Trimipramine

Identification

Summary

Trimipramine is a tricyclic antidepressant used to treat depression.

Generic Name
Trimipramine
DrugBank Accession Number
DB00726
Background

Tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 294.4338
Monoisotopic: 294.209598842
Chemical Formula
C20H26N2
Synonyms
  • 10,11-dihydro-N,N,β-trimethyl-5H-dibenz[b,f]azepine-5-propanamine
  • 5-(γ-dimethylamino-β-methylpropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine
  • 5-[3-(dimethylamino)-2-methylpropyl]-10,11-dihydro-5H-dibenz[b,f]azepine
  • beta-Methylimipramine
  • Trimeprimina
  • Trimeprimine
  • Trimeproprimine
  • Trimipramina
  • Trimipramine
  • Trimipraminum
  • β-methylimipramine
External IDs
  • IF 6120
  • IL 6001
  • RP 7162
  • RP-7162

Pharmacology

Indication

For the treatment of depression and depression accompanied by anxiety, agitation or sleep disturbance

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofDepression••••••••••••
Treatment ofInsomnia••• •••••
Treatment ofNocturnal enuresis••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Trimipramine is a tricyclic antidepressant. It was thought that tricyclic antidepressants work by inhibiting the re-uptake of the neurotransmitters norepinephrine and serotonin by nerve cells. However, this response occurs immediately, yet mood does not lift for around two weeks. It is now thought that changes occur in receptor sensitivity in the cerebral cortex and hippocampus. The hippocampus is part of the limbic system, a part of the brain involved in emotions. Presynaptic receptors are affected: a1 and b1 receptors are sensitized, a2 receptors are desensitised (leading to increased noradrenaline production). Tricyclics are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain. A precise mechanism for their analgesic action is unknown, but it is thought that they modulate anti-pain opioid systems in the CNS via an indirect serotonergic route. They are also effective in migraine prophylaxis, but not in abortion of acute migraine attack. The mechanism of their anti-migraine action is also thought to be serotonergic.

Mechanism of action

Trimipramine's mechanism of action differs from other tricyclic antidepressants. Trimipramine acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
ASodium-dependent noradrenaline transporter
inhibitor
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
U5-hydroxytryptamine receptor 2A
agonist
Humans
U5-hydroxytryptamine receptor 1A
antagonist
Humans
UAlpha-1A adrenergic receptor
antagonist
Humans
UAlpha-1B adrenergic receptor
antagonist
Humans
UDopamine D2 receptor
other/unknown
Humans
UAlpha-2B adrenergic receptor
other/unknown
Humans
UHistamine H1 receptor
antagonist
Humans
U5-hydroxytryptamine receptor 2C
antagonist
Humans
U5-hydroxytryptamine receptor 3A
binder
Humans
U5-hydroxytryptamine receptor 1D
binder
Humans
UAlpha-2A adrenergic receptor
antagonist
Humans
UD(1) dopamine receptor
binder
Humans
UBeta adrenergic receptor
binder
Humans
UMuscarinic acetylcholine receptor
binder
Humans
U5-hydroxytryptamine receptor 1C
binder
Rat
Absorption

Rapid absorption

Volume of distribution

Not Available

Protein binding

93%-96% (to plasma proteins)

Metabolism

Hepatic

Route of elimination

Not Available

Half-life

11-18 hrs

Clearance

Not Available

Adverse Effects
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Toxicity

Side effects include agitation, coma, confusion, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high fever, irregular heart rate, low body temperature, muscle rigidity, overactive reflexes, severely low blood pressure, stupor, vomiting

