doxepin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
tricyclic compounds 956 1668-19-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • P-3693A
  • doxepin
  • doxepine
  • doxepin hydrochloride
  • silenor
  • doxepin HCl
A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.
  • Molecular weight: 279.38
  • Formula: C19H21NO
  • CLOGP: 4.09
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -3.94
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 17.90 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 14 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 15 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MET,NTRK2,PDK2,PDK4,PDPK1,PIM2,PRKDC,SIK2,SIK3,STK33,TEK,TGFBR1,TTK 39
kinase-selectivity-class AXL,BRAF,PDK4,TTK 4
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 0.608 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 1 High 1
rat-kpuu-brain Rat brain Kpuu 1.028 % High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 23, 1969 FDA

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 953.46 13.59 535 21822 144523 90461567
Toxicity to various agents 641.79 13.59 545 21812 287301 90318789
Respiratory depression 283.40 13.59 116 22241 15459 90590631
Cardio-respiratory arrest 201.19 13.59 148 22209 62992 90543098
Bezoar 136.38 13.59 43 22314 2691 90603399
Drug abuse 117.26 13.59 122 22235 82225 90523865
Depressed level of consciousness 114.87 13.59 114 22243 72670 90533420
Respiratory arrest 103.61 13.59 77 22280 33234 90572856
Chronic spontaneous urticaria 84.07 13.59 27 22330 1793 90604297
Drug interaction 74.24 13.59 191 22166 276262 90329828
Cardiac arrest 70.88 13.59 107 22250 104828 90501262
Suicide attempt 70.61 13.59 90 22267 75309 90530781
Systemic lupus erythematosus 70.02 13.59 5 22352 361891 90244199
Suicidal ideation 64.23 13.59 85 22272 73770 90532320
Intentional overdose 63.82 13.59 96 22261 93738 90512352
Corneal reflex decreased 63.74 13.59 15 22342 306 90605784
Glossodynia 63.56 13.59 4 22353 321775 90284315
Infusion related reaction 61.08 13.59 14 22343 416766 90189324
Pruritus 56.14 13.59 273 22084 541252 90064838
Joint swelling 54.66 13.59 28 22329 503272 90102818
Synovitis 52.65 13.59 9 22348 329743 90276347
Maternal exposure during pregnancy 50.97 13.59 13 22344 360050 90246040
Sleep-related eating disorder 50.95 13.59 16 22341 988 90605102
Urticaria 50.74 13.59 181 22176 312553 90293537
Skin plaque 50.02 13.59 31 22326 9944 90596146
Decreased bronchial secretion 47.20 13.59 9 22348 62 90606028
Pupillary reflex impaired 46.42 13.59 19 22338 2526 90603564
Areflexia 46.03 13.59 21 22336 3632 90602458
Dermatitis atopic 45.07 13.59 41 22316 23431 90582659
Electrocardiogram QRS complex prolonged 45.07 13.59 26 22331 7322 90598768
Coma 44.74 13.59 71 22286 72561 90533529
Hepatic enzyme increased 43.97 13.59 17 22340 360719 90245371
Paranasal sinus inflammation 40.15 13.59 12 22345 627 90605463
Depression 39.71 13.59 163 22194 300438 90305652
Pulmonary congestion 39.39 13.59 35 22322 19398 90586692
Overdose 39.25 13.59 106 22251 157603 90448487
Contraindicated product administered 39.15 13.59 15 22342 320124 90285966
Somnolence 39.14 13.59 127 22230 208957 90397133
Bradypnoea 38.29 13.59 20 22337 4638 90601452
Nail avulsion 37.55 13.59 10 22347 342 90605748
Rheumatoid arthritis 32.68 13.59 25 22332 362589 90243501
Muscle injury 32.59 13.59 3 22354 176651 90429439
Exposure via ingestion 32.56 13.59 15 22342 2652 90603438
Suspected suicide 31.73 13.59 23 22334 9545 90596545
Osteosclerosis 31.15 13.59 17 22340 4303 90601787
Scratch 31.10 13.59 23 22334 9843 90596247
Jaundice neonatal 30.92 13.59 11 22346 999 90605091
Lipohypertrophy 30.23 13.59 10 22347 729 90605361
Stomatitis 30.21 13.59 15 22342 274683 90331407
Inadequate analgesia 29.86 13.59 15 22342 3209 90602881
Death 29.40 13.59 203 22154 456348 90149742
Insomnia 28.84 13.59 160 22197 333314 90272776
