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Identification
NameImipramine
Accession NumberDB00458  (APRD00672, DB08002)
TypeSmall Molecule
GroupsApproved
Description

Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative 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, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. 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. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. See toxicity section below for a complete listing of side effects. Imipramine may be used to treat depression and nocturnal enuresis in children. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD).

Structure
Thumb
Synonyms
10,11-dihydro-N,N-Dimethyl-5H-dibenz[b,F]azepine-5-propanamine
3-(5H-DIBENZO[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine
5-[3-(dimethylamino)Propyl]-10,11-dihydro-5H-dibenz[b,F]azepine
Antideprin
Imipramin
Imipramine
Imipraminum
Imizine
Irmin
Melipramine
N-(gamma-Dimethylaminopropyl)iminodibenzyl
N-(γ-dimethylaminopropyl)iminodibenzyl
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Imipraminetablet10 mgoralAa Pharma Inc1976-12-31Not applicableCanada
Imipraminetablet50 mgoralAa Pharma Inc1975-12-31Not applicableCanada
Imipraminetablet25 mgoralAa Pharma Inc1975-12-31Not applicableCanada
Imipraminetablet75 mgoralAa Pharma Inc1989-12-31Not applicableCanada
Imipramine 10tabtablet10 mgoralPro Doc Limitee1976-12-312010-07-13Canada
Imipramine 25tabtablet25 mgoralPro Doc Limitee1976-12-312010-07-13Canada
Imipramine 50 Tab 50mgtablet50 mgoralPro Doc Limitee1978-12-312010-07-13Canada
Imipramine Hydrochloride Tablets 25mgtablet25 mgoralD.C. Labs Limited1977-12-312003-07-11Canada
Imipramine Hydrochloride Tablets 50mgtablet50 mgoralD.C. Labs Limited1977-12-312003-07-11Canada
Imipramine Pamoatecapsule75 mg/1oralSTAT Rx USA LLC2009-10-15Not applicableUs
Imipramine Pamoatecapsule150 mg/1oralMallinckrodt, Inc.2009-10-15Not applicableUs
Imipramine Pamoatecapsule125 mg/1oralMallinckrodt, Inc.2009-10-15Not applicableUs
Imipramine Pamoatecapsule100 mg/1oralMallinckrodt, Inc.2009-10-15Not applicableUs
Imipramine Pamoatecapsule75 mg/1oralMallinckrodt, Inc.2009-10-15Not applicableUs
Imipramine Tab 25mgtablet25 mgoralDuchesnay Inc1978-12-312003-07-18Canada
Impriltablet75 mgoralValeant Canada Lp Valeant Canada S.E.C.1988-12-312014-07-30Canada
Impriltablet10 mgoralValeant Canada Lp Valeant Canada S.E.C.1974-12-312014-07-30Canada
Impriltablet50 mgoralValeant Canada Lp Valeant Canada S.E.C.1974-12-312014-07-30Canada
Impriltablet25 mgoralValeant Canada Lp Valeant Canada S.E.C.1974-12-312014-07-30Canada
Novo-pramine Tab 10mgtablet10 mgoralNovopharm Limited1971-12-31Not applicableCanada
Novo-pramine Tab 25mgtablet25 mgoralNovopharm Limited1971-12-31Not applicableCanada
Novo-pramine Tab 50mgtablet50 mgoralNovopharm Limited1971-12-31Not applicableCanada
PMS Imipramine Tab 10mgtablet10 mgoralPharmascience Inc1988-12-31Not applicableCanada
PMS Imipramine Tab 25mgtablet25 mgoralPharmascience Inc1988-12-31Not applicableCanada
PMS Imipramine Tab 50mgtablet50 mgoralPharmascience Inc1988-12-31Not applicableCanada
Tofranil 10mgtablet10 mgoralNovartis Pharmaceuticals Canada Inc1960-12-312001-07-30Canada
Tofranil 25mgtablet25 mgoralNovartis Pharmaceuticals Canada Inc1959-12-312008-07-18Canada
Tofranil 50mgtablet50 mgoralNovartis Pharmaceuticals Canada Inc1962-12-312010-11-29Canada
Tofranil 75mgtablet75 mgoralNovartis Pharmaceuticals Canada Inc1974-12-312008-07-18Canada
Tofranil-PMcapsule75 mg/1oralMallinckrodt, Inc.2009-11-04Not applicableUs
Tofranil-PMcapsule150 mg/1oralMallinckrodt, Inc.2009-11-04Not applicableUs
Tofranil-PMcapsule125 mg/1oralMallinckrodt, Inc.2009-11-04Not applicableUs
Tofranil-PMcapsule100 mg/1oralMallinckrodt, Inc.2009-11-04Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-imipraminetablet50 mgoralApotex IncNot applicableNot applicableCanada
Apo-imipraminetablet75 mgoralApotex IncNot applicableNot applicableCanada
Apo-imipraminetablet25 mgoralApotex IncNot applicableNot applicableCanada
Apo-imipraminetablet10 mgoralApotex IncNot applicableNot applicableCanada
Imipramine Hydrochloridetablet, film coated50 mg/1oralPhysicians Total Care, Inc.1992-11-12Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralMutual Pharmaceutical Company, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet25 mg/1oralREMEDYREPACK INC.2011-09-21Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralExcellium Pharmaceutical, Inc2012-11-01Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralPd Rx Pharmaceuticals, Inc.1976-04-20Not applicableUs
