Protriptyline

Identification

Summary

Protriptyline is a tricyclic antidepressant that is indicated in the treatment of depression only under close clinical supervision.

Generic Name
Protriptyline
DrugBank Accession Number
DB00344
Background

Protriptyline hydrochloride is a dibenzocycloheptene-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, protriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, protriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs 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, alpha1-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. Protriptyline may be used for the treatment of depression.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 263.3767
Monoisotopic: 263.167399677
Chemical Formula
C19H21N
Synonyms
  • 3-(5H-dibenzo[a,d][7]annulen-5-yl)-N-methylpropan-1-amine
  • 3-(5H-dibenzo[a,d]cyclohepten-5-yl)-N-methyl-1-propanamine
  • 5-(3-methylaminopropyl)-5H-dibenzo[a,d]cycloheptene
  • 7-(3-methylaminopropyl)-1,2:5,6-dibenzocycloheptatriene
  • Amimetilina
  • N-methyl-5H-dibenzo[a,d]cycloheptene-5-propanamine
  • N-methyl-5H-dibenzo[a,d]cycloheptene-5-propylamine
  • Protriptilina
  • Protriptylin
  • Protriptyline
  • Protriptylinum
External IDs
  • MK 240
  • MK-240

Pharmacology

Indication

For the treatment of depression.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDepression••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Protriptyline is a tricyclic antidepressant. It was thought that tricyclic antidepressants work by inhibiting the reuptake of the neurotransmitters norepinephrine and serotonin by nerve cells. The effectiveness of antidepressants appear after approximately two weeks following recommended adminsitration schedule. Gradual changes are thought to occur in the cerebral cortex and hippocampus, involved in emotion regulation as part of the limbic system, as receptor sensitivity is enhanced. While α1 and β1 receptors are sensitized, α2 receptors are desensitized (leading to increased noradrenaline production). Tricyclics are also reported to alter the perceptions of pain, including neuropathic or neuralgic pain, so they may exhibit analgesic properties. The mechanism of action behind this analgesic property is not fully understood; however, it is thought to involve modulation of endogenous opioid systems in the CNS via an indirect serotonergic route. Tricyclic antidepressants are also effective in relieving migraine prophylaxis, but not in abortion of acute migraine attack, potentially via their serotonergic effects.

Mechanism of action

Protriptyline acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inhibitor
Humans
ASodium-dependent serotonin transporter
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Protriptyline is reported to undergo cumulative urinary excretion during 16 days, which accounts for approximately 50% of the total drug administered. The fecal excretion pathway seems to play a minimal role in drug elimination.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Side effects include anxiety, blood disorders, confusion, decreased libido, dizziness, flushing, headache, impotence, insomnia, low blood pressure, nightmares, rapid or irregular heartbeat, rash, seizures, sensitivity to sunlight, stomach and intestinal discomfort, sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableC alleleEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Protriptyline is combined with 1,2-Benzodiazepine.
AcarboseProtriptyline may decrease the hypoglycemic activities of Acarbose.
AcebutololProtriptyline may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Protriptyline is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Protriptyline is combined with Acemetacin.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Protriptyline hydrochloride44665V00O81225-55-4OGQDIIKRQRZXJH-UHFFFAOYSA-N
Product Images
International/Other Brands
Triptil
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Triptil Tab 10mgTablet10 mg / tabOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1966-12-312001-01-25Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Protriptyline hydrochlorideTablet, film coated5 mg/1OralHi-Tech Pharmacal Co., Inc.2013-10-28Not applicableUS flag
Protriptyline HydrochlorideTablet10 mg/1Oralbryant ranch prepack2008-09-16Not applicableUS flag
Protriptyline HydrochlorideTablet, film coated10 mg/1OralBarr Laboratories2008-12-232013-06-30US flag
Protriptyline HydrochlorideTablet, film coated10 mg/1OralSigmapharm Laboratories, LLC2020-03-02Not applicableUS flag
Protriptyline HydrochlorideTablet, film coated5 mg/1OralRising Pharmaceuticals, Inc2010-06-11Not applicableUS flag

Categories

ATC Codes
N06AA11 — Protriptyline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Dibenzocycloheptenes
Sub Class
Not Available
Direct Parent
Dibenzocycloheptenes
Alternative Parents
Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homopolycyclic compound / Dibenzocycloheptene / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Secondary aliphatic amine / Secondary amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
organic tricyclic compound (CHEBI:8597)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4NDU154T12
CAS number
438-60-8
InChI Key
BWPIARFWQZKAIA-UHFFFAOYSA-N
InChI
InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-10,12-13,19-20H,6,11,14H2,1H3
IUPAC Name
methyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-yl}propyl)amine
SMILES
CNCCCC1C2=CC=CC=C2C=CC2=CC=CC=C12