Wound 28.44 13.59 20 22337 302960 90303130
Mandibular mass 28.06 13.59 7 22350 184 90605906
Defaecation disorder 27.99 13.59 10 22347 919 90605171
Therapeutic product effect decreased 27.85 13.59 17 22340 277554 90328536
Somnambulism 27.84 13.59 18 22339 6210 90599880
Diverticulum oesophageal 27.74 13.59 7 22350 193 90605897
Junctional ectopic tachycardia 27.04 13.59 7 22350 214 90605876
Acute lung injury 26.70 13.59 11 22346 1487 90604603
Poisoning 26.17 13.59 25 22332 15192 90590898
Congestive hepatopathy 24.87 13.59 13 22344 3020 90603070
Therapeutic product effect increased 24.73 13.59 10 22347 1289 90604801
Stress 24.71 13.59 59 22298 81336 90524754
Mobility decreased 24.27 13.59 16 22341 250718 90355372
Febrile neutropenia 23.81 13.59 5 22352 158344 90447746
Product use issue 23.58 13.59 28 22329 329891 90276199
Osteoporosis postmenopausal 23.42 13.59 7 22350 366 90605724
Abdominal discomfort 23.35 13.59 52 22305 477276 90128814
Foramen magnum stenosis 23.19 13.59 6 22351 183 90605907
Fear-related avoidance of activities 23.13 13.59 6 22351 185 90605905
Ventricular arrhythmia 23.12 13.59 14 22343 4307 90601783
Visceral congestion 23.11 13.59 7 22350 383 90605707
Blood pressure systolic increased 23.04 13.59 47 22310 58298 90547792
Psoriatic arthropathy 22.88 13.59 14 22343 228321 90377769
Arrhythmia 22.85 13.59 39 22318 42293 90563797
Sinobronchitis 22.85 13.59 8 22349 693 90605397
Pyrexia 22.76 13.59 85 22272 660400 89945690
Major depression 22.20 13.59 19 22338 10016 90596074
Myofascial pain syndrome 22.15 13.59 12 22345 2995 90603095
Restlessness 22.10 13.59 35 22322 35685 90570405
Drug withdrawal syndrome neonatal 22.10 13.59 11 22346 2308 90603782
Seizure 21.92 13.59 85 22272 152544 90453546
Mental disorder 21.86 13.59 33 22324 32285 90573805
Peripheral nerve lesion 21.72 13.59 7 22350 470 90605620
Self esteem decreased 21.66 13.59 8 22349 808 90605282
Blood glucose fluctuation 21.04 13.59 14 22343 5069 90601021
Angioedema 20.75 13.59 48 22309 64828 90541262
Gastrointestinal infection 20.71 13.59 19 22338 10971 90595119
Drug withdrawal syndrome 20.39 13.59 30 22327 28693 90577397
Hypothermia 20.24 13.59 22 22335 15553 90590537
Eczema 20.18 13.59 42 22315 52828 90553262
Lung disorder 20.09 13.59 6 22351 149877 90456213
Anxiety 20.07 13.59 138 22219 309634 90296456
Radial nerve palsy 20.02 13.59 7 22350 604 90605486
Hepatic lesion 19.65 13.59 14 22343 5659 90600431
Serotonin syndrome 19.27 13.59 34 22323 37853 90568237
Choking 19.25 13.59 19 22338 12014 90594076
Iliotibial band syndrome 19.05 13.59 6 22351 374 90605716
General physical health deterioration 18.77 13.59 37 22320 355078 90251012
Gastritis fungal 18.64 13.59 5 22352 176 90605914
Generalised tonic-clonic seizure 18.63 13.59 32 22325 34871 90571219
Dyshidrotic eczema 18.52 13.59 7 22350 754 90605336
Breast adenoma 18.48 13.59 4 22353 55 90606035
Vertebral lesion 18.42 13.59 7 22350 765 90605325
Patellofemoral pain syndrome 18.35 13.59 7 22350 773 90605317
Dysaesthesia 18.27 13.59 13 22344 5242 90600848
Brain oedema 18.27 13.59 22 22335 17363 90588727
Rotator cuff syndrome 18.14 13.59 21 22336 15898 90590192
Blood pressure increased 17.95 13.59 96 22261 197121 90408969
Nocturia 17.92 13.59 17 22340 10238 90595852
Product prescribing error 17.91 13.59 29 22328 30116 90575974
Blister 17.83 13.59 22 22335 254976 90351114
Arthropathy 17.81 13.59 40 22317 366202 90239888
Urticaria physical 17.77 13.59 3 22354 9 90606081
Gait inability 17.66 13.59 7 22350 146449 90459641
Quality of life decreased 17.60 13.59 18 22339 11871 90594219
Nasal turbinate hypertrophy 17.22 13.59 7 22350 914 90605176
Joint range of motion decreased 17.17 13.59 6 22351 135637 90470453
Sedation complication 17.09 13.59 21 22336 16923 90589167
Allergic oedema 17.01 13.59 7 22350 943 90605147
Multiple drug therapy 17.01 13.59 14 22343 6995 90599095
Mastocytosis 16.97 13.59 7 22350 949 90605141