Imipramine Hydrochloridetablet50 mg/1oralREMEDYREPACK INC.2011-09-20Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralSandoz Inc1976-04-20Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralExcellium Pharmaceutical, Inc2012-11-01Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralREMEDYREPACK INC.2011-04-21Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralPhysicians Total Care, Inc.1993-02-02Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralREMEDYREPACK INC.2013-07-08Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralExcellium Pharmaceutical, Inc2012-11-01Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralLeading Pharma, Llc2016-04-07Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralAv Kare, Inc.2015-12-09Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralRichmond Pharmaceuticals, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralNorthwind Pharmaceuticals, LLC2015-03-06Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralbryant ranch prepack2010-12-21Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralLeading Pharma, Llc2016-04-07Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralAv Kare, Inc.2015-12-09Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralRichmond Pharmaceuticals, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralA S Medication Solutions Llc1990-06-05Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralbryant ranch prepack1990-06-05Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralLeading Pharma, Llc2016-04-07Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralAv Kare, Inc.2015-12-09Not applicableUs
Imipramine Hydrochloridetablet10 mg/1oralKAISER FOUNDATION HOSPITALS2012-05-31Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralRichmond Pharmaceuticals, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet25 mg/1oralA S Medication Solutions Llc1983-10-21Not applicableUs
Imipramine Hydrochloridetablet50 mg/1oralGolden State Medical Supply, Inc.1999-08-27Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralLupin Pharmaceuticals, Inc.2010-12-21Not applicableUs
Imipramine Hydrochloridetablet50 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC1983-10-21Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralA S Medication Solutions Llc1990-06-05Not applicableUs
Imipramine Hydrochloridetablet50 mg/1oralPar Pharmaceutical Inc.1983-10-21Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralSandoz Inc1976-04-20Not applicableUs
Imipramine Hydrochloridetablet, film coated50 mg/1oralMutual Pharmaceutical Company, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet25 mg/1oralPar Pharmaceutical Inc.1983-10-21Not applicableUs
Imipramine Hydrochloridetablet25 mg/1oralGolden State Medical Supply, Inc.1999-08-27Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralLupin Pharmaceuticals, Inc.2010-12-21Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralSandoz Inc1976-04-20Not applicableUs
Imipramine Hydrochloridetablet, film coated25 mg/1oralMutual Pharmaceutical Company, Inc.1990-06-05Not applicableUs
Imipramine Hydrochloridetablet10 mg/1oralPar Pharmaceutical Inc.1983-10-21Not applicableUs
Imipramine Hydrochloridetablet10 mg/1oralCarilion Materials Management1983-10-21Not applicableUs
Imipramine Hydrochloridetablet10 mg/1oralGolden State Medical Supply, Inc.1999-08-27Not applicableUs
Imipramine Hydrochloridetablet, film coated10 mg/1oralLupin Pharmaceuticals, Inc.2010-12-21Not applicableUs
Imipramine Pamoatecapsule75 mg/1oralRoxane Laboratories, Inc2010-04-19Not applicableUs
Imipramine Pamoatecapsule150 mg/1oralLupin Pharmaceuticals, Inc.2010-04-16Not applicableUs
Imipramine Pamoatecapsule125 mg/1oralLupin Pharmaceuticals, Inc.2010-04-16Not applicableUs
Imipramine Pamoatecapsule100 mg/1oralLupin Pharmaceuticals, Inc.2010-04-16Not applicableUs
Imipramine Pamoatecapsule150 mg/1oralRoxane Laboratories, Inc2010-04-19Not applicableUs
Imipramine Pamoatecapsule125 mg/1oralRoxane Laboratories, Inc2010-04-19Not applicableUs
Imipramine Pamoatecapsule75 mg/1oralLupin Pharmaceuticals, Inc.2010-04-16Not applicableUs
Imipramine Pamoatecapsule100 mg/1oralRoxane Laboratories, Inc2010-04-19Not applicableUs
Tofraniltablet, sugar coated50 mg/1oralMallinckrodt, Inc.2011-01-24Not applicableUs
Tofraniltablet, sugar coated25 mg/1oralMallinckrodt, Inc.2011-01-24Not applicableUs
Tofraniltablet, sugar coated10 mg/1oralMallinckrodt, Inc.2011-01-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AntidepTorrent
DepsonilAbbott
Depsonil-PMAbbott
ElaminBaroda
FronilJohnson
ImidolTanabe Mitsubishi Pharma
Imipramin DakNycomed
ImiprexDumex
PraminIncepta
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Imipramine Hydrochloride
113-52-0
Thumb
  • InChI Key: XZZXIYZZBJDEEP-UHFFFAOYSA-N
  • Monoisotopic Mass: 316.170626517
  • Average Mass: 316.868
DBSALT000099
Imipramine Pamoate
Thumb
  • InChI Key: SBDXQUVAAJKLDH-UHFFFAOYSA-N
  • Monoisotopic Mass: 668.288637022
  • Average Mass: 668.7768
DBSALT000100
Categories
UNIIOGG85SX4E4
CAS number50-49-7
WeightAverage: 280.4073
Monoisotopic: 280.193948778
Chemical FormulaC19H24N2
InChI KeyInChIKey=BCGWQEUPMDMJNV-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
IUPAC Name
(3-{2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine
SMILES
CN(C)CCCN1C2=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 aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used to manage panic disorders, with or without agoraphobia, as a second line agent in ADHD, management of eating disorders, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, and for symptomatic treatment of postherpetic neuralgia.
PharmacodynamicsImipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. A tertiary amine, imipramine inhibits the reuptake of serotonin more so than most secondary amine tricyclics, meaning that it blocks the reuptake of neurotransmitters serotonin and noradrenaline almost equally. With chronic use, imipramine also down-regulates cerebral cortical β-adrenergic receptors and sensitizes post-synaptic sertonergic receptors, which also contributes to increased serotonergic transmission. It takes approximately 2 - 4 weeks for antidepressants effects to occur. The onset of action may be longer, up to 8 weeks, in some individuals. It is also effective in migraine prophylaxis, but not in abortion of acute migraine attack.
Mechanism of actionImipramine works by inhibiting the neuronal reuptake of the neurotransmitters norepinephrine and serotonin. It binds the sodium-dependent serotonin transporter and sodium-dependent norepinephrine transporter preventing or reducing the reuptake of norepinephrine and serotonin by nerve cells. Depression has been linked to a lack of stimulation of the post-synaptic neuron by norepinephrine and serotonin. Slowing the reuptake of these neurotransmitters increases their concentration in the synaptic cleft, which is thought to contribute to relieving symptoms of depression. In addition to acutely inhibiting neurotransmitter re-uptake, imipramine causes down-regulation of cerebral cortical beta-adrenergic receptors and sensitization of post-synaptic serotonergic receptors with chronic use. This leads to enhanced serotonergic transmission.
Related Articles
AbsorptionRapidly and well absorbed after oral administration. Bioavailability is approximately 43%. Peak plasma concentrations usually attained 1 - 2 hours following oral administration. Absorption is unaffected by food.
Volume of distributionNot Available
Protein binding60-95%
Metabolism

Exclusively metabolized by the liver. Imipramine is converted in the liver by various CYP isoenzymes (e.g. CYP1A2, CYP2D6, CYP3A4, CYP2C9) to active metabolites desipramine and 2-hydroxydesipramine.

SubstrateEnzymesProduct
Imipramine
2-hydroxyimipramineDetails
Imipramine
DesipramineDetails
2-hydroxyimipramine
Not Available
2-hydroxy-imipramine glucuronideDetails
Route of eliminationApproximately 40% of an orally administered dose is eliminated in urine within 24 hours, 70% in 72 hours. Small amounts are eliminated in feces via the biliary elimination.
Half lifeImipramine - 8-20 hours; Desipramine (active metabolite) - up to 125 hours
ClearanceNot Available
ToxicityOral, rat LD50: 355 to 682 mg/kg. Toxic signs proceed progressively from depression, irregular respiration and ataxia to convulsions and death. Antagonism of the histamine H1 and α1 receptors can lead to sedation and hypotension. Antimuscarinic and anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of imipramine. 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
Imipramine Metabolism PathwayDrug metabolismSMP00625
Imipramine Action PathwayDrug actionSMP00422
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 Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs3892097 CYP2D6*4C > TThose that are homozygous for the poorly metabolizing CYP2D6 alleles are at an increased risk of side effects and decrease drug metabolism18070221
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs3892097 CYP2D6*4C > TThose that are homozygous for the poorly metabolizing CYP2D6 alleles are at an increased risk of side effects and decrease drug metabolism9918137
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9822
Blood Brain Barrier+0.9865
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7684
P-glycoprotein inhibitor IInhibitor0.8662
P-glycoprotein inhibitor IIInhibitor0.6205
Renal organic cation transporterInhibitor0.8541
CYP450 2C9 substrateNon-substrate0.7799
CYP450 2D6 substrateSubstrate0.9532
CYP450 3A4 substrateSubstrate0.6718
CYP450 1A2 substrateNon-inhibitor0.7583
CYP450 2C9 inhibitorNon-inhibitor0.9089
CYP450 2D6 inhibitorInhibitor0.9017
CYP450 2C19 inhibitorNon-inhibitor0.9304
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8399
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9329
BiodegradationNot ready biodegradable0.9819
