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 acts as both a direct and indirect sympathomimetic. It is an alpha- and beta-adrenergic receptor agonist; however, it also causes the indirect release of norepinephrine from sympathetic neurons, inhibiting norepinephrine reuptake and displacing more norepinephrine from storage vesicles.^4,8 Ephedrine is used for its vasoconstrictive, positive chronotropic, and positive inotropic effects.⁸ Ephedrine and phenylephrine are still 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

Similar Structures

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

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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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Dose Form
Treatment of	Allergic disorder		••• •••••	•••••••••
Treatment of	Bronchial asthma		••• •••••	•••••••••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Dextromethorphan (DB00514), Promethazine (DB01069)	••••••••••••	•••••
Used in combination for symptomatic treatment of	Coughing	Combination Product in combination with: Promethazine (DB01069), Dextromethorphan (DB00514)	••••••••••••	•••••
Used in combination for symptomatic treatment of	Coughing	Combination Product in combination with: Dextromethorphan (DB00514), Diphenhydramine (DB01075)	••••••••••••	•••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Ephedrine increases blood pressure by stimulating heart rate and cardiac output and variably increasing peripheral resistance.⁹ It causes bronchodilation due to the activation of beta-adrenergic receptors in the lungs. By stimulating alpha-adrenergic receptors in bladder smooth muscle cells, ephedrine also increases the resistance to the outflow of urine.^8,9 The therapeutic window of ephedrine 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 Also, the use of ephedrine for hypotension prophylaxis is associated with a higher risk of hypertension, compared to when ephedrine is used to treat hypotension.⁹

Mechanism of action

Ephedrine is a direct and indirect sympathomimetic amine.⁴ As a direct effect, ephedrine activates alpha-adrenergic and beta-adrenergic receptors. As an indirect effect, it inhibits norepinephrine reuptake and increases the release of norepinephrine from vesicles in nerve cells.⁴ These actions combined lead to larger quantities of norepinephrine present in the synapse for more extended periods of time, increasing stimulation of the sympathetic nervous system.⁴

Ephedrine acts as an agonist of alpha-1, beta-1 and beta-2-adrenergic receptors. The stimulation of alpha-1-adrenergic receptors causes the constriction of veins and a rise in blood pressure, the stimulation of beta-1-adrenergic receptors increases cardiac chronotropy and inotropy, and the stimulation of beta-2-adrenergic receptors causes vasodilation and bronchodilation.⁴

Target	Actions	Organism
AAlpha-1A adrenergic receptor	agonist	Humans
ABeta-1 adrenergic receptor	agonist	Humans
ABeta-2 adrenergic receptor	agonist	Humans
USodium-dependent noradrenaline transporter	inverse agonist	Humans

Absorption

Oral ephedrine reaches an average C_max of 79.5ng/mL, with a T_max 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

Ephedrine
- Norephedrine
- 1,2-dihydroxypropylbenzene

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

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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

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Interactions

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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.

Drug	Interaction
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Acebutolol	The therapeutic efficacy of Acebutolol can be increased when used in combination with Ephedrine.
Aceclofenac	The risk or severity of hypertension can be increased when Ephedrine is combined with Aceclofenac.
Acemetacin	The risk or severity of hypertension can be increased when Ephedrine is combined with Acemetacin.
Acetazolamide	The risk or severity of Cardiac Arrhythmia can be increased when Ephedrine is combined with Acetazolamide.
Acetyldigitoxin	The risk or severity of Cardiac Arrhythmia can be increased when Ephedrine is combined with Acetyldigitoxin.

Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ephedrine hydrochloride	NLJ6390P1Z	50-98-6	BALXUFOVQVENIU-GNAZCLTHSA-N
Ephedrine sulfate	U6X61U5ZEG	134-72-5	CAVQBDOACNULDN-KHFUBBAMSA-N
Ephedrine tannate	1M92VL7U3I	1405-94-3	FGPQMDDYPJHDFD-RDVHWUOCSA-N

