dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine

• ChemBase ID: 794
• Molecular Formular: C17H25N3O2S
• Molecular Mass: 335.4643
• Monoisotopic Mass: 335.16674806
• SMILES: S(=O)(=O)(N1CCCC1)Cc1cc2c(CCN(C)C)c[nH]c2cc1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(cc2)CS(=O)(=O)N1CCCC1)C
• InChI: InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3
• InChIKey: WKEMJKQOLOHJLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
• IUPAC Traditional name: almotriptan
• Brand Name: Axert; Almogran
• Synonyms: almotriptan; Almotriptan

Database IDs

• CAS Number: 181183-52-8
• PubChem SID: 46505165; 160964257
• PubChem CID: 123606

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.136013
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.8689746
• LogD (pH = 7.4): -0.6067433
• Log P: 1.5233824
• Molar Refractivity: 94.5219 cm^3
• Polarizability: 38.129585 Å^3
• Polar Surface Area: 56.41 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.04
• LOG S: -3.44
• Solubility (Water): 1.21e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.6

DETAILS

DrugBank - DB00918

• Drug Groups: approved; investigational
• Description: Almotriptan is a triptan drug for the treatment of migraine headaches. Almotriptan is in a class of medications called selective serotonin receptor agonists. It works by narrowing blood vessels in the brain, stopping pain signals from being sent to the brain, and stopping the release of certain natural substances that cause pain, nausea, and other symptoms of migraine. Almotriptan does not prevent migraine attacks.
• Indication: For the treatment of acute migraine headache in adults
• Pharmacology: Almotriptan is a selective 5-hydroxytryptamine receptor subtype agonist indicated for the acute treatment of migraine attacks with or without aura in adults. Almotriptan is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. Almotriptan is an agonist for a vascular 5-hydroxytryptamine receptor subtype (probably a member of the 5-HT_1D family) having only a weak affinity for 5-HT_1A, 5-HT_5A, and 5-HT₇ receptors and no significant affinity or pharmacological activity at 5-HT₂, 5-HT₃ or 5-HT₄ receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Almotriptan also activates 5-HT₁ receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Almotriptan in humans.
• Affected Organisms: Humans and other mammals
• Half Life: 3-4 hours
• Protein Binding: 35%
• 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.
• Distribution: * 180 to 200 L
• Clearance: * 57 L/h [healthy]; * 34.2 L/h [moderate renal impairment (creatinine clearance between 31 and 71 mL/min)]; * 9.8 L/h [severe renal impairment (creatinine clearance between 10 and 30 mL/min)]
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