Rat acute toxicity3.0187 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9172
hERG inhibition (predictor II)Inhibitor0.7771
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Actavis totowa llc
  • Lederle laboratories div american cyanamid co
  • Lupin ltd
  • Mutual pharmaceutical co inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Vangard laboratories inc div midway medical co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Abbott laboratories pharmaceutical products div
  • Alra laboratories inc
  • Sanofi aventis us llc
  • Tyco healthcare group lp
  • Odyssey pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral75 mg
Tabletoral10 mg/1
Tabletoral25 mg/1
Tabletoral50 mg/1
Tablet, film coatedoral10 mg/1
Tablet, film coatedoral25 mg/1
Tablet, film coatedoral50 mg/1
Capsuleoral100 mg/1
Capsuleoral125 mg/1
Capsuleoral150 mg/1
Capsuleoral75 mg/1
Tabletoral10 mg
Tabletoral25 mg
Tabletoral50 mg
Tablet, sugar coatedoral10 mg/1
Tablet, sugar coatedoral25 mg/1
Tablet, sugar coatedoral50 mg/1
Prices
Unit descriptionCostUnit
Tofranil-PM 30 125 mg capsule Bottle588.33USD bottle
Tofranil-PM 30 150 mg capsule Bottle588.33USD bottle
Tofranil-PM 30 75 mg capsule Bottle588.33USD bottle
Tofranil 30 50 mg tablet Bottle185.09USD bottle
Trimipramine maleate powder51.0USD g
Tofranil-pm 100 mg capsule19.23USD capsule
Tofranil-pm 150 mg capsule18.86USD capsule
Tofranil-pm 75 mg capsule18.86USD capsule
Tofranil-pm 125 mg capsule18.68USD capsule
Imipramine pamoate 75 mg capsule16.35USD capsule
Imipramine pamoate 100 mg capsule15.17USD capsule
Imipramine pamoate 125 mg capsule15.17USD capsule
Imipramine pamoate 150 mg capsule15.17USD capsule
Tofranil 50 mg tablet6.64USD tablet
Surmontil 100 mg capsule5.92USD capsule
Tofranil 25 mg tablet4.97USD tablet
Tofranil 10 mg tablet4.73USD tablet
Surmontil 50 mg capsule4.07USD capsule
Trimipramine Maleate 50 mg capsule3.27USD capsule
Trimipramine 50 mg capsule3.14USD capsule
Surmontil 25 mg capsule2.49USD capsule
Cenestin 0.3 mg tablet2.21USD tablet
Cenestin 0.45 mg tablet2.21USD tablet
Cenestin 0.625 mg tablet2.21USD tablet
Cenestin 0.9 mg tablet2.21USD tablet
Cenestin 1.25 mg tablet2.21USD tablet
Trimipramine 25 mg capsule1.92USD capsule
Apo-Trimip 100 mg Tablet0.97USD tablet
Imipramine hcl powder0.77USD g
Apo-Trimip 75 mg Capsule0.77USD capsule
Apo-Imipramine 75 mg Tablet0.58USD tablet
Tofranil 50 mg Tablet0.57USD tablet
Apo-Trimip 50 mg Tablet0.57USD tablet
Imipramine hcl 10 mg tablet0.46USD tablet
Imipramine hcl 50 mg tablet0.44USD tablet
Apo-Imipramine 50 mg Tablet0.4USD tablet
Imipramine hcl 25 mg tablet0.35USD tablet
Apo-Trimip 25 mg Tablet0.29USD tablet
Apo-Imipramine 25 mg Tablet0.25USD tablet
Apo-Trimip 12.5 mg Tablet0.23USD tablet
Apo-Imipramine 10 mg Tablet0.14USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point174-175U.S. Patent 2,554,736.
boiling point160 °C at 1.00E-01 mm HgPhysProp
water solubility18.2 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.80HANSCH,C ET AL. (1995)
logS-4.19ADME Research, USCD
Caco2 permeability-4.85ADME Research, USCD
pKa9.4SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0664 mg/mLALOGPS
logP4.53ALOGPS
logP4.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.61 m3·mol-1ChemAxon
Polarizability33.39 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.2 KB)
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-55d924fd00e5b357ce9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-eb3c0ecdffc5d9d95e33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ab9-9432000000-033c51459b692622ee7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0019-7490000000-bb99ef31a755d9f6ba14View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0543-8890000000-6cf8e84f007ce7c750f2View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

U.S. Patent 2,554,736.

General ReferencesNot Available
External Links
ATC CodesN06AA02
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 Imipramine can be increased when it is combined with Abiraterone.
AcepromazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Acetophenazine.
Acetylsalicylic acidImipramine may increase the antiplatelet activities of Acetylsalicylic acid.
AclidiniumAclidinium may increase the anticholinergic activities of Imipramine.