Thrombocytopenia 16.82 13.59 16 22341 208709 90397381
Solar urticaria 16.80 13.59 4 22353 86 90606004
Restless legs syndrome 16.72 13.59 24 22333 22446 90583644
Bradycardia 16.64 13.59 52 22305 83795 90522295
Psychotic symptom 16.61 13.59 9 22348 2247 90603843
Cardiogenic shock 16.57 13.59 25 22332 24443 90581647
Myoclonus 16.56 13.59 22 22335 19146 90586944
Neutropenia 16.15 13.59 19 22338 224885 90381205
Injection site pain 16.11 13.59 85 22272 173614 90432476
Type 2 diabetes mellitus 15.89 13.59 16 22341 203228 90402862
Treatment failure 15.77 13.59 32 22325 303896 90302194
Feeling abnormal 15.62 13.59 82 22275 167153 90438937
Dissociation 15.44 13.59 13 22344 6702 90599388
Scar 15.39 13.59 19 22338 15376 90590714
Drooling 15.24 13.59 11 22346 4535 90601555
Drug intolerance 15.14 13.59 58 22299 447533 90158557
Gastrointestinal disorder 15.12 13.59 25 22332 256662 90349428
Ill-defined disorder 15.10 13.59 14 22343 184877 90421213
Meniscus injury 15.06 13.59 14 22343 8223 90597867
Blood test abnormal 15.04 13.59 22 22335 20930 90585160
Tinnitus 15.02 13.59 33 22324 43069 90563021
Impaired work ability 14.91 13.59 21 22336 19305 90586785
Iritis 14.89 13.59 10 22347 3676 90602414
Osteoporotic fracture 14.84 13.59 11 22346 4725 90601365
Flatulence 14.79 13.59 32 22325 41335 90564755
Hypersensitivity 14.69 13.59 60 22297 454617 90151473
Impaired healing 14.56 13.59 22 22335 234177 90371913
Microcephaly 14.49 13.59 7 22350 1377 90604713
Dysplasia 14.44 13.59 7 22350 1387 90604703
Irritability 14.40 13.59 29 22328 35633 90570457
Musculoskeletal pain 13.94 13.59 13 22344 171238 90434852
C-reactive protein abnormal 13.93 13.59 7 22350 127422 90478668
Migraine 13.64 13.59 87 22270 190305 90415785

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
Completed suicide 545.79 18.17 322 10161 96143 42514709
Toxicity to various agents 327.67 18.17 338 10145 228798 42382054
Needle fatigue 186.15 18.17 46 10437 1167 42609685
Gait spastic 179.31 18.17 46 10437 1363 42609489
Relapsing-remitting multiple sclerosis 176.61 18.17 46 10437 1449 42609403
Hypertonic bladder 155.42 18.17 46 10437 2335 42608517
Monoparesis 145.54 18.17 46 10437 2914 42607938
Drug abuse 142.51 18.17 151 10332 104620 42506232
Muscle spasticity 108.08 18.17 46 10437 6776 42604076
Ataxia 104.40 18.17 59 10424 16066 42594786
Central nervous system lesion 101.77 18.17 46 10437 7824 42603028
Nocturia 96.94 18.17 51 10432 12061 42598791
Pollakiuria 88.67 18.17 60 10423 22445 42588407
Micturition urgency 86.51 18.17 47 10436 11851 42599001
Movement disorder 79.84 18.17 48 10435 14650 42596202
Multiple sclerosis relapse 78.56 18.17 47 10436 14217 42596635
Memory impairment 72.81 18.17 75 10408 50147 42560705
Insomnia 71.15 18.17 114 10369 118139 42492713
Erectile dysfunction 69.75 18.17 54 10429 24859 42585993
Dissociation 68.18 18.17 28 10455 3770 42607082
Dysarthria 66.09 18.17 64 10419 39743 42571109
Pulmonary oedema 52.33 18.17 65 10418 53207 42557645
Anxiety 47.76 18.17 96 10387 118464 42492388
Brain oedema 44.84 18.17 35 10448 16292 42594560
Substance use 42.28 18.17 16 10467 1735 42609117
Reduced facial expression 40.64 18.17 15 10468 1518 42609334
Protein S decreased 38.55 18.17 8 10475 89 42610763
Suspected suicide 38.27 18.17 22 10461 6177 42604675
Brugada syndrome 38.17 18.17 13 10470 1040 42609812
Balance disorder 37.28 18.17 52 10431 47593 42563259
Cardio-respiratory arrest 35.84 18.17 57 10426 58579 42552273
Dissociative disorder 35.35 18.17 11 10472 661 42610191
Drug dependence 34.33 18.17 39 10444 29055 42581797
Electrocardiogram QRS complex prolonged 34.18 18.17 20 10463 5803 42605049
Hypoaesthesia 32.57 18.17 61 10422 71402 42539450
Overdose 29.72 18.17 74 10409 105190 42505662
Soft tissue haemorrhage 29.10 18.17 7 10476 158 42610694
Illness anxiety disorder 28.26 18.17 7 10476 179 42610673
Pruritus 27.28 18.17 105 10378 188666 42422186
Disease prodromal stage 26.69 18.17 5 10478 31 42610821
