Chemical Component Summary

NameAmitriptyline
Synonyms3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine
Identifiersn/a
FormulaC20 H23 N
Molecular Weight277.403
TypeNON-POLYMER
Isomeric SMILESCN(C)CCC=C1c2ccccc2CCc3c1cccc3
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

Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count0
Bond Count46
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB00321 
NameAmitriptyline
Groups approved
DescriptionAmitriptyline is a tricyclic antidepressant that has been used to treat depression for decades. ELAVIL, a previously approved branded product of amitriptyline, was first approved by the FDA in 1961.[A259342] Amitriptyline has been investigated in the treatment of pain-related conditions, attributed to its analgesic properties.[A174661]
Synonyms
  • Amitriptyline hydrochloride
  • 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • 10,11-dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene
  • Amitriptyline
  • 5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene
Brand Names
  • Amitriptyline Hydrochloride
  • Amitriptyline HCL
  • Novo-triptyn Tab 50mg
  • Apo Peram Tab 3-15
  • Zyvodol
IndicationThis drug in indicated for the following conditions [FDA label]: Major depressive disorder in adults [L46357] Management of neuropathic pain in adults Prophylactic treatment of chronic tension-type headache (CTTH) in adults Prophylactic treatment of migraine in adults Treatment of nocturnal enuresis in children aged 6 years and above when organic pathology, including spina bifida and related disorders, have been excluded and no response has been achieved to all other non-drug and drug treatments, including antispasmodics and vasopressin-related products. This product should only be prescribed by a healthcare professional with expertise in the management of persistent enuresis [FDA label] Off-label uses: irritable bowel syndrome, sleep disorders, diabetic neuropathy, agitation, fibromyalgia, and insomnia
Categories
  • Adrenergic alpha-1 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Adrenergic Uptake Inhibitors
  • Agents producing tachycardia
ATC-Code
  • N06AA09
  • N06CA01
CAS number50-48-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Sodium-dependent noradrenaline transporterMLLARMNPQVQPENNGADTGPEQPLRARKTAELLVVKERNGVQCLLAPRD...unknowninhibitor
Sodium-dependent serotonin transporterMETTPLNSQKQLSACEDGEDCQENGVLQKVVPTPGDKVESGQISNGYSAV...unknowninhibitor
5-hydroxytryptamine receptor 2AMDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...unknownantagonist
5-hydroxytryptamine receptor 1AMDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...unknowninhibitor,inducer
Delta-type opioid receptorMEPAPSAGAELQPPLFANASDAYPSACPSAGANASGPPGARSASSLALAI...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL629
PubChem 2160
ChEMBL CHEMBL629
ChEBI CHEBI:2666
CCDC/CSD YOVZEO