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Identification
NamePropranolol
Accession NumberDB00571  (APRD00194)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A widely used non-cardioselective beta-adrenergic antagonist. Propranolol is used in the treatment or prevention of many disorders including acute myocardial infarction, arrhythmias, angina pectoris, hypertension, hypertensive emergencies, hyperthyroidism, migraine, pheochromocytoma, menopause, and anxiety. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanolNot AvailableNot Available
1-(isopropylamino)-3-(1-naphthyloxy)propan-2-olNot AvailableNot Available
beta-PropranololNot AvailableNot Available
PropanalolNot AvailableNot Available
PropanololNot AvailableNot Available
PropranololNot AvailableNot Available
PropranololoNot AvailableNot Available
PropranololumNot AvailableNot Available
β-PropranololNot AvailableNot Available
Salts
Name/CAS Structure Properties
Propranolol Hydrochloride
318-98-9
Thumb
  • InChI Key: ZMRUPTIKESYGQW-UHFFFAOYNA-N
  • Monoisotopic Mass: 295.13390666
  • Average Mass: 295.804
DBSALT000549
Brand names
NameCompany
AngilolNot Available
Bedranol SRNot Available
CardinolNot Available
CiplarNot Available
DeralinNot Available
DocitonNot Available
DuranolNot Available
HEMANGEOLNot Available
InderalNot Available
Inderal LANot Available
IndoblocNot Available
INNOPRANNot Available
Innopran XLNot Available
ProphyluxNot Available
SumialNot Available
Brand mixtures
Brand NameIngredients
Inderidepropranolol hydrochloride + hydrochlorothiazide
Categories
CAS number525-66-6
WeightAverage: 259.3434
Monoisotopic: 259.157228921
Chemical FormulaC16H21NO2
InChI KeyAQHHHDLHHXJYJD-UHFFFAOYSA-N
InChI
InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3
IUPAC Name
[2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine
SMILES
CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassAcenes and Derivatives
SubclassNaphthalenes
Direct parentNaphthalenes
Alternative parentsPhenol Ethers; Alkyl Aryl Ethers; Secondary Alcohols; 1,2-Aminoalcohols; Polyamines; Dialkylamines
Substituentsphenol ether; alkyl aryl ether; benzene; 1,2-aminoalcohol; secondary alcohol; secondary aliphatic amine; secondary amine; ether; polyamine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Pharmacology
IndicationFor the prophylaxis of migraine.
PharmacodynamicsPropranolol, the prototype of the beta-adrenergic receptor antagonists, is a competitive, nonselective beta-blocker similar to nadolol without intrinsic sympathomimetic activity. Propanolol is a racemic compound; the l-isomer is responsible for adrenergic blocking activity.
Mechanism of actionPropranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.
AbsorptionPropranolol is almost completely absorbed from the GI tract; however, plasma concentrations attained are quite variable among individuals.
Volume of distribution
  • 4 L
Protein bindingMore than 90%
Metabolism

