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Identification
NameDesipramine
Accession NumberDB01151  (APRD00022, DB07682)
TypeSmall Molecule
GroupsApproved
Description

Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).

Structure
Thumb
Synonyms
3-(10,11-DIHYDRO-5H-dibenzo[b,F]azepin-5-yl)-N-methylpropan-1-amine
5-(gamma-Methylaminopropyl)iminodibenzyl
5-(γ-methylaminopropyl)iminodibenzyl
Déméthylimipramine
Desipramin
Desipramina
Desipramine
Desipraminum
Desmethylimipramine
DMI
Monodemethylimipramine
N-(3-methylaminopropyl)iminobibenzyl
Norimipramine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desipraminetablet50 mgoralAa Pharma Inc1996-12-31Not applicableCanada
Desipraminetablet75 mgoralAa Pharma Inc1996-12-31Not applicableCanada
Desipraminetablet100 mgoralAa Pharma Inc1996-12-31Not applicableCanada
Desipraminetablet25 mgoralAa Pharma Inc1996-12-31Not applicableCanada
Desipraminetablet10 mgoralAa Pharma Inc1996-12-31Not applicableCanada
Desipramine Hydrochloridetablet, sugar coated10 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine Hydrochloridetablet, sugar coated150 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine Hydrochloridetablet, sugar coated100 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine Hydrochloridetablet, sugar coated75 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine Hydrochloridetablet, sugar coated50 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine Hydrochloridetablet, sugar coated25 mg/1oralWinthrop U.S.2014-04-01Not applicableUs
Desipramine-10 - Tab 10mgtablet10 mgoralPro Doc Limitee1996-12-042010-07-13Canada
Desipramine-25 - Tab 25mgtablet25 mgoralPro Doc Limitee1997-04-302010-07-13Canada
Desipramine-50 - Tab 50mgtablet50 mgoralPro Doc Limitee1996-12-062010-07-13Canada
Desipramine-75 - Tab 75mgtablet75 mgoralPro Doc Limitee1997-02-272010-07-13Canada
Dom-desipramine Tablets - 25mgtablet25 mgoralDominion Pharmacal1996-12-31Not applicableCanada
Dom-desipramine Tablets - 50mgtablet50 mgoralDominion Pharmacal1996-12-31Not applicableCanada
Norpramintablet, sugar coated10 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramintablet, sugar coated150 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramintablet, sugar coated100 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramintablet, sugar coated75 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramintablet, sugar coated50 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramintablet, sugar coated25 mg/1oralSanofi Aventis U.S. Llc1964-11-20Not applicableUs
Norpramin 100mg Tabtablet100 mgoralAventis Pharma Inc1995-12-312002-07-29Canada
Norpramin 10mg Tabtablet10 mgoralAventis Pharma Inc1995-12-312003-07-22Canada
Norpramin 25mg Tabtablet25 mgoralSanofi Aventis Canada Inc1995-12-312007-08-01Canada
Norpramin 50mg Tabtablet50 mgoralSanofi Aventis Canada Inc1995-12-312007-08-01Canada
Norpramin 75mg Tabtablet75 mgoralAventis Pharma Inc1996-12-312000-08-16Canada
Norpramin Tab 25mgtablet25 mgoralMerrell Pharms Inc., Division Of Merrell Dow (Can)1976-12-311996-09-09Canada
Norpramin Tab 50mgtablet50 mgoralMerrell Pharms Inc., Division Of Merrell Dow (Can)1976-12-311997-08-05Canada
Norpramin Tab 75mgtablet75 mgoralMerrell Pharms Inc., Division Of Merrell Dow (Can)1978-12-311997-08-05Canada
Novo-desipramine Fc - 50mg Tabtablet50 mgoralNovopharm Limited1996-11-27Not applicableCanada
Novo-desipramine Sc - Tab 10mgtablet10 mgoralNovopharm Limited1996-11-27Not applicableCanada
Novo-desipramine Sc - Tab 25mgtablet25 mgoralNovopharm Limited1996-11-27Not applicableCanada
Novo-desipramine Sc -tab 75mgtablet75 mgoralNovopharm Limited1996-11-27Not applicableCanada
Nu-desipramine - Tab 100mgtablet100 mgoralNu Pharm Inc1996-09-132012-09-04Canada
Nu-desipramine - Tab 10mgtablet10 mgoralNu Pharm Inc1996-12-312012-09-04Canada
Nu-desipramine - Tab 25mgtablet25 mgoralNu Pharm Inc1996-12-312012-09-04Canada
Nu-desipramine - Tab 50mgtablet50 mgoralNu Pharm Inc1996-12-312012-09-04Canada
Nu-desipramine - Tab 75mgtablet75 mgoralNu Pharm Inc1996-12-312012-09-04Canada
