Ephedrine

Identification

Summary

Ephedrine is an alpha and beta-adrenergic agonist indicated to treat hypotension under anesthesia, allergic conditions, bronchial asthma, and nasal congestion.

Brand Names
Akovaz, Bronkaid, Corphedra, Emerphed, Primatene, Rezipres
Generic Name
Ephedrine
DrugBank Accession Number
DB01364
Background

Ephedrine was first described in western literature in 1888, as a naturally occurring component of the ephedra plant, along with pseudoephedrine.5 Ephedrine is an adrenergic receptor agonist used for its vasoconstrictive, positive chronotropic, and positive inotropic effects.8 Ephedrine and phenylephrine are still commonly used to treat hypotension but their use in other indications has decreased due to the development of more selective adrenergic agonists.6,7,9

Ephedrine was granted a type 7 FDA Approval on 29 April 2016.9

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 165.2322
Monoisotopic: 165.115364107
Chemical Formula
C10H15NO
Synonyms
  • (-)-Ephedrine
  • (1R,2S)-1-Phenyl-1-hydroxy-2-methylaminopropane
  • Efedrina
  • Ephedrine
  • L-Ephedrine
  • L-erythro-2-(Methylamino)-1-phenylpropan-1-ol
  • L(−)-ephedrine
External IDs
  • NSC-170951
  • NSC-8971

Pharmacology

Indication

Ephedrine intravenous injections are indicated to treat hypotension under anesthesia,8,13 ephedrine injections by multiple routes are indicated to treat allergic conditions such as bronchial asthma,12 ephedrine nasal spray is and OTC medication used as a decongestant.11

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Ephedrine is a sympathomimetic amine that activates adrenergic receptors, increasing heart rate and blood pressure, and causing bronchodilation.4 The therapeutic window is wide as patients can be given doses of 5mg up to 50mg.11 Patients should be counselled regarding the pressor effects of sympathomimetic amines and the risk of tachyphylaxis.4

Mechanism of action

Ephedrine is a direct and indirect sympathomimetic amine.4 Ephedrine activates adrenergic α and β-receptors as well as inhibiting norepinephrine reuptake, and increasing the release of norepinephrine from vesicles in nerve cells.4 These actions combined lead to larger quantities of norepinephrine present in the synapse, for longer periods of time, increasing stimulation of the sympathetic nervous system.4 Ephedrine's stimulation of α-1 receptors causes constriction of veins and a rise in blood pressure, stimulation of β-1 adrenergic receptors increase cardiac chronotropy and inotropy, stimulation of β-2 adrenergic receptors causes bronchodilation.4

TargetActionsOrganism
USodium-dependent noradrenaline transporter
inverse agonist
Humans
AAlpha-1A adrenergic receptor
agonist
Humans
ABeta-1 adrenergic receptor
agonist
Humans
ABeta-2 adrenergic receptor
agonist
Humans
Absorption

Oral ephedrine reaches an average Cmax of 79.5ng/mL, with a Tmax of 1.81h, and a bioavailability of 88%.2

Volume of distribution

Oral ephedrine has an average volume of distribution of 215.6L.2

Protein binding

(-) Ephedrine is 4.9±0.3% bound to human serum albumin and (+) Ephedrine is 6.9±1.4% bound to human serum albumin.3

Metabolism

Ephedrine is largely unmetabolized in the body.1 Ephedrine can be N-demethylated to norephedrine, or demethylated and deaminized to benzoic acid conjugates and 1,2-hydroxypropylbenzene.1

Hover over products below to view reaction partners

Route of elimination

Ephedrine is mainly eliminated in the urine.1,8 Approximately 60% is eliminated as the unmetabolized parent compound, 13% as benzoic acid conjugates, and 1% as 1,2-dihydroxypropylbenzene.1

Half-life

Oral ephedrine has a plasma elimination half life of approximately 6 hours, but there is a large degree of inter-patient variability.2,8,13