Product Images

International/Other Brands

Rezipres (Eton Pharmaceuticals, Inc.)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Akovaz	Injection	50 mg/1mL	Intravenous	BluePoint Laboratories	2017-06-30	2022-11-30
Akovaz	Injection	5 mg/1mL	Intravenous	Exela Pharma Sciences, LLC	2021-05-10	Not applicable
Akovaz	Injection	50 mg/1mL	Intravenous	Exela Pharma Sciences, LLC	2021-04-15	Not applicable
Akovaz	Injection	50 mg/1mL	Intravenous	Avadel Legacy Pharmaceuticals, Llc	2016-08-01	2023-09-30
Corphedra	Injection, solution	500 mg/10mL	Intravenous	Par Pharmaceutical, Inc.	2019-01-18	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ephedrine Sulfate	Injection	50 mg/1mL	Intravenous	NorthStar Rx LLC	2020-12-02	Not applicable
Ephedrine Sulfate	Injection	50 mg/1mL	Intravenous	Xiromed, Llc	2022-04-21	Not applicable
Ephedrine Sulfate	Injection	50 mg/1mL	Intravenous	Fresenius Kabi USA, LLC	2020-10-31	Not applicable
Ephedrine Sulfate	Injection	50 mg/1mL	Intravenous	Medical Purchasing Solutions, Llc	2021-06-14	Not applicable
Ephedrine Sulfate	Injection	50 mg/1mL	Intravenous	Civica, Inc.	2021-08-23	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Bronkaid Max	Tablet, coated	25 mg/1	Oral	Foundation Consumer Healthcare LLC	2020-09-01	Not applicable
Ephedrine HCl	Capsule	25 mg / cap	Oral	Kaizen Inc.	1997-04-22	1999-03-15
Ephedrine HCl	Tablet	8 mg	Oral	Kaizen Inc.	2004-01-01	2010-02-26
Ephedrine HCl	Tablet	8 mg	Oral	Added Dimensions	2002-04-30	2006-09-25
Ephedrine HCl - Tab 25mg	Tablet	25 mg	Oral	Added Dimensions	1996-07-30	2002-02-25

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ALCOUGH MIXTURE	Ephedrine hydrochloride (6 mg/5ml) + Guaifenesin (50 mg/5ml)	Solution	Oral	ALCARE PHARMACEUTICALS PTE LTD	1989-06-21	Not applicable
ANTI-PHLEGM COUGH MIXTURE	Ephedrine hydrochloride (4 mg/5ml) + Ammonium chloride (100 mg/5ml) + Sodium citrate (150 mg/5ml)	Solution	Oral	LI TA SHEN MEDICAL TRADER	1989-11-05	Not applicable
ANTIBEKSIN SURUP, 100 ML	Ephedrine hydrochloride (5 mg/5ml) + Pheniramine maleate (15 mg/5ml) + Potassium guaiacolsulfonate (175 mg/5ml) + Sodium citrate (65 mg/5ml)	Syrup	Oral	YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş.	2009-02-06	Not applicable
ARKODIN SIROP, 125 ML	Ephedrine hydrochloride (10 mg/5ml) + Codeine phosphate (12.5 mg/5ml)	Syrup	Oral	GÜNSA GÜNEY İLAÇ VE HAMMADDELER SAN. VE TİC. A.Ş.	1972-03-16	Not applicable
ARTU 100 ML SURUP	Ephedrine hydrochloride (5 mg/5ml) + Sodium benzoate (5 mg/5ml) + Potassium guaiacolsulfonate (175 mg/5ml) + Promethazine hydrochloride (5 mg/5ml)	Syrup	Oral	GÜNSA GÜNEY İLAÇ VE HAMMADDELER SAN. VE TİC. A.Ş.	1972-03-16	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Ephedrine	Ephedrine sulfate (10 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2016-03-18	2017-12-06
Ephedrine Sulfate	Ephedrine sulfate (50 mg/1mL)	Injection	Intramuscular; Intravenous; Subcutaneous	Cardinal Health	2009-04-01	2016-02-29
Ephedrine Sulfate	Ephedrine sulfate (50 mg/1mL)	Injection, solution	Intravenous	Nexus Pharmaceuticals Inc	2015-06-08	Not applicable
Ephedrine Sulfate	Ephedrine sulfate (50 mg/1mL)	Injection	Intramuscular; Intravenous; Subcutaneous	Akorn	2009-04-01	Not applicable
Ephedrine Sulfate	Ephedrine sulfate (50 mg/1mL)	Injection	Intramuscular; Intravenous; Subcutaneous	Akorn	2012-03-11	2017-06-01