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2C19CYP2C19*2Not Available681G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2C19CYP2C19*3Not Available636G>AEffect Directly StudiedThe presence of this polymorphism in CYP2C19 is associated with reduced or poor metabolism of trimipramine.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details
Cytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with poor metabolism of trimipramine.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Trimipramine is combined with 1,2-Benzodiazepine.
AbataceptThe metabolism of Trimipramine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Trimipramine can be decreased when combined with Abiraterone.
AbrocitinibThe serum concentration of Trimipramine can be increased when it is combined with Abrocitinib.
AcarboseTrimipramine may decrease the hypoglycemic activities of Acarbose.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the risk of adverse effects of trimipramine such as sedation and orthostatic hypotension.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Trimipramine maleate269K6498LD521-78-8YDGHCKHAXOUQOS-BTJKTKAUSA-N
Trimipramine mesylateY62G268P6X25332-13-2KPPOZKAGJSXVND-UHFFFAOYSA-N
Product Images
International/Other Brands
Herphonal (Temmler) / Sapilent (ExtractumPharma) / Stangyl (Sanofi-Aventis) / Trimidura (Mylan dura) / Trimineurin (Hexal) / Tripress (Mylan) / Tydamine (Aspen Pharmacare)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RhotrimineTablet100 mgOralSanofi Aventis1988-12-312007-03-29Canada flag
RhotrimineTablet12.5 mgOralSanofi Aventis1988-12-312006-07-28Canada flag
RhotrimineTablet50 mgOralSanofi Aventis1988-12-312006-07-28Canada flag
RhotrimineCapsule75 mgOralSanofi Aventis1988-12-312007-03-29Canada flag
RhotrimineTablet25 mgOralSanofi Aventis1988-12-312006-07-28Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-trimipramineTablet50 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-trimipramineCapsule75 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-trimipramineTablet25 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-trimipramineTablet100 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-trimipramineTablet12.5 mgOralApotex CorporationNot applicableNot applicableCanada flag

Categories

ATC Codes
N06AA06 — Trimipramine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Dibenzazepines
Direct Parent
Dibenzazepines
Alternative Parents
Alkyldiarylamines / Azepines / Benzenoids / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzenoid / Dibenzazepine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, dibenzoazepine (CHEBI:9738)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6S082C9NDT
CAS number
739-71-9
InChI Key
ZSCDBOWYZJWBIY-UHFFFAOYSA-N
InChI
InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
IUPAC Name
(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}-2-methylpropyl)dimethylamine
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2CCC2=CC=CC=C12