AltretamineAltretamine may increase the orthostatic hypotensive activities of Imipramine.
AmisulprideThe risk or severity of adverse effects can be increased when Imipramine is combined with Amisulpride.
AmphetamineImipramine may increase the stimulatory activities of Amphetamine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Imipramine.
AzelastineImipramine 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 Imipramine.
BatimastatThe serum concentration of Imipramine can be increased when it is combined with Batimastat.
BenzquinamideThe risk or severity of adverse effects can be increased when Imipramine is combined with Benzquinamide.
BortezomibThe metabolism of Imipramine can be decreased when combined with Bortezomib.
Botulinum Toxin Type AImipramine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BImipramine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Imipramine.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
BuprenorphineImipramine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
BupropionThe metabolism of Imipramine can be decreased when combined with Bupropion.
ButabarbitalThe metabolism of Imipramine can be increased when combined with Butabarbital.
ButethalThe metabolism of Imipramine can be increased when combined with Butethal.
CarphenazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Carphenazine.
CathinoneImipramine may increase the stimulatory activities of Cathinone.
ChlormezanoneThe risk or severity of adverse effects can be increased when Imipramine is combined with Chlormezanone.
ChlorpromazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Chlorpromazine.
ChlorpropamideImipramine may increase the hypoglycemic activities of Chlorpropamide.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Imipramine is combined with Chlorprothixene.
CimetidineThe metabolism of Imipramine can be decreased when combined with Cimetidine.
Cimetropium BromideImipramine may increase the anticholinergic activities of Cimetropium Bromide.
CinacalcetThe serum concentration of Imipramine can be increased when it is combined with Cinacalcet.
CitalopramThe risk or severity of adverse effects can be increased when Imipramine is combined with Citalopram.
ClozapineThe risk or severity of adverse effects can be increased when Imipramine is combined with Clozapine.
CobicistatThe serum concentration of Imipramine can be increased when it is combined with Cobicistat.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Imipramine.
DabrafenibThe serum concentration of Imipramine can be decreased when it is combined with Dabrafenib.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Imipramine.
DarunavirThe serum concentration of Imipramine can be increased when it is combined with Darunavir.
DesmopressinThe risk or severity of adverse effects can be increased when Imipramine is combined with Desmopressin.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Dexmethylphenidate is combined with Imipramine.
DicoumarolImipramine may increase the anticoagulant activities of Dicoumarol.
DipivefrinThe therapeutic efficacy of Dipivefrin can be decreased when used in combination with Imipramine.
DofetilideImipramine may increase the QTc-prolonging activities of Dofetilide.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Imipramine.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
DuloxetineDuloxetine may increase the serotonergic activities of Imipramine.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Imipramine.
EluxadolineImipramine may increase the activities of Eluxadoline.
EscitalopramThe risk or severity of adverse effects can be increased when Imipramine is combined with Escitalopram.
EthanolImipramine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FencamfamineThe risk or severity of adverse effects can be increased when Imipramine is combined with Fencamfamine.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Imipramine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Imipramine.
FlupentixolThe risk or severity of adverse effects can be increased when Imipramine is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Imipramine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Imipramine.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Imipramine is combined with Glucagon recombinant.
GoserelinImipramine may increase the QTc-prolonging activities of Goserelin.
GranisetronGranisetron may increase the serotonergic activities of Imipramine.
HaloperidolThe risk or severity of adverse effects can be increased when Imipramine is combined with Haloperidol.
HeptabarbitalThe metabolism of Imipramine can be increased when combined with Heptabarbital.
HexobarbitalThe metabolism of Imipramine can be increased when combined with Hexobarbital.
HydrocodoneImipramine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
IcosapentImipramine may increase the antiplatelet activities of Icosapent.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Imipramine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Imipramine.
IsoflurophateThe serum concentration of Imipramine can be increased when it is combined with Isoflurophate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Imipramine.
LeuprolideImipramine may increase the QTc-prolonging activities of Leuprolide.
LinezolidLinezolid may increase the serotonergic activities of Imipramine.
LiothyronineLiothyronine may increase the arrhythmogenic activities of Imipramine.
LithiumLithium may increase the neurotoxic activities of Imipramine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Imipramine.
LoxapineThe risk or severity of adverse effects can be increased when Imipramine is combined with Loxapine.
LuliconazoleThe serum concentration of Imipramine can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Imipramine can be decreased when it is combined with Lumacaftor.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
MesoridazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Mesoridazine.
MethohexitalThe metabolism of Imipramine can be increased when combined with Methohexital.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Methotrimeprazine.
Methylene blueImipramine may increase the serotonergic activities of Methylene blue.
MethylphenidateThe risk or severity of adverse effects can be increased when Methylphenidate is combined with Imipramine.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Imipramine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Imipramine.
MetyrosineImipramine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Imipramine.
MidodrineImipramine may increase the activities of Midodrine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Imipramine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
MirabegronThe risk or severity of adverse effects can be increased when Imipramine is combined with Mirabegron.