References

General References
Not Available
Human Metabolome Database
HMDB0014488
KEGG Drug
D08447
KEGG Compound
C07408
PubChem Compound
4976
PubChem Substance
46505128
ChemSpider
4805
BindingDB
50176062
RxNav
8886
ChEBI
8597
ChEMBL
CHEMBL668
ZINC
ZINC000001530764
Therapeutic Targets Database
DAP000863
PharmGKB
PA451168
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Protriptyline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentDepression1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Pfizer laboratories div pfizer inc
  • Roxane laboratories inc
  • Sigmapharm laboratories llc
  • Odyssey pharmaceuticals inc
Packagers
  • Barr Pharmaceuticals
  • Duramed
  • Mallinckrodt Inc.
  • Pliva Inc.
  • Qualitest
  • Rising Pharmaceuticals
  • Roxane Labs
  • Sanofi-Aventis Inc.
Dosage Forms
FormRouteStrength
TabletOral10 mg/1
TabletOral5 mg/1
TabletOral10 mg / tab
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 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
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
Anafranil 25 mg capsule13.51USD capsule
Anafranil 50 mg capsule13.51USD capsule
Anafranil 75 mg capsule13.24USD capsule
Tofranil 50 mg tablet6.64USD tablet
Norpramin 150 mg tablet6.23USD tablet
Surmontil 100 mg capsule5.92USD capsule
Tofranil 25 mg tablet4.97USD tablet
Tofranil 10 mg tablet4.73USD tablet
Norpramin 100 mg tablet4.27USD tablet
Surmontil 50 mg capsule4.15USD capsule
Vivactil 10 mg tablet4.05USD tablet
Norpramin 75 mg tablet3.27USD tablet
Protriptyline hcl 10 mg tablet3.07USD tablet
Vivactil 5 mg tablet2.86USD tablet
Norpramin 50 mg tablet2.59USD tablet
Surmontil 25 mg capsule2.49USD capsule
Protriptyline hcl 5 mg tablet2.12USD tablet
Norpramin 25 mg tablet1.4USD tablet
Norpramin 10 mg tablet1.16USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)169-171 °C (Protriptyline HCl)Not Available
water solubility1.04 mg/LNot Available
logP4.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000231 mg/mLALOGPS
logP4.65ALOGPS
logP4.5Chemaxon
logS-6.1ALOGPS
pKa (Strongest Basic)10.54Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area12.03 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity87.3 m3·mol-1Chemaxon
Polarizability31.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9862
Caco-2 permeable+0.7821
P-glycoprotein substrateSubstrate0.7406
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.5597
Renal organic cation transporterInhibitor0.6622
CYP450 2C9 substrateNon-substrate0.7206
CYP450 2D6 substrateSubstrate0.9034
CYP450 3A4 substrateSubstrate0.5285
CYP450 1A2 substrateNon-inhibitor0.7595
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.641
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7512
Ames testNon AMES toxic0.6
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.7732
Rat acute toxicity3.0087 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.736
hERG inhibition (predictor II)Inhibitor0.8132
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9040000000-6498574fa1f4eead1816
Mass Spectrum (Electron Ionization)MSsplash10-006x-8910000000-ec599ee02d998905757e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0090000000-318361a180d9ffd4202a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-4dbc79d75d4f434716de
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-04a235c7acf72488ebad
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-1090000000-1a96cdfe59b3bbf1d166
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfu-0490000000-d3a0815d2f9adaf3ad96
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06r5-0940000000-99cc73279511930e358e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.7080806
predicted
DarkChem Lite v0.1.0
[M-H]-175.6112806
predicted
DarkChem Lite v0.1.0
[M-H]-160.15425
predicted
DeepCCS 1.0 (2019)
[M+H]+174.4481806
predicted
DarkChem Lite v0.1.0
[M+H]+176.8254806
predicted
DarkChem Lite v0.1.0
[M+H]+162.51225
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.5791806
predicted
DarkChem Lite v0.1.0
[M+Na]+176.0537806
predicted
DarkChem Lite v0.1.0
[M+Na]+168.60541
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
  4. Cheetham SC, Viggers JA, Butler SA, Prow MR, Heal DJ: [3H]nisoxetine--a radioligand for noradrenaline reuptake sites: correlation with inhibition of [3H]noradrenaline uptake and effect of DSP-4 lesioning and antidepressant treatments. Neuropharmacology. 1996 Jan;35(1):63-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. McDougle CJ, Epperson CN, Price LH, Gelernter J: Evidence for linkage disequilibrium between serotonin transporter protein gene (SLC6A4) and obsessive compulsive disorder. Mol Psychiatry. 1998 May;3(3):270-3. [Article]
  2. Rouillon F, Blachier C, Dreyfus JP, Bouhassira M, Allicar MP: [Pharmaco-epidemiologic study of the use of antidepressant drugs in the general population]. Encephale. 1996 May;22 Spec No 1:39-48. [Article]
  3. Frazer A, Daws LC: Serotonin transporter function in vivo: assessment by chronoamperometry. Ann N Y Acad Sci. 1998 Dec 15;861:217-29. [Article]
  4. Daws LC, Toney GM, Gerhardt GA, Frazer A: In vivo chronoamperometric measures of extracellular serotonin clearance in rat dorsal hippocampus: contribution of serotonin and norepinephrine transporters. J Pharmacol Exp Ther. 1998 Aug;286(2):967-76. [Article]
  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. [Article]
  6. Kovachich GB, Aronson CE, Brunswick DJ: Effect of repeated administration of antidepressants on serotonin uptake sites in limbic and neocortical structures of rat brain determined by quantitative autoradiography. Neuropsychopharmacology. 1992 Dec;7(4):317-24. [Article]

Transporters

Kind
Protein
Organism
Humans
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
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:24