Almotriptan Malate
Basic information
- CAS
181183-52-8- Standard SMILES
CN(C)CCc1c[nH]c2ccc(CS(=O)(=O)N3CCCC3)cc12.O=C(O)CC(O)C(=O)O- InChIKey
QHATUKWEVNMHRY-UHFFFAOYSA-N- Molecular formula
- C21H31N3O7S
- Average molar mass
- 469.6 g/mol
- Monoisotopic mass
- 469.18827151
Overview
Almotriptan malate is the malate salt of almotriptan. It has a role as a non-steroidal anti-inflammatory drug, a serotonergic agonist and a vasoconstrictor agent. It contains an almotriptan.
Names & identifiers
- Preferred name
- Almotriptan Malate
- IUPAC
- N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine;2-hydroxybutanedioic acid
- English name
- Almotriptan malate
- Molecular formula
- C21H31N3O7S
- Molecular weight
- 469.55
Names & synonyms
Almotriptan malate181183-52-8Almotriptan maleateLAS 31416 D,L-malate acidPNU-180638EPJP312605EDTXSID1044225CHEBI:53781RefChem:57721DTXCID9024225815-382-1Axert
Show more names
AlmogranPNU 180638PNU-180638AlmotriptanLAS-31416 Malate1-[[[3-[2-(dimethAmotriptan malateAlmotriptanMaleate
MFCD08067740Almotriptan (malate)Almotriptan malate [USAN]Almotriptan d,l-hydrogenmalateN,N-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)methyl)-1H-indol-3-yl)ethan-1-amine 2-hydroxysuccinateN,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine;2-hydroxybutanedioic acidLAS-31416 D,L-Malate acid1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine Malate
Database identifiers
- CAS
181183-52-8- PubChem CID
- 123607
- DTXSID
DTXSID1044225- ChEMBL
CHEMBL1200521- ChEBI
CHEBI:53781- UNII
- PJP312605E
- EC Number
- 815-382-1
Properties
Computed structural properties
- Topological polar surface area
- 160 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 9
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 611
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 170 · 170-172°C
- storage temp.
- 2 · 2-8°C
- solubility
- Basic Alcohol (Very Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
- form
- powder
- color
- white to beige
- Water Solubility
- 2 O: · H2O: 10mg/mL, clear
- InChIKey
- QHATUKWEVNMHRY-UHFFFAOYSA-N
- SMILES
- [S](=O)(=O)(N3CCCC3)Cc1cc2c([nH]cc2CCN(C)C)cc1.OC(CC(=O)O)C(=O)O
- FDA UNII
- 312605 E · PJP312605E
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 312 · H312-H332
- Precautionary statements
- 261 · P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
- WGK Germany
- 3 · WGK 3
- HS Code
- 2935904000 · 2935904000
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P261, P271, P280, P302+P352, P304+P340, P317, P321, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Treatment
Gastrointestinal decontamination (i.e., gastric lavage followed by activated charcoal) should be considered in patients suspected of an overdose with Almotriptan. Clinical and electrocardiographic monitoring should be continued for at least 20 hours, even if clinical symptoms are not observed. (L1712)
Exposure RoutesOral
Toxicity SummaryAlmotriptan binds with high affinity to human 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors leading to cranial blood vessel constriction.
Signs and SymptomsNausea, drowsiness, dizziness, diarrhea, headache, sweating, or dry mouth may occur.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Almotriptan malate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- WGK 3
- hs_code
- 2935904000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H312-H332
- Precautionary statements
- P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Hepatic. Route of Elimination: Almotriptan is eliminated primarily by renal excretion (about 75% of the oral dose), with approximately 40% of an administered dose excreted unchanged in urine. Approximately 13% of the administered dose is excreted via feces, both unchanged and metabolized. Half Life: 3-4 hours
FDA Pharmacological Classification
ALMOTRIPTAN MALATE
Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]
MeSH Pharmacological ClassificationEndogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Uses & manufacturing
UsesAlmotriptan is indicated for the acute treatment of migraine with or without aura in adults. [Wikipedia]
Applications
DescriptionAlmotriptan is a kind of triptan drug which can be used for the treatment of migraine headaches. It is belong to a drug category of selective serotonin receptor agonists. It has a high and specificity affinity for serotonin 5-HT receptors, further leading to vascoconstriction of the brain blood vessel and affecting the redistribution of blood flow. These effects stop pain signals from being sent to the brain, and further suppressing the release of certain natural substances which cause pain, nausea and other migraine symptoms. However, it doesn’t prevent migraine attacks.
DescriptionAlmotriptan 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.
UsesAlmotriptan is a serotonin 5HT-1B/1D-receptor agonist; antimigraine.
UsesAlmotriptan is a serotonin 5HT1B /1D-receptor agonist used for treatment of migraine.
Usesanti-migraine agent
General DescriptionAlmotriptan, 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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: The malate salt of almotriptan.
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