Penta-desipramine Tabletstablet50 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-desipramine Tabletstablet25 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-desipramine Tabletstablet10 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-desipramine Tabletstablet75 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Pertofrane 25mgtablet25 mgoralNovartis Pharmaceuticals Canada Inc1964-12-311999-08-04Canada
Pertofrane Tab 50mgtablet50 mgoralGeigy Pharmaceuticals, Ciba Geigy Canada Ltd.1990-12-311996-11-08Canada
PHL-desipraminetablet100 mgoralPharmel IncNot applicableNot applicableCanada
PHL-desipraminetablet75 mgoralPharmel Inc1998-02-172009-10-26Canada
PHL-desipraminetablet50 mgoralPharmel Inc1998-02-172009-10-26Canada
PHL-desipraminetablet25 mgoralPharmel Inc1998-02-172009-10-26Canada
PHL-desipraminetablet10 mgoralPharmel Inc1998-02-172009-10-26Canada
PMS Desipramine Hydro Tab 10mgtablet10 mgoralPharmascience Inc1993-12-31Not applicableCanada
PMS Desipramine Hydro Tab 25mgtablet25 mgoralPharmascience Inc1993-12-31Not applicableCanada
PMS Desipramine Hydro Tab 50mgtablet50 mgoralPharmascience Inc1993-12-31Not applicableCanada
PMS Desipramine Hydro Tab 75mgtablet75 mgoralPharmascience Inc1993-12-31Not applicableCanada
PMS-desipramine - Tab 100mgtablet100 mgoralPharmascience Inc1995-12-31Not applicableCanada
Ratio-desipramine Tab 100mgtablet100 mgoralRatiopharm Inc Division Of Teva Canada Limited2002-07-262006-08-04Canada
Ratio-desipramine Tab 10mgtablet10 mgoralRatiopharm Inc Division Of Teva Canada Limited1994-12-312006-08-04Canada
Ratio-desipramine Tab 25mgtablet25 mgoralRatiopharm Inc Division Of Teva Canada Limited1992-12-312008-08-01Canada
Ratio-desipramine Tab 50mgtablet50 mgoralRatiopharm Inc Division Of Teva Canada Limited1992-12-312008-08-01Canada
Ratio-desipramine Tab 75mgtablet75 mgoralRatiopharm Inc Division Of Teva Canada Limited1992-12-312006-08-04Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Desipramine Hydrochloridetablet, film coated25 mg/1oralActavis Pharma, Inc.2006-05-01Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralPreferred Pharmaceuticals, Inc2012-04-05Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralKAISER FOUNDATION HOSPITALS2012-05-31Not applicableUs
Desipramine Hydrochloridetablet, film coated75 mg/1oralActavis Pharma, Inc.2006-05-08Not applicableUs
Desipramine Hydrochloridetablet, film coated150 mg/1oralSandoz Inc1988-06-20Not applicableUs
Desipramine Hydrochloridetablet50 mg/1oralREMEDYREPACK INC.2011-09-19Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralActavis Pharma, Inc.2006-05-09Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralCarilion Materials Management1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated100 mg/1oralSandoz Inc1988-06-20Not applicableUs
Desipramine Hydrochloridetablet, film coated50 mg/1oralREMEDYREPACK INC.2011-04-21Not applicableUs
Desipramine Hydrochloridetablet10 mg/1oralRebel Distributors Corp1996-02-09Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralAmerican Health Packaging2015-09-01Not applicableUs
Desipramine Hydrochloridetablet, film coated150 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated75 mg/1oralSandoz Inc1988-06-20Not applicableUs
Desipramine Hydrochloridetablet10 mg/1oralREMEDYREPACK INC.2011-04-18Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralRebel Distributors Corp1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated50 mg/1oralbryant ranch prepack2006-06-04Not applicableUs
Desipramine Hydrochloridetablet, film coated100 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated50 mg/1oralSandoz Inc1988-05-24Not applicableUs
Desipramine Hydrochloridetablet50 mg/1oralREMEDYREPACK INC.2011-04-04Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralSTAT Rx USA LLC1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated100 mg/1oralbryant ranch prepack1988-06-20Not applicableUs
Desipramine Hydrochloridetablet, film coated75 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralSandoz Inc1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated150 mg/1oralActavis Pharma, Inc.2006-05-09Not applicableUs
Desipramine Hydrochloridetablet, film coated100 mg/1oralSTAT Rx USA LLC1988-06-20Not applicableUs
