Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C9H13NO3.ClH |
| Molecular Weight | 219.6656 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNCC(c1ccc(c(c1)O)O)O.Cl
InChI
InChIKey=ATADHKWKHYVBTJ-UHFFFAOYSA-N
InChI=1S/C9H13NO3.ClH/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;/h2-4,9-13H,5H2,1H3;1H
| Molecular Formula | C9H13NO3 |
| Molecular Weight | 183.2048 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.4609 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Racepinephrine or racemic epinephrine is a mixture of levo and dextro isomers of epinephrine act as a nonselective agonist at adrenergic receptors. It is a bronchodilator used in the temporary relief of mild symptoms of intermittent asthma including wheezing, shortness of breath. Inhaled racepinephrine became available in September 2012 as a nonprescription treatment for bronchospasm based on a 1986 US Food and Drug Administration rule. Besides, racemic epinephrine relieves respiratory distress in hospitalized infants with bronchiolitis and is safe but does not abbreviate hospital stay. Morbidity associated with bronchiolitis as identified by parents persists for at least one week after hospital discharge in most infants.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2331074 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseFor temporary relief of mild symptoms of intermittent asthma: wheezing, tightness of chest, shortness of breath |
|||
| Palliative | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50 mg single, oral Overdose |
unknown, 2 years n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 Sources: |
Disc. AE: Hypertension, Tachycardia... AEs leading to discontinuation/dose reduction: Hypertension (5.4%) Sources: Tachycardia (5.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hypertension | 5.4% Disc. AE |
50 mg single, oral Overdose |
unknown, 2 years n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 Sources: |
| Tachycardia | 5.4% Disc. AE |
50 mg single, oral Overdose |
unknown, 2 years n = 1 Health Status: unknown Age Group: 2 years Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors. | 1988 Dec |
|
| Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor. | 1993 Dec |
|
| Carazolol: a potent, selective beta 3-adrenoceptor agonist. | 1995 Nov 30 |
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| Ligand efficacy and potency at recombinant alpha2 adrenergic receptors: agonist-mediated [35S]GTPgammaS binding. | 1998 Apr 1 |
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| [Experimental study of puerarin injection on the hemorheology in acute blood-stasis model rats]. | 2003 Dec |
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| Exercise-induced changes in plasma composition increase erythrocyte Na+,K+-ATPase, but not Na+-K+-2Cl- cotransporter, activity to stimulate net and unidirectional K+ transport in humans. | 2003 Dec 15 |
|
| Cardiovascular and autonomic responses to lower body negative pressure: do not explain gender differences in orthostatic tolerance. | 2003 Feb |
|
| Beta-adrenergic or parasympathetic inhibition, heart rate and cardiac output during normoxic and acute hypoxic exercise in humans. | 2003 Jul 15 |
|
| [Surface architectonics and cytoskeleton of erythrocytes and their modulation by adrenergic agents in patients with bronchial asthma]. | 2004 |
|
| Long-term stability study of L-adrenaline injections: Kinetics of sulfonation and racemization pathways of drug degradation. | 2004 Apr |
|
| Stereospecificity of horseradish peroxidase. | 2004 Dec |
|
| Cardiovascular responses of Chinook salmon (Oncorhynchus tshawytscha) during rapid anaesthetic induction and recovery. | 2004 Feb |
|
| Extravasation of blood-borne immunoglobulin G through blood-brain barrier during adrenaline-induced transient hypertension in the rat. | 2004 Jun |
|
| MAPK-dependent regulation of IL-1- and beta-adrenoreceptor-induced inflammatory cytokine production from mast cells: implications for the stress response. | 2004 Sep 21 |
|
| Transfusion-free pediatric burn surgery: techniques and strategies. | 2005 Feb |
|
| Catecholamines potentiate the effect of thyroid hormone on intestinal absorption of glucose in the rat. | 2005 Jun |
|
| Plasma levobupivacaine concentrations following scalp block in patients undergoing awake craniotomy. | 2005 Jun |
|
| Single dose oral clonidine premedication does not enhance postoperative, single low dose epidural morphine analgesia in hysterectomy patients. | 2005 Mar |
|
| Proinflammatory cytokine responses induced by influenza A (H5N1) viruses in primary human alveolar and bronchial epithelial cells. | 2005 Nov 11 |
