dimethyl({2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl})amine

• ChemBase ID: 829
• Molecular Formular: C15H19N5
• Molecular Mass: 269.34486
• Monoisotopic Mass: 269.16404563
• SMILES: [nH]1c2c(c(CCN(C)C)c1)cc(cc2)Cn1ncnc1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(cc2)Cn1cncn1)C
• InChI: InChI=1S/C15H19N5/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3
• InChIKey: ULFRLSNUDGIQQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl({2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl})amine
• IUPAC Traditional name: maxalt; rizatriptan
• Brand Name: Maxalt; Maxalt-MLT; Maxalt MLT
• Synonyms: 2-(5-((1H-1,2,4-Triazol-1-yl)methyl)-1H-indol-3-yl)-N,N-dimethylethanamine; Rizatriptan benzoat; Rizatriptan benzoate; Risatriptan; MK 462 Free Base; Rizatriptan

Database IDs

• CAS Number: 144034-80-0; 145202-66-0
• MDL Number: MFCD03840591
• PubChem SID: 46506557; 160964292
• PubChem CID: 5078

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.23522
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.6272316
• LogD (pH = 7.4): -0.37320176
• Log P: 1.7678794
• Molar Refractivity: 93.1323 cm^3
• Polarizability: 31.647243 Å^3
• Polar Surface Area: 49.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.67
• LOG S: -2.9
• Solubility (Water): 3.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: 42 mg/mL (for free base)
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00953

• Drug Groups: approved
• Description: Rizatriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.
• Indication: For treatment of acute migraine attacks with or without aura.
• Pharmacology: Rizatriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonists and has 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 Rizatriptan 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 Rizatriptan in humans.
• Toxicity: Symptoms of overdose include dizziness, fainting, heart and blood vessel problems, high blood pressure, loss of bowel and bladder control, slow heartbeat, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Rizatriptan is metabolized by monoamine oxidase A isoenzyme (MAO-A) to an inactive indole acetic acid metabolite. In addition, several other inactive metabolites are formed. An active metabolite, N-monodesmethyl-rizatriptan, with pharmacological activity similar to that of the parent compound has been identified in small concentrations (14%) in the plasma.
• Absorption: Rapid following oral administration. Bioavailability is 45%. Food has no effect on the bioavailability of rizatriptan. However, administering rizatriptan with food will delay by 1 hour the time to reach peak plasma concentration. The rate of absorption is not affected by the presence of a migraine attack.
• Half Life: 2-3 hours
• Protein Binding: 14%
• Elimination: Approximately 14% of an oral dose is excreted in urine as unchanged rizatriptan while 51% is excreted as indole acetic acid metabolite, indicating substantial first pass metabolism.
• Distribution: * 140 L [male]; * 110 L [female]
• References: Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. [Pubmed] ; Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. [Pubmed] ; Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance] Nippon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. [Pubmed] ; Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. [Pubmed] ; Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Wellington K, Plosker GL: Rizatriptan: an update of its use in the management of migraine. Drugs. 2002;62(10):1539-74. Pubmed
• Wellington K, Jarvis B: Spotlight on rizatriptan in migraine. CNS Drugs. 2002;16(10):715-20. Pubmed
• Ikemoto F, Toru T, Aijima H, Natsumeda Y: [Rizatriptan (Maxalt), a new entity of triptan for migraine: pharmacology and therapeutic relevance] Nippon Yakurigaku Zasshi. 2004 Apr;123(4):295-302. Pubmed
• Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. Pubmed
• Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. Pubmed