Racepinephrine

Identification

Name
Racepinephrine
Accession Number
DB11124
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.

Type
Small Molecule
Groups
Approved
Synonyms
Not Available

Pharmacology

Indication

Indicated for temporary relief of mild symptoms of intermittent asthma.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Humans
AAlpha-1B adrenergic receptor
agonist
Humans
AAlpha-2A adrenergic receptor
agonist
Humans
AAlpha-2B adrenergic receptor
agonist
Humans
AAlpha-2C adrenergic receptor
agonist
Humans
ABeta-1 adrenergic receptor
agonist
Humans
ABeta-2 adrenergic receptor
agonist
Humans
AAlpha-1D adrenergic receptor
antagonist
Humans
ABeta-3 adrenergic receptor
agonist
Humans
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.

Adverse Effects
Learn about our commercial Adverse Effects data.
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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
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 Racepinephrine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Racepinephrine.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Racepinephrine.
AcemetacinThe risk or severity of hypertension can be increased when Racepinephrine is combined with Acemetacin.
AcetazolamideThe risk or severity of Cardiac Arrhythmia can be increased when Racepinephrine is combined with Acetazolamide.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Racepinephrine is combined with Acetyldigitoxin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Racepinephrine.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Racepinephrine.
AcrivastineThe therapeutic efficacy of Racepinephrine can be increased when used in combination with Acrivastine.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Racepinephrine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid caffeine.

Products

Product Ingredients
IngredientUNIICASInChI Key
Racepinephrine hydrochloride336096P2WE329-63-5ATADHKWKHYVBTJ-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cord No2 Gingival RetractionPackingDentalGingi Pak Labs, Division Of Belport Co., Inc.1979-12-312004-08-16Canada flag
Cord No3PackingDentalGingi Pak Labs, Division Of Belport Co., Inc.1979-12-312004-08-16Canada flag
Cotton CoilPackingDentalGingi Pak Labs, Division Of Belport Co., Inc.1979-12-312004-08-16Canada flag
Crown Pak Retraction CordPackingDentalGingi Pak Labs, Division Of Belport Co., Inc.1979-12-312004-08-16Canada flag
Epidri 6%DentalPascal International Corporation1951-12-312005-06-23Canada flag
Epifrin 1/2%Solution / dropsOphthalmicAllergan1970-12-312010-01-26Canada flag
Epifrin 1%Solution / dropsOphthalmicAllergan1970-12-312010-01-26Canada flag
Epifrin 2%Solution / dropsOphthalmicAllergan1964-12-312010-01-26Canada flag
Epinephrine Inj 1:10000 SterileLiquidIntracardiac; IntravenousInternational Medication Systems, Limited1977-12-311997-08-15Canada flag
Gingi Pak CordPackingDentalGingi Pak Labs, Division Of Belport Co., Inc.1981-12-312004-08-16Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AsthmanefrinSolution11.25 mg/0.5mLRespiratory (inhalation)Nephron Sc, Inc.2012-08-01Not applicableUS flag
Epi-MistAerosol, spray.594 mg/.120mLRespiratory (inhalation)Drnaturalhealing Inc2015-05-15Not applicableUS flag
RacepinephrineSolution11.25 mg/0.5mLRespiratory (inhalation)Nucare Pharmaceuticals,inc.2000-01-01Not applicableUS flag
S2Solution11.25 mg/0.5mLRespiratory (inhalation)Nephron Sc, Inc.2000-01-01Not applicableUS flag
S2Solution11.25 mg/.5mLRespiratory (inhalation)Cardinal Health2000-01-012018-07-31US flag
S2 Racepinephrine MULTI-DOSESolution11.25 mg/0.5mLRespiratory (inhalation)Nephron Sc, Inc.1992-08-12Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Gingibraid W Alum Pot Sulf and Epin 0eRacepinephrine hydrochloride (0.2 mg) + Potassium alum (0.15 mg)PackingDentalVan R Dental Products Inc.1981-12-312007-07-31Canada flag
Gingibraid W Epineph and Alum 1eRacepinephrine hydrochloride (0.4 mg) + Potassium alum (0.25 mg)PackingDentalVan R Dental Products Inc.1981-12-312007-07-31Canada flag
Gingibraid W Epineph and Alum 2eRacepinephrine hydrochloride (0.6 mg) + Potassium alum (0.35 mg)PackingDentalVan R Dental Products Inc.1981-12-312007-07-31Canada flag
Gingibraid W Epineph and Alum 3eRacepinephrine hydrochloride (0.9 mg) + Potassium alum (0.55 mg)PackingDentalVan R Dental Products Inc.1981-12-312007-07-31Canada flag
Gingicord W Epineph and Alum Size No 1Racepinephrine hydrochloride (.4 mg) + Potassium alum (.2 mg)PackingDentalVan R Dental Products Inc.1981-12-312005-08-04Canada flag
Gingicord W Epineph and Alum Size No 3Racepinephrine hydrochloride (1.7 mg) + Potassium alum (.95 mg)PackingDentalVan R Dental Products Inc.1981-12-312005-08-04Canada flag
Gingicord W/epineph and Alum Size 2Racepinephrine hydrochloride (.7 mg) + Potassium alum (.37 mg)PackingDentalVan R Dental Products Inc.1981-12-312005-08-04Canada flag
Racord Two 7Racepinephrine hydrochloride (.225 mg) + Zinc phenolsulfonate (.4 mg)PackingDentalPascal International Corporation1992-12-311998-07-23Canada flag
Racord Two No 10Racepinephrine hydrochloride (.3 mg) + Zinc phenolsulfonate (1.45 mg)PackingDentalPascal International Corporation1996-08-141998-07-23Canada flag
Racord Two No 8Racepinephrine hydrochloride (.23 mg) + Zinc phenolsulfonate (.4 mg)PackingDentalPascal International Corporation1997-08-121998-07-23Canada flag

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
GR0L9S3J0F
CAS number
329-65-7

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]
  4. DailyMed: Asthmanefrin (racepinephrine) solution [Link]
PubChem Substance
347911128
RxNav
66887
Wikipedia
Epinephrine_(medication)
AHFS Codes
  • 12:12.12 — Alpha-and Beta-adrenergic Agonists
FDA label
Download (625 KB)
MSDS
Download (59.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentBronchiolitis1
3CompletedPreventionUlcerative Colitis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentUlcerative Colitis1
3RecruitingTreatmentHypogonadism1
2CompletedTreatmentPlasmodium Infections1
2RecruitingTreatmentIron Deficiency Anemia (IDA) / Iron-Deficiency Anemias1
2, 3Unknown StatusTreatmentTobacco Dependence1
1Active Not RecruitingTreatmentPeyronie's Disease1
1CompletedNot AvailableHealthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Aerosol, sprayRespiratory (inhalation).594 mg/.120mL
Solution / dropsOphthalmic
LiquidIntracardiac; Intravenous
PackingTopical
LiquidDental
LiquidDental8 %
SwabDental
SolutionRespiratory (inhalation)11.25 mg
SolutionRespiratory (inhalation)11.25 mg/.5mL
SolutionRespiratory (inhalation)11.25 mg/0.5mL
SolutionRespiratory (inhalation)22.5 mg/1mL
PackingDental
PackingDental
SolutionRespiratory (inhalation)
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

Targets

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
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
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
Molecular Weight
56835.375 Da
Kind
Protein
Organism
Humans
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
Humans
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
Humans
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
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
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
Kind
Protein
Organism
Humans
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
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. 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 September 17, 2020 23:28

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