amitriptyline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
75 mg O
75 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1000 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 15.45 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 48 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 8.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.07 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 17 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 7, 1961 FDA ASTRAZENECA

FDA Adverse Event Reporting System (Female)

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 3849.17 44.68 922 3810 20112 2333241
Toxicity to various agents 3251.05 44.68 882 3850 31872 2321481
Drug abuse 1122.97 44.68 313 4419 11713 2341640
Overdose 1104.60 44.68 346 4386 19561 2333792
Cardiac arrest 1095.71 44.68 322 4410 14608 2338745
Cardio-respiratory arrest 958.74 44.68 261 4471 8885 2344468
Respiratory arrest 954.50 44.68 240 4492 5938 2347415
Intentional overdose 710.71 44.68 217 4515 11104 2342249
Death 544.84 44.68 314 4418 81154 2272199
Coma 531.25 44.68 165 4567 8891 2344462
Drug hypersensitivity 479.98 44.68 240 4492 46403 2306950
Electrocardiogram QRS complex prolonged 434.48 44.68 92 4640 1010 2352343
Suicide attempt 428.48 44.68 148 4584 11134 2342219
Poisoning 426.47 44.68 108 4624 2712 2350641
Serotonin syndrome 416.33 44.68 111 4621 3429 2349924
Hypotension 411.79 44.68 193 4539 32243 2321110
Electrocardiogram QT prolonged 406.45 44.68 130 4602 7684 2345669
Drug interaction 402.74 44.68 184 4548 28979 2324374
Drug ineffective 391.49 44.68 277 4455 101347 2252006
Somnolence 387.70 44.68 168 4564 23317 2330036
Loss of consciousness 351.79 44.68 147 4585 18620 2334733
Depressed level of consciousness 328.58 44.68 110 4622 7494 2345859
Intentional product misuse 319.83 44.68 114 4618 9375 2343978
Confusional state 296.49 44.68 141 4591 24203 2329150
Pain 232.95 44.68 167 4565 61690 2291663
Tachycardia 227.26 44.68 104 4628 16305 2337048
Agitation 221.66 44.68 91 4641 10960 2342393
Anticholinergic syndrome 220.35 44.68 42 4690 254 2353099
Fibromyalgia 217.88 44.68 66 4666 3234 2350119
Delirium 215.31 44.68 73 4659 5150 2348203
Fall 209.56 44.68 141 4591 46958 2306395
Suicidal ideation 207.83 44.68 87 4645 11000 2342353
Cognitive disorder 205.39 44.68 71 4661 5310 2348043
Seizure 204.59 44.68 110 4622 24356 2328997
Bradycardia 202.90 44.68 83 4649 9898 2343455
Dizziness 199.45 44.68 149 4583 58516 2294837
Respiratory depression 198.91 44.68 56 4676 2114 2351239
Shock 193.08 44.68 63 4669 3941 2349412
Mydriasis 188.66 44.68 54 4678 2165 2351188
Sinus tachycardia 187.77 44.68 59 4673 3266 2350087
Accidental overdose 185.48 44.68 61 4671 3911 2349442
Dry mouth 182.74 44.68 73 4659 8180 2345173
Synovial fluid analysis 182.52 44.68 26 4706 5 2353348
Rheumatoid arthritis 176.74 44.68 92 4640 19048 2334305
Ventricular tachycardia 176.59 44.68 55 4677 2956 2350397
Pulseless electrical activity 163.78 44.68 41 4691 974 2352379
Vomiting 161.09 44.68 143 4589 71459 2281894
Tenosynovitis stenosans 157.47 44.68 28 4704 107 2353246
Depression 146.25 44.68 93 4639 28039 2325314
Musculoskeletal stiffness 145.83 44.68 70 4662 12177 2341176
Circulatory collapse 141.56 44.68 49 4683 3671 2349682
Scleritis 140.24 44.68 29 4703 279 2353074
Hyponatraemia 137.26 44.68 69 4663 13256 2340097
Coma scale abnormal 136.76 44.68 34 4698 784 2352569