|
| Opposite changes in imidazoline I2 receptors and alpha2-adrenoceptors density in rat frontal cortex after induced gliosis. | 2005 Nov 26 |
|
| Characterization of porcine beta1- and beta2-adrenergic receptors in heart, skeletal muscle, and adipose tissue, and the identification of an atypical beta-adrenergic binding site. | 2005 Oct |
|
| Method development for the enantiomeric purity determination of low concentrations of adrenaline in local anaesthetic solutions by capillary electrophoresis. | 2006 Apr 11 |
|
| [Adrenaline]. | 2006 Aug-Sep |
|
| [Experimental studies of rhizoma Astilbes chinensis on its effects in abirritation, blood activation, cough relieving and sputum elimination]. | 2006 Dec |
|
| Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006 Jan |
|
| [European Resuscitation Council guidelines for cardiopulmonary resuscitation in 2005]. | 2006 Jan-Feb |
|
| Strategies for enantioseparations of catecholamines and structurally related compounds by capillary zone electrophoresis using sulfated beta-cyclodextrins as chiral selectors. | 2006 Sep |
|
| Extracellular signal-regulated kinase 1/2-mediated transcriptional regulation of G-protein-coupled receptor kinase 3 expression in neuronal cells. | 2007 Apr |
|
| More PKA independent beta-adrenergic signalling via cAMP: is Rap1-mediated glucose uptake in vascular smooth cells physiologically important? | 2007 Jun |
|
| Stereospecificity of mushroom tyrosinase immobilized on a chiral and a nonchiral support. | 2007 May 30 |
|
| End-column chemiluminescence detection for pressurized capillary electrochromatographic analysis of norepinephrine and epinephrine. | 2007 Nov 2 |
|
| Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin. | 2008 |
|
| Optimal vasopressor drug therapy during resuscitation. | 2008 |
|
| Analysis of the antimicrobial activity of local anaesthetics used for dental analgesia. | 2008 Jan |
|
| Neuronal nitric oxide synthase gene inactivation reduces the expression of vasopressin in the hypothalamic paraventricular nucleus and of catecholamine biosynthetic enzymes in the adrenal gland of the mouse. | 2008 Jan |
|
| Electrical nerve stimulation or ultrasound guidance for lateral sagittal infraclavicular blocks: a randomized, controlled, observer-blinded, comparative study. | 2008 Jun |
|
| Analysis of efficacy of chiral adrenergic agonists. | 2008 Mar |
|
| The methylation, neurotransmitter, and antioxidant connections between folate and depression. | 2008 Sep |
|
| Caffeine and anaerobic performance: ergogenic value and mechanisms of action. | 2009 |
|
| Adrenaline-induced chronic ocular hypertension in adult rabbits. | 2009 Apr |
|
| Simultaneous separation of epinephrine and norepinephrine enantiomers by EKC: application to the analysis of pharmaceutical formulations. | 2009 Aug |
|
| Simultaneous determination of epinephrine, uric acid and xanthine in the presence of ascorbic acid using an ultrathin polymer film of 5-amino-1,3,4-thiadiazole-2-thiol modified electrode. | 2009 Aug 4 |
|
| Characteristics and outcome of cardiopulmonary resuscitation in hospitalised African children. | 2009 Jan |
|
| The impact of platelet function or C-reactive protein, on cardiovascular events after an acute myocardial infarction. | 2009 Jul 7 |
|
| Enhanced voltammetric detection of epinephrine at a carbon nanotube/nafion composite electrode in the presence of ascorbic acid. | 2009 Nov |
|
| Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse. | 2009 Oct |
|
| Activation of AMP-activated protein kinase by interleukin-6 in rat skeletal muscle: association with changes in cAMP, energy state, and endogenous fuel mobilization. | 2009 Sep |
|
| Job insecurity and change over time in health among older men and women. | 2010 Jan |
|
| Calcium deficiency in the early stages after weaning is associated with the enhancement of a low level of adrenaline-stimulated lipolysis and reduction of adiponectin release in isolated rat mesenteric adipocytes. | 2010 Jul |
|
| Vesicular monoamine transporters (VMATs) in adrenal chromaffin cells: stress-triggered induction of VMAT2 and expression in epinephrine synthesizing cells. | 2010 Nov |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:52:21 UTC 2021
by
admin
on
Fri Jun 25 20:52:21 UTC 2021
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| Record UNII |
336096P2WE
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C319
Created by
admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
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CFR |
21 CFR 341.16
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admin on Fri Jun 25 20:52:21 UTC 2021 