MolindoneThe risk or severity of adverse effects can be increased when Imipramine is combined with Molindone.
MorphineThe risk or severity of adverse effects can be increased when Imipramine is combined with Morphine.
MoxonidineThe therapeutic efficacy of Moxonidine can be decreased when used in combination with Imipramine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Imipramine.
NicorandilImipramine may increase the hypotensive activities of Nicorandil.
OlanzapineThe risk or severity of adverse effects can be increased when Imipramine is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Imipramine is combined with Ondansetron.
OrciprenalineThe risk or severity of adverse effects can be increased when Imipramine is combined with Orciprenaline.
OrphenadrineImipramine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PaliperidoneThe risk or severity of adverse effects can be increased when Imipramine is combined with Paliperidone.
PanobinostatThe serum concentration of Imipramine can be increased when it is combined with Panobinostat.
ParaldehydeImipramine 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 Imipramine.
Peginterferon alfa-2bThe serum concentration of Imipramine can be decreased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe metabolism of Imipramine can be increased when combined with Pentobarbital.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
PerphenazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Perphenazine.
PhenelzinePhenelzine may increase the serotonergic activities of Imipramine.
PhenytoinThe metabolism of Imipramine can be increased when combined with Phenytoin.
PimozideThe risk or severity of adverse effects can be increased when Imipramine is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Piperacetazine.
Potassium ChlorideImipramine may increase the ulcerogenic activities of Potassium Chloride.
PramipexoleImipramine may increase the sedative activities of Pramipexole.
PramlintidePramlintide may increase the anticholinergic activities of Imipramine.
PrimidoneThe metabolism of Imipramine can be increased when combined with Primidone.
ProchlorperazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Prochlorperazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Imipramine.
PromazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Promazine.
PropafenoneThe serum concentration of Imipramine can be increased when it is combined with Propafenone.
QuetiapineThe risk or severity of adverse effects can be increased when Imipramine is combined with Quetiapine.
QuinidineImipramine may increase the QTc-prolonging activities of Quinidine.
RamosetronImipramine may increase the activities of Ramosetron.
RemoxiprideThe risk or severity of adverse effects can be increased when Imipramine is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Imipramine is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Imipramine is combined with Risperidone.
RitonavirThe metabolism of Imipramine can be decreased when combined with Ritonavir.
RopiniroleImipramine may increase the sedative activities of Ropinirole.
RotigotineImipramine may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Imipramine.
SecobarbitalThe metabolism of Imipramine can be increased when combined with Secobarbital.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Imipramine.
SertindoleThe risk or severity of adverse effects can be increased when Imipramine is combined with Sertindole.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Imipramine.
SimeprevirThe serum concentration of Imipramine can be increased when it is combined with Simeprevir.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
St. John's WortThe metabolism of Imipramine can be increased when combined with St. John's Wort.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Imipramine.
SuvorexantImipramine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Imipramine 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 Imipramine resulting in a loss in efficacy.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Imipramine.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Imipramine.
TerbinafineThe metabolism of Imipramine can be decreased when combined with Terbinafine.
ThalidomideImipramine 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 Imipramine.
ThiothixeneThe risk or severity of adverse effects can be increased when Imipramine is combined with Thiothixene.
TiclopidineThe metabolism of Imipramine can be decreased when combined with Ticlopidine.
TiotropiumImipramine may increase the anticholinergic activities of Tiotropium.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Imipramine.
TopiramateThe risk or severity of adverse effects can be increased when Imipramine is combined with Topiramate.
TramadolImipramine may increase the neuroexcitatory activities of Tramadol.
TranylcypromineTranylcypromine may increase the serotonergic activities of Imipramine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Imipramine.
TrifluoperazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Imipramine is combined with Triflupromazine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Imipramine.
Valproic AcidThe serum concentration of Imipramine can be increased when it is combined with Valproic Acid.
YohimbineThe serum concentration of Yohimbine can be increased when it is combined with Imipramine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Imipramine is combined with Ziprasidone.
ZolpidemImipramine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Imipramine is combined with Zuclopenthixol.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (caffeine).
  • Avoid St.John's Wort.
  • Do not take fibers at the same time.
  • Take with food.

