T3DB: Almotriptan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2009-07-21 20:27:58 UTC

Update Date

2014-12-24 20:25:53 UTC

Accession Number

T3D2931

Identification

Common Name

Almotriptan

Class

Small Molecule

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.

Compound Type

Amide
Amine
Anti-Inflammatory Agent
Anti-Migraine Agent
Drug
Metabolite
Organic Compound
Selective Serotonin Agonist
Serotonin Agonist
Serotonin Antagonist
Serotonin Receptor Agonist
Synthetic Compound
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-(((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine
Almogran
Axert

Chemical Formula

C₁₇H₂₅N₃O₂S

Average Molecular Mass

335.464 g/mol

Monoisotopic Mass

335.167 g/mol

CAS Registry Number

181183-52-8

IUPAC Name

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

Traditional Name

almotriptan

SMILES

CN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C2

InChI Identifier

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

InChI Key

InChIKey=WKEMJKQOLOHJLZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
3-alkylindole
Indole
Aralkylamine
Substituted pyrrole
Organic sulfonic acid amide
Benzenoid
Organosulfonic acid amide
Pyrrole
Pyrrolidine
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Sulfonyl
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:520985 )
sulfonamide (CHEBI:520985 )
indoles (CHEBI:520985 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

serotonergic agonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.21e-01 g/L
LogP	1.6

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.52	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	17.14	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.41 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.52 m³·mol⁻¹	ChemAxon
Polarizability	37.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9120000000-8636aefe6f44933ba51b	2017-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2169000000-911884b25f81ab3a7184	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-8691000000-449e57d16a963ed1b74e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9510000000-6004be92a59ee97c688d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1926000000-1904ba0b8d011df20b74	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3931000000-ce8a83db474ffb7c1720	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9210000000-cd68178eac1c4d05f3f4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-946584fd7a8aeaa09963	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1695000000-9e83c6cf357b6d2f2b99	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9410000000-4ebc2e87bfec77e89c93	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0903000000-b62a8e072289815a1db0	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2529000000-c131caf01f261a061ede	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3792000000-25e1db8e7ba47860dbf0	2021-10-11	View Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

Almotriptan binds with high affinity to human 5-HT_1B and 5-HT_1D receptors leading to cranial blood vessel constriction.

Metabolism

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Almotriptan is indicated for the acute treatment of migraine with or without aura in adults. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Nausea, drowsiness, dizziness, diarrhea, headache, sweating, or dry mouth may occur.

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. (2)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

520985

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Almotriptan

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Almotriptan

References

Synthesis Reference

Ramasubramanian Sridharan, Vandanapu Purushotham, Kori Algooram, Nitin Pradhan, “Crystalline forms of almotriptan and processes for their preparation.” U.S. Patent US20070112055, issued May 17, 2007.

MSDS

T3D2931.pdf

General References

Drugs.com [Link]
RxList: The Internet Drug Index (2009). [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. 5-hydroxytryptamine receptor 1B

General Function:: Serotonin receptor activity
Specific Function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior. Besides, plays a role in vasoconstriction of cerebral arteries.
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular Weight:: 43567.535 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [10193663 ]
Bou J, Domenech T, Puig J, Heredia A, Gras J, Fernandez-Forner D, Beleta J, Palacios JM: Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist for the treatment of migraine. Eur J Pharmacol. 2000 Dec 20;410(1):33-41. [11134654 ]
Fleishaker JC, Sisson TA, Carel BJ, Azie NE: Pharmacokinetic interaction between verapamil and almotriptan in healthy volunteers. Clin Pharmacol Ther. 2000 May;67(5):498-503. [10824628 ]
van den Broek RW, MaassenVanDenBrink A, de Vries R, Bogers AJ, Stegmann AP, Avezaat CJ, Saxena PR: Pharmacological analysis of contractile effects of eletriptan and sumatriptan on human isolated blood vessels. Eur J Pharmacol. 2000 Oct 27;407(1-2):165-73. [11050304 ]
Knyihar-Csillik E, Tajti J, Csillik AE, Chadaide Z, Mihaly A, Vecsei L: Effects of eletriptan on the peptidergic innervation of the cerebral dura mater and trigeminal ganglion, and on the expression of c-fos and c-jun in the trigeminal complex of the rat in an experimental migraine model. Eur J Neurosci. 2000 Nov;12(11):3991-4002. [11069595 ]

Target Details

2. 5-hydroxytryptamine receptor 1D

General Function:: Serotonin receptor activity
Specific Function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Regulates the release of 5-hydroxytryptamine in the brain, and thereby affects neural activity. May also play a role in regulating the release of other neurotransmitters. May play a role in vasoconstriction.
Gene Name:: HTR1D
Uniprot ID:: P28221
Molecular Weight:: 41906.38 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [10193663 ]
Bou J, Domenech T, Puig J, Heredia A, Gras J, Fernandez-Forner D, Beleta J, Palacios JM: Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist for the treatment of migraine. Eur J Pharmacol. 2000 Dec 20;410(1):33-41. [11134654 ]
Gras J, Llupia J, Llenas J, Palacios JM: Safety profile of almotriptan, a new antimigraine agent. Effects on central nervous system, renal function and respiratory dynamics. Arzneimittelforschung. 2001 Sep;51(9):726-32. [11642004 ]

Almotriptan (T3D2931)

Structure for T3D2931: Almotriptan

Targets

References

References