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Identification
NameEphedrine
Accession NumberDB01364
Typesmall molecule
Groupsapproved
Description

An alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number299-42-3
WeightAverage: 165.2322
Monoisotopic: 165.115364107
Chemical FormulaC10H15NO
InChI KeyInChIKey=KWGRBVOPPLSCSI-WPRPVWTQSA-N
InChI
InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
IUPAC Name
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
SMILES
CN[C@@H](C)[C@H](O)C1=CC=CC=C1
Mass Specshow(7.84 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsSecondary Alcohols; 1,2-Aminoalcohols; Dialkylamines; Polyamines
Substituents1,2-aminoalcohol; secondary alcohol; secondary amine; secondary aliphatic amine; polyamine; alcohol; amine; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationEphedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.
PharmacodynamicsEphedrine is similar in structure to the derivatives amphetamine and methamphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors.
Mechanism of actionEphedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its direct and indirect actions on the adrenergic receptor system, which is part of the sympathetic nervous system. Ephedrine increases post-synaptic noradrenergic receptor activity by (weakly) directly activating post-synaptic α-receptors and β-receptors, but the bulk of its effect comes from the pre-synaptic neuron being unable to distinguish between real adrenaline or noradrenaline from ephedrine. The ephedrine, mixed with noradrenaline, is transported through the noradrenaline reuptake complex and packaged (along with real noradrenaline) into vesicles that reside at the terminal button of a nerve cell. Ephedrine's action as an agonist at most major noradrenaline receptors and its ability to increase the release of both dopamine and to a lesser extent, serotonin by the same mechanism is presumed to have a major role in its mechanism of action.
Absorption85%
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationmainly renal
Half life3-6 hours
ClearanceNot Available
ToxicityCardiovascular: tachycardia, cardiac arrhythmias, angina pectoris, vasoconstriction with hypertension
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9645
Blood Brain Barrier + 0.5638
Caco-2 permeable + 0.8866
P-glycoprotein substrate Non-substrate 0.7182
P-glycoprotein inhibitor I Non-inhibitor 0.9795
P-glycoprotein inhibitor II Non-inhibitor 0.984
Renal organic cation transporter Non-inhibitor 0.8965
CYP450 2C9 substrate Non-substrate 0.8001
CYP450 2D6 substrate Non-substrate 0.7839
CYP450 3A4 substrate Non-substrate 0.7235
CYP450 1A2 substrate Non-inhibitor 0.5595
CYP450 2C9 substrate Non-inhibitor 0.7209
CYP450 2D6 substrate Inhibitor 0.5846
CYP450 2C19 substrate Non-inhibitor 0.5737
CYP450 3A4 substrate Non-inhibitor 0.9431
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.907
Ames test Non AMES toxic 0.9517
Carcinogenicity Non-carcinogens 0.7739
Biodegradation Not ready biodegradable 0.7807
Rat acute toxicity 2.3882 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9329
hERG inhibition (predictor II) Non-inhibitor 0.9277
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
LiquidIntramuscular
LiquidIntravenous
PowderOral
SolutionIntramuscular
TabletOral
Prices
Unit descriptionCostUnit
Ephedrine sulfate 250 mg/5 ml7.82USDml
Ephedrine-ns 50 mg/5 ml syr2.91USDml
Ephedrine-ns 100 mg/10 ml syr2.07USDml
Ephedrine su 50 mg/ml vial1.75USDml
Ephedrine 50 mg/ml ampul0.76USDml
Ephedrine powder0.47USDg
Ephedrine sulfate powder0.46USDg
Ephedrine su 25 mg capsule0.3USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point34 °CPhysProp
boiling point255 °CPhysProp
water solubility6.36E+004 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.13AVDEEF,A (1997)
pKa10.3 (at 0 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
water solubility8.26e+00 g/lALOGPS
logP1ALOGPS
logP1.32ChemAxon
logS-1.3ALOGPS
pKa (strongest acidic)13.89ChemAxon
pKa (strongest basic)9.52ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area32.26ChemAxon
rotatable bond count3ChemAxon
refractivity49.69ChemAxon
polarizability18.8ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Thomas Moest, Uwe Loeffler, Hans Waiblinger, “Production of pellets composed of an ephedrine derivative.” U.S. Patent US5453280, issued March, 1994.