Desipramine Hydrochloridetablet, film coated25 mg/1oralbryant ranch prepack1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated50 mg/1oralActavis Pharma, Inc.2006-06-04Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated50 mg/1oralAmneal Pharmaceuticals of New York, LLC2016-03-21Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralSandoz Inc1988-05-24Not applicableUs
Desipramine Hydrochloridetablet, film coated100 mg/1oralActavis Pharma, Inc.2006-07-19Not applicableUs
Desipramine Hydrochloridetablet, film coated10 mg/1oralSandoz Inc2015-06-24Not applicableUs
Desipramine Hydrochloridetablet25 mg/1oralREMEDYREPACK INC.2011-10-12Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PertofranCiba
PertofraneUSV
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Desipramine Hydrochloride
Thumb
  • InChI Key: XAEWZDYWZHIUCT-UHFFFAOYSA-N
  • Monoisotopic Mass: 302.154976453
  • Average Mass: 302.842
DBSALT000042
Categories
UNIITG537D343B
CAS number50-47-5
WeightAverage: 266.3807
Monoisotopic: 266.178298714
Chemical FormulaC18H22N2
InChI KeyInChIKey=HCYAFALTSJYZDH-UHFFFAOYSA-N
InChI
InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
IUPAC Name
(3-{2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine
SMILES
CNCCCN1C2=CC=CC=C2CCC2=CC=CC=C12
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Alkyldiarylamine
  • Azepine
  • Benzenoid
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management.
PharmacodynamicsDesipramine, a secondary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is the active metabolite of imipramine, a tertiary amine TCA. The acute effects of desipramine include inhibition of noradrenaline re-uptake at noradrenergic nerve endings and inhibition of serotonin (5-hydroxy tryptamine, 5HT) re-uptake at the serotoninergic nerve endings in the central nervous system. Desipramine exhibits greater noradrenergic re-uptake inhibition compared to the tertiary amine TCA imipramine. In addition to inhibiting neurotransmitter re-uptake, desipramine down-regulates beta-adrenergic receptors in the cerebral cortex and sensitizes serotonergic receptors with chronic use. The overall effect is increased serotonergic transmission. Antidepressant effects are typically observed 2 - 4 weeks following the onset of therapy though some patients may require up to 8 weeks of therapy prior to symptom improvement. Patients experiencing more severe depressive episodes may respond quicker than those with mild depressive symptoms.
Mechanism of actionDesipramine is a tricyclic antidepressant (TCA) that selectively blocks reuptake of norepinephrine (noradrenaline) from the neuronal synapse. It also inhibits serotonin reuptake, but to a lesser extent compared to tertiary amine TCAs such as imipramine. Inhibition of neurotransmitter reuptake increases stimulation of the post-synaptic neuron. Chronic use of desipramine also leads to down-regulation of beta-adrenergic receptors in the cerebral cortex and sensitization of serotonergic receptors. An overall increase in serotonergic transmission likely confers desipramine its antidepressant effects. Desipramine also possesses minor anticholinergic activity, through its affinity for muscarinic receptors. TCAs are believed to act by restoring normal levels of neurotransmitters via synaptic reuptake inhibition and by increasing serotonergic neurotransmission via serotonergic receptor sensitization in the central nervous system.
Related Articles
AbsorptionDesipramine hydrochloride is rapidly and almost completely absorbed from the gastrointestinal tract. It undergoes extensive first-pass metabolism. Peak plasma concentrations are attained 4 - 6 hours following oral administration.
Volume of distributionNot Available
Protein binding73-92% bound to plasma proteins
Metabolism

Desipramine is extensively metabolized in the liver by CYP2D6 (major) and CYP1A2 (minor) to 2-hydroxydesipramine, an active metabolite. 2-hydroxydesipramine is thought to retain some amine reuptake inhibition and may possess cardiac depressant activity. The 2-hydroxylation metabolic pathway of desipramine is under genetic control.

SubstrateEnzymesProduct
Desipramine
2-hydroxydesipramineDetails
2-hydroxydesipramine
Not Available
2-hydroxy-desipramine glucuronideDetails
Route of eliminationDesipramine is metabolized in the liver, and approximately 70% is excreted in the urine.
