amitriptyline indications/contra

Stem definitionDrug idCAS RN
antidepressants, dibenzo[a,d]cycloheptane or cyclopheptene derivatives 180 50-48-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • amitriptyline
  • amitriprolidine
  • amitriptylin
  • damitriptyline
  • amitriptyline hydrochloride
  • amitryptiline
  • amitryptiline hydrochloride
  • amitriptyline HCl
  • amitryptiline HCl
Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.
  • Molecular weight: 277.41
  • Formula: C20H23N
  • CLOGP: 4.85
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 0
  • TPSA: 3.24
  • ALOGS: -4.79
  • ROTB: 3

Drug dosage:

DoseUnitRoute
75 mg O
75 mg P

Approvals:

DateAgencyCompanyOrphan
April 7, 1961 FDA ASTRAZENECA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 4349.21 42.79 1063 4279 30051 3350466
Toxicity to various agents 3130.46 42.79 896 4446 46158 3334359
Overdose 1591.34 42.79 498 4844 33480 3347037
Cardiac arrest 1401.46 42.79 430 4912 26889 3353628
Drug abuse 1372.01 42.79 387 4955 17943 3362574
Respiratory arrest 1331.04 42.79 342 5000 11026 3369491
Cardio-respiratory arrest 1018.57 42.79 296 5046 15144 3365373
Intentional overdose 960.42 42.79 282 5060 14943 3365574
Poisoning 626.22 42.79 160 5182 4952 3375565
Suicide attempt 556.16 42.79 188 5154 15659 3364858
Death 540.65 42.79 370 4972 151954 3228563
Serotonin syndrome 506.79 42.79 137 5205 5286 3375231
Intentional product misuse 498.44 42.79 164 5178 12537 3367980
Electrocardiogram QRS complex prolonged 482.63 42.79 101 5241 1245 3379272
Confusional state 427.85 42.79 198 5144 37800 3342717
Coma 412.86 42.79 142 5200 12410 3368107
Drug hypersensitivity 392.43 42.79 183 5159 35497 3345020
Electrocardiogram QT prolonged 389.76 42.79 131 5211 10664 3369853
Agitation 385.30 42.79 152 5190 19554 3360963
Loss of consciousness 377.95 42.79 166 5176 27981 3352536
Drug interaction 373.98 42.79 193 5149 46619 3333898
Somnolence 328.71 42.79 157 5185 32047 3348470
Hypotension 286.38 42.79 165 5177 49349 3331168
Depressed level of consciousness 279.57 42.79 104 5238 11361 3369156
Delirium 240.77 42.79 89 5253 9539 3370978
Mydriasis 231.56 42.79 65 5277 2869 3377648
Seizure 228.98 42.79 133 5209 40267 3340250
Respiratory depression 222.99 42.79 67 5275 3767 3376750
Ventricular tachycardia 202.84 42.79 69 5273 5793 3374724
Tachycardia 196.49 42.79 100 5242 23271 3357246

Pharmacologic Action:

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SourceCodeDescription
ATC N06AA09 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
ATC N06CA01 NERVOUS SYSTEM
PSYCHOANALEPTICS
PSYCHOLEPTICS AND PSYCHOANALEPTICS IN COMBINATION
Antidepressants in combination with psycholeptics
FDA EPC N0000175752 Tricyclic Antidepressant
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007 DOID:2848
Mixed anxiety and depressive disorder indication 231504006
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
Sinus tachycardia contraindication 11092001
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Chronic disease of respiratory system contraindication 17097001
Disorder of lung contraindication 19829001 DOID:850
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002 DOID:13548
Hyperthyroidism contraindication 34486009 DOID:7998
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Paralytic ileus contraindication 55525008 DOID:8442
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Sleep apnea contraindication 73430006 DOID:0050848
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
Chronic idiopathic constipation contraindication 82934008
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Kidney disease contraindication 90708001 DOID:2527
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Hypoalbuminemia contraindication 119247004
Acute disease of cardiovascular system contraindication 128487001
Bipolar affective disorder, current episode manic contraindication 191618007
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Metabolic syndrome X contraindication 237602007 DOID:14221
Hyperprolactinemia contraindication 237662005 DOID:12700
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Retention of urine contraindication 267064002
Syncope contraindication 271594007
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Severe chronic obstructive pulmonary disease contraindication 313299006
Coma contraindication 371632003
At risk for aspiration contraindication 371736008
Angle-closure glaucoma contraindication 392291006 DOID:13550
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004 DOID:13268
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002
Posttraumatic stress disorder off-label use 47505003 DOID:2055
Bulimia nervosa off-label use 78004001 DOID:12129
Fibromyalgia off-label use 203082005 DOID:631
Neuropathic pain off-label use 247398009
Migraine Prevention off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.66 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR Kd 8.37 WOMBAT-PK CHEMBL
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Kd 7.46 WOMBAT-PK CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.88 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 8.07 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 8.25 DRUG MATRIX
Sodium channel protein type 5 subunit alpha Ion channel IC50 5.80 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 5.21 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.77 CHEMBL
Sodium channel protein type 9 subunit alpha Ion channel IC50 6 CHEMBL
Sodium channel protein type 2 subunit alpha Ion channel IC50 5.51 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 8.10 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7.96 WOMBAT-PK
Solute carrier family 22 member 2 Transporter IC50 4.85 WOMBAT-PK
Histamine H4 receptor GPCR Ki 8.14 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR IC50 8 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR IC50 7.90 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.05 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 7.40 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 7.05 WOMBAT-PK
Sigma non-opioid intracellular receptor 1 Membrane receptor IC50 6.25 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 6.59 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 7.80 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 8.14 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 7.89 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8.10 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 7.83 WOMBAT-PK
Histamine H2 receptor GPCR IC50 6.80 WOMBAT-PK
Histamine H1 receptor GPCR ANTAGONIST Ki 9.30 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 6.77 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 6.69 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 6.40 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.72 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 6.71 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5 WOMBAT-PK
High affinity nerve growth factor receptor Kinase IC50 4.22 CHEMBL
Proto-oncogene tyrosine-protein kinase receptor Ret Kinase IC50 6 CHEMBL
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 8.10 IUPHAR
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 8.40 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 6.40 IUPHAR
G protein-activated inward rectifier potassium channel 2 Ion channel BLOCKER IC50 4 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.38 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.77 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter IC50 5.07 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 10.70 CHEMBL
Transporter Transporter IC50 5.60 CHEMBL
Muscarinic acetylcholine receptor GPCR IC50 6.52 CHEMBL
Histamine H1 receptor GPCR IC50 10.70 CHEMBL
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 7.20 IUPHAR
5-hydroxytryptamine receptor 1A GPCR IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7 IUPHAR

External reference:

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IDSource
DB00321 DRUGBANK_ID
200 IUPHAR_LIGAND_ID
4019607 VUID
N0000147702 NUI
C0002600 UMLSCUI
D00809 KEGG_DRUG
CHEMBL629 ChEMBL_ID
1806D8D52K UNII
976 INN_ID
549-18-8 SECONDARY_CAS_RN
2160 PUBCHEM_CID
4019607 VANDF
704 RXNORM
372726002 SNOMEDCT_US
40589005 SNOMEDCT_US
d00146 MMSL
N0000005763 NDFRT
N0000147702 NDFRT
004600 NDDF
CHEBI:2666 CHEBI
CHEMBL1200964 ChEMBL_ID
D000639 MESH_DESCRIPTOR_UI
TP0 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0042 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0073 TABLET, FILM COATED 50 mg ORAL ANDA 13 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0211 TABLET, FILM COATED 14 mg ORAL ANDA 14 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0277 TABLET, FILM COATED 27.98 mg ORAL ANDA 14 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0330 TABLET, FILM COATED 10 mg ORAL ANDA 13 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0442 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Perphenazine and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0574 TABLET, FILM COATED 25 mg ORAL ANDA 13 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2610 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2625 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2650 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2675 TABLET, FILM COATED 75 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2685 TABLET, FILM COATED 100 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2695 TABLET, FILM COATED 150 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0463-6351 TABLET, FILM COATED 25 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0463-6352 TABLET, FILM COATED 50 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0463-6354 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2212 TABLET, FILM COATED 10 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2213 TABLET, FILM COATED 25 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2214 TABLET, FILM COATED 50 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2215 TABLET, FILM COATED 75 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2216 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-2217 TABLET, FILM COATED 150 mg ORAL ANDA 16 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-0828 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-0829 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-0830 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1486 TABLET, FILM COATED 10 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1487 TABLET, FILM COATED 25 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1488 TABLET, FILM COATED 50 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1489 TABLET, FILM COATED 75 mg ORAL ANDA 15 sections
Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-1490 TABLET, FILM COATED 100 mg ORAL ANDA 15 sections