a
amitriptyline
Medicine used to treat cyclic vomiting syndrome (CVS), depression and a variety of pain syndromes
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
- Formula
- C₂₀H₂₃N
1
- C₂₀H₂₃N
- Mass
- 277.183 Da
1
- 277.183 Da
Overview
Chemistry
All data
289 statements · 72% with external sources · numbers in brackets are citations
- Significant drug interaction
- isocarboxazid
- phenelzine
- procarbazine
- (±)-deprenyl
- tranylcypromine
- loxapine side effect: hypotension
- trimipramine side effect: hyponatremia
- nabumetone side effect: hyponatremia
Show 52 moreShow less
- naproxen side effect: hyponatremia
- celecoxib side effect: hyponatremia
- Diclofenac side effect: hyponatremia
- piroxicam side effect: hyponatremia
- meloxicam side effect: hyponatremia
- (RS)-fenoprofen side effect: hyponatremia
- (±)-flurbiprofen side effect: hyponatremia
- ibuprofen side effect: hyponatremia
- indomethacin side effect: hyponatremia
- (RS)-ketoprofen side effect: hyponatremia
- (RS)-etodolac side effect: hyponatremia
- sulindac side effect: hyponatremia
- parecoxib side effect: hyponatremia
- aceclofenac side effect: hyponatremia
- tenoxicam side effect: hyponatremia
- (S)-duloxetine side effect: hyponatremia
- paroxetine side effect: hyponatremia
- (E/Z)-doxepin side effect: hyponatremia
- sertraline side effect: hyponatremia
- fluvoxamine side effect: hyponatremia
- fluoxetine side effect: hyponatremia
- imipramine side effect: hyponatremia
- (RS)-citalopram side effect: hyponatremia
- clomipramine side effect: hyponatremia
- paliperidone side effect: hypotension
- trimipramine side effect: hypotension
- methyldopa side effect: hypotension
- guanfacine side effect: hypotension
- propranolol side effect: hypotension
- sotalol side effect: hypotension
- clonidine side effect: hypotension
- zuclopenthixol side effect: hypotension
- (RS)-sulpiride side effect: hypotension
- (RS)-baclofen side effect: hypotension
- phenelzine side effect: hypotension
- risperidone side effect: hypotension
- (E/Z)-doxepin side effect: hypotension
- droperidol side effect: hypotension
- pimozide side effect: hypotension
- aripiprazole side effect: hypotension
- haloperidol side effect: hypotension
- quetiapine side effect: hypotension
- imipramine side effect: hypotension
- chlorpromazine side effect: hypotension
- clomipramine side effect: hypotension
- clozapine side effect: hypotension
- lithium side effect: toxic encephalopathy
- disopyramide side effect: torsades de pointes
- disopyramide side effect: long QT syndrome
- disopyramide side effect: pulseless electrical activity
- disopyramide side effect: cardiotoxicity
- sotalol side effect: torsades de pointes
- World Health Organisation international non-proprietary name
- amitriptyline
1
- amitriptyline
- Medical condition treated
- pain
1
- neurotic disorder
1
- fibromyalgia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- insomnia
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- migraine
1
Sources- 1.Stated in Drug Indications Extracted from FAERSRetrieved 2018-10-02
- pain
- Canonical SMILES
- CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
1
- CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
- Subject has role
- selective serotonin reuptake inhibitor
1
- adrenergic uptake inhibitors
2
Sources- 1.Stated in NDF-RTRetrieved 2018-03-05
- 2.Stated in Medical Subject HeadingsRetrieved 2018-03-15
- non-opioid analgesic
1
- tricyclic antidepressant
1
- WHO essential medicines
- selective serotonin reuptake inhibitor
- Physically interacts with
- 5-hydroxytryptamine receptor 6 subject has role: antagonist
1
- 5-hydroxytryptamine (serotonin) receptor 7 subject has role: antagonist
1
- Histamine receptor H1 subject has role: antagonist
1
- Potassium inwardly-rectifying channel, subfamily J, member 6 subject has role: antagonist
1
- Potassium inwardly-rectifying channel, subfamily J, member 5 subject has role: antagonist
1
- Cholinergic receptor muscarinic 1 subject has role: antagonist
1
- Cholinergic receptor muscarinic 2 subject has role: antagonist
1
- Cholinergic receptor muscarinic 3 subject has role: antagonist
1
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- Cholinergic receptor muscarinic 4 subject has role: antagonist
1
- Cholinergic receptor muscarinic 5 subject has role: antagonist
1
- Solute carrier family 6 member 2 subject has role: antagonist
1
- solute carrier family 6 member 4 subject has role: antagonist
1
- 5-hydroxytryptamine receptor 6 subject has role: antagonist
- LiverTox likelihood score
- LiverTox toxicity likelihood category B
1
Sources- 1.Stated in LiverToxncbi.nlm.nih.gov/books/n/livertox/AmitriptylineRetrieved 2021-04-08
- LiverTox toxicity likelihood category B
- Defined daily dose
- 75 milligram route of administration: oral administration
- 75 milligram route of administration: parenteral route of administration
- Legal status (medicine)
- boxed warning
1
Sources- 1.“FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.”nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
- boxed warning
On other databases
49 identifiers linking amitriptyline across the web's reference databases
- ATC codeN06AA09
- CAS Registry Number50-48-6
- ChEBI ID2666
- ChEMBL IDCHEMBL629
- ChemSpider ID2075
- DeCS ID652
- DrugBank IDDB00321
- DrugCentral ID180
- DSSTOX compound identifierDTXCID502594
- DSSTox substance IDDTXSID7022594
- EC number200-041-6
- ECHA Substance Infocard ID100.000.038
- Electronic Essential Medicines List medicine ID19
- Encyclopædia Britannica Online IDscience/amitriptyline
- Freebase ID/m/02sff3
- Gran Enciclopèdia Catalana IDamitriptilina
- Gran Enciclopèdia Catalana ID (former scheme)0077786
- Guide to Pharmacology Ligand ID200
- HSDB ID3007
- Human Metabolome Database IDHMDB0014466
- InChIInChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
- InChIKeyKRMDCWKBEZIMAB-UHFFFAOYSA-N
- KBpedia IDAmitriptyline
- KEGG IDC06824
- LiverTox IDAmitriptyline
- MassBank accession IDSM859203
- MedlinePlus drug identifiera682388
- MeSH descriptor IDD000639
- MeSH tree codeD02.455.426.559.847.181.384.100
- Microsoft Academic ID (discontinued)2780216858
- NDF-RT IDN0000147702
- OpenAlex IDC2780216858
- PatientsLikeMe treatment IDamitriptyline
- PDB ligand IDTP0
- PDB structure ID3APV
- Probes And Drugs IDPD010103
- PubChem CID2160
- Quora topic IDAmitriptyline-1
- Reaxys registry number2217885
- RxNorm CUI704
- SPLASHsplash10-001i-1590000000-35080e23f36a6ed30005
- SureChEMBL ID7824
- UMLS CUIC0002600
- UniChem compound ID10791
- UNII1806D8D52K
- Wellcome Collection concept IDshjxv563
- WikiProjectMed IDAmitriptyline
- Wolfram Language entity codeEntity["Concept", "Amitriptyline::dpg47"]
- WordNet 3.1 Synset ID02705434-n