nortriptyline Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
antidepressants, dibenzo[a,d]cycloheptane or cyclopheptene derivatives 1971 72-69-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nortryptyline
  • nortriptyline
  • demethylamitriptylin
  • desitriptilina
  • desmethylamitriptyline
  • noramitriptyline
  • nortriptyline hydrochloride
  • nortriptyline HCl
A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.
  • Molecular weight: 263.38
  • Formula: C19H21N
  • CLOGP: 4.31
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 1
  • TPSA: 12.03
  • ALOGS: -5.48
  • ROTB: 3

Drug dosage:

DoseUnitRoute
75 mg O
30 mg P

Approvals:

DateAgencyCompanyOrphan
Nov. 6, 1964 FDA

FDA Adverse Event Reporting System

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 2027.40 48.35 489 1761 41956 4594786
Toxicity to various agents 1770.47 48.35 489 1761 71551 4565191
Drug hypersensitivity 620.24 48.35 220 2030 68180 4568562
Pneumonia aspiration 568.14 48.35 134 2116 9572 4627170
Somnolence 509.21 48.35 170 2080 43490 4593252
Coma 508.32 48.35 138 2112 17381 4619361
Gastrooesophageal reflux disease 477.47 48.35 127 2123 14766 4621976
Overdose 403.55 48.35 143 2107 43416 4593326
Cardiac arrest 342.62 48.35 119 2131 33888 4602854
Drug abuse 325.18 48.35 109 2141 27838 4608904
Suicidal ideation 269.99 48.35 89 2161 21494 4615248
Cardio-respiratory arrest 269.22 48.35 87 2163 19735 4617007
Temperature regulation disorder 221.58 48.35 36 2214 338 4636404
Intentional overdose 210.24 48.35 74 2176 21692 4615050
Food allergy 186.58 48.35 36 2214 954 4635788
Electrocardiogram QRS complex prolonged 182.79 48.35 40 2210 1996 4634746
Respiratory arrest 178.23 48.35 58 2192 13362 4623380
Coeliac disease 176.55 48.35 36 2214 1273 4635469
Sedation 173.52 48.35 50 2200 7667 4629075
Immunodeficiency 166.44 48.35 36 2214 1699 4635043
Death 166.32 48.35 129 2121 198034 4438708
Hypotension 166.22 48.35 87 2163 67313 4569429
Bursitis 155.55 48.35 37 2213 2681 4634061
Suicide attempt 153.25 48.35 58 2192 20784 4615958
Poisoning 144.54 48.35 41 2209 5933 4630809
Drug ineffective 142.70 48.35 115 2135 185946 4450796
Brugada syndrome 135.27 48.35 24 2226 394 4636348
Accidental overdose 135.06 48.35 43 2207 9212 4627530
Hyperhidrosis 132.95 48.35 58 2192 29859 4606883
Accidental death 130.15 48.35 26 2224 826 4635916
Respiratory depression 127.80 48.35 36 2214 5074 4631668
Tachycardia 111.69 48.35 52 2198 31093 4605649
Constipation 108.16 48.35 56 2194 42098 4594644
Fluid retention 106.86 48.35 38 2212 11383 4625359
Serotonin syndrome 103.35 48.35 33 2217 7119 4629623
Rash erythematous 102.25 48.35 36 2214 10473 4626269
Substance abuse 101.86 48.35 24 2226 1664 4635078
Asthma 101.62 48.35 41 2209 17333 4619409
Hypersensitivity 98.41 48.35 51 2199 38370 4598372
Hepatic enzyme increased 96.83 48.35 40 2210 17951 4618791
Upper respiratory tract infection 96.29 48.35 37 2213 13750 4622992
Delirium 95.45 48.35 36 2214 12716 4624026
Pain 94.07 48.35 68 2182 92802 4543940
Seizure 93.55 48.35 54 2196 50183 4586559
Ventricular arrhythmia 88.68 48.35 21 2229 1487 4635255
Rheumatoid arthritis 87.27 48.35 41 2209 24958 4611784
Ventricular tachycardia 86.29 48.35 29 2221 7335 4629407
Long QT syndrome 86.14 48.35 19 2231 979 4635763
Intentional product misuse 82.50 48.35 36 2214 18457 4618285
Drug interaction 81.11 48.35 54 2196 64454 4572288
Headache 79.51 48.35 69 2181 122304 4514438
Agitation 79.28 48.35 38 2212 24162 4612580
Sleep disorder 77.81 48.35 30 2220 11233 4625509
Back pain 77.54 48.35 48 2202 50551 4586191
Electrocardiogram QT prolonged 75.53 48.35 32 2218 15263 4621479
Psychotic disorder 75.45 48.35 29 2221 10766 4625976
Fatigue 74.89 48.35 72 2178 145494 4491248
Confusional state 71.47 48.35 45 2205 48789 4587953
Miosis 70.58 48.35 20 2230 2870 4633872
Depression 69.89 48.35 44 2206 47689 4589053
Traumatic coma 69.68 48.35 9 2241 10 4636732
Hyperreflexia 62.19 48.35 16 2234 1594 4635148
Erythema 59.71 48.35 38 2212 41902 4594840
Tremor 57.02 48.35 35 2215 36224 4600518
Condition aggravated 55.11 48.35 41 2209 58130 4578612
Presbyacusis 54.38 48.35 9 2241 95 4636647
Pleural thickening 51.52 48.35 9 2241 134 4636608
Hypertension 50.80 48.35 37 2213 50761 4585981
Deafness neurosensory 50.76 48.35 13 2237 1271 4635471
Dizziness 50.45 48.35 49 2201 99822 4536920
Blood magnesium increased 49.28 48.35 10 2240 343 4636399

