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HomeProduct name listALMOTRIPTAN

ALMOTRIPTAN

Synonym(s):3-[2-(Dimethylamino)ethyl]-5-(pyrrolidin-1-ylsulfonylmethyl )-1H-indole malate;PNU 180638

  • CAS NO.:181183-52-8
  • Empirical Formula: C21H31N3O7S
  • Molecular Weight: 469.55
  • MDL number: MFCD08067740
  • EINECS: 815-382-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
ALMOTRIPTAN Structural

What is ALMOTRIPTAN?

Description

Almotriptan is an agonist of the serotonin (5-HT) receptor subtypes 5-HT1B and 5-HT1D (IC50s = 12 and 13 nM, respectively, in a radioligand binding assay). It is selective for human 5-HT1B and 5-HT1D receptors over rat 5-HT1A and human 5-HT2A and 5-HT4 receptors (IC50s = 0.85, 25.1, and 140 μM, respectively). Almotriptan induces contractions in isolated canine saphenous veins (EC50 = 394 nM) but not isolated rabbit renal or mesenteric arteries. It increases carotid vascular resistance in anesthetized cats (ED100 = 11 μg/kg, i.v.) without increasing blood pressure or heart rate. Formulations containing almotriptan have been used in the treatment of migraine headaches.

Chemical properties

Pale Yellow Solid

Originator

Almogran ,Lundbeck

The Uses of ALMOTRIPTAN

Almotriptan is a serotonin 5HT1B /1D-receptor agonist used for treatment of migraine.

The Uses of ALMOTRIPTAN

anti-migraine agent

The Uses of ALMOTRIPTAN

Almotriptan is a serotonin 5HT-1B/1D-receptor agonist; antimigraine.

What are the applications of Application

Almotriptan Malate is a serotonin 5HT1B /1D-receptor agonist used for treatment of migraines

Definition

ChEBI: The malate salt of almotriptan.

Manufacturing Process

To a solution of previously dried 1-[[2-carboxy-3-(2-dimethylaminoethyl)-5- indolyl]methanesulphonyl]-pyrrolidine (1.6 g; 0.0442 moles) in anhydrous quinoline (75 ml) and under atmosphere of nitrogen, cuprous oxide (160 mg; 0.0011 moles) was added. The reaction mixture was heated to 190°C for 15 minutes, stirred to room temperature, poured into a mixture of 1 N hydrochloric acid (150 ml) and ethyl acetate (50 ml), shaken and decanted. The aqueous solution was washed several times with ethyl acetate, then solid sodium bicarbonate was added until pH = 7.8, and washed with n-hexane to eliminate the quinoline. The aqueous solution was made alkaline with solid potassium carbonate and extracted with ethyl acetate. The organic solution was dried (Na2SO4), the solvent removed under reduced pressure when a dark oil was obtained (1.3 g; yield 92%). This product was purified by column chromatography with silica gel and methylene chloride:ethanol:ammonium hydroxide (60:8:1) as eluent and a white foam (0.8 g) of 1-[[3-(2- dimethylaminoethyl)-5-indolyl]methanesulphonyl]-pyrrolidine was obtained. To a solution of the above product (0.8 g) in acetone (30 ml), a few drops of hydrogen chloride saturated dioxan solution, were added. The precipitated solid was collected by filtration, washed with acetone and dried to give 1-[(3- (2-(dimethylamino)ethyl)-5-indolyl)methanesulphonyl]-pyrrolidine hydrochloride (0.75 g). Melting point 218°-220°C.
In practice it is usually used as malate salt.

brand name

Axert (Ortho-McNeil).

Therapeutic Function

Migraine therapy

General Description

Almotriptan, marketed in 2000, has the highest oralbioavailability among all triptans. It is metabolizedby both MAO-A and CYP3A4, thus has a more favorableside effects profile when compared with sumatriptan.However, it is only available in a 12.5 mg tablet form.

Biochem/physiol Actions

Almotriptan is a serotonin 5HT-1B/1D-receptor agonist used to treat migraine. Almotriptan has low nanomolar affinity for the 5-HT(1B) and 5-HT(1D) receptors while affinity for 5-HT receptors other than 5-HT(1B/1D) is substantially lower. Affinity for 5-HT(7) and 5-HT(1A) receptors was approximately 40 and 60 times lower than that for 5-HT(1B/1D) receptors, respectively.

Properties of ALMOTRIPTAN

Melting point: 170-172°C
storage temp.  2-8°C
solubility  Basic Alcohol (Very Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
form  powder
color  white to beige

Safety information for ALMOTRIPTAN

Computed Descriptors for ALMOTRIPTAN

ALMOTRIPTAN manufacturer

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CSD Labs

Hyderabad
product: Almotriptan malate
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