Half life7-60+ hours; 70% eliminated renally
ClearanceNot Available
ToxicityMale mice: LD50 = 290 mg/kg, female rats: LD50 = 320 mg/kg. Antagonism of the histamine H1 and α1 receptors can lead to sedation and hypotension. Antimuscarinic activity confers anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of desipramine. Cardiovascular side effects in postural hypotension, tachycardia, hypertension, ECG changes and congestive heart failure. Psychotoxic effects include impaired memory and delirium. Induction of hypomanic or manic episodes may occur in patients with a history of bipolar disorder. Withdrawal symptoms include GI disturbances (e.g. nausea, vomiting, abdominal pain, diarrhea), anxiety, insomnia, nervousness, headache and malaise.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Desipramine Action PathwayDrug actionSMP00423
Imipramine Action PathwayDrug actionSMP00422
Imipramine Metabolism PathwayDrug metabolismSMP00625
Desipramine Metabolism PathwayDrug metabolismSMP00626
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs3892097 CYP2D6*4A AllelePoor drug metabolizer, lower dose requirements, higher risk for adverse side effects18070221
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9854
Caco-2 permeable+0.8868
P-glycoprotein substrateSubstrate0.7945
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.6353
Renal organic cation transporterInhibitor0.7955
CYP450 2C9 substrateNon-substrate0.7684
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5117
CYP450 1A2 substrateInhibitor0.9029
CYP450 2C9 inhibitorNon-inhibitor0.9125
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9241
CYP450 3A4 inhibitorInhibitor0.744
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8478
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9476
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity2.8197 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8569
hERG inhibition (predictor II)Inhibitor0.8604
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg/1
Tabletoral25 mg/1
Tabletoral50 mg/1
Tablet, film coatedoral10 mg/1
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral150 mg/1
Tablet, film coatedoral25 mg/1
Tablet, film coatedoral50 mg/1
Tablet, film coatedoral75 mg/1
Tablet, sugar coatedoral10 mg/1
Tablet, sugar coatedoral100 mg/1
Tablet, sugar coatedoral150 mg/1
Tablet, sugar coatedoral25 mg/1
Tablet, sugar coatedoral50 mg/1
Tablet, sugar coatedoral75 mg/1
Tabletoral10 mg
Tabletoral25 mg
Tabletoral50 mg
Tabletoral75 mg
Tabletoral100 mg
Prices
Unit descriptionCostUnit
Desipramine hcl powder14.4USD g
Norpramin 150 mg tablet6.08USD tablet
Desipramine HCl 150 mg tablet4.67USD tablet
Norpramin 100 mg tablet4.2USD tablet
Norpramin 75 mg tablet3.19USD tablet
Desipramine HCl 100 mg tablet2.81USD tablet
Desipramine HCl 75 mg tablet2.63USD tablet
Norpramin 50 mg tablet2.51USD tablet
Desipramine 150 mg tablet2.18USD tablet
Desipramine HCl 50 mg tablet1.64USD tablet
Desipramine 100 mg tablet1.5USD tablet
Norpramin 25 mg tablet1.33USD tablet
Desipramine 75 mg tablet1.15USD tablet
Norpramin 10 mg tablet1.11USD tablet
Apo-Desipramine 75 mg Tablet0.93USD tablet
Desipramine 50 mg tablet0.92USD tablet
Desipramine HCl 10 mg tablet0.87USD tablet
Desipramine HCl 25 mg tablet0.83USD tablet
Apo-Desipramine 50 mg Tablet0.7USD tablet
Desipramine 25 mg tablet0.49USD tablet
Desipramine 10 mg tablet0.4USD tablet
Apo-Desipramine 10 mg Tablet0.4USD tablet
Apo-Desipramine 25 mg Tablet0.4USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point214-218 °CNot Available
water solubility58.6 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.90HANSCH,C ET AL. (1995)
logS-3.66ADME Research, USCD
Caco2 permeability-4.67ADME Research, USCD
pKa10.4SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0396 mg/mLALOGPS
logP4.02ALOGPS
logP3.9ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity85.31 m3·mol-1ChemAxon
Polarizability31.74 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-4970000000-810535cb33c37107abc5View in MoNA
References
Synthesis Reference

Biel, J.H.and Judd, C.I.; US. Patent 3,454,554; July 8,1969; assigned to Colgate Palmolive Co.

General ReferencesNot Available
External Links
ATC CodesN06AA01
AHFS Codes
  • 28:16.04.28
PDB EntriesNot Available
FDA labelDownload (152 KB)
MSDSDownload (73.6 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Desipramine can be increased when it is combined with Abiraterone.
AcepromazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Acetophenazine.
AclidiniumAclidinium may increase the anticholinergic activities of Desipramine.
AltretamineAltretamine may increase the orthostatic hypotensive activities of Desipramine.
