Identification

Name
Racepinephrine
Accession Number
DB11124
Type
Small Molecule
Groups
Approved
Description

Racepinephrine is a racemic mixture consisting of d-Epinephrine and l-Epinephrine enantiomers. Epinephrine is a non-selective α- and β-adrenergic receptor agonist. It is a bronchodilator used in the temporary relief of mild symptoms of intermittent asthma including wheezing, tightness of chest and shortness of breath. It is an active ingredient in oral inhalation over-the-counter products as racepinephrine hydrochloride.

Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Racepinephrine hydrochloride336096P2WE329-63-5ATADHKWKHYVBTJ-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
S2Solution2.25 %Respiratory (inhalation)Nephron Pharmaceuticals Corporation1998-10-02Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AsthmanefrinSolution11.25 mg/0.5mLRespiratory (inhalation)Nephron Sc, Inc.2012-08-01Not applicableUs
Epi-MistAerosol, spray.594 mg/.120mLRespiratory (inhalation)Drnaturalhealing Inc2015-05-15Not applicableUs
S2Solution11.25 mg/0.5mLRespiratory (inhalation)Nephron Sc, Inc.2000-01-01Not applicableUs
S2Solution11.25 mg/.5mLRespiratory (inhalation)Cardinal Health2000-01-01Not applicableUs
Categories
UNII
GR0L9S3J0F
CAS number
329-65-7
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

Indicated for temporary relief of mild symptoms of intermittent asthma.

Pharmacodynamics

Epinephrine acts on α- and β-adrenergic receptors. When given subcutaneously or intramuscularly, epinephrine has a rapid onset and short duration of action [Label]. Epinephrine induces bronchial smooth muscle relaxation to relieve respiratory distress in asthma. In a clinical trial of paediatric patients with bronchiolitis, administration of aerosolized racemic epinephrine via inhalation resulted in improved clinical symptoms such as wheezing and retractions [1]. The clinical efficacy of racemic epinephrine was comparable to that of salbutamol or albuterol, which are commonly used bronchodilators [1, 2].

Mechanism of action

Epinephrine is a non-selective agonist at α- and β-adrenergic receptors, which are all G-protein-coupled receptors. The main therapeutic effect of epinephrine arises from its agonist action on β2-adrenergic receptors, which activate adenylyl cyclase and increase intracellular cyclic AMP production. Epinephrine causes smooth muscle relaxation on various tissues, including bronchial smooth muscles [3]. As a result, epinephrine serves to alleviate bronchospasm, wheezing and tightness of chest that may occur during asthmatic attacks [Label]. Via its relaxer effects on the smooth muscle of the stomach, intestine, uterus and urinary bladder, epinephrine may also alleviate pruritus, urticaria, and angioedema and may relieve gastrointestinal and genitourinary symptoms associated with anaphylaxis.

Epinephrine also acts on the α-adrenergic receptors on vascular smooth muscles, particularly in the skin and splanchnic vascular beds, to cause constriction. Epinephrine is thought to reduce capillary leakage by constricting precapillary arterioles, reducing hydrostatic pressure and consequently bronchial mucosal edema [1].

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-1B adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
AAlpha-2C adrenergic receptor
agonist
Human
ABeta-1 adrenergic receptor
agonist
Human
ABeta-2 adrenergic receptor
agonist
Human
AAlpha-1D adrenergic receptor
antagonist
Human
ABeta-3 adrenergic receptor
agonist
Human
Absorption

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Volume of distribution

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Protein binding

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Metabolism

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Route of elimination

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Half life

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Clearance

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for Epinephrine.

Toxicity

Oral LD50 of racepinephrine hydrochloride in mouse is 90 mg/kg [MSDS].

Overdosage of epinephrine may cause extremely elevated arterial pressure, which may further lead to cerebrovascular hemorrhage, particularly in elderly patients. Peripheral vascular constriction in conjunction with cardiac stimulation may produce pulmonary oedema. Treatment consists of rapidly acting vasodilators or alpha-adrenergic blocking drugs and/or respiratory support. Transient bradycardia followed by tachycardia may also be observed, and may be accompanied by potentially fatal cardiac arrhythmias. remature ventricular contractions may appear within one minute after injection and may be followed by multifocal ventricular tachycardia (prefibrillation rhythm). Subsidence of the ventricular effects may be followed by atrial tachycardia and occasionally by atrioventricular block. In case of arrhythmias, treatment should involve administration of a beta­ adrenergic blocking drug such as propranolol. Overdosage may also produce extreme pallor and coldness of the skin, metabolic acidosis, and kidney failure, which should each be treated with suitable corrective measures [Label].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-benzylimidazole1-benzylimidazole may decrease the hypertensive activities of Racepinephrine.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of 2,5-Dimethoxy-4-ethylamphetamine can be increased when used in combination with Racepinephrine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of 2,5-Dimethoxy-4-ethylthioamphetamine can be increased when used in combination with Racepinephrine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Racepinephrine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe therapeutic efficacy of 3,4-Methylenedioxyamphetamine can be increased when used in combination with Racepinephrine.
3,5-diiodothyropropionic acidThe therapeutic efficacy of Racepinephrine can be increased when used in combination with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyamphetamine can be increased when used in combination with Racepinephrine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Racepinephrine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Racepinephrine is combined with 7-Deazaguanine.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Racepinephrine is combined with 7,9-Dimethylguanine.
Food Interactions
Not Available

References

General References
  1. Langley JM, Smith MB, LeBlanc JC, Joudrey H, Ojah CR, Pianosi P: Racemic epinephrine compared to salbutamol in hospitalized young children with bronchiolitis; a randomized controlled clinical trial [ISRCTN46561076]. BMC Pediatr. 2005 May 5;5(1):7. doi: 10.1186/1471-2431-5-7. [PubMed:15876347]
  2. Reijonen T, Korppi M, Pitkakangas S, Tenhola S, Remes K: The clinical efficacy of nebulized racemic epinephrine and albuterol in acute bronchiolitis. Arch Pediatr Adolesc Med. 1995 Jun;149(6):686-92. [PubMed:7767427]
  3. 14. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 174-175, 181-182). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
External Links
PubChem Substance
347911128
Wikipedia
Racepinephrine
FDA label
Download (625 KB)
MSDS
Download (59.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableNot Yet RecruitingPreventionDysphonia / Postoperative pain / Swallowing Disorders1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Aerosol, sprayRespiratory (inhalation).594 mg/.120mL
SolutionRespiratory (inhalation)11.25 mg/0.5mL
SolutionRespiratory (inhalation)11.25 mg/.5mL
SolutionRespiratory (inhalation)2.25 %
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
PropertyValueSource
melting point (°C)157MSDS
water solubilitySolubleMSDS
Predicted Properties
Not Available
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
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
Kind
Protein
Organism
Human
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
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Epinephrine binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
Molecular Weight
49565.8 Da
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name
ADRA2C
Uniprot ID
P18825
Uniprot Name
Alpha-2C adrenergic receptor
Molecular Weight
49521.585 Da
Kind
Protein
Organism
Human
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
Kind
Protein
Organism
Human
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
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Alpha1-adrenergic receptor activity
Specific Function
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name
ADRA1D
Uniprot ID
P25100
Uniprot Name
Alpha-1D adrenergic receptor
Molecular Weight
60462.205 Da
Kind
Protein
Organism
Human
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. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 08:53