Hepatic

SubstrateEnzymesProduct
Propranolol
N-desisopropylpropranololDetails
Propranolol
4'-hydroxypropanololDetails
Route of eliminationPropranolol is extensively metabolized with most metabolites appearing in the urine.
Half life4 hours
ClearanceNot Available
ToxicitySymptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm. LD50=565 mg/kg (orally in mice).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9944
Blood Brain Barrier - 0.9031
Caco-2 permeable + 0.6942
P-glycoprotein substrate Substrate 0.7079
P-glycoprotein inhibitor I Inhibitor 0.5588
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Non-inhibitor 0.8177
CYP450 2C9 substrate Non-substrate 0.7898
CYP450 2D6 substrate Substrate 0.8918
CYP450 3A4 substrate Non-substrate 0.6463
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.924
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8487
Ames test Non AMES toxic 0.9392
Carcinogenicity Non-carcinogens 0.9097
Biodegradation Not ready biodegradable 0.9871
Rat acute toxicity 2.5625 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9185
hERG inhibition (predictor II) Inhibitor 0.7092
Pharmacoeconomics
Manufacturers
  • Akrimax pharmaceuticals llc
  • Glaxosmithkline llc
  • Actavis elizabeth llc
  • Inwood laboratories inc sub forest laboratories inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical
  • Upsher smith laboratories inc
  • Roxane laboratories inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hikma farmaceutica (portugal) sa
  • Sandoz canada inc
  • Smith and nephew solopak div smith and nephew
  • Solopak medical products inc
  • Morton grove pharmaceuticals inc
  • Wyeth ayerst laboratories
  • Clonmel healthcare ltd
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Interpharm inc
  • Ipca laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lederle laboratories div american cyanamid co
  • Mutual pharmaceutical co inc
  • Northstar healthcare holdings ltd
  • Par pharmaceutical inc
  • Pliva inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Schering corp sub schering plough corp
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals
  • Warner chilcott div warner lambert co
  • Warner chilcott inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseOral
SolutionIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Propranolol hcl powder11.63USDg
Propranolol 1 mg/ml vial10.0USDml
Inderal la 160 mg capsule8.41USDcapsule
Inderal LA 160 mg 24 Hour Capsule7.6USDcapsule
Inderal la 160 mg capsule sa7.01USDcapsule
Inderal la 120 mg capsule6.42USDcapsule
Inderal LA 120 mg 24 Hour Capsule5.8USDcapsule
Inderal la 120 mg capsule sa5.36USDcapsule
Inderal la 80 mg capsule5.18USDcapsule
Inderal LA 60 mg 24 Hour Capsule4.79USDcapsule
Inderal LA 80 mg 24 Hour Capsule4.68USDcapsule
Inderal la 60 mg capsule4.43USDcapsule
Inderal la 80 mg capsule sa4.32USDcapsule
Inderal la 60 mg capsule sa3.7USDcapsule
Propranolol HCl CR 160 mg 24 Hour Capsule2.62USDcapsule
InnoPran XL 80 mg 24 Hour Capsule2.5USDcapsule
InnoPran XL 120 mg 24 Hour Capsule2.46USDcapsule
Innopran xl 120 mg capsule2.41USDcapsule
Innopran xl 80 mg capsule2.41USDcapsule
Inderide 80-25 mg tablet2.17USDtablet
Propranolol HCl CR 120 mg 24 Hour Capsule2.0USDcapsule
Inderide 40-25 mg tablet1.74USDtablet
Propranolol HCl CR 80 mg 24 Hour Capsule1.61USDcapsule
Propranolol HCl CR 60 mg 24 Hour Capsule1.38USDcapsule
Propranolol HCl 60 mg tablet1.27USDtablet
Inderal-La 160 mg Sustained-Release Capsule1.26USDcapsule
Inderal-La 120 mg Sustained-Release Capsule1.07USDcapsule
Inderal-La 80 mg Sustained-Release Capsule0.69USDcapsule
Propranolol HCl 80 mg tablet0.66USDtablet
Propranolol-HCTZ 80-25 mg tablet0.65USDtablet
Inderal-La 60 mg Sustained-Release Capsule0.62USDcapsule
Propranolol-HCTZ 40-25 mg tablet0.61USDtablet
Propranolol 80 mg tablet0.58USDtablet
Propranolol 60 mg tablet0.56USDtablet
Propranolol HCl 40 mg tablet0.53USDtablet
Propranolol 40 mg tablet0.45USDtablet
Propranolol HCl 20 mg tablet0.36USDtablet
Propranolol 20 mg tablet0.33USDtablet
Apo-Propranolol 120 mg Tablet0.32USDtablet
Propranolol HCl 10 mg tablet0.29USDtablet
Propranolol 10 mg tablet0.22USDtablet
Propranolol HCl 20 mg/5ml Solution0.11USDml
Apo-Propranolol 80 mg Tablet0.06USDtablet
Novo-Pranol 80 mg Tablet0.06USDtablet
Pms-Propranolol 80 mg Tablet0.06USDtablet
Apo-Propranolol 20 mg Tablet0.04USDtablet
Apo-Propranolol 40 mg Tablet0.04USDtablet
Novo-Pranol 20 mg Tablet0.04USDtablet
Novo-Pranol 40 mg Tablet0.04USDtablet
Apo-Propranolol 10 mg Tablet0.02USDtablet
Novo-Pranol 10 mg Tablet0.02USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States65004542002-12-312022-12-31
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point96 °CPhysProp
water solubility61.7 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP3.48AVDEEF,A (1997)
Caco2 permeability-4.58ADME Research, USCD
pKa9.42SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0794ALOGPS
logP3.03ALOGPS
logP2.58ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.83 m3·mol-1ChemAxon
Polarizability29.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