US5453280
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00124
KEGG CompoundC01575
PubChem Compound9294
PubChem Substance46507538
ChemSpider8935
ChEBI15407
ChEMBLCHEMBL211456
Therapeutic Targets DatabaseDAP000228
PharmGKBPA449466
IUPHAR556
Guide to Pharmacology556
Drug Product Database38121
RxListhttp://www.rxlist.com/cgi/generic/ephedrine.htm
Drugs.comhttp://www.drugs.com/ephedrine.html
WikipediaEphedrine
ATC CodesC01CA26S01FB02R03CA02R01AB05R01AA03
AHFS Codes
  • 12:12.12
  • 92:01.00*
  • 12:12.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of ephedrine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of ephedrine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of ephedrine.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of ephedrine.
DesvenlafaxineDesvenlafaxine may increase the tachycardic and vasopressor effects of ephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of ephedrine.
GuanethidineEphedrine may decrease the effect of guanethidine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of ephedrine.
IobenguaneSympathomimetic that increase chances of producing a false negative imaging result
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of ephedrine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of ephedrine.
PhenelzineIncreased arterial pressure
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
RotigotineRisk of sedation may decrease with concomitant therapy. Monitor therapy closely.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Ephedrine. Concomitant therapy should be avoided.
VenlafaxineVenlafaxine may increase the tachycardic and vasopressor effects of ephedrine. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
Food InteractionsNot Available

1. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inverse agonist

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S: The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? Anesth Analg. 2003 Nov;97(5):1239-45. Pubmed
  2. McMahon LR, Cunningham KA: Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands. Drug Alcohol Depend. 2003 Jun 5;70(3):255-64. Pubmed
  3. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. Pubmed
  4. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed

2. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Ma G, Bavadekar SA, Davis YM, Lalchandani SG, Nagmani R, Schaneberg BT, Khan IA, Feller DR: Pharmacological effects of ephedrine alkaloids on human alpha(1)- and alpha(2)-adrenergic receptor subtypes. J Pharmacol Exp Ther. 2007 Jul;322(1):214-21. Epub 2007 Apr 3. Pubmed
  2. Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Synaptic vesicular amine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Synaptic vesicular amine transporter Q05940 Details

References:

  1. Ellis JD, German CL, Birdsall E, Hanson JE, Crosby MA, Rowley SD, Sawada NA, West JN, Hanson GR, Fleckenstein AE: Ephedrine decreases vesicular monoamine transporter-2 function. Synapse. 2010 Dec 15. Pubmed
  2. Horton DB, Siripurapu KB, Norrholm SD, Culver JP, Hojahmat M, Beckmann JS, Harrod SB, Deaciuc AG, Bardo MT, Crooks PA, Dwoskin LP: meso-Transdiene Analogs Inhibit Vesicular Monoamine Transporter-2 Function and Methamphetamine-evoked Dopamine Release. J Pharmacol Exp Ther. 2010 Dec 21. Pubmed
  3. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
  4. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. Pubmed
  5. Yasumoto S, Tamura K, Karasawa J, Hasegawa R, Ikeda K, Yamamoto T, Yamamoto H: Inhibitory effect of selective serotonin reuptake inhibitors on the vesicular monoamine transporter 2. Neurosci Lett. 2009 May 1;454(3):229-32. Epub 2009 Mar 18. Pubmed
  6. Fleckenstein AE, Volz TJ, Riddle EL, Gibb JW, Hanson GR: New insights into the mechanism of action of amphetamines. Annu Rev Pharmacol Toxicol. 2007;47:681-98. Pubmed

4. Acetylcholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Acetylcholinesterase P22303 Details

References:

  1. Singh AK, Spassova D: Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Jan;119(1):97-105. Pubmed

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

  1. Maizel’ EB, Rozengart EV, Khakimov IuP, Abduvakhabov AA, Aslanov KhA: [Ephedrine, salsoline and cytisine derivatives as substrates and inhibitirs of cholinesterases]. Biokhimiia. 1978 Jul;43(7):1150-6. Pubmed

Comments
Drug created on July 06, 2007 13:56 / Updated on September 16, 2013 17:14