AmisulprideThe risk or severity of adverse effects can be increased when Desipramine is combined with Amisulpride.
AmphetamineDesipramine may increase the stimulatory activities of Amphetamine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Desipramine.
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Desipramine resulting in a loss in efficacy.
AzelastineDesipramine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Desipramine.
BatimastatThe serum concentration of Desipramine can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Desipramine is combined with Benzquinamide.
BoceprevirThe serum concentration of Desipramine can be increased when it is combined with Boceprevir.
Botulinum Toxin Type ADesipramine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BDesipramine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Desipramine.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
BuprenorphineDesipramine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
BupropionThe metabolism of Desipramine can be decreased when combined with Bupropion.
ButabarbitalThe metabolism of Desipramine can be increased when combined with Butabarbital.
ButethalThe metabolism of Desipramine can be increased when combined with Butethal.
CarbamazepineThe metabolism of Desipramine can be increased when combined with Carbamazepine.
CarphenazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Carphenazine.
CathinoneDesipramine may increase the stimulatory activities of Cathinone.
ChlormezanoneThe risk or severity of adverse effects can be increased when Desipramine is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Chlorpromazine.
ChlorpropamideDesipramine may increase the hypoglycemic activities of Chlorpropamide.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Desipramine is combined with Chlorprothixene.
CimetidineThe metabolism of Desipramine can be decreased when combined with Cimetidine.
CimetropiumDesipramine may increase the anticholinergic activities of Cimetropium Bromide.
CinacalcetThe serum concentration of Desipramine can be increased when it is combined with Cinacalcet.
CitalopramThe risk or severity of adverse effects can be increased when Desipramine is combined with Citalopram.
ClozapineThe risk or severity of adverse effects can be increased when Desipramine is combined with Clozapine.
CobicistatThe serum concentration of Desipramine can be increased when it is combined with Cobicistat.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Desipramine.
DarunavirThe serum concentration of Desipramine can be increased when it is combined with Darunavir.
DesmopressinThe risk or severity of adverse effects can be increased when Desipramine is combined with Desmopressin.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Desipramine.
DicoumarolDesipramine may increase the anticoagulant activities of Dicoumarol.
DipivefrinThe therapeutic efficacy of Dipivefrin can be decreased when used in combination with Desipramine.
DofetilideDesipramine may increase the QTc-prolonging activities of Dofetilide.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Desipramine.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
DuloxetineDuloxetine may increase the serotonergic activities of Desipramine.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Desipramine.
EluxadolineDesipramine may increase the activities of Eluxadoline.
EscitalopramThe risk or severity of adverse effects can be increased when Desipramine is combined with Escitalopram.
EthanolDesipramine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FencamfamineThe risk or severity of adverse effects can be increased when Desipramine is combined with Fencamfamine.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Desipramine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Desipramine.
FlupentixolThe risk or severity of adverse effects can be increased when Desipramine is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Desipramine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Desipramine.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Desipramine is combined with Glucagon recombinant.
GoserelinDesipramine may increase the QTc-prolonging activities of Goserelin.
GranisetronGranisetron may increase the serotonergic activities of Desipramine.
HaloperidolThe risk or severity of adverse effects can be increased when Desipramine is combined with Haloperidol.
HeptabarbitalThe metabolism of Desipramine can be increased when combined with Heptabarbital.
HexobarbitalThe metabolism of Desipramine can be increased when combined with Hexobarbital.
HydrocodoneDesipramine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Desipramine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Desipramine.
IsoflurophateThe serum concentration of Desipramine can be increased when it is combined with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Desipramine.
LeuprolideDesipramine may increase the QTc-prolonging activities of Leuprolide.
LinezolidLinezolid may increase the serotonergic activities of Desipramine.
LiothyronineLiothyronine may increase the arrhythmogenic activities of Desipramine.
LithiumLithium may increase the neurotoxic activities of Desipramine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Desipramine.
LoxapineThe risk or severity of adverse effects can be increased when Desipramine is combined with Loxapine.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
MesoridazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Mesoridazine.
MethadoneThe metabolism of Methadone can be decreased when combined with Desipramine.
MethohexitalThe metabolism of Desipramine can be increased when combined with Methohexital.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Methotrimeprazine.
Methylene blueDesipramine may increase the serotonergic activities of Methylene blue.
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Desipramine.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Desipramine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Desipramine.
MetyrosineDesipramine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Desipramine.
MidodrineDesipramine may increase the activities of Midodrine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Desipramine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
MirabegronThe serum concentration of Desipramine can be increased when it is combined with Mirabegron.