Clearance

Oral ephedrine has a clearance of 23.3L/h but there is a high degree of inter-patient variability.2

Adverse Effects
Adverseeffects
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Toxicity

Patients experiencing an overdose of ephedrine will present with rapidly increasing blood pressure.8,13 Manage overdose with blood pressure monitoring, and possibly the administration of parenteral antihypertensives.8,13 The LD50 in mice after oral administration is 785mg/kg, after intraperitoneal administration if 248mg/kg, and after subcutaneous administration is 425mg/kg.10

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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
AbaloparatideThe risk or severity of adverse effects can be increased when Ephedrine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Ephedrine.
AceclofenacThe risk or severity of hypertension can be increased when Ephedrine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Ephedrine is combined with Acemetacin.
AcetazolamideThe risk or severity of Cardiac Arrhythmia can be increased when Ephedrine is combined with Acetazolamide.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Ephedrine is combined with Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Ephedrine.
AclidiniumThe risk or severity of Tachycardia can be increased when Ephedrine is combined with Aclidinium.
AcrivastineThe therapeutic efficacy of Ephedrine can be increased when used in combination with Acrivastine.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Ephedrine.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Ephedrine hydrochlorideNLJ6390P1Z50-98-6BALXUFOVQVENIU-GNAZCLTHSA-N
Ephedrine sulfateU6X61U5ZEG134-72-5CAVQBDOACNULDN-KHFUBBAMSA-N
Ephedrine tannate1M92VL7U3I1405-94-3FGPQMDDYPJHDFD-RDVHWUOCSA-N
Product Images
International/Other Brands
Rezipres (Eton Pharmaceuticals, Inc.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AkovazInjection50 mg/1mLIntravenousExela Pharma Sciences, LLC2021-04-15Not applicableUS flag
AkovazInjection50 mg/1mLIntravenousAvadel Legacy Pharmaceuticals, Llc2016-08-012023-09-30US flag
AkovazInjection50 mg/1mLIntravenousExela Pharma Sciences, LLC2021-05-10Not applicableUS flag
AkovazInjection50 mg/1mLIntravenousBluePoint Laboratories2017-06-302022-11-30US flag
CorphedraInjection, solution50 mg/1mLIntravenousPar Pharmaceutical, Inc.2017-02-16Not applicableUS flag
EmerphedInjection5 mg/1mLIntravenousNexus Pharmaceuticals Inc2020-05-15Not applicableUS flag
EphedrineInjection, solution10 mg/1mLIntravenousCantrell Drug Company2016-03-182017-12-06US flag
Ephedrine SulfateInjection, solution50 mg/1mLIntravenousPar Pharmaceutical, Inc.2017-02-16Not applicableUS flag
Ephedrine SulfateInjection, solution50 mg/1mLIntravenousNexus Pharmaceuticals Inc2015-06-08Not applicableUS flag
Ephedrine SulfateInjection, solution50 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-09-082013-08-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ephedrine SulfateInjection50 mg/1mLIntravenousMedical Purchasing Solutions, Llc2019-10-23Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousHikma Pharmaceuticals USA Inc.2020-12-15Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousSandoz Inc2017-10-01Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousAuroMedics Pharma LLC2021-06-14Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousNorthStar Rx LLC2020-12-02Not applicableUS flag16714 03720201220 14367 x99o4m
Ephedrine SulfateInjection50 mg/1mLIntravenousAmneal Pharmaceuticals LLC2019-10-23Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousCivica, Inc.2021-08-23Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousCivica, Inc.2021-03-29Not applicableUS flag
Ephedrine SulfateInjection50 mg/1mLIntravenousFresenius Kabi USA, LLC2020-10-31Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bronkaid MaxTablet, coated25 mg/1OralFoundation Consumer Healthcare LLC2020-09-01Not applicableUS flag
