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

Stem definitionDrug idCAS RN
2717 19794-93-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • trazodone
  • trazodon
  • trazodone hydrochloride
  • trazodone HCl
A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309)
  • Molecular weight: 371.87
  • Formula: C19H22ClN5O
  • CLOGP: 3.85
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 0
  • TPSA: 42.39
  • ALOGS: -3.11
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.30 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.20 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 23.05 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 81 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.52 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 24, 1981 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 5345.32 41.17 1154 2810 19880 2334241
Toxicity to various agents 2853.85 41.17 766 3198 31988 2322133
Drug abuse 1399.45 41.17 358 3606 11668 2342453
Cardio-respiratory arrest 1159.21 41.17 292 3672 8854 2345267
Respiratory arrest 1065.70 41.17 253 3711 5925 2348196
Cardiac arrest 941.21 41.17 275 3689 14655 2339466
Serotonin syndrome 719.74 41.17 166 3798 3374 2350747
Overdose 664.38 41.17 226 3738 19681 2334440
Death 550.30 41.17 297 3667 81171 2272950
Drug hypersensitivity 496.47 41.17 232 3732 46411 2307710
Poisoning 487.09 41.17 116 3848 2704 2351417
Intentional overdose 301.27 41.17 109 3855 11212 2342909
Electrocardiogram QT prolonged 288.10 41.17 96 3868 7718 2346403
Suicide attempt 271.89 41.17 101 3863 11181 2342940
Hypotension 264.47 41.17 135 3829 32301 2321820
Somnolence 261.41 41.17 121 3843 23364 2330757
Coma 228.86 41.17 84 3880 8972 2345149
Intentional product misuse 214.10 41.17 81 3883 9408 2344713
Depressed level of consciousness 201.24 41.17 73 3891 7531 2346590
Drug interaction 169.18 41.17 97 3867 29066 2325055
Agitation 154.79 41.17 67 3897 10984 2343137
Insomnia 152.80 41.17 87 3877 25700 2328421
Asphyxia 150.95 41.17 37 3927 967 2353154
Drug ineffective 143.97 41.17 145 3819 101479 2252642
Torsade de pointes 143.14 41.17 42 3922 2204 2351917
Confusional state 135.82 41.17 79 3885 24265 2329856
Arteriosclerosis coronary artery 130.59 41.17 34 3930 1139 2352982
Exposure via ingestion 128.46 41.17 31 3933 757 2353364
Myocardial stunning 124.13 41.17 19 3945 25 2354096
Tremor 109.78 41.17 65 3899 20596 2333525
Hyperreflexia 109.46 41.17 28 3936 873 2353248
Mental status changes 105.67 41.17 42 3922 5540 2348581
Myoclonus 105.40 41.17 34 3930 2449 2351672
Mydriasis 104.97 41.17 33 3931 2186 2351935
Vomiting 104.43 41.17 104 3860 71498 2282623
Encephalopathy 102.95 41.17 39 3925 4522 2349599
Poisoning deliberate 101.72 41.17 28 3936 1163 2352958
Unresponsive to stimuli 100.42 41.17 39 3925 4837 2349284
Lethargy 96.84 41.17 45 3919 8685 2345436
Depression 96.08 41.17 67 3897 28065 2326056
Condition aggravated 95.09 41.17 70 3894 31909 2322212
Neuroleptic malignant syndrome 94.52 41.17 30 3934 2050 2352071
Accidental death 92.13 41.17 20 3944 299 2353822
Pulmonary congestion 92.02 41.17 29 3935 1936 2352185
Drug screen positive 89.65 41.17 24 3940 896 2353225
Sedation 84.08 41.17 31 3933 3331 2350790
Spleen congestion 82.84 41.17 14 3950 46 2354075
Aspiration 81.76 41.17 25 3939 1509 2352612
Hyponatraemia 81.57 41.17 46 3918 13279 2340842
Loss of personal independence in daily activities 80.20 41.17 34 3930 5277 2348844
Nausea 74.09 41.17 109 3855 112080 2242041
Aortic valve calcification 71.75 41.17 13 3951 70 2354051
Akathisia 67.28 41.17 22 3942 1652 2352469
Fatigue 67.16 41.17 90 3874 84783 2269338
Pulmonary oedema 66.58 41.17 33 3931 7330 2346791
Dry mouth 65.89 41.17 34 3930 8219 2345902
Fall 65.88 41.17 67 3897 47032 2307089
Respiratory depression 65.49 41.17 23 3941 2147 2351974
Cerebellar syndrome 65.42 41.17 17 3947 564 2353557
Disorientation 64.95 41.17 31 3933 6341 2347780
Delirium 64.42 41.17 29 3935 5194 2348927
Small for dates baby 63.09 41.17 17 3947 650 2353471
Medication error 63.02 41.17 30 3934 6101 2348020
Anxiety 62.87 41.17 53 3911 29306 2324815
Visual perseveration 60.74 41.17 11 3953 59 2354062
Metabolic acidosis 60.58 41.17 29 3935 5969 2348152
Generalised tonic-clonic seizure 60.50 41.17 28 3936 5344 2348777
Respiratory failure 57.60 41.17 37 3927 13491 2340630
Rhabdomyolysis 57.52 41.17 29 3935 6675 2347446
Bradycardia 57.14 41.17 33 3931 9948 2344173
Substance abuse 56.70 41.17 15 3949 534 2353587
Tachycardia 55.74 41.17 39 3925 16370 2337751
Syncope 54.76 41.17 39 3925 16836 2337285
Accidental poisoning 54.38 41.17 11 3953 114 2354007
Headache 54.37 41.17 79 3885 80100 2274021
Suicidal ideation 53.93 41.17 33 3931 11054 2343067
Muscle rigidity 53.70 41.17 19 3945 1812 2352309
Miosis 52.90 41.17 17 3947 1207 2352914
Accidental overdose 52.00 41.17 23 3941 3949 2350172
Intentional self-injury 51.16 41.17 23 3941 4104 2350017
Compartment syndrome 50.75 41.17 13 3951 407 2353714
Urinary tract infection 50.05 41.17 47 3917 29895 2324226
Sopor 48.68 41.17 22 3942 3973 2350148
Delusion 47.81 41.17 18 3946 2047 2352074
Apallic syndrome 47.00 41.17 10 3954 135 2353986
Constipation 46.17 41.17 39 3925 21590 2332531
Cardiomegaly 45.21 41.17 18 3946 2378 2351743
Off label use 44.83 41.17 69 3895 73529 2280592
Hyperhidrosis 44.03 41.17 33 3931 15389 2338732
Hypomagnesaemia 44.03 41.17 18 3946 2546 2351575
Purpura senile 42.69 41.17 7 3957 18 2354103
Inappropriate antidiuretic hormone secretion 42.36 41.17 17 3947 2292 2351829
Ventricular tachycardia 41.24 41.17 18 3946 2993 2351128

