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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
Synonyms
(-)-Ephedrine
(1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropane
Ephedrine
L-Ephedrine
L-erythro-2-(Methylamino)-1-phenylpropan-1-ol
L(-)-Ephedrine
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ephedrineinjection, solution50 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2005-09-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection, solution50 mg/mLintramuscular; intravenous; subcutaneousAndersen Pharma Llc2014-11-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection, solution50 mg/mLintramuscular; intravenous; subcutaneousSandoz Inc2004-03-26Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection50 mg/mLintramuscular; intravenous; subcutaneousCardinal Health2009-04-012016-02-29Us 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection50 mg/mLintramuscular; intravenous; subcutaneousAkorn, Inc.2012-03-11Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection50 mg/mLintramuscular; intravenous; subcutaneousAkorn, Inc.2009-04-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ephedrine Sulfateinjection, solution50 mg/mLintravenousNexus Pharmaceuticals Inc2015-06-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ultra T-M - Tablettablet8 mgNutrion Health & Fitness Inc.1995-12-311999-08-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ephedrine Sulfatecapsule25 mg/1oralWest ward Pharmaceutical Corp1993-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sinuplex - Tabtablet10 mgoralMetagenics, Inc.1995-12-312002-12-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Bronchial Asthma ReliefWalgreens Company
Broncho DilateContract Pharmacal Corp
Bronkaid Dual Action FormulaBayer Health Care Consumer Care
Ephed AsthmaDickey Consumer Products DBA DMD
PrimatenePfizer Consumer Healthcare
Vasopro EphedrineOptimal Research Inc
Salts
Name/CASStructureProperties
Ephedrine hydrochloride
ThumbNot applicableDBSALT001513
Ephedrine sulfate
ThumbNot applicableDBSALT001503
CategoriesNot Available
UNIIGN83C131XS
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9645
Blood Brain Barrier+0.5638
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.7182
P-glycoprotein inhibitor INon-inhibitor0.9795
P-glycoprotein inhibitor IINon-inhibitor0.984
Renal organic cation transporterNon-inhibitor0.8965
CYP450 2C9 substrateNon-substrate0.8001
CYP450 2D6 substrateNon-substrate0.7839
CYP450 3A4 substrateNon-substrate0.7235
CYP450 1A2 substrateNon-inhibitor0.5595
CYP450 2C9 inhibitorNon-inhibitor0.7209
CYP450 2D6 inhibitorInhibitor0.5846
CYP450 2C19 inhibitorNon-inhibitor0.5737
CYP450 3A4 inhibitorNon-inhibitor0.9431
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.907
Ames testNon AMES toxic0.9517
CarcinogenicityNon-carcinogens0.7739
BiodegradationNot ready biodegradable0.7807
Rat acute toxicity2.3882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9329
hERG inhibition (predictor II)Non-inhibitor0.9277
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Tablet, coatedoral
Injection, solutionintramuscular; intravenous; subcutaneous50 mg/mL
Capsuleoral25 mg/1
Injectionintramuscular; intravenous; subcutaneous50 mg/mL
Injection, solutionintravenous50 mg/mL
Tabletoral10 mg
Tablet8 mg
Prices
Unit descriptionCostUnit
Ephedrine sulfate 250 mg/5 ml7.82USD ml
Ephedrine-ns 50 mg/5 ml syr2.91USD ml
Ephedrine-ns 100 mg/10 ml syr2.07USD ml
Ephedrine su 50 mg/ml vial1.75USD ml
Ephedrine 50 mg/ml ampul0.76USD ml
Ephedrine powder0.47USD g
Ephedrine sulfate powder0.46USD g
Ephedrine su 25 mg capsule0.3USD capsule
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 Solubility8.26 mg/mLALOGPS
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 Area32.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.69 m3·mol-1ChemAxon
Polarizability18.8 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.84 KB)
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-z200000000-bcc578719d003732d7f8View in MoNA
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 ReferencesNot Available
External Links
ATC CodesC01CA26R01AA03R01AB05R03CA02S01FB02
AHFS Codes
  • 12:12.00
  • 12:12.12
  • 92:01.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Ephedrine.
AcetazolamideThe serum concentration of Ephedrine can be increased when it is combined with Acetazolamide.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Ephedrine.
Ammonium chlorideThe serum concentration of Ephedrine can be decreased when it is combined with Ammonium chloride.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Ephedrine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Ephedrine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Ephedrine.
Benzylpenicilloyl PolylysineEphedrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
CabergolineCabergoline may increase the hypertensive activities of Ephedrine.
Calcium AcetateThe serum concentration of Ephedrine can be increased when it is combined with Calcium Acetate.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Ephedrine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Ephedrine.
DesfluraneEphedrine may increase the arrhythmogenic activities of Desflurane.
DiclofenamideThe serum concentration of Ephedrine can be increased when it is combined with Diclofenamide.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Ephedrine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Ephedrine.
DoxofyllineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Ephedrine.
DroxidopaEphedrine may increase the hypertensive activities of Droxidopa.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Ephedrine.
EthoxzolamideThe serum concentration of Ephedrine can be increased when it is combined with Ethoxzolamide.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Ephedrine.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Ephedrine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Ephedrine.
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Ephedrine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedrine.
IsofluraneEphedrine may increase the arrhythmogenic activities of Isoflurane.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Ephedrine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Ephedrine.
LinezolidLinezolid may increase the hypertensive activities of Ephedrine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Ephedrine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ephedrine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Ephedrine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ephedrine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Ephedrine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Ephedrine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Ephedrine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Ephedrine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Ephedrine.
PhenelzinePhenelzine may increase the hypertensive activities of Ephedrine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Ephedrine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Ephedrine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Ephedrine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Ephedrine.
PrazosinPrazosin may decrease the vasoconstricting activities of Ephedrine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Ephedrine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Ephedrine.
SevofluraneEphedrine may increase the arrhythmogenic activities of Sevoflurane.
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Ephedrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Ephedrine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Ephedrine.
TranylcypromineTranylcypromine may increase the hypertensive activities of Ephedrine.
VenlafaxineVenlafaxine may increase the tachycardic activities of Ephedrine.
Food InteractionsNot Available

Targets

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

Enzymes

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

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Drug created on July 06, 2007 13:56 / Updated on December 03, 2015 09:51