MolindoneThe risk or severity of adverse effects can be increased when Desipramine is combined with Molindone.
MorphineThe risk or severity of adverse effects can be increased when Desipramine is combined with Morphine.
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Desipramine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Desipramine.
NicorandilDesipramine may increase the hypotensive activities of Nicorandil.
OlanzapineThe risk or severity of adverse effects can be increased when Desipramine is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Desipramine is combined with Ondansetron.
OrciprenalineThe risk or severity of adverse effects can be increased when Desipramine is combined with Orciprenaline.
OrphenadrineDesipramine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PaliperidoneThe risk or severity of adverse effects can be increased when Desipramine is combined with Paliperidone.
PanobinostatThe serum concentration of Desipramine can be increased when it is combined with Panobinostat.
ParaldehydeDesipramine may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Desipramine.
Peginterferon alfa-2bThe serum concentration of Desipramine can be decreased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe metabolism of Desipramine can be increased when combined with Pentobarbital.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
PerphenazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Perphenazine.
PhenelzinePhenelzine may increase the serotonergic activities of Desipramine.
PimozideThe risk or severity of adverse effects can be increased when Desipramine is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Piperacetazine.
Potassium ChlorideDesipramine may increase the ulcerogenic activities of Potassium Chloride.
PramipexoleDesipramine may increase the sedative activities of Pramipexole.
PramlintidePramlintide may increase the anticholinergic activities of Desipramine.
PrimidoneThe metabolism of Desipramine can be increased when combined with Primidone.
ProchlorperazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Prochlorperazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Desipramine.
PromazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Promazine.
PropafenoneThe serum concentration of Desipramine can be increased when it is combined with Propafenone.
QuetiapineThe risk or severity of adverse effects can be increased when Desipramine is combined with Quetiapine.
QuinidineDesipramine may increase the QTc-prolonging activities of Quinidine.
RamosetronDesipramine may increase the activities of Ramosetron.
RemoxiprideThe risk or severity of adverse effects can be increased when Desipramine is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Desipramine is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Desipramine is combined with Risperidone.
RitonavirThe metabolism of Desipramine can be decreased when combined with Ritonavir.
RopiniroleDesipramine may increase the sedative activities of Ropinirole.
RotigotineDesipramine may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Desipramine.
SecobarbitalThe metabolism of Desipramine can be increased when combined with Secobarbital.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Desipramine.
SertindoleThe risk or severity of adverse effects can be increased when Desipramine is combined with Sertindole.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Desipramine.
SimeprevirThe serum concentration of Desipramine can be increased when it is combined with Simeprevir.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
St. John's WortThe metabolism of Desipramine can be increased when combined with St. John's Wort.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Desipramine.
SuvorexantDesipramine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Desipramine can be decreased when used in combination with Tacrine.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Desipramine resulting in a loss in efficacy.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Desipramine.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Desipramine.
TegafurThe serum concentration of the active metabolites of Tegafur can be reduced when Tegafur is used in combination with Desipramine resulting in a loss in efficacy.
TerbinafineThe metabolism of Desipramine can be decreased when combined with Terbinafine.
ThalidomideDesipramine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Desipramine.
ThiothixeneThe risk or severity of adverse effects can be increased when Desipramine is combined with Thiothixene.
TiclopidineThe metabolism of Desipramine can be decreased when combined with Ticlopidine.
TiotropiumDesipramine may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Desipramine is combined with Topiramate.
TramadolDesipramine may increase the neuroexcitatory activities of Tramadol.
TranylcypromineTranylcypromine may increase the serotonergic activities of Desipramine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Desipramine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Desipramine is combined with Triflupromazine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Desipramine.
Valproic AcidThe serum concentration of Desipramine can be increased when it is combined with Valproic Acid.
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Desipramine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Desipramine is combined with Ziprasidone.
ZolpidemDesipramine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Desipramine is combined with Zuclopenthixol.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation, limit caffeine intake.