Pharmacologic Action:

SourceCodeDescription
ATC N06AA10 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
MeSH PA D018663 Adrenergic Agents
FDA EPC N0000175752 Tricyclic Antidepressant
MeSH PA D018759 Adrenergic Uptake Inhibitors
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35610 antineoplastic agent
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 D011619 Psychotropic Drugs

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007
Neuropathic pain off-label use 247398009
Smoking cessation assistance off-label use 384742004
Attention deficit hyperactivity disorder off-label use 406506008
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Sinus tachycardia contraindication 11092001
Lowered convulsive threshold contraindication 19260006
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Torsades de pointes contraindication 31722008
Hyperthyroidism contraindication 34486009 DOID:7998
Renal failure syndrome contraindication 42399005 DOID:1074
Conduction disorder of the heart contraindication 44808001
Hepatic failure contraindication 59927004
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Bipolar affective disorder, current episode manic contraindication 191618007
Cerebrovascular accident contraindication 230690007
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Non-Q wave myocardial infarction contraindication 314207007
Breastfeeding (mother) contraindication 413712001
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.5 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 Ki 7.34 WOMBAT-PK CHEMBL
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Kd 8.36 WOMBAT-PK CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.56 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 7.07 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 7.21 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.64 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 7.52 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.91 DRUG MATRIX
Cytochrome P450 2C19 Enzyme IC50 5.52 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.67 CHEMBL
Cytochrome P450 2D6 Enzyme Km 6.22 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 6.07 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 7.01 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 7.08 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 7.30 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 6.96 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 7.40 WOMBAT-PK
Histamine H1 receptor GPCR Kd 8.03 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 7 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.26 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 8 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7.36 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.51 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 5.59 PDSP
ATP-sensitive inward rectifier potassium channel 10 Ion channel BLOCKER IC50 4.80 SCIENTIFIC LITERATURE
Proto-oncogene tyrosine-protein kinase receptor Ret Kinase IC50 5.82 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 5.92 PDSP
D(1A) dopamine receptor GPCR Ki 6.57 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 6.94 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 5.84 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 10.40 CHEMBL
Histamine H1 receptor GPCR IC50 10.30 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 5.73 CHEMBL

External reference:

IDSource
4019860 VUID
N0000147946 NUI
C0028420 UMLSCUI
D00816 KEGG_DRUG
00FN6IH15D UNII
894-71-3 SECONDARY_CAS_RN
13432000 SNOMEDCT_US
4019860 VANDF
2740 MMSL
7531 RXNORM
372652004 SNOMEDCT_US
d00144 MMSL
004601 NDDF
1328 INN_ID
CHEBI:7640 CHEBI
CHEMBL445 ChEMBL_ID
DB00540 DRUGBANK_ID
21B PDB_CHEM_ID
4543 PUBCHEM_CID
CHEMBL1201156 ChEMBL_ID
D009661 MESH_DESCRIPTOR_UI
2404 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0810 CAPSULE 10 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0811 CAPSULE 25 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0812 CAPSULE 50 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-0813 CAPSULE 75 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0121-0678 SOLUTION 10 mg ORAL ANDA 14 sections
PAMELOR HUMAN PRESCRIPTION DRUG LABEL 1 0406-9910 CAPSULE 10 mg ORAL NDA 13 sections
PAMELOR HUMAN PRESCRIPTION DRUG LABEL 1 0406-9911 CAPSULE 25 mg ORAL NDA 13 sections
PAMELOR HUMAN PRESCRIPTION DRUG LABEL 1 0406-9912 CAPSULE 50 mg ORAL NDA 13 sections
PAMELOR HUMAN PRESCRIPTION DRUG LABEL 1 0406-9913 CAPSULE 75 mg ORAL NDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-567 CAPSULE 10 mg ORAL ANDA 13 sections
NORTRIPTYLINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-171 CAPSULE 25 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-093 CAPSULE 10 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-094 CAPSULE 25 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-599 CAPSULE 50 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-600 CAPSULE 75 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-348 CAPSULE 25 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-532 CAPSULE 10 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-692 CAPSULE 50 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-804 CAPSULE 75 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-722 CAPSULE 25 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-897 CAPSULE 25 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 45865-371 CAPSULE 10 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0507 CAPSULE 25 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0537 CAPSULE 10 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-603 CAPSULE 10 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-604 CAPSULE 25 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50268-605 CAPSULE 50 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50436-4022 CAPSULE 25 mg ORAL ANDA 14 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50436-6652 CAPSULE 10 mg ORAL ANDA 13 sections
Nortriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51672-4001 CAPSULE 10 mg ORAL ANDA 14 sections