ChemicalBook > CAS DataBase List > Almotriptan

Almotriptan

Product Name
Almotriptan
CAS No.
154323-57-6
Chemical Name
Almotriptan
Synonyms
LAS-31416;Almotriptan;LAS-31416-d6;ALMOTRIPTAN-D6;AlMotriptan API;ALMOTRIPTAN(SUBJECTTOPATENETFREE);1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine;N,N-dimethyl-5-[(1-pyrrolidinylsulfonyl)methyl]-1H-Indole-3-ethanamine;1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine-d6;1-[[[2-(Dimethyl-amino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidine
CBNumber
CB7716603
Molecular Formula
C17H25N3O2S
Formula Weight
335.46
MOL File
154323-57-6.mol
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Almotriptan Property

Boiling point:
538.7±60.0 °C(Predicted)
Density 
1.27±0.1 g/cm3(Predicted)
pka
16.92±0.30(Predicted)
CAS DataBase Reference
154323-57-6(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P233Keep container tightly closed.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304IF INHALED:

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P340Remove victim to fresh air and keep at rest in a position comfortable for breathing.

P362Take off contaminated clothing and wash before reuse.

P403Store in a well-ventilated place.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0002140
Product name
Almotriptan for system suitability
Purity
CRS, European Pharmacopoeia (EP) Reference Standard
Packaging
Y0002140
Price
$156
Updated
2024/03/01
Usbiological
Product number
A1358-90
Product name
Almotriptan
Packaging
10mg
Price
$375
Updated
2021/12/16
Matrix Scientific
Product number
091207
Product name
N,N-Dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)-methyl)-1H-indol-3-yl)ethanamine
Purity
95+%
Packaging
1g
Price
$457
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
RDL0006650
Product name
ALMOTRIPTAN-D6
Purity
95.00%
Packaging
5MG
Price
$497.17
Updated
2021/12/16
Biorbyt Ltd
Product number
orb134783
Product name
Almotriptan
Purity
>99%
Packaging
100mg
Price
$510
Updated
2021/12/16
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Almotriptan Chemical Properties,Usage,Production

Description

Almotriptan was first marketed in Spain as a new medicine against acute attacks of migraine. It is the fifth agent belonging to the “triptan” class to be launched after sumatriptan, naratriptan, zolmitriptan and rizatriptan. This close structural analog of sumatriptan can be prepared in six steps from 4-nitrobenzylsulfonyl chloride with a Fischer indole synthesis as the key step. Almotriptan acts as a dual 5-HT1D/1B agonist with a 35 to 51-fold selectivity versus 5-HT1A and 5-HT7 receptors respectively as well as having insignificant affinity for the most relevant nonserotonergic receptors (K1>1μM). Its agonistic effect on 5-HT,n receptors of trigeminal sensory neurons turns off neurogenic inflammation by inhibiting the release of neuropeptides such as calcitonin gene-related peptide, neurokinin A and substance P. Concomitantly, its action on the 5-HT1B receptors in meningeal arteries relieves the vasodilatation of these vessels associated with migraine attacks. Almotriptan causes selective concentration-dependent vasoconstriction of human meningeal and temporal arteries (with EC50 of 0.03 and 0.7 μM) compared to basilar (EC50 = 3.5 μM) and pulmonary arteries (EC50>10μM) or rabbit mesenteric and renal arteries (EC50>100 μM). Although it is predominantly cleared by the kidneys as unchanged drug (45%) or transformed into inactive metabolites by monoamine oxidase A (MAO-A) and CYP3A4 enzymes in the liver, almotriptan has the highest oral bioavailability (70%) of the triptans and has a half-life of 3.5 h. The therapeutic dose of 12.5 mg is well tolerated, shows a rapid onset of action (30 min) and low recurrence rate compared to sumatriptan.

Originator

Almirall Prodesfarma (Spain)

Uses

Serotonin 5HT1B /1D-receptor agonist

Definition

ChEBI: An indole compound having a 2-(dimethylamino)ethyl group at the 3-position and a (pyrrolidin-1-ylsulfonyl)methyl group at the 5-position.

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

Almogran

Therapeutic Function

Migraine therapy

Clinical Use

5HT1 receptor agonist:
Acute relief of migraine

Drug interactions

Potentially hazardous interactions with other drugs
Antidepressants: increased risk of CNS toxicity with citalopram - avoid; possibly increased serotonergic effects with duloxetine or venlafaxine; increased serotonergic effects with St John’s wort - avoid.
Antifungals: concentration increased by ketoconazole (increased risk of toxicity).
Dapoxetine: possible increased risk of serotonergic effects - avoid for 2 weeks after stopping 5HT1 agonists.
Ergot alkaloids: increased risk of vasospasm - avoid.

Metabolism

The major biotransformation route is via monoamine oxidase (MAO-A) mediated oxidative deamination to the indole acetic metabolite. Cytochrome P450 (3A4 and 2D6 isozymes) and flavin mono-oxygenase are other enzymes involved in the metabolism of almotriptan. None of the metabolites are significantly active pharmacologically. More than 75% of a dose is eliminated in urine, and the remainder in faeces. Approximately, 50% of the urinary and faecal excretion is unchanged almotriptan.

Almotriptan Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Almotriptan manufacturers

Career Henan Chemical Co
Product
Almotriptan 154323-57-6
Price
US $7.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-21

154323-57-6, AlmotriptanRelated Search:


  • LAS-31416-d6
  • ALMOTRIPTAN(SUBJECTTOPATENETFREE)
  • Almotriptan
  • N,N-Dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]-ethanamine
  • dimethyl-[2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethyl]amine
  • AlMotriptan API
  • N,N-dimethyl-5-[(1-pyrrolidinylsulfonyl)methyl]-1H-Indole-3-ethanamine
  • ALMOTRIPTAN-D6
  • 1-[[[2-(Dimethyl-amino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidine
  • 1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine
  • LAS-31416
  • 1-[[[2-(Dimethyl-amino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidine-d6
  • 1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine-d6
  • 1H-Indole-3-ethanamine, N,N-dimethyl-5-[(1-pyrrolidinylsulfonyl)methyl]-
  • AlmotriptanQ: What is Almotriptan Q: What is the CAS Number of Almotriptan Q: What is the storage condition of Almotriptan Q: What are the applications of Almotriptan
  • 154323-57-6
  • C17H19D6N3O2S
  • Intermediates & Fine Chemicals
  • Isotope Labeled Compounds
  • Pharmaceuticals
  • APIs
  • Isotope Labelled Compounds
  • Heterocyclic Compounds