Metabolic acidosis 136.00 44.68 54 4678 5944 2347409
Impaired work ability 135.88 44.68 40 4692 1770 2351583
Arthralgia 131.08 44.68 113 4619 54172 2299181
Insomnia 130.89 44.68 84 4648 25703 2327650
Crepitations 128.17 44.68 31 4701 635 2352718
Poisoning deliberate 119.46 44.68 33 4699 1158 2352195
Joint effusion 117.21 44.68 33 4699 1243 2352110
Hallucination, visual 116.27 44.68 40 4692 2939 2350414
Muscle spasms 116.25 44.68 73 4659 21493 2331860
Feeling jittery 116.22 44.68 36 4696 1896 2351457
Cushingoid 115.37 44.68 28 4704 582 2352771
Rheumatoid nodule 115.01 44.68 28 4704 590 2352763
Nausea 110.94 44.68 145 4587 112044 2241309
Synovial cyst 110.28 44.68 29 4703 841 2352512
Generalised tonic-clonic seizure 110.15 44.68 45 4687 5327 2348026
Drug withdrawal syndrome 109.44 44.68 48 4684 6773 2346580
Pleuritic pain 108.52 44.68 27 4705 624 2352729
Drug intolerance 107.00 44.68 59 4673 13658 2339695
Pain in extremity 105.50 44.68 90 4642 42450 2310903
Bursitis 104.11 44.68 33 4699 1875 2351478
Sacroiliitis 102.09 44.68 22 4710 262 2353091
Akathisia 99.87 44.68 31 4701 1643 2351710
Tenderness 99.81 44.68 32 4700 1886 2351467
Tremor 99.11 44.68 65 4667 20596 2332757
Exposure via ingestion 98.60 44.68 26 4706 762 2352591
Orthostatic hypotension 98.32 44.68 35 4697 2844 2350509
Malaise 97.73 44.68 97 4635 55488 2297865
Dyspnoea 97.36 44.68 114 4618 78619 2274734
Sedation 96.67 44.68 36 4696 3326 2350027
Myoclonus 95.57 44.68 33 4699 2450 2350903
Brain injury 94.64 44.68 26 4706 893 2352460
Constipation 94.00 44.68 64 4668 21565 2331788
Balance disorder 93.11 44.68 48 4684 9699 2343654
Heart rate increased 92.78 44.68 50 4682 11055 2342298
Hyperhidrosis 92.72 44.68 56 4676 15366 2337987
Psychotic disorder 91.85 44.68 38 4694 4641 2348712
Musculoskeletal pain 91.14 44.68 49 4683 10781 2342572
Dry eye 90.98 44.68 36 4696 3920 2349433
Unresponsive to stimuli 90.34 44.68 38 4694 4838 2348515
Eye pain 90.23 44.68 38 4694 4853 2348500
Flank pain 89.61 44.68 28 4704 1517 2351836
Restlessness 89.38 44.68 37 4695 4526 2348827
Conjunctivitis 89.00 44.68 31 4701 2362 2350991
Respiratory failure 88.82 44.68 52 4680 13476 2339877
Haemodynamic instability 88.23 44.68 26 4706 1153 2352200
Condition aggravated 88.22 44.68 72 4660 31907 2321446
Pruritus 88.16 44.68 82 4650 43258 2310095
Cardiogenic shock 87.78 44.68 31 4701 2460 2350893
Atelectasis 86.95 44.68 29 4703 1936 2351417
Antinuclear antibody positive 85.99 44.68 25 4707 1057 2352296
Headache 85.91 44.68 108 4624 80071 2273282
Mental status changes 85.40 44.68 38 4694 5544 2347809
Neuroleptic malignant syndrome 85.34 44.68 29 4703 2051 2351302
Drug dependence 85.33 44.68 32 4700 3013 2350340
Aggression 84.35 44.68 36 4696 4750 2348603
Ulcer 84.20 44.68 28 4704 1852 2351501
Nodule 83.41 44.68 29 4703 2197 2351156
Pneumonia 82.87 44.68 84 4648 49212 2304141
Somatic symptom disorder 82.72 44.68 19 4713 308 2353045
Treatment noncompliance 82.50 44.68 37 4695 5497 2347856
Lung disorder 81.51 44.68 38 4694 6174 2347179
Dystonia 79.96 44.68 28 4704 2166 2351187
Photophobia 78.80 44.68 28 4704 2261 2351092
Psychotic disorder due to a general medical condition 77.68 44.68 13 4719 31 2353322
Abdominal pain 77.62 44.68 69 4663 34305 2319048
Hallucination 77.44 44.68 40 4692 8108 2345245
Swelling face 77.21 44.68 42 4690 9451 2343902
Arrhythmia 76.38 44.68 36 4696 5992 2347361
Acute respiratory distress syndrome 75.84 44.68 30 4702 3262 2350091