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 2187.12 46.99 556 2282 15756 1728187
Toxicity to various agents 1621.35 46.99 500 2338 28641 1715302
Priapism 1106.44 46.99 209 2629 1255 1742688
Drug abuse 1069.99 46.99 308 2530 13381 1730562
Serotonin syndrome 870.65 46.99 191 2647 2597 1741346
Cardio-respiratory arrest 534.57 46.99 166 2672 9127 1734816
Respiratory arrest 486.37 46.99 139 2699 5700 1738243
Cardiac arrest 424.76 46.99 160 2678 15770 1728173
Intentional overdose 325.40 46.99 109 2729 7561 1736382
Overdose 319.09 46.99 132 2706 16569 1727374
Death 266.94 46.99 206 2632 87237 1656706
Drug interaction 256.92 46.99 133 2705 27825 1716118
Electrocardiogram QT prolonged 235.62 46.99 79 2759 5466 1738477
Poisoning 217.83 46.99 62 2776 2470 1741473
Intentional product misuse 195.45 46.99 74 2764 7284 1736659
Suicide attempt 177.29 46.99 69 2769 7312 1736631
Somnolence 142.78 46.99 76 2762 16663 1727280
Agitation 138.09 46.99 65 2773 10961 1732982
Accidental overdose 136.72 46.99 49 2789 4115 1739828
Insomnia 125.11 46.99 69 2769 16207 1727736
Ventricular tachyarrhythmia 113.24 46.99 19 2819 47 1743896
Mental status changes 111.97 46.99 47 2791 6028 1737915
Hypotension 102.77 46.99 76 2762 29578 1714365
Myoclonus 98.46 46.99 33 2805 2262 1741681
Acute pulmonary oedema 96.48 46.99 28 2810 1189 1742754
Confusional state 95.69 46.99 64 2774 21214 1722729
Drug hypersensitivity 94.32 46.99 56 2782 15079 1728864
Unresponsive to stimuli 89.25 46.99 37 2801 4592 1739351
Shock 86.14 46.99 35 2803 4126 1739817
Anxiety 85.29 46.99 53 2785 15474 1728469
Muscle rigidity 84.96 46.99 28 2810 1820 1742123
Pneumonia aspiration 78.20 46.99 35 2803 5231 1738712
Lethargy 76.64 46.99 38 2800 7146 1736797
Coma 76.25 46.99 38 2800 7224 1736719
Tremor 72.53 46.99 45 2793 13086 1730857
Sedation 71.60 46.99 29 2809 3388 1740555
Bradycardia 70.89 46.99 41 2797 10493 1733450
Hypoglycaemia 68.07 46.99 37 2801 8401 1735542
Metabolic acidosis 67.96 46.99 32 2806 5370 1738573
Depression 65.06 46.99 46 2792 16623 1727320
Suicidal ideation 64.98 46.99 36 2802 8482 1735461
Exposure via ingestion 64.49 46.99 18 2820 662 1743281
Drug ineffective 64.45 46.99 83 2755 63718 1680225
Hyperreflexia 61.47 46.99 17 2821 604 1743339
Environmental exposure 60.77 46.99 11 2827 48 1743895
Symptom masked 57.99 46.99 11 2827 65 1743878
Depressed level of consciousness 56.21 46.99 30 2808 6562 1737381
Fall 54.79 46.99 51 2787 27163 1716780
Disorientation 52.65 46.99 27 2811 5442 1738501
Painful erection 52.62 46.99 11 2827 113 1743830
Poisoning deliberate 52.08 46.99 16 2822 826 1743117
Lactic acidosis 51.34 46.99 26 2812 5103 1738840
Acute kidney injury 51.03 46.99 55 2783 34889 1709054
Tachycardia 49.59 46.99 35 2803 12593 1731350
Dizziness 48.28 46.99 53 2785 34308 1709635
Hallucination, visual 47.51 46.99 20 2818 2572 1741371
Clonus 47.08 46.99 13 2825 459 1743484