Targets

Kind
Protein
Organism
Human
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
Molecular Weight:
69331.42 Da
References
  1. Zavosh A, Schaefer J, Ferrel A, Figlewicz DP: Desipramine treatment decreases 3H-nisoxetine binding and norepinephrine transporter mRNA in SK-N-SHSY5Y cells. Brain Res Bull. 1999 Jul 1;49(4):291-5. [PubMed:10424850 ]
  2. Weinshenker D, White SS, Javors MA, Palmiter RD, Szot P: Regulation of norepinephrine transporter abundance by catecholamines and desipramine in vivo. Brain Res. 2002 Aug 16;946(2):239-46. [PubMed:12137927 ]
  3. Bryan-Lluka LJ, Bonisch H, Lewis RJ: chi-Conopeptide MrIA partially overlaps desipramine and cocaine binding sites on the human norepinephrine transporter. J Biol Chem. 2003 Oct 10;278(41):40324-9. Epub 2003 Jul 1. [PubMed:12837768 ]
  4. Zhu MY, Kyle PB, Hume AS, Ordway GA: The persistent membrane retention of desipramine causes lasting inhibition of norepinephrine transporter function. Neurochem Res. 2004 Feb;29(2):419-27. [PubMed:15002740 ]
  5. Ordway GA, Jia W, Li J, Zhu MY, Mandela P, Pan J: Norepinephrine transporter function and desipramine: residual drug effects versus short-term regulation. J Neurosci Methods. 2005 Apr 30;143(2):217-25. Epub 2004 Dec 30. [PubMed:15814154 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. 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. [PubMed:9537821 ]
Kind
Protein
Organism
Human
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 the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 Da
References
  1. Holmes A, Yang RJ, Murphy DL, Crawley JN: Evaluation of antidepressant-related behavioral responses in mice lacking the serotonin transporter. Neuropsychopharmacology. 2002 Dec;27(6):914-23. [PubMed:12464448 ]
  2. Gould GG, Altamirano AV, Javors MA, Frazer A: A comparison of the chronic treatment effects of venlafaxine and other antidepressants on serotonin and norepinephrine transporters. Biol Psychiatry. 2006 Mar 1;59(5):408-14. Epub 2005 Sep 2. [PubMed:16140280 ]
  3. Zhou L, Huang KX, Kecojevic A, Welsh AM, Koliatsos VE: Evidence that serotonin reuptake modulators increase the density of serotonin innervation in the forebrain. J Neurochem. 2006 Jan;96(2):396-406. Epub 2005 Nov 21. [PubMed:16300628 ]
  4. Hoffman AF, Gerhardt GA: In vivo electrochemical studies of dopamine clearance in the rat substantia nigra: effects of locally applied uptake inhibitors and unilateral 6-hydroxydopamine lesions. J Neurochem. 1998 Jan;70(1):179-89. [PubMed:9422361 ]
  5. 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. [PubMed:9537821 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Matsumoto K, Ojima K, Ohta H, Watanabe H: Beta 2- but not beta 1-adrenoceptors are involved in desipramine enhancement of aggressive behavior in long-term isolated mice. Pharmacol Biochem Behav. 1994 Sep;49(1):13-8. [PubMed:7816863 ]
  2. Sapena R, Morin D, Zini R, Morin C, Tillement JP: Desipramine treatment differently down-regulates beta-adrenoceptors of freshly isolated neurons and astrocytes. Eur J Pharmacol. 1996 Apr 4;300(1-2):159-62. [PubMed:8741184 ]
  3. Abadie C, Foucart S, Page P, Nadeau R: Modulation of noradrenaline release from isolated human atrial appendages. J Auton Nerv Syst. 1996 Dec 14;61(3):269-76. [PubMed:8988485 ]
  4. Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [PubMed:17417877 ]
  5. Osadchii OE, Woodiwiss AJ, Deftereos D, Norton GR: Temporal changes in myocardial adrenergic regulation with the progression to pump dysfunction after chronic beta-adrenoreceptor activation in rats. Pflugers Arch. 2007 Nov;455(2):251-60. Epub 2007 Jun 9. [PubMed:17558518 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Sapena R, Morin D, Zini R, Morin C, Tillement JP: Desipramine treatment differently down-regulates beta-adrenoceptors of freshly isolated neurons and astrocytes. Eur J Pharmacol. 1996 Apr 4;300(1-2):159-62. [PubMed:8741184 ]
  2. Burgi S, Baltensperger K, Honegger UE: Antidepressant-induced switch of beta 1-adrenoceptor trafficking as a mechanism for drug action. J Biol Chem. 2003 Jan 10;278(2):1044-52. Epub 2002 Oct 21. [PubMed:12393876 ]
  3. Matsumoto K, Ojima K, Ohta H, Watanabe H: Beta 2- but not beta 1-adrenoceptors are involved in desipramine enhancement of aggressive behavior in long-term isolated mice. Pharmacol Biochem Behav. 1994 Sep;49(1):13-8. [PubMed:7816863 ]
  4. Samnick S, Scheuer C, Munks S, El-Gibaly AM, Menger MD, Kirsch CM: Technetium-99m labeled 1-(4-fluorobenzyl)-4-(2-mercapto-2-methyl-4-azapentyl)-4-(2-mercapto-2-methylprop ylamino)-piperidine and iodine-123 metaiodobenzylguanidine for studying cardiac adrenergic function: a comparison of the uptake characteristics in vascular smooth muscle cells and neonatal cardiac myocytes, and an investigation in rats. Nucl Med Biol. 2004 May;31(4):511-22. [PubMed:15093822 ]