DrugSyn.org

US3520919
General Reference
  1. Brunet A, Orr SP, Tremblay J, Robertson K, Nader K, Pitman RK: Effect of post-retrieval propranolol on psychophysiologic responding during subsequent script-driven traumatic imagery in post-traumatic stress disorder. J Psychiatr Res. 2007 Jun 21;. Pubmed
  2. Ohnishi ST, Sadanaga KK, Katsuoka M, Weidanz WP: Effects of membrane acting-drugs on plasmodium species and sickle cell erythrocytes. Mol Cell Biochem. 1989 Nov 23-Dec 19;91(1-2):159-65. Pubmed
  3. Singh N, Puri SK: Interaction between chloroquine and diverse pharmacological agents in chloroquine resistant Plasmodium yoelii nigeriensis. Acta Trop. 2000 Nov 2;77(2):185-93. Pubmed
  4. Murphy SC, Harrison T, Hamm HE, Lomasney JW, Mohandas N, Haldar K: Erythrocyte G protein as a novel target for malarial chemotherapy. PLoS Med. 2006 Dec;3(12):e528. Pubmed
External Links
ResourceLink
KEGG CompoundC07407
PubChem Compound4946
PubChem Substance46505387
ChemSpider4777
BindingDB25761
ChEBI8499
ChEMBLCHEMBL27
Therapeutic Targets DatabaseDAP000089
PharmGKBPA451145
IUPHAR564
Guide to Pharmacology564
Drug Product Database663719
RxListhttp://www.rxlist.com/cgi/generic/propran.htm
Drugs.comhttp://www.drugs.com/propranolol.html
WikipediaPropranolol
ATC CodesC07AA05
AHFS Codes
  • 24:24.00
PDB EntriesNot Available
FDA labelshow(256 KB)
MSDSshow(74.7 KB)
Interactions
Drug Interactions
Drug
AcetohexamideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
AminophyllineAntagonism of action and increased effect of theophylline
BromazepamCo-administration with propranolol will cause a reduction in bromazepam clearance and increases half-life.
ChlorpromazineIncreased effect of both drugs
ChlorpropamideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
CimetidineCimetidine may increase the serum concentration of propranolol by decreasing its metabolism.
CitalopramThe SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
ClonidineIncreased hypertension when clonidine stopped
DihydroergotamineIschemia with risk of gangrene
DiltiazemIncreased risk of bradycardia
DisopyramideThe beta-blocker, propranolol, may increase the toxicity of disopyramide.
DronedaronePropranolol is a CYP2D6 substrate and because dronedarone inhibits this enzyme, will increase propranolol exposure 1.3-fold. Lower dose of metoprolol.
DyphyllineAntagonism of action and increased effect of theophylline
EpinephrineHypertension, then bradycardia
ErgonovineIschemia with risk of gangrene
ErgotamineIschemia with risk of gangrene
EscitalopramThe SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
FenoterolAntagonism
FluoxetineThe SSRI, fluoxetine, may increase the bradycardic effect of the beta-blocker, propranolol.
FormoterolAntagonism
GliclazideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
GlipizideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
GlisoxepideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
GlyburideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
GlycodiazineThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
HaloperidolIncreased effect of both drugs
HydralazineIncreased effect of both drugs
IbuprofenRisk of inhibition of renal prostaglandins
IndacaterolBeta-adrenergic antagonists, especially those that are not cardioselective, may interfere with the effect of indacaterol when administered concurrently. Beta-blockers may exacerbate bronchospasms in patients with COPD.
IndomethacinRisk of inhibition of renal prostaglandins
Insulin GlargineThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
IsoprenalineAntagonism
LidocaineThe beta-blocker, propranolol, may increase the effect and toxicity of lidocaine.
MaprotilinePropranolol increases the serum levels of cisapride
MesoridazineIncreased risk of cardiotoxicity and arrhythmias
MethyldopaPossible hypertensive crisis
MethysergideIschemia with risk of gangrene
OrciprenalineAntagonism
OxtriphyllineAntagonism of action and increased effect of theophylline
ParoxetineThe SSRI, paroxetine, may increase the bradycardic effect of the beta-blocker, propranolol.
PhenobarbitalThe barbiturate decreases the effect of the metabolized beta-blocker
PipobromanAntagonism
PirbuterolAntagonism
PiroxicamRisk of inhibition of renal prostaglandins
PrazosinRisk of hypotension at the beginning of therapy
PrimidoneThe barbiturate decreases the effect of metabolized beta-blocker
ProcaterolAntagonism
PropafenonePropafenone may increase the effect of the beta-blocker, propranolol.
RepaglinideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
RifampicinRifampin may decrease the serum concentration of propranolol by increasing its metabolism.
RizatriptanPropranolol increases the effect and toxicity of rizatriptan
SalbutamolAntagonism
SalmeterolAntagonism
SertralineThe SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
TerazosinIncreased risk of hypotension. Initiate concomitant therapy cautiously.
TerbinafineTerbinafine may reduce the metabolism and clearance of Propranolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Propranolol if Terbinafine is initiated, discontinued or dose changed.
TerbutalineAntagonism
TheophyllineAntagonism of action and increased effect of theophylline
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
TolazamideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
TolbutamideThe beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
TopotecanThe p-glycoprotein inhibitor, Propranolol, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
VerapamilIncreased effect of both drugs
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take with food.