Disturbance in attention 75.27 44.68 35 4697 5650 2347703
Cardiotoxicity 73.99 44.68 23 4709 1224 2352129
Feeling abnormal 73.34 44.68 57 4675 23524 2329829
Maternal exposure during pregnancy 71.81 44.68 47 4685 14816 2338537
Atrioventricular block first degree 70.93 44.68 21 4711 946 2352407
Product use in unapproved indication 70.74 44.68 42 4690 11158 2342195
Anxiety 70.40 44.68 61 4671 29298 2324055
Pulmonary eosinophilia 70.10 44.68 14 4718 111 2353242
Erythema 70.08 44.68 57 4675 25102 2328251
Joint swelling 68.86 44.68 48 4684 16771 2336582
Dysarthria 68.85 44.68 34 4698 6268 2347085
Disorientation 68.49 44.68 34 4698 6338 2347015
Dyskinesia 68.15 44.68 31 4701 4758 2348595
Speech disorder 68.03 44.68 34 4698 6430 2346923
Hyperreflexia 67.99 44.68 20 4712 881 2352472
Urinary retention 65.99 44.68 28 4704 3639 2349714
Hypertension 65.90 44.68 57 4675 27304 2326049
Exposure during pregnancy 65.78 44.68 55 4677 25164 2328189
Wheezing 65.48 44.68 33 4699 6351 2347002
Withdrawal syndrome 65.14 44.68 27 4705 3310 2350043
Visual impairment 63.77 44.68 40 4692 11715 2341638
Pyrexia 63.29 44.68 76 4656 53632 2299721
Bradypnoea 62.42 44.68 16 4716 418 2352935
Thrombosis 62.24 44.68 36 4696 9108 2344245
Accidental death 62.14 44.68 15 4717 304 2353049
Rash 61.72 44.68 79 4653 59479 2293874
Treatment failure 61.57 44.68 33 4699 7206 2346147
Paraesthesia 61.41 44.68 50 4682 22038 2331315
Infection 61.36 44.68 46 4686 17983 2335370
Myofascial pain syndrome 59.55 44.68 13 4719 165 2353188
Respiratory rate decreased 57.99 44.68 16 4716 558 2352795
Emotional disorder 57.81 44.68 22 4710 2155 2351198
Aspiration 57.52 44.68 20 4712 1514 2351839
Eye irritation 57.22 44.68 25 4707 3487 2349866
Neoplasm malignant 57.18 44.68 28 4704 5065 2348288
Ocular hyperaemia 56.90 44.68 26 4706 4030 2349323
Therapeutic product effect decreased 56.74 44.68 36 4696 10753 2342600
Amnesia 55.96 44.68 31 4701 7222 2346131
Gastrointestinal disorder 55.15 44.68 33 4699 8884 2344469
Myalgia 54.94 44.68 48 4684 23285 2330068
Hypoglycaemia 54.31 44.68 32 4700 8375 2344978
Fatigue 53.52 44.68 89 4643 84784 2268569
Acute kidney injury 52.87 44.68 51 4681 28071 2325282
Mood altered 52.85 44.68 22 4710 2724 2350629
Pneumonia aspiration 52.53 44.68 24 4708 3718 2349635
Clonus 52.50 44.68 15 4717 595 2352758
Gait disturbance 52.31 44.68 46 4686 22499 2330854
Blood pH decreased 51.05 44.68 14 4718 477 2352876
Sleep disorder 50.78 44.68 28 4704 6461 2346892
Muscular weakness 50.65 44.68 38 4694 14859 2338494
Asthenia 49.75 44.68 63 4669 46863 2306490
Swelling 49.66 44.68 39 4693 16311 2337042
Fracture 49.62 44.68 21 4711 2710 2350643
Stubbornness 48.44 44.68 8 4724 17 2353336
Delusion 48.19 44.68 19 4713 2046 2351307
Back pain 47.79 44.68 51 4681 31608 2321745
Migraine 47.35 44.68 32 4700 10621 2342732
Ventricular fibrillation 47.01 44.68 19 4713 2182 2351171
Immune thrombocytopenic purpura 46.51 44.68 17 4715 1487 2351866
Hypoaesthesia 46.40 44.68 41 4691 20174 2333179
Foetal death 46.05 44.68 18 4714 1894 2351459
Interstitial lung disease 45.95 44.68 28 4704 7784 2345569
Pulse absent 45.81 44.68 15 4717 944 2352409
Movement disorder 45.64 44.68 20 4712 2808 2350545
Asthma 45.60 44.68 32 4700 11282 2342071
Therapeutic product effect incomplete 45.30 44.68 31 4701 10500 2342853
Peripheral swelling 45.06 44.68 38 4694 17559 2335794
Status epilepticus 44.84 44.68 19 4713 2459 2350894

