1% of rasagiline was excreted as unchanged drug in urine.
Rasagiline is rapidly absorbed; following oral administration, peak plasma concentrations are achieved in approximately 1 hour. The absolute bioavailability of rasagiline is about 36%. Following administration with a high-fat meal, peak plasma rasagiline concentrations and area under the plasma concentration-time curve (AUC) decreased by approximately 60 and 20%, respectively; because AUC is not substantially affected, rasagiline may be administered with or without food. Rasagiline readily crosses the blood-brain barrier. The mean steady-state or terminal half-life of rasagiline is 31 or 1.342 hours, respectively; however, there is no correlation between rasagiline's pharmacokinetic profile and its pharmacologic effects because the drug irreversibly inhibits MAO-B, and restoration of normal enzyme activity depends on the rate of de novo enzyme synthesis. Rasagiline is approximately 88-94% bound to plasma proteins, with 61-63% bound to albumin.
IV studies in rats and dogs show that the volume of distribution (Vd) of rasagiline is several times that of total body water, indicating extensive tissue distribution. Tissue distribution of (14)C-rasagiline was studied in albino and pigmented rats, revealing peaks of tissue radioactivity between 0.25 and 0.5 hours. Distribution to large intestine, urinary bladder and lacrimal glands takes longer, whilst persistence (up to 24 hrs) was seen in eyes, skin and arterial walls of pigmented animals. In-vitro protein binding in plasma of animals is in the range of 70 to 90% and in human plasma in the range of 88 to 94%.
Oral studies with (14)C-rasagiline show that absorption is rapid in all species, with Cmax attained in less than 2 hours. Absolute bioavailability has been estimated as 53-69% in rats, 13-22% in dogs, and 36% in humans. Toxicokinetic analyses during the toxicology studies showed that exposure was linear at doses higher than the pharmacological selectivity for inhibition of MOA-B and was maintained up to about 5 mg/kg/day. However, kinetics became non-linear at higher doses, possibly indicating saturation of the elimination processes for both rasagiline and its metabolite aminoindan. Accumulation was seen only at the highest doses in the mouse and dog studies (60 and 21 mg/kg/day respectively).
The clearance of rasagiline is greater than the combined predicted renal and hepatic blood flow, suggesting extra hepatic, extra renal modes of elimination, possibly through non-reversible binding to target sites in the tissues. Mass balance studies conducted following oral administration in mice, rats and dogs showed a large proportion (>90%) of the administered radioactivity in the excreta, particularly urine (70-85%). Despite the rapid elimination half-life for rasagiline, repeat doses were seen to give greater exposure than seen after single doses. ...This observation is compatible with the mechanism of irreversible binding of rasagiline to MAO-B, leading to saturation of binding site. Excess unbound product appears in the plasma after the saturation threshold has been reached.
The pharmacokinetic disposition of rasagiline is best characterized by a two-compartment open model with first-order absorption and first-order elimination. Rasagiline appears to be widely distributed, with a mean apparent volume of distribution (Vd) of about 243 L following a single dose IV administration (2 mg). The large Vd is related to the irreversible binding of rasagiline to MAO in the body and is consistent with the findings in the population PK studies. The blood cell-to-plasma ratio for rasagiline derived radioactive material ranged from 0.1 to 1.2 with a mean ratio across time of 0.2 to 0.7, indicating that association and/or distribution of rasagiline and/or its metabolites into blood cells is not extensive.

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