Fall 26.52 18.17 121 10362 234399 42376453
Somatic symptom disorder 25.89 18.17 9 10474 766 42610086
Hydrocholecystis 25.39 18.17 8 10475 501 42610351
Acute kidney injury 25.30 18.17 32 10451 367305 42243547
Kidney enlargement 24.54 18.17 9 10474 894 42609958
Dermatitis atopic 24.53 18.17 22 10461 12382 42598470
Measles 24.52 18.17 7 10476 312 42610540
Crime 24.31 18.17 5 10478 53 42610799
Albuminuria 24.02 18.17 8 10475 598 42610254
Bradyphrenia 23.06 18.17 15 10468 5247 42605605
Thrombocytopenia 23.03 18.17 9 10474 190270 42420582
Toxic cardiomyopathy 22.38 18.17 7 10476 428 42610424
Helplessness 22.07 18.17 5 10478 86 42610766
Neutropenia 21.68 18.17 11 10472 199420 42411432
Skin wrinkling 21.67 18.17 7 10476 475 42610377
Persistent depressive disorder 21.43 18.17 7 10476 492 42610360
Oral dysaesthesia 20.95 18.17 5 10478 109 42610743
Depressed mood 20.53 18.17 27 10456 23357 42587495
Change in seizure presentation 20.07 18.17 6 10477 315 42610537

FDA Adverse Event Reporting System (Geriatric)

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 1515.67 13.62 868 26761 241513 110320157
Toxicity to various agents 957.41 13.62 857 26772 479698 110081972
Drug abuse 248.72 13.62 262 27367 177149 110384521
Cardio-respiratory arrest 231.76 13.62 208 27421 115628 110446042
Respiratory depression 178.73 13.62 107 27522 31894 110529776
Needle fatigue 178.52 13.62 45 27584 1219 110560451
Gait spastic 164.70 13.62 44 27585 1505 110560165
Relapsing-remitting multiple sclerosis 151.82 13.62 44 27585 2038 110559632
Hypertonic bladder 125.69 13.62 48 27581 5254 110556416
Monoparesis 121.68 13.62 45 27584 4508 110557162
Bezoar 119.23 13.62 43 27586 4011 110557659
Respiratory arrest 115.15 13.62 104 27525 58195 110503475
Ataxia 93.74 13.62 70 27559 30038 110531632
Insomnia 82.73 13.62 237 27392 360353 110201317
Nocturia 82.58 13.62 52 27577 16938 110544732
Chronic spontaneous urticaria 81.33 13.62 27 27602 1966 110559704
Electrocardiogram QRS complex prolonged 79.14 13.62 46 27583 12975 110548695
Cardiac arrest 75.85 13.62 158 27471 196595 110365075
Overdose 75.69 13.62 175 27454 233619 110328051
Erectile dysfunction 73.58 13.62 50 27579 18506 110543164
Dissociation 71.27 13.62 39 27590 9803 110551867
Micturition urgency 69.43 13.62 49 27580 19271 110542399
Intentional overdose 69.08 13.62 121 27508 132380 110429290
Suspected suicide 67.62 13.62 44 27585 15155 110546515
Central nervous system lesion 66.70 13.62 44 27585 15509 110546161
Anxiety 60.79 13.62 207 27422 344871 110216799
Suicide attempt 59.94 13.62 99 27530 103295 110458375
Depressed level of consciousness 56.54 13.62 101 27528 112177 110449493
Corneal reflex decreased 55.45 13.62 15 27614 538 110561132
Pollakiuria 54.35 13.62 61 27568 44134 110517536
Drug interaction 53.59 13.62 257 27372 499926 110061744
Pruritus 51.99 13.62 284 27345 581276 109980394
Systemic lupus erythematosus 51.45 13.62 3 27626 254335 110307335
Infusion related reaction 50.80 13.62 16 27613 381146 110180524
Dermatitis atopic 49.31 13.62 45 27584 25496 110536174
Pulmonary congestion 49.22 13.62 49 27580 30917 110530753
Brain oedema 49.04 13.62 49 27580 31049 110530621
Decreased bronchial secretion 46.83 13.62 9 27620 64 110561606
Substance use 46.47 13.62 19 27610 2487 110559183
Maternal exposure during pregnancy 46.02 13.62 5 27624 254878 110306792
Suicidal ideation 45.38 13.62 83 27546 93854 110467816
Skin plaque 45.27 13.62 32 27597 12613 110549057
Urticaria 44.95 13.62 178 27451 318679 110242991
Death 43.48 13.62 311 27318 698558 109863112
Scratch 42.24 13.62 31 27598 12948 110548722
Self esteem decreased 41.60 13.62 14 27615 1063 110560607
Dysarthria 40.22 13.62 74 27555 84047 110477623
Exposure via ingestion 39.92 13.62 21 27608 4879 110556791
Muscle spasticity 39.83 13.62 47 27582 35868 110525802
Movement disorder 39.32 13.62 47 27582 36357 110525313
Synovitis 39.30 13.62 10 27619 274082 110287588
