amitriptilina

Also known as amitryptiline, 5-(gamma-dimethylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptadiene, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine, 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene, 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptatriene, 10,11-dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(5),gamma-propylamine, 10,11-dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene, 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]heptalene-delta(5),gamma-propylamine

composto químico

OverviewAI-generated

Amitriptyline is a chemical compound with the formula C₂₀H₂₃N. Its IUPAC name is N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine. The compound has a mass of 277.183 and a defined daily dose of 75.

Chemical properties include an xlogp of 5, a topological polar surface area of 3.2, and a charge of 0. It has zero hydrogen bond donors and one hydrogen bond acceptor. The canonical SMILES notation for the molecule is CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.

Amitriptyline is referenced by 4,158 other encyclopedia articles. A search for the term in PubMed yields a count of 10,509 entries.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

In the Vinony graph

Vinony's link graph records 4,158 inbound references to amitriptilina, and connects out to Hypericum perforatum, benzodiazepine drug and propranolol.

Vinony files it under Alpha-1 blockers, Alpha-2 blockers and Dibenzocycloheptenes.

Vinony links it to 48 Wikipedia language editions.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 477169407
Drug.image: Amitriptyline2DACS.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Amitriptyline-from-picrate-xtal-3D-balls.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Elavil, others
Drug.MedlinePlus: a682388
Drug.DailyMedID: Amitriptyline
Drug.pregnancy_AU: C
Drug.routes_of_administration: Oral, intramuscular injection
Drug.class: Tricyclic antidepressant (TCA)
Drug.ATC_prefix: N06
Drug.ATC_suffix: AA09
Drug.legal_AU: S4
Drug.legal_BR: C1

via Wikipedia infobox

Chemical data

Formula: C20H23N
Molecular weight: 277.4 g/mol
IUPAC name: N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine
SMILES: CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
InChIKey: KRMDCWKBEZIMAB-UHFFFAOYSA-N
XLogP: 5
Polar surface area: 3.2 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1961
Admin. routes: oral, parenteral
Indications: diabetes mellitus, reproductive system disease, pain, neuropathy

via ChEMBL · EBI

Research

10,509 papers

Amitriptyline's anticholinergic adverse drug reactions-A systematic multiple-indication review and meta-analysis.PloS one · 2023
Classics in Chemical Neuroscience: Amitriptyline.ACS chemical neuroscience · 2021
[Amitriptyline].Therapeutique (La Semaine des hopitaux) · 1969
Amitriptyline for the treatment of fibromyalgia: a comprehensive review.Expert review of neurotherapeutics · 2015
Amitriptyline intoxication in bullfrogs causes widening of QRS complexes in electrocardiogram.The Journal of veterinary medical science · 2023

via PubMed

Wikidata facts

Has part: carbon
Mass: 277.183
Has use: medication

Show 11 more facts

chemical formula: C₂₀H₂₃N
significant drug interaction: fluvoxamine
Commons category: Amitriptyline
World Health Organisation international non-proprietary name: amitriptyline
medical condition treated: migraine
canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
subject has role: essential medicine
physically interacts with: solute carrier family 6 member 4
legal status (medicine): boxed warning
route of administration: intravenous infusion and defusion
defined daily dose: 75

Sources (7)

via Wikidata · CC0

Article · Português

A amitriptilina (nomes comerciais: Amytril, Elavil, entre outros) é um fármaco utilizado para tratar várias condições que afectam o SNC. Entre elas estão principalmente a depressão e problemas de ansiedade, mas também a enurese. É eficaz na prevenção das enxaquecas, cefaleias de tensão e no controlo da dor neuropática. Para além disso, é utilizado em casos de insónia, fibromialgia, síndrome do cólon irritável, entre outros, embora o seu uso não esteja oficialmente aprovado em muitos países para essas condições. Segundo uma meta análise em grande escala feita em 2018, que comparou 21 antidepressivos disponíveis atualmente no mercado, tanto a nível de eficácia como de tolerabilidade, a amitriptilina foi considerado o mais eficaz com uma diferença significativa. Já a nível de tolerabilidade, algo no qual os antidepressivos tricíclicos possuem uma má reputação, ficou na sexta posição.

Abstract from DBpedia / Wikipedia · CC BY-SA