Targets

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Lewis CJ, Gong H, Brown MJ, Harding SE: Overexpression of beta 1-adrenoceptors in adult rat ventricular myocytes enhances CGP 12177A cardiostimulation: implications for ‘putative’ beta 4-adrenoceptor pharmacology. Br J Pharmacol. 2004 Mar;141(5):813-24. Epub 2004 Feb 2. Pubmed
  3. Rouget C, Barthez O, Goirand F, Leroy MJ, Breuiller-Fouche M, Rakotoniaina Z, Guerard P, Morcillo EJ, Advenier C, Sagot P, Cabrol D, Dumas M, Bardou M: Stimulation of the ADRB3 adrenergic receptor induces relaxation of human placental arteries: influence of preeclampsia. Biol Reprod. 2006 Jan;74(1):209-16. Epub 2005 Sep 21. Pubmed
  4. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. Pubmed
  5. Rezmann-Vitti LA, Louis SN, Nero TL, Jackman GP, Machida CA, Louis WJ: Site-directed mutagenesis of the rat beta1-adrenoceptor. Involvement of Tyr356 (7.43) in (/-)cyanopindolol but not (/-)[125Iodo]cyanopindolol binding. Eur J Med Chem. 2004 Jul;39(7):625-31. Pubmed
  6. Yazawa K, Wang JW, Hao LY, Onoue Y, Kameyama M: Verrucotoxin, a stonefish venom, modulates calcium channel activity in guinea-pig ventricular myocytes. Br J Pharmacol. 2007 Aug;151(8):1198-203. Epub 2007 Jun 18. Pubmed

2. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

References:

  1. Isaza C, Henao J, Ramirez E, Cuesta F, Cacabelos R: Polymorphic variants of the beta2-adrenergic receptor (ADRB2) gene and ADRB2-related propanolol-induced dyslipidemia in the Colombian population. Methods Find Exp Clin Pharmacol. 2005 May;27(4):237-44. Pubmed
  2. Rouget C, Barthez O, Goirand F, Leroy MJ, Breuiller-Fouche M, Rakotoniaina Z, Guerard P, Morcillo EJ, Advenier C, Sagot P, Cabrol D, Dumas M, Bardou M: Stimulation of the ADRB3 adrenergic receptor induces relaxation of human placental arteries: influence of preeclampsia. Biol Reprod. 2006 Jan;74(1):209-16. Epub 2005 Sep 21. Pubmed
  3. Illingworth CJ, Gooding SR, Winn PJ, Jones GA, Ferenczy GG, Reynolds CA: Classical polarization in hybrid QM/MM methods. J Phys Chem A. 2006 May 25;110(20):6487-97. Pubmed
  4. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Beta-3 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Berg T, Piercey BW, Jensen J: Role of beta1-3-adrenoceptors in blood pressure control at rest and during tyramine-induced norepinephrine release in spontaneously hypertensive rats. Hypertension. 2010 May;55(5):1224-30. Epub 2010 Mar 15. Pubmed

4. 5-hydroxytryptamine receptor 1A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

References:

  1. Smejkal-Jagar L, Boranic M: Serotonin and serotoninergic agents affect proliferation of normal and transformed lymphoid cells. Immunopharmacol Immunotoxicol. 1995 Feb;17(1):151-62. Pubmed

5. 5-hydroxytryptamine receptor 1B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1B P28222 Details

References:

  1. Bailey SR, Elliott J: Evidence for different 5-HT1B/1D receptors mediating vasoconstriction of equine digital arteries and veins. Eur J Pharmacol. 1998 Aug 21;355(2-3):175-87. Pubmed
  2. Choppin A, O’Connor SE: Presence of vasoconstrictor 5HT1-like receptors revealed by precontraction of rabbit isolated mesenteric artery. Br J Pharmacol. 1995 Jan;114(2):309-14. Pubmed

Enzymes

1. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T: Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers—N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995 Apr;39(4):421-31. Pubmed
  2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  3. 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. Epub 2009 Nov 24. Pubmed
  4. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. Pubmed

3. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T: Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers—N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995 Apr;39(4):421-31. Pubmed
  2. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. Pubmed
  3. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. Pubmed
  4. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  5. 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. Epub 2009 Nov 24. Pubmed
  6. Carrillo JA, Benitez J: Clinically significant pharmacokinetic interactions between dietary caffeine and medications. Clin Pharmacokinet. 2000 Aug;39(2):127-53. Pubmed
  7. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S: Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15. Pubmed

5. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  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. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

Carriers

1. Alpha-1-acid glycoprotein 1

Kind: protein

Organism: Human

Pharmacological action: no

Components

Name UniProt ID Details
Alpha-1-acid glycoprotein 1 P02763 Details

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

Transporters

1. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

References:

  1. Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. Pubmed

2. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. 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
  2. D’Emanuele A, Jevprasesphant R, Penny J, Attwood D: The use of a dendrimer-propranolol prodrug to bypass efflux transporters and enhance oral bioavailability. J Control Release. 2004 Mar 24;95(3):447-53. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:25