Joint swelling 39.05 13.62 32 27597 442813 110118857
Generalised tonic-clonic seizure 38.12 13.62 57 27572 54623 110507047
Pupillary reflex impaired 37.90 13.62 19 27610 3996 110557674
Coma 37.85 13.62 88 27541 117781 110443889
Febrile neutropenia 37.63 13.62 16 27613 316751 110244919
Multiple sclerosis relapse 37.38 13.62 54 27575 50186 110511484
Poisoning 37.21 13.62 41 27588 29064 110532606
Depression 36.84 13.62 167 27462 317168 110244502
Thrombocytopenia 36.35 13.62 21 27608 348864 110212806
Bradycardia 36.35 13.62 103 27526 155414 110406256
Congestive hepatopathy 35.91 13.62 20 27609 5200 110556470
Sleep-related eating disorder 35.63 13.62 12 27617 913 110560757
Illness anxiety disorder 35.11 13.62 9 27620 261 110561409
Visceral congestion 34.86 13.62 13 27616 1332 110560338
Protein S decreased 34.48 13.62 8 27621 151 110561519
Areflexia 33.60 13.62 21 27608 6748 110554922
Stomatitis 33.15 13.62 13 27616 270229 110291441
Neutropenia 33.11 13.62 27 27602 374593 110187077
Brugada syndrome 32.76 13.62 13 27616 1575 110560095
Depressed mood 29.70 13.62 54 27575 60755 110500915
Blood glucose fluctuation 28.76 13.62 20 27609 7678 110553992
Contraindicated product administered 28.76 13.62 13 27616 248254 110313416
Dissociative disorder 28.49 13.62 11 27618 1240 110560430
Pyrexia 28.25 13.62 122 27507 898143 109663527
Hepatic enzyme increased 27.28 13.62 24 27605 320868 110240802
Diverticulum oesophageal 27.21 13.62 7 27622 206 110561464
Lipohypertrophy 27.09 13.62 10 27619 996 110560674
Pulmonary oedema 26.85 13.62 70 27559 100589 110461081
Bradypnoea 26.67 13.62 20 27609 8629 110553041
Mandibular mass 26.30 13.62 7 27622 236 110561434
Drug intolerance 26.28 13.62 38 27591 406474 110155196
Restlessness 26.27 13.62 49 27580 56210 110505460
Dyshidrotic eczema 25.99 13.62 9 27620 745 110560925
Panic attack 25.88 13.62 34 27595 28906 110532764
Acute kidney injury 25.44 13.62 78 27551 635352 109926318
Fear-related avoidance of activities 25.08 13.62 6 27623 130 110561540
Therapeutic product effect increased 25.07 13.62 11 27618 1714 110559956
Obsessive-compulsive personality disorder 25.03 13.62 6 27623 131 110561539
Somnolence 25.00 13.62 143 27486 297306 110264364
Intentional product misuse 24.48 13.62 81 27548 132823 110428847
Mental impairment 24.07 13.62 29 27600 22610 110539060
Hydrocholecystis 24.01 13.62 8 27621 589 110561081
Feeling guilty 24.00 13.62 9 27620 937 110560733
Crime 23.67 13.62 5 27624 60 110561610
Rheumatoid arthritis 23.60 13.62 24 27605 299589 110262081
Disease progression 23.60 13.62 16 27613 244018 110317652
Disease prodromal stage 23.51 13.62 5 27624 62 110561608
Serotonin syndrome 23.34 13.62 48 27581 59105 110502565
Helplessness 23.16 13.62 7 27622 375 110561295
Product prescribing error 23.09 13.62 44 27585 51287 110510383
Reduced facial expression 22.46 13.62 13 27616 3638 110558032
Arrhythmia 22.39 13.62 52 27577 69523 110492147
Bursitis 22.33 13.62 3 27626 129915 110431755
Dizziness 22.12 13.62 269 27360 697924 109863746
Feeling abnormal 21.62 13.62 96 27533 180615 110381055
Somatic symptom disorder 21.45 13.62 12 27617 3147 110558523
Drug dependence 21.43 13.62 42 27587 49978 110511692
Product use issue 21.28 13.62 28 27601 311667 110250003
Inadequate analgesia 20.89 13.62 14 27615 5063 110556607
Muscle injury 20.44 13.62 5 27624 140802 110420868
Fear 20.35 13.62 27 27602 23166 110538504
Somnambulism 20.17 13.62 15 27614 6390 110555280
Memory impairment 20.17 13.62 100 27529 196844 110364826
Renal impairment 20.11 13.62 11 27618 188434 110373236
Albuminuria 19.90 13.62 8 27621 1003 110560667
Kidney enlargement 19.70 13.62 9 27620 1542 110560128
Spinal disorder 19.45 13.62 19 27610 11709 110549961
Measles 19.29 13.62 7 27622 664 110561006
Psoriatic arthropathy 18.89 13.62 13 27616 196748 110364922
Liver disorder 18.88 13.62 6 27623 142237 110419433
Breast adenoma 18.86 13.62 4 27625 49 110561621
Acute lung injury 18.80 13.62 11 27618 3140 110558530
Lung disorder 18.51 13.62 11 27618 180036 110381634
Joint range of motion decreased 18.33 13.62 4 27625 121828 110439842
Interstitial lung disease 18.28 13.62 6 27623 139328 110422342
Toxic cardiomyopathy 18.19 13.62 7 27622 782 110560888
Soft tissue haemorrhage 17.99 13.62 6 27623 443 110561227
Change in seizure presentation 17.81 13.62 7 27622 827 110560843
Aggression 17.69 13.62 43 27586 59167 110502503
Mobility decreased 17.60 13.62 20 27609 237402 110324268
Impaired healing 17.59 13.62 14 27615 196703 110364967
Urticaria physical 17.49 13.62 3 27626 10 110561660
Injection site pain 17.28 13.62 89 27540 177833 110383837
Allergic oedema 16.94 13.62 7 27622 941 110560729
Irritable bowel syndrome 16.93 13.62 10 27619 164205 110397465
Abdominal discomfort 16.72 13.62 47 27582 393811 110167859
Libido decreased 16.71 13.62 13 27616 5922 110555748
Oral dysaesthesia 16.60 13.62 5 27624 265 110561405
Neutrophil count decreased 16.23 13.62 5 27624 120936 110440734
Malignant neoplasm progression 16.15 13.62 12 27617 174555 110387115
Blister 15.95 13.62 20 27609 227356 110334314
Fall 15.95 13.62 225 27404 603257 109958413
Stress 15.78 13.62 60 27569 105288 110456382
Neuroendocrine carcinoma of the skin 15.71 13.62 8 27621 1737 110559933
Anticholinergic syndrome 15.71 13.62 11 27618 4269 110557401
Solar urticaria 15.71 13.62 4 27625 113 110561557
Blood pressure systolic increased 15.65 13.62 51 27578 82940 110478730
Therapeutic product effect decreased 15.62 13.62 23 27606 244293 110317377
Gastritis fungal 15.61 13.62 5 27624 325 110561345
Major depression 15.40 13.62 16 27613 10605 110551065
Multiple drug therapy 15.23 13.62 14 27615 8000 110553670
Seizure 15.21 13.62 101 27528 221084 110340586
Pancytopenia 15.17 13.62 18 27611 209595 110352075
Drug withdrawal syndrome 15.16 13.62 31 27598 38023 110523647
Sleep apnoea syndrome 15 13.62 32 27597 40415 110521255
Hypothermia 14.98 13.62 25 27604 26277 110535393
Product dose omission issue 14.91 13.62 134 27495 321648 110240022
Encephalopathy 14.56 13.62 49 27580 81006 110480664
Septic shock 14.35 13.62 11 27618 157517 110404153
Sedation complication 14.27 13.62 21 27608 19834 110541836
Postprandial hypoglycaemia 14.22 13.62 4 27625 166 110561504
Bronchitis 14.18 13.62 77 27552 156955 110404715
Alanine aminotransferase increased 14.15 13.62 15 27614 183758 110377912
Pulmonary fibrosis 14.09 13.62 4 27625 102038 110459632
Musculoskeletal pain 14.02 13.62 15 27614 183008 110378662
Persistent depressive disorder 13.97 13.62 7 27622 1470 110560200
General physical health deterioration 13.80 13.62 57 27572 425238 110136432
Blood pressure increased 13.76 13.62 111 27518 258262 110303408
Exposure during pregnancy 13.65 13.62 13 27616 167411 110394259
Skin wrinkling 13.64 13.62 7 27622 1546 110560124

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D04AX01 DERMATOLOGICALS
ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
Other antipruritics
ATC N06AA12 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
MeSH PA D000068776 Sleep Aids, Pharmaceutical
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D006633 Histamine Antagonists
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:35469 antidepressant
FDA EPC N0000175752 Tricyclic Antidepressant

Related Drugs by ATC class:

N06AA Non-selective monoamine reuptake inhibitors 20 drugs
amineptineamitriptylineamoxapinebutriptylineclomipraminedesipraminedibenzepindimetacrinedosulepinimipramineimipramine oxideiprindole show all 20 →

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Atopic dermatitis indication 24079001 DOID:3310
Depressive disorder indication 35489007
Anxiety indication 48694002
Lichen simplex chronicus indication 53891004
Severe major depression with psychotic features indication 73867007
Bipolar affective disorder, current episode depression indication 191627008 DOID:3312
Insomnia indication 193462001
Itching of skin indication 418363000
Cholestatic pruritus off-label use 707150004
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Hepatic failure contraindication 59927004
Sleep apnea contraindication 73430006 DOID:0050847
Chronic idiopathic constipation contraindication 82934008
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Prolonged QT interval contraindication 111975006
Bipolar affective disorder, current episode manic contraindication 191618007
Sleep automatism contraindication 247962006
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Syncope contraindication 271594007
Angle-closure glaucoma contraindication 392291006 DOID:13550
Breastfeeding (mother) contraindication 413712001
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10238620 May 18, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10653662 May 18, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 12083090 May 18, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9486437 May 18, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9861607 May 18, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10238620 May 18, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10653662 May 18, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 12083090 May 18, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9486437 May 18, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9861607 May 18, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10653660 July 20, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11110074 July 20, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9572814 July 20, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10653660 July 20, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11110074 July 20, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9572814 July 20, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 7915307 Aug. 24, 2027 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 7915307 Aug. 24, 2027 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11234954 Jan. 18, 2028 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11234954 Jan. 18, 2028 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10548871 April 11, 2028 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11096920 April 11, 2028 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 10548871 April 11, 2028 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 11096920 April 11, 2028 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9107898 May 1, 2028 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 9107898 May 1, 2028 TREATMENT OF INSOMNIA
EQ 3MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 8513299 Sept. 7, 2030 TREATMENT OF INSOMNIA
EQ 6MG BASE SILENOR CURRAX N022036 March 17, 2010 RX TABLET ORAL 8513299 Sept. 7, 2030 TREATMENT OF INSOMNIA

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Kd 7.53 WOMBAT-PK CHEMBL
Histamine H1 receptor GPCR ANTAGONIST Ki 9.75 WOMBAT-PK DRUG LABEL
Alpha-2A adrenergic receptor GPCR Ki 6.30 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.58 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter INHIBITOR Kd 7.17 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.54 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR EC50 7.45 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR EC50 7.20 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR EC50 7 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 6.98 CHEMBL
5-hydroxytryptamine receptor 7 GPCR WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 7.63 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR IC50 7.21 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 6.33 DRUG MATRIX
D(1A) dopamine receptor GPCR EC50 6.50 WOMBAT-PK
Histamine H4 receptor GPCR EC50 6.79 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 7.42 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 6.80 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 7.28 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 7.09 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 7.13 WOMBAT-PK
Alpha-2C adrenergic receptor GPCR IC50 7 WOMBAT-PK
Alpha-1D adrenergic receptor GPCR Ki 7.37 DRUG MATRIX
Solute carrier family 22 member 1 Transporter IC50 4.95 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.89 WOMBAT-PK
Histamine H2 receptor GPCR Ki 5.74 DRUG MATRIX
D(2) dopamine receptor GPCR EC50 6.50 WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 7.48 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 11 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 6.70 CHEMBL

External reference:

IDSource
4019736 VUID
N0000147828 NUI
D00814 KEGG_DRUG
1229-29-4 SECONDARY_CAS_RN
4017851 VANDF
4019736 VANDF
C0013085 UMLSCUI
CHEBI:4710 CHEBI
CHEMBL1628227 ChEMBL_ID
CHEMBL1628234 ChEMBL_ID
DB01142 DRUGBANK_ID
D004316 MESH_DESCRIPTOR_UI
3158 PUBCHEM_CID
1225 IUPHAR_LIGAND_ID
1855 INN_ID
5ASJ6HUZ7D UNII
203179 RXNORM
172015 MMSL
239355 MMSL
27123 MMSL
278670 MMSL
3183 MMSL
4638 MMSL
d00217 MMSL
001509 NDDF
004607 NDDF
11841005 SNOMEDCT_US
372587005 SNOMEDCT_US
85037008 SNOMEDCT_US
5ASJ6HUZ7D INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
doxepin hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-9609 CREAM 50 mg TOPICAL ANDA 18 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 0228-3315 TABLET, FILM COATED 3 mg ORAL ANDA 31 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 0228-3316 TABLET, FILM COATED 6 mg ORAL ANDA 31 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1049 CAPSULE 10 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1049 CAPSULE 10 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3125 CAPSULE 25 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3125 CAPSULE 25 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-4250 CAPSULE 50 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-4250 CAPSULE 50 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5375 CAPSULE 75 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5375 CAPSULE 75 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6410 CAPSULE 100 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6410 CAPSULE 100 mg ORAL ANDA 35 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-8117 CREAM 50 mg TOPICAL NDA authorized generic 18 sections
Zonalon HUMAN PRESCRIPTION DRUG LABEL 1 0378-8123 CREAM 50 mg TOPICAL NDA 19 sections
PRUDOXIN HUMAN PRESCRIPTION DRUG LABEL 1 0378-8130 CREAM 50 mg TOPICAL NDA 18 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7052 CAPSULE 10 mg ORAL ANDA 16 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7053 CAPSULE 25 mg ORAL ANDA 16 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7054 CAPSULE 50 mg ORAL ANDA 16 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7055 CAPSULE 100 mg ORAL ANDA 16 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 10135-758 TABLET, FILM COATED 3 mg ORAL ANDA 32 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 10135-758 TABLET, FILM COATED 3 mg ORAL ANDA 32 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 10135-764 TABLET, FILM COATED 6 mg ORAL ANDA 32 sections
Doxepin HUMAN PRESCRIPTION DRUG LABEL 1 10135-764 TABLET, FILM COATED 6 mg ORAL ANDA 32 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10267-5059 CAPSULE 10 mg ORAL ANDA 15 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10267-5060 CAPSULE 25 mg ORAL ANDA 15 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10267-5061 CAPSULE 50 mg ORAL ANDA 15 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10267-5062 CAPSULE 75 mg ORAL ANDA 15 sections
Doxepin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10267-5063 CAPSULE 100 mg ORAL ANDA 15 sections
DOXEPIN HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-081 CAPSULE 50 mg ORAL ANDA 13 sections