Ephedrine HClTablet8 mgOralKaizen Inc.2004-01-012010-02-26Canada flag
Ephedrine HClTablet8 mgOralAdded Dimensions2002-04-302006-09-25Canada flag
Ephedrine HClCapsule25 mg / capOralKaizen Inc.1997-04-221999-03-15Canada flag
Ephedrine HCl - Tab 25mgTablet25 mgOralAdded Dimensions1996-07-302002-02-25Canada flag
Ephedrine HCl 8 mgTablet8 mgOralNutrition Zone Products Inc.2002-09-202008-07-27Canada flag
Ephedrine Hydrochloride Tablets 25mgTablet25 mgOralProdemdis Enr.1998-05-042002-08-30Canada flag
Ephedrine SulfateCapsule25 mg/1OralHikma Pharmaceuticals USA Inc.1993-09-012015-12-31US flag
Ephedrine Tab 15mgTablet15 mg / tabOralGlaxo Canada Inc1991-12-311996-09-10Canada flag
Ephedrine Tab 30mgTablet30 mg / tabOralGlaxo Canada Inc1991-12-311996-09-10Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ANTIBEKSIN SURUP, 100 MLEphedrine hydrochloride (5 mg/5ml) + Pheniramine maleate (15 mg/5ml) + Potassium guaiacolsulfonate (175 mg/5ml) + Sodium citrate (65 mg/5ml)SyrupOralYAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ARKODIN SIROP, 125 MLEphedrine hydrochloride (10 mg/5ml) + Codeine phosphate (12.5 mg/5ml)SyrupOralGÜNSA GÜNEY İLAÇ VE HAMMADDELER SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ARTU 100 ML SURUPEphedrine hydrochloride (5 mg/5ml) + Sodium benzoate (5 mg/5ml) + Potassium guaiacolsulfonate (175 mg/5ml) + Promethazine hydrochloride (5 mg/5ml)SyrupOralGÜNSA GÜNEY İLAÇ VE HAMMADDELER SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Balminil Nasal OintmentEphedrine hydrochloride (6 mg / g) + Camphor (4 mg / g) + Chlorobutanol (2 mg / g) + Eucalyptol (6 mg / g) + Levomenthol (4 mg / g)OintmentNasalRougier Pharma Division Of Ratiopharm Inc1995-12-312003-09-22Canada flag
BROKSIN 6.66 MG/5 ML+100 MG/5 ML SURUP, 150 MLEphedrine hydrochloride (6.66 mg/5ml) + Guaifenesin (100 mg/5ml)SyrupOralTRIPHARMA İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Bronch EzeEphedrine hydrochloride (4 mg / 5 mL) + Ammonium chloride (100 mg / 5 mL)SyrupOralPharmavite Laboratories (1987) Inc.1984-12-312000-08-18Canada flag
Bronchial Asthma ReliefEphedrine hydrochloride (12.5 mg/1) + Guaifenesin (200 mg/1)TabletOralWalgreens2002-02-13Not applicableUS flag
Bronchial Asthma ReliefEphedrine hydrochloride (12.5 mg/1) + Guaifenesin (200 mg/1)TabletOralWalgreen Company2020-04-26Not applicableUS flag
Broncho DilateEphedrine hydrochloride (12.5 mg/1) + Guaifenesin (200 mg/1)TabletOralContract Pharmacal Corporation2002-02-132012-01-18US flag
Broncho Tuss AdultEphedrine hydrochloride (7.5 mg / sup) + Guaifenesin (100 mg / sup) + Sodium camphorsulfonate (60 mg / sup)SuppositoryRectalProduits Francais Labs Inc.1981-12-311997-05-30Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EphedrineEphedrine sulfate (10 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2016-03-182017-12-06US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousAkorn, Inc.2009-04-01Not applicableUS flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousAkorn2012-03-112017-06-01US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousCardinal Health2004-03-262015-02-28US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousAndersen Pharma Llc2014-11-012015-11-30US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousSandoz2004-03-262017-09-30US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousCardinal Health2009-04-012016-02-29US flag
Ephedrine SulfateEphedrine sulfate (50 mg/1mL)Injection, solutionIntravenousNexus Pharmaceuticals Inc2015-06-08Not applicableUS flag
Ephedrine SulphateEphedrine sulfate (50 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousClaris Lifesciences, Inc.2009-10-072010-11-04US flag
Ephedrine SulphateEphedrine sulfate (50 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousClaris Lifesciences Limited2009-10-072010-11-04US flag