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. Mitchell HA, Ahern TH, Liles LC, Javors MA, Weinshenker D: The effects of norepinephrine transporter inactivation on locomotor activity in mice. Biol Psychiatry. 2006 Nov 15;60(10):1046-52. Epub 2006 Aug 7. [PubMed:16893531 ]
  2. Dziedzicka-Wasylewska M, Faron-Gorecka A, Kusmider M, Drozdowska E, Rogoz Z, Siwanowicz J, Caron MG, Bonisch H: Effect of antidepressant drugs in mice lacking the norepinephrine transporter. Neuropsychopharmacology. 2006 Nov;31(11):2424-32. Epub 2006 Mar 22. [PubMed:16554743 ]
  3. Anton M, Wagner B, Haubner R, Bodenstein C, Essien BE, Bonisch H, Schwaiger M, Gansbacher B, Weber WA: Use of the norepinephrine transporter as a reporter gene for non-invasive imaging of genetically modified cells. J Gene Med. 2004 Jan;6(1):119-26. [PubMed:14716684 ]
  4. Kantor L, Hewlett GH, Park YH, Richardson-Burns SM, Mellon MJ, Gnegy ME: Protein kinase C and intracellular calcium are required for amphetamine-mediated dopamine release via the norepinephrine transporter in undifferentiated PC12 cells. J Pharmacol Exp Ther. 2001 Jun;297(3):1016-24. [PubMed:11356924 ]
  5. Tatsumi M, Jansen K, Blakely RD, Richelson E: Pharmacological profile of neuroleptics at human monoamine transporters. Eur J Pharmacol. 1999 Mar 5;368(2-3):277-83. [PubMed:10193665 ]
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. Leboyer M, Quintin P, Manivet P, Varoquaux O, Allilaire JF, Launay JM: Decreased serotonin transporter binding in unaffected relatives of manic depressive patients. Biol Psychiatry. 1999 Dec 15;46(12):1703-6. [PubMed:10624553 ]
  2. Scholze P, Zwach J, Kattinger A, Pifl C, Singer EA, Sitte HH: Transporter-mediated release: a superfusion study on human embryonic kidney cells stably expressing the human serotonin transporter. J Pharmacol Exp Ther. 2000 Jun;293(3):870-8. [PubMed:10869387 ]
  3. Quintin P, Benkelfat C, Launay JM, Arnulf I, Pointereau-Bellenger A, Barbault S, Alvarez JC, Varoquaux O, Perez-Diaz F, Jouvent R, Leboyer M: Clinical and neurochemical effect of acute tryptophan depletion in unaffected relatives of patients with bipolar affective disorder. Biol Psychiatry. 2001 Aug 1;50(3):184-90. [PubMed:11513817 ]
  4. Goulet M, Miller GM, Bendor J, Liu S, Meltzer PC, Madras BK: Non-amines, drugs without an amine nitrogen, potently block serotonin transport: novel antidepressant candidates? Synapse. 2001 Dec 1;42(3):129-40. [PubMed:11746710 ]
  5. Barkan T, Gurwitz D, Levy G, Weizman A, Rehavi M: Biochemical and pharmacological characterization of the serotonin transporter in human peripheral blood lymphocytes. Eur Neuropsychopharmacol. 2004 May;14(3):237-43. [PubMed:15056483 ]
  6. Schloss P, Betz H: Heterogeneity of antidepressant binding sites on the recombinant rat serotonin transporter SERT1. Biochemistry. 1995 Oct 3;34(39):12590-5. [PubMed:7548008 ]
  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
unknown
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 ]
  2. Zanoveli JM, Nogueira RL, Zangrossi H Jr: Chronic imipramine treatment sensitizes 5-HT1A and 5-HT 2 A receptors in the dorsal periaqueductal gray matter: evidence from the elevated T-maze test of anxiety. Behav Pharmacol. 2005 Nov;16(7):543-52. [PubMed:16170231 ]
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. 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:
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.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 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. Nojimoto FD, Mueller A, Hebeler-Barbosa F, Akinaga J, Lima V, Kiguti LR, Pupo AS: The tricyclic antidepressants amitriptyline, nortriptyline and imipramine are weak antagonists of human and rat alpha1B-adrenoceptors. Neuropharmacology. 2010 Jul-Aug;59(1-2):49-57. doi: 10.1016/j.neuropharm.2010.03.015. Epub 2010 Apr 2. [PubMed:20363235 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
antagonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Nojimoto FD, Mueller A, Hebeler-Barbosa F, Akinaga J, Lima V, Kiguti LR, Pupo AS: The tricyclic antidepressants amitriptyline, nortriptyline and imipramine are weak antagonists of human and rat alpha1B-adrenoceptors. Neuropharmacology. 2010 Jul-Aug;59(1-2):49-57. doi: 10.1016/j.neuropharm.2010.03.015. Epub 2010 Apr 2. [PubMed:20363235 ]
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 ]
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 ]
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
no
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity
Specific Function:
Voltage-gated potassium channel that mediates transmembrane potassium transport in excitable membranes, primarily in the brain. Mediates the major part of the dendritic A-type current I(SA) in brain neurons (By similarity). This current is activated at membrane potentials that are below the threshold for action potentials. It regulates neuronal excitability, prolongs the latency before the firs...
Gene Name:
KCND2
Uniprot ID:
Q9NZV8
Molecular Weight:
70535.825 Da
References
  1. Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated by interactions with other alpha subunits and with regulatory subunits.