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

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]
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]
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]
Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
Stehle RL: Ephedrine-A New (?) Sympathomimetic Drug. Can Med Assoc J. 1925 Nov;15(11):1158-60. [Article]
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]
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]
FDA Approved Drug Products: Emerphed Ephedrine Sulfate Intravenous Injection [Link]
FDA Approved Drug Products: Akovaz Ephedrine Sulfare Intravenous Injection [Link]
Cayman Chemical: Ephedrine MSDS [Link]
Dailymed: Ephedrine Nasal Spray [Link]
Dailymed: Ephedrine Intravenous, Intramuscular, and Subcutaneous Injection [Link]
FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Other	Endovascular Carotid Surgery / Preoperative Hypotension	1
4	Completed	Prevention	Anesthesia; Adverse Effect, Spinal and Epidural / Complications; Cesarean Section / Hypotension	1
4	Completed	Prevention	Bradycardia	1
4	Completed	Prevention	Bradycardia / Dexmedetomidine / Spinal Anesthesia therapy	1
4	Completed	Prevention	Hypotension	1

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

Form	Route	Strength
Capsule
Solution	Oral	6 mg/5ml
Solution	Oral
Solution / drops	Nasal
Tablet, film coated	Oral
Ointment	Nasal
Solution	Oral	100 mg/5ml
Suppository	Rectal
Tablet, coated	Oral
Tablet, coated	Oral	25 mg/1
Syrup	Oral
Injection, solution	Intravenous	500 mg/10mL
Injection	Intramuscular; Intravenous; Subcutaneous	30 mg/ml
Spray	Nasal
Syrup
Syrup	Oral	9 mg/5ml
Elixir	Oral
Tablet	Oral	50 mg
Injection; solution	Intramuscular; Intravenous; Subcutaneous	0.05 g/ml
Injection, solution		3 MG/ML
Syrup
Syrup	Nasal; Topical
Tablet	Oral
Injection, solution		10 MG/ML
Injection, solution		25 MG/ML
Injection, solution
Injection	Intravenous	5 mg/1mL
Liquid	Oral
Injection, solution	Parenteral
Injection, solution	Parenteral	10 mg/ml
Injection, solution	Parenteral	50 mg/ml
Injection, solution	Intravenous	10 mg/1mL
Capsule	Oral	25 mg / cap
Tablet	Oral	8 mg
Tablet	Oral	25 mg
Solution	Nasal	0.5 % w/v
Capsule	Oral	25 mg/1
Injection	Intramuscular; Intravenous; Subcutaneous	50 mg/1mL
Injection	Intravenous	50 mg/1mL
Injection, solution	Intravenous	50 mg/1mL
Tablet, film coated	Oral	25 mg/1
Liquid	Intramuscular; Intravenous; Subcutaneous	50 mg / mL
Solution	Intramuscular; Intravenous; Subcutaneous	50 mg / 1 mL
Injection	Intramuscular; Intravenous; Subcutaneous	50 mg/ml
Injection, solution	Intramuscular; Intravenous; Subcutaneous	50 mg/1mL
Solution	Intramuscular; Intravenous; Subcutaneous	50 mg / mL
Tablet	Oral	15 mg / tab
Tablet	Oral	30 mg / tab
Tablet	Oral	.13 mg
Liquid	Nasal	1.5 %
Tablet	Oral	5.34 mg/8g
Bead	Oral	4.6 mg/4g
Ointment	Topical
Injection, solution	Intravenous	30 mg/ml
Jelly	Nasal
Injection		30 mg/ml
Solution	Oral	80 mg/5ml
Tablet	Oral	12.5 mg/1
Injection, solution	Intravenous	4.7 mg/1mL
Injection, solution	Intravenous	47 mg/1mL
Injection, solution	Intravenous	47 mg/10mL
Injection, solution	Intravenous	9.4 mg/1mL
Solution / drops	Nasal	1 %
Spray	Nasal	5 mg/1mL
Spray	Topical	5 mg/1mL
Tablet	Oral
Syrup	Oral	100 mg/5ml
Tablet	Oral	10 mg
Elixir	Oral	4 mg/5ml
Liquid	Infiltration
Liquid	Infiltration; Subcutaneous
Elixir	Oral	9 mg/5ml
Elixir	Oral	10.0 mg/5ml
Solution	Intramuscular	50.000 mg
Tablet
Elixir	Oral	10 mg/5ml
Injection