Categories

ATC Codes
S01FB02 — EphedrineR01AB05 — EphedrineC01CA26 — EphedrineR03CA02 — EphedrineA08AA56 — Ephedrine, combinationsR01AA03 — Ephedrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines, phenethylamine alkaloid (CHEBI:15407) / Alkaloids, Phenylalanine derived alkaloids (C01575)
Affected organisms
  • Humans

Chemical Identifiers

UNII
GN83C131XS
CAS number
299-42-3
InChI Key
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

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 References
  1. Sever PS, Dring LG, Williams RT: The metabolism of (-)-ephedrine in man. Eur J Clin Pharmacol. 1975 Dec 19;9(2-3):193-8. doi: 10.1007/bf00614017. [Article]
  2. Pickup ME, May CS, Ssendagire R, Paterson JW: The pharmacokinetics of ephedrine after oral dosage in asthmatics receiving acute and chronic treatment. Br J Clin Pharmacol. 1976 Feb;3(1):123-34. doi: 10.1111/j.1365-2125.1976.tb00579.x. [Article]
  3. Volpp M, Holzgrabe U: Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration. Eur J Pharm Sci. 2019 Jan 15;127:175-184. doi: 10.1016/j.ejps.2018.10.027. Epub 2018 Oct 31. [Article]
  4. Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
  5. Stehle RL: Ephedrine-A New (?) Sympathomimetic Drug. Can Med Assoc J. 1925 Nov;15(11):1158-60. [Article]
  6. Wang X, Mao M, Liu S, Xu S, Yang J: A Comparative Study of Bolus Norepinephrine, Phenylephrine, and Ephedrine for the Treatment of Maternal Hypotension in Parturients with Preeclampsia During Cesarean Delivery Under Spinal Anesthesia. Med Sci Monit. 2019 Feb 9;25:1093-1101. doi: 10.12659/MSM.914143. [Article]
  7. Kinsella SM, Carvalho B, Dyer RA, Fernando R, McDonnell N, Mercier FJ, Palanisamy A, Sia ATH, Van de Velde M, Vercueil A: International consensus statement on the management of hypotension with vasopressors during caesarean section under spinal anaesthesia. Anaesthesia. 2018 Jan;73(1):71-92. doi: 10.1111/anae.14080. Epub 2017 Nov 1. [Article]
  8. FDA Approved Drug Products: Emerphed Ephedrine Sulfate Intravenous Injection [Link]
  9. FDA Approved Drug Products: Akovaz Ephedrine Sulfare Intravenous Injection [Link]
  10. Cayman Chemical: Ephedrine MSDS [Link]
  11. Dailymed: Ephedrine Nasal Spray [Link]
  12. Dailymed: Ephedrine Intravenous, Intramuscular, and Subcutaneous Injection [Link]
  13. FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]
Human Metabolome Database
HMDB0015451
KEGG Drug
D00124
KEGG Compound
C01575
PubChem Compound
9294
PubChem Substance
46507538
ChemSpider
8935
RxNav
3966
ChEBI
15407
ChEMBL
CHEMBL211456
ZINC
ZINC000000074836
Therapeutic Targets Database
DAP000228
PharmGKB
PA449466
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ephedrine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherEndovascular Carotid Surgery / Preoperative Hypotension1
4CompletedPreventionAnesthesia; Adverse Effect, Spinal and Epidural / Complications; Cesarean Section / Hypotension1
4CompletedPreventionBradycardia1
4CompletedPreventionBradycardia / Dexmedetomidine / Spinal Anaesthesia1
4CompletedPreventionHypotension1
4CompletedPreventionInfluence of Vasoactive Medication on Spinal Oxygenation1
4CompletedPreventionPain, Labor1
4CompletedTreatmentCesarean Sections / Hypotension / Pregnant State / Spinal Anaesthesia1
4CompletedTreatmentComplications; Cesarean Section1
4CompletedTreatmentGall Stone Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Akorn Inc.
  • Allergy Laboratories Inc.
  • Ben Venue Laboratories Inc.
  • C.O. Truxton Inc.
  • Cardinal Health
  • Claris Lifesciences Inc.
  • Consolidated Midland Corp.
  • Ebewe Pharma
  • Hospira Inc.
  • Jordan Pharmaceuticals Inc.
  • Mallinckrodt Inc.
  • Parenta Pharmaceuticals
  • Pharmedium
  • Taylor Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Capsule
Solution / dropsNasal
Tablet, film coatedOral
OintmentNasal
SuppositoryRectal
Tablet, coatedOral
Tablet, coatedOral25 mg/1
SyrupOral
SprayNasal
Syrup
ElixirOral
Injection; solutionIntramuscular; Intravenous; Subcutaneous
Injection, solution3 MG/ML
Syrup
SyrupNasal; Topical
TabletOral
Injection, solution10 MG/ML
InjectionIntravenous5 mg/1mL
LiquidOral
Injection, solutionParenteral
Injection, solutionIntravenous10 mg/1mL
CapsuleOral25 mg / cap
TabletOral8 mg
TabletOral25 mg
CapsuleOral25 mg/1
InjectionIntramuscular; Intravenous; Subcutaneous50 mg/1mL
InjectionIntravenous50 mg/1mL
Injection, solutionIntravenous50 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous50 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous50 mg / 1 mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous50 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous50 mg / mL
TabletOral15 mg / tab
TabletOral30 mg / tab
Injection, solution
TabletOral.13 mg
LiquidNasal1.5 %
OintmentTopical
JellyNasal
TabletOral12.5 mg/1
Injection, solutionIntravenous4.7 mg/1mL
Injection, solutionIntravenous47 mg/1mL
Injection, solutionIntravenous9.4 mg/1mL
SprayNasal5 mg/1mL
SprayTopical5 mg/1mL
TabletOral
TabletOral10 mg
LiquidInfiltration
LiquidInfiltration; Subcutaneous
Tablet
Injection
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10869845No2020-01-222040-01-22US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)34 °CPhysProp
boiling point (°C)255 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (7.84 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-9000000000-bcc578719d003732d7f8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-33d551e262321705ae8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0900000000-32a84e7b7e5332fe2026
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-82640acc94773485568a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-bdfb6079227a418eb706
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-c04df5fb623578be67ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00l2-1900000000-3a68bc210684b52a9fd8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-2900000000-e12bf9df640426404f1c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0900000000-0218a677989aab76b176
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-3dd538034653edb47df1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-553c930e0970a8c1a866
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-0499cdf7955d013fca29
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-015a-1900000000-f6b6229ef8c2d7fd24ab
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-2900000000-7c8549f8cd727886d67d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-bcbf5073df33d11415cc

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inverse agonist
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. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
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. [Article]
  2. Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. [Article]
  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. [Article]
  4. Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
  5. FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
  2. FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
  2. FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
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. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Volpp M, Holzgrabe U: Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration. Eur J Pharm Sci. 2019 Jan 15;127:175-184. doi: 10.1016/j.ejps.2018.10.027. Epub 2018 Oct 31. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
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. 2011 May;65(5):449-51. doi: 10.1002/syn.20896. [Article]
  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. 2011 Mar;336(3):940-51. doi: 10.1124/jpet.110.175117. Epub 2010 Dec 21. [Article]
  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. [Article]
  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. [Article]
  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. doi: 10.1016/j.neulet.2009.03.049. Epub 2009 Mar 18. [Article]
  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. [Article]

Drug created on July 06, 2007 19:56 / Updated on September 19, 2021 19:53