FDA Adverse Event Reporting System (Male)

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
Toxicity to various agents 1698.35 50.65 503 2023 28638 1715617
Completed suicide 1533.32 50.65 411 2115 15901 1728354
Overdose 699.60 50.65 227 2299 16474 1727781
Drug abuse 654.64 50.65 206 2320 13483 1730772
Respiratory arrest 407.23 50.65 118 2408 5721 1738534
Coma 369.13 50.65 115 2411 7147 1737108
Cardiac arrest 362.01 50.65 138 2388 15792 1728463
Intentional overdose 350.49 50.65 112 2414 7558 1736697
Serotonin syndrome 342.04 50.65 88 2438 2700 1741555
Cardio-respiratory arrest 321.51 50.65 110 2416 9183 1735072
Electrocardiogram QRS complex prolonged 315.56 50.65 65 2461 710 1743545
Confusional state 267.79 50.65 121 2405 21157 1723098
Suicide attempt 245.73 50.65 85 2441 7296 1736959
Poisoning 229.70 50.65 63 2463 2469 1741786
Agitation 198.64 50.65 81 2445 10945 1733310
Drug interaction 182.46 50.65 102 2424 27856 1716399
Electrocardiogram QT prolonged 169.51 50.65 60 2466 5485 1738770
Intentional product misuse 163.64 50.65 63 2463 7295 1736960
Death 159.17 50.65 146 2380 87297 1656958
Depressed level of consciousness 148.54 50.65 57 2469 6535 1737720
Sedation 127.70 50.65 43 2483 3374 1740881
Drug hypersensitivity 122.93 50.65 64 2462 15071 1729184
Fall 121.76 50.65 78 2448 27136 1717119
Somnolence 116.86 50.65 64 2462 16675 1727580
Tachycardia 115.87 50.65 58 2468 12570 1731685
Loss of consciousness 112.53 50.65 60 2466 14815 1729440
Unresponsive to stimuli 111.30 50.65 42 2484 4587 1739668
Foetal exposure during pregnancy 101.70 50.65 43 2483 6316 1737939
Disturbance in attention 96.66 50.65 37 2489 4197 1740058
Drug ineffective 95.44 50.65 96 2430 63705 1680550
Delirium 95.05 50.65 41 2485 6321 1737934
Respiratory depression 94.79 50.65 31 2495 2216 1742039
Mydriasis 92.94 50.65 27 2499 1297 1742958
Hallucination 91.36 50.65 43 2483 8127 1736128
Accidental overdose 90.10 50.65 35 2491 4129 1740126
Cardiotoxicity 86.19 50.65 23 2503 805 1743450
Poisoning deliberate 85.80 50.65 23 2503 819 1743436
Brugada syndrome 84.48 50.65 18 2508 232 1744023
Generalised tonic-clonic seizure 83.97 50.65 33 2493 4013 1740242
Seizure 82.46 50.65 55 2471 20386 1723869
Hypotension 78.97 50.65 62 2464 29592 1714663
Hyponatraemia 72.76 50.65 38 2488 8962 1735293
Ventricular tachycardia 71.92 50.65 29 2497 3769 1740486
Aggression 70.60 50.65 36 2490 8079 1736176
Depression 69.96 50.65 46 2480 16623 1727632
Delusion of replacement 68.78 50.65 11 2515 21 1744234
Acute respiratory distress syndrome 66.84 50.65 27 2499 3524 1740731
Exposure via ingestion 66.57 50.65 18 2508 662 1743593
Substance abuse 63.99 50.65 19 2507 984 1743271
Pulmonary congestion 60.66 50.65 21 2505 1784 1742471
Quality of life decreased 60.44 50.65 16 2510 542 1743713
Arrhythmia 59.12 50.65 29 2497 5987 1738268
Myoclonus 55.74 50.65 21 2505 2274 1741981
Nervous system disorder 54.37 50.65 21 2505 2433 1741822
Heart rate increased 54.05 50.65 28 2498 6482 1737773
Pulmonary oedema 53.74 50.65 28 2498 6558 1737697
Constipation 52.45 50.65 37 2489 14963 1729292
Arteriosclerosis coronary artery 52.14 50.65 19 2507 1873 1742382
Migraine 51.99 50.65 20 2506 2291 1741964
Dyskinesia 51.75 50.65 23 2503 3796 1740459

Pharmacologic Action:

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
MeSH PA D018663 Adrenergic Agents
FDA EPC N0000175752 Tricyclic Antidepressant
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)

DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007
Mixed anxiety and depressive disorder indication 231504006
Posttraumatic stress disorder off-label use 47505003 DOID:2055
Bulimia nervosa off-label use 78004001
Fibromyalgia off-label use 203082005 DOID:631
Neuropathic pain off-label use 247398009
Migraine Prevention off-label use
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
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:0050847
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:557
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
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
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

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:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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