References

General References
Not Available
Human Metabolome Database
HMDB0014864
KEGG Drug
D00394
PubChem Compound
5584
PubChem Substance
46507121
ChemSpider
5382
BindingDB
50240410
RxNav
10834
ChEBI
9738
ChEMBL
CHEMBL644
Therapeutic Targets Database
DAP001153
PharmGKB
PA451791
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Trimipramine
FDA label
Download (152 KB)
MSDS
Download (75 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusNot AvailableMajor Depressive Disorder (MDD)1
3TerminatedTreatmentAnxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Duramed
  • Professional Co.
Dosage Forms
FormRouteStrength
Solution / dropsOral40 MG/ML
Tablet, film coatedOral25 MG
CapsuleOral75 mg / cap
Tablet, film coatedOral100 MG
SolutionOral40 MG/ML
SolutionOral40 mg
TabletOral75 MG
CapsuleOral75 mg
TabletOral100 mg
TabletOral12.5 mg
TabletOral50 mg
CapsuleOral100 mg/1
CapsuleOral25 mg/1
CapsuleOral50 mg/1
TabletOral25 mg
Prices
Unit descriptionCostUnit
Trimipramine maleate powder51.0USD g
Surmontil 100 mg capsule5.92USD capsule
Surmontil 50 mg capsule4.15USD capsule
Trimipramine Maleate 50 mg capsule3.27USD capsule
Trimipramine 50 mg capsule3.14USD capsule
Surmontil 25 mg capsule2.49USD capsule
Trimipramine 25 mg capsule1.92USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)45 °CPhysProp
water solubilitySlightly solubleNot Available
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 mg/mLALOGPS
logP4.67ALOGPS
logP4.76Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)9.42Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area6.48 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity95.02 m3·mol-1Chemaxon
Polarizability35.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9739
Blood Brain Barrier+0.9861
Caco-2 permeable+0.8059
P-glycoprotein substrateSubstrate0.6559
P-glycoprotein inhibitor IInhibitor0.8838
P-glycoprotein inhibitor IIInhibitor0.8826
Renal organic cation transporterInhibitor0.7098
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6698
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9094
CYP450 3A4 inhibitorNon-inhibitor0.6132
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6083
Ames testNon AMES toxic0.8109
CarcinogenicityNon-carcinogens0.9021
BiodegradationNot ready biodegradable0.9886
Rat acute toxicity2.8709 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9065
hERG inhibition (predictor II)Inhibitor0.8271
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-8190000000-adf34fd522dfa7cde9c9
Mass Spectrum (Electron Ionization)MSsplash10-0a4m-5790000000-53c724efbeeb45818f39
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-68bace4e48742b76d7b4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-683044c8af33df070967
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udj-1960000000-2c69c2591b0ff915ccc2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfr-3920000000-7c68e89e7f53026fdb80
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfr-4930000000-f1fe2a4f61bfbec6d778
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-7920000000-b085a14dd7e5d88d4922
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-9810000000-b67a0e6866c4bcb27488
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-90da643ba602b4854ad4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udj-1960000000-953dd8f5d50ce412ae55
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfr-2920000000-493d39be6384cb3b09d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfr-4920000000-02c877be6bc360fbe70e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pb9-6920000000-eb3878e47d12e4792744
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-8910000000-5341bd1feea3e6a75bc8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-875e7a40df38e129227c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0390000000-ba9e7ad393ed66ddaf58
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-472dd752080dc3aaf00d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052k-5290000000-17148781816b0166b661
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0390000000-6e715c64a237e096281e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0690000000-340906ee99deff4ca70e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9520000000-733bf3d5c478f772c096
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.8511081
predicted
DarkChem Lite v0.1.0
[M-H]-164.04424
predicted
DeepCCS 1.0 (2019)
[M+H]+186.6998081
predicted
DarkChem Lite v0.1.0
[M+H]+166.40224
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.0479081
predicted
DarkChem Lite v0.1.0
[M+Na]+172.4954
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Diamond M, Kelly JP, Connor TJ: Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90. Epub 2006 Jan 4. [Article]
  2. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
  2. Haenisch B, Hiemke C, Bonisch H: Inhibitory potencies of trimipramine and its main metabolites at human monoamine and organic cation transporters. Psychopharmacology (Berl). 2011 Sep;217(2):289-95. doi: 10.1007/s00213-011-2281-9. Epub 2011 Apr 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Details
10. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. PDSP Ki Database [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.

Components:
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...

Components:
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...

Components:
References
  1. Eikmeier G, Muszynski K, Berger M, Gastpar M: High-dose trimipramine in acute schizophrenia. Preliminary results of an open trial. Pharmacopsychiatry. 1990 Sep;23(5):212-4. [Article]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
Htr2c
Uniprot ID
P08909
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51916.005 Da
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Kirchheiner J, Muller G, Meineke I, Wernecke KD, Roots I, Brockmoller J: Effects of polymorphisms in CYP2D6, CYP2C9, and CYP2C19 on trimipramine pharmacokinetics. J Clin Psychopharmacol. 2003 Oct;23(5):459-66. doi: 10.1097/01.jcp.0000088909.24613.92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  2. Bolaji OO, Coutts RT, Baker GB: Metabolism of trimipramine in vitro by human CYP2D6 isozyme. Res Commun Chem Pathol Pharmacol. 1993 Oct;82(1):111-20. [Article]
  3. Kirchheiner J, Muller G, Meineke I, Wernecke KD, Roots I, Brockmoller J: Effects of polymorphisms in CYP2D6, CYP2C9, and CYP2C19 on trimipramine pharmacokinetics. J Clin Psychopharmacol. 2003 Oct;23(5):459-66. doi: 10.1097/01.jcp.0000088909.24613.92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Kirchheiner J, Muller G, Meineke I, Wernecke KD, Roots I, Brockmoller J: Effects of polymorphisms in CYP2D6, CYP2C9, and CYP2C19 on trimipramine pharmacokinetics. J Clin Psychopharmacol. 2003 Oct;23(5):459-66. doi: 10.1097/01.jcp.0000088909.24613.92. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Uhr M, Grauer MT: abcb1ab P-glycoprotein is involved in the uptake of citalopram and trimipramine into the brain of mice. J Psychiatr Res. 2003 May-Jun;37(3):179-85. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48