  5. Mudunkotuwa NT, Horton RW: Desipramine administration in the olfactory bulbectomized rat: changes in brain beta-adrenoceptor and 5-HT2A binding sites and their relationship to behaviour. Br J Pharmacol. 1996 Apr;117(7):1481-6. [PubMed:8730743 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sphingomyelin phosphodiesterase activity
Specific Function:
Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:
SMPD1
Uniprot ID:
P17405
Molecular Weight:
69751.3 Da
References
  1. Testai FD, Landek MA, Dawson G: Regulation of sphingomyelinases in cells of the oligodendrocyte lineage. J Neurosci Res. 2004 Jan 1;75(1):66-74. [PubMed:14689449 ]
  2. Kolzer M, Werth N, Sandhoff K: Interactions of acid sphingomyelinase and lipid bilayers in the presence of the tricyclic antidepressant desipramine. FEBS Lett. 2004 Feb 13;559(1-3):96-8. [PubMed:14960314 ]
  3. Erdreich-Epstein A, Tran LB, Cox OT, Huang EY, Laug WE, Shimada H, Millard M: Endothelial apoptosis induced by inhibition of integrins alphavbeta3 and alphavbeta5 involves ceramide metabolic pathways. Blood. 2005 Jun 1;105(11):4353-61. Epub 2005 Feb 10. [PubMed:15705795 ]
  4. Zeidan YH, Pettus BJ, Elojeimy S, Taha T, Obeid LM, Kawamori T, Norris JS, Hannun YA: Acid ceramidase but not acid sphingomyelinase is required for tumor necrosis factor-{alpha}-induced PGE2 production. J Biol Chem. 2006 Aug 25;281(34):24695-703. Epub 2006 Jun 27. [PubMed:16803890 ]
  5. Hurwitz R, Ferlinz K, Sandhoff K: The tricyclic antidepressant desipramine causes proteolytic degradation of lysosomal sphingomyelinase in human fibroblasts. Biol Chem Hoppe Seyler. 1994 Jul;375(7):447-50. [PubMed:7945993 ]
  6. Kornhuber J, Tripal P, Reichel M, Muhle C, Rhein C, Muehlbacher M, Groemer TW, Gulbins E: Functional Inhibitors of Acid Sphingomyelinase (FIASMAs): a novel pharmacological group of drugs with broad clinical applications. Cell Physiol Biochem. 2010;26(1):9-20. doi: 10.1159/000315101. Epub 2010 May 18. [PubMed:20502000 ]
Kind
Protein
Organism
Human
Pharmacological action
no
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Sawynok J, Esser MJ, Reid AR: Peripheral antinociceptive actions of desipramine and fluoxetine in an inflammatory and neuropathic pain test in the rat. Pain. 1999 Aug;82(2):149-58. [PubMed:10467920 ]
  2. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein group
Organism
Human
Pharmacological action
no
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Components:
NameUniProt IDDetails
Alpha-1A adrenergic receptorP35348 Details
Alpha-1B adrenergic receptorP35368 Details
Alpha-1D adrenergic receptorP25100 Details
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor 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 action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
General Function:
Receptor 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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
General Function:
Guanyl-nucleotide exchange factor 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 action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular Weight:
60073.205 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
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. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular Weight:
46106.335 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein
Organism
Human
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-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
References
  1. Palvimaki EP, Roth BL, Majasuo H, Laakso A, Kuoppamaki M, Syvalahti E, Hietala J: Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor. Psychopharmacology (Berl). 1996 Aug;126(3):234-40. [PubMed:8876023 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
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
Molecular Weight:
50618.91 Da
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
binder
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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
Components:
NameUniProt IDDetails
Alpha-2A adrenergic receptorP08913 Details
Alpha-2B adrenergic receptorP18089 Details
Alpha-2C adrenergic receptorP18825 Details
References
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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. [PubMed:8968657 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [PubMed:11996013 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
General Function:
Not Available
Specific Function:
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Molecular Weight:
23511.38 Da
References
  1. Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. [PubMed:2870173 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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
Molecular Weight:
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
  2. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
  3. Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [PubMed:7990927 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [PubMed:10966924 ]
  2. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [PubMed:9632645 ]
  3. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23