Gene Name:
KCND3
Uniprot ID:
Q9UK17
Molecular Weight:
73450.53 Da
References
  1. Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonistbinder
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 ]
  2. Roth BL: Multiple serotonin receptors: clinical and experimental aspects. Ann Clin Psychiatry. 1994 Jun;6(2):67-78. [PubMed:7804391 ]
Kind
Protein
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Nojimoto FD, Mueller A, Hebeler-Barbosa F, Akinaga J, Lima V, Kiguti LR, Pupo AS: The tricyclic antidepressants amitriptyline, nortriptyline and imipramine are weak antagonists of human and rat alpha1B-adrenoceptors. Neuropharmacology. 2010 Jul-Aug;59(1-2):49-57. doi: 10.1016/j.neuropharm.2010.03.015. Epub 2010 Apr 2. [PubMed:20363235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Serotonin receptor 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. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase.
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular Weight:
53554.43 Da
References
  1. Lucchelli A, Santagostino-Barbone MG, D'Agostino G, Masoero E, Tonini M: The interaction of antidepressant drugs with enteric 5-HT7 receptors. Naunyn Schmiedebergs Arch Pharmacol. 2000 Sep;362(3):284-9. [PubMed:10997731 ]
  2. Roth BL: Multiple serotonin receptors: clinical and experimental aspects. Ann Clin Psychiatry. 1994 Jun;6(2):67-78. [PubMed:7804391 ]
Kind
Protein group
Organism
Human
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:
NameUniProt IDDetails
D(1A) dopamine receptorP21728 Details
D(1B) dopamine receptorP21918 Details
References
  1. Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, Schwartz RW, Haggart D, O'Brien A, White A, Kennedy JM, Craymer K, Farrington L, Auh JS: Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res Monogr. 1998 Mar;178:440-66. [PubMed:9686407 ]
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. Peddi S, Roth BL, Glennon RA, Westkaemper RB: Structural determinants for high 5-HT(2A) receptor affinity of spiro[9,10-dihydroanthracene]-9,3(')-pyrrolidine (SpAMDA). Bioorg Med Chem Lett. 2004 May 3;14(9):2279-83. [PubMed:15081025 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Teschemacher AG, Seward EP, Hancox JC, Witchel HJ: Inhibition of the current of heterologously expressed HERG potassium channels by imipramine and amitriptyline. Br J Pharmacol. 1999 Sep;128(2):479-85. [PubMed:10510461 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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
Molecular Weight:
68494.255 Da
References
  1. Melikian HE, Buckley KM: Membrane trafficking regulates the activity of the human dopamine transporter. J Neurosci. 1999 Sep 15;19(18):7699-710. [PubMed:10479674 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
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. Haddjeri N, Blier P, de Montigny C: Long-term antidepressant treatments result in a tonic activation of forebrain 5-HT1A receptors. J Neurosci. 1998 Dec 1;18(23):10150-6. [PubMed:9822768 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Serotonin receptor 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. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs (By similarity). Controls pyramidal neurons migration during corticogenesis, through...
Gene Name:
HTR6
Uniprot ID:
P50406
Molecular Weight:
46953.625 Da
References
  1. Grimaldi B, Bonnin A, Fillion MP, Ruat M, Traiffort E, Fillion G: Characterization of 5-ht6 receptor and expression of 5-ht6 mRNA in the rat brain during ontogenetic development. Naunyn Schmiedebergs Arch Pharmacol. 1998 Apr;357(4):393-400. [PubMed:9606024 ]
  2. Roth BL: Multiple serotonin receptors: clinical and experimental aspects. Ann Clin Psychiatry. 1994 Jun;6(2):67-78. [PubMed:7804391 ]

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. 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 ]
  2. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
  3. 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. Shin JG, Park JY, Kim MJ, Shon JH, Yoon YR, Cha IJ, Lee SS, Oh SW, Kim SW, Flockhart DA: Inhibitory effects of tricyclic antidepressants (TCAs) on human cytochrome P450 enzymes in vitro: mechanism of drug interaction between TCAs and phenytoin. Drug Metab Dispos. 2002 Oct;30(10):1102-7. [PubMed:12228186 ]
  2. Morinobu S, Tanaka T, Kawakatsu S, Totsuka S, Koyama E, Chiba K, Ishizaki T, Kubota T: Effects of genetic defects in the CYP2C19 gene on the N-demethylation of imipramine, and clinical outcome of imipramine therapy. Psychiatry Clin Neurosci. 1997 Aug;51(4):253-7. [PubMed:9316174 ]
  3. Madsen H, Rasmussen BB, Brosen K: Imipramine demethylation in vivo: impact of CYP1A2, CYP2C19, and CYP3A4. Clin Pharmacol Ther. 1997 Mar;61(3):319-24. [PubMed:9084457 ]
  4. 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 ]
  5. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
  6. Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [PubMed:8846619 ]
  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. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 ]
  2. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 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. 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
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
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:
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. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 ]
  3. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]
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. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  2. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
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 ]
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 January 12, 2016 15:51