阿米替林

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

Amitriptyline, formerly sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.

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.

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 · 中文

阿米替林（Amitriptyline），商品名稱Elavil，是使用最广泛的一种止痛药。阿米替林可以治疗许多精神障碍，包括重度抑郁症和焦虑症，有时候也用来治疗精神病、注意力缺陷多动障碍（ADHD，多动症）和双相情感障碍。阿米替林也可以預防偏头痛、治療包括纖維肌痛症及在内的神經性疼痛，偶爾也會被用於治療失眠。該藥屬於口服藥物。常見的副作用包含口乾、視覺障礙、姿位性低血壓、嗜睡，以及便秘等等。嚴重的副作用可能會造成癲癇發作、尿滯留、青光眼，或是其他心臟問題，25歲以下的用藥者甚至會有增加自殺念頭的風險。該藥切忌與单胺氧化酶抑制剂或等藥物合用。妊娠時服用阿米替林可能具有風險，哺乳期間用藥目前認為是安全的。該藥為使用最廣泛的一種三環類抗抑鬱藥（TCA），然其詳細機轉仍不清楚。在1960年首次發現阿米替林，並於1961年被美國食品藥品監督管理局核准。該藥列名世界衛生組織基本藥物標準清單當中，為基礎醫療體系的必備用藥之一。該藥屬於通用名藥物，2014年每劑的批發價價格區間位於0.01至0.04美金之間，美國境內則約一劑0.20美金左右。

Abstract from DBpedia / Wikipedia · CC BY-SA