Prices

Unit description	Cost	Unit
Ephedrine sulfate 250 mg/5 ml	7.82USD	ml
Ephedrine-ns 50 mg/5 ml syr	2.91USD	ml
Ephedrine-ns 100 mg/10 ml syr	2.07USD	ml
Ephedrine su 50 mg/ml vial	1.75USD	ml
Ephedrine 50 mg/ml ampul	0.76USD	ml
Ephedrine powder	0.47USD	g
Ephedrine sulfate powder	0.46USD	g
Ephedrine su 25 mg capsule	0.3USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US10869845	No	2020-12-22	2040-01-22
US11090278	No	2021-08-17	2040-05-16
US11241400	No	2020-05-16	2040-05-16
US11464752	No	2020-05-16	2040-05-16
US11478436	No	2020-05-16	2040-05-16
US11571398	No	2020-05-16	2040-05-16

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	34 °C	PhysProp
boiling point (°C)	255 °C	PhysProp
water solubility	6.36E+004 mg/L (at 30 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	1.13	AVDEEF,A (1997)
pKa	10.3 (at 0 °C)	PERRIN,DD (1965)

Predicted Properties

Property	Value	Source
Water Solubility	8.26 mg/mL	ALOGPS
logP	1	ALOGPS
logP	1.32	Chemaxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	13.89	Chemaxon
pKa (Strongest Basic)	9.52	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	32.26 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	49.69 m³·mol^-1	Chemaxon
Polarizability	18.8 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

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 inhibitor	Non-inhibitor	0.7209
CYP450 2D6 inhibitor	Inhibitor	0.5846
CYP450 2C19 inhibitor	Non-inhibitor	0.5737
CYP450 3A4 inhibitor	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (7.84 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-9300000000-5bdf33e08e94f0c0bd26
Mass Spectrum (Electron Ionization)	MS	splash10-0a4i-9000000000-bcc578719d003732d7f8
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-33d551e262321705ae8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014j-0900000000-32a84e7b7e5332fe2026
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-82640acc94773485568a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-bdfb6079227a418eb706
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-c04df5fb623578be67ea
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00l2-1900000000-3a68bc210684b52a9fd8
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0159-2900000000-e12bf9df640426404f1c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014j-0900000000-0218a677989aab76b176
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-3dd538034653edb47df1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-553c930e0970a8c1a866
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-0499cdf7955d013fca29
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-015a-1900000000-f6b6229ef8c2d7fd24ab
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0159-2900000000-7c8549f8cd727886d67d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0002-0900000000-bcbf5073df33d11415cc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kb-0900000000-4a2a7c918368930693fa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014l-6900000000-125aac34eca51135b9d1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0900000000-56b8f9c6cad6a483eb62
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-9200000000-a1773c8925eed519e99d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0aor-5900000000-e23ee25dd8123c9b13ad
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a6u-9300000000-01a6c30b0567e12cc866
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	140.5843286	predicted	DarkChem Lite v0.1.0
[M-H]-	139.9190286	predicted	DarkChem Lite v0.1.0
[M-H]-	140.1475286	predicted	DarkChem Lite v0.1.0
[M-H]-	139.83556	predicted	DeepCCS 1.0 (2019)
[M+H]+	141.3247286	predicted	DarkChem Lite v0.1.0
[M+H]+	140.7224286	predicted	DarkChem Lite v0.1.0
[M+H]+	140.4529286	predicted	DarkChem Lite v0.1.0
[M+H]+	142.23112	predicted	DeepCCS 1.0 (2019)
[M+Na]+	140.5780286	predicted	DarkChem Lite v0.1.0
[M+Na]+	140.2162286	predicted	DarkChem Lite v0.1.0
[M+Na]+	140.3267286	predicted	DarkChem Lite v0.1.0
[M+Na]+	148.14365	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Alpha-1A adrenergic receptor

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

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]
Wellman PJ, Miller DK, Ho DH: Noradrenergic modulation of ephedrine-induced hypophagia. Synapse. 2003 Apr;48(1):18-24. [Article]
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]
Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]

Details2. Beta-1 adrenergic receptor

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

Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]

Details3. Beta-2 adrenergic receptor

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

Statler AK, Maani CV, Kohli A: Ephedrine . [Article]
FDA Approved Drug Products: Rezipres (Ephedrine Hydrochloride) Intravenous Injection [Link]

Details4. Sodium-dependent noradrenaline transporter

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

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]
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]
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]
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]

Enzymes

Details1. Cholinesterase

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

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]

Details2. Acetylcholinesterase

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

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

Details1. Serum albumin

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

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

Details1. Synaptic vesicular amine transporter

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

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]
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]
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]
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]
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]
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 at July 06, 2007 19:56 / Updated at February 20, 2024 23:54

Ephedrine

Identification

Structure for Ephedrine (DB01364)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Enzymes

References

References

Carriers

References

Transporters

References