Pharmacologic Action:

SourceCodeDescription
ATC N06AX05 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
FDA EPC N0000175696 Serotonin Reuptake Inhibitor
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D000928 Antidepressive Agents
MeSH PA D018687 Antidepressive Agents, Second-Generation
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018490 Serotonin Agents
MeSH PA D017367 Serotonin Uptake Inhibitors
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:37887 adrenergic antagonist
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:50949 serotonin uptake inhibitor
CHEBI has role CHEBI:35474 anxiolytic drug
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Major depressive disorder indication 370143000
Insomnia off-label use 193462001
Priapism contraindication 6273006 DOID:9286
Suicidal thoughts contraindication 6471006
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Heart disease contraindication 56265001 DOID:114
Blood coagulation disorder contraindication 64779008 DOID:1247
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Benign prostatic hyperplasia contraindication 266569009
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 6.98 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
150MG **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** OLEPTRO ANGELINI PHARMA N022411 Feb. 2, 2010 DISCN TABLET, EXTENDED RELEASE ORAL 7829120 March 27, 2027 METHOD OF TREATING DEPRESSION
300MG **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** OLEPTRO ANGELINI PHARMA N022411 Feb. 2, 2010 DISCN TABLET, EXTENDED RELEASE ORAL 7829120 March 27, 2027 METHOD OF TREATING DEPRESSION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 6.65 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 7.35 WOMBAT-PK CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR Kd 6.80 WOMBAT-PK CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 6.81 PDSP
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.03 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.75 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.90 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.33 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Kd 5.13 WOMBAT-PK
Histamine H1 receptor GPCR Ki 6.21 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR IC50 9.55 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 7.08 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 7.02 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Kd 5.07 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.54 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.58 WOMBAT-PK
D(4) dopamine receptor GPCR Ki 6.15 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 5.75 PDSP
D(2) dopamine receptor GPCR Ki 5.46 PDSP
D(1A) dopamine receptor GPCR Ki 5.43 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 6.97 PDSP
Histamine H2 receptor GPCR Ki 5.48 PDSP
Alpha-1B adrenergic receptor GPCR Ki 7.21 DRUG MATRIX
5-hydroxytryptamine receptor 1B GPCR Ki 6.08 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.08 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR IC50 7.77 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 6.65 CHEMBL
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 6.70 IUPHAR
Alpha-1A adrenergic receptor GPCR IC50 6.93 CHEMBL

External reference:

IDSource
4019954 VUID
N0000148039 NUI
C0040805 UMLSCUI
D00820 KEGG_DRUG
6E8ZO8LRNM UNII
25332-39-2 SECONDARY_CAS_RN
7336002 SNOMEDCT_US
4019954 VANDF
10737 RXNORM
372829000 SNOMEDCT_US
004610 NDDF
d00395 MMSL
CHEMBL621 ChEMBL_ID
DB00656 DRUGBANK_ID
CHEMBL1200798 ChEMBL_ID
CHEBI:9654 CHEBI
2878 INN_ID
D014196 MESH_DESCRIPTOR_UI
5533 PUBCHEM_CID
213 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0733 TABLET 300 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-6160 TABLET, FILM COATED 50 mg ORAL ANDA 20 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-6161 TABLET, FILM COATED 100 mg ORAL ANDA 20 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-2578 TABLET 50 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-2579 TABLET 100 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8155 TABLET 150 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6554 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6555 TABLET 100 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6868 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6869 TABLET 100 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-532 TABLET 100 mg ORAL ANDA 20 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-533 TABLET 150 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-534 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-867 TABLET 150 mg ORAL ANDA 20 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 12634-193 TABLET, FILM COATED 50 mg ORAL ANDA 21 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13107-079 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13107-080 TABLET 100 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13107-081 TABLET 150 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13107-082 TABLET 300 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13668-330 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13668-331 TABLET 100 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13668-332 TABLET 150 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13668-333 TABLET 300 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-231 TABLET 50 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-232 TABLET 100 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16590-585 TABLET 150 mg ORAL ANDA 14 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-299 TABLET 50 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-300 TABLET 100 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-301 TABLET 150 mg ORAL ANDA 19 sections
Trazodone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-302 TABLET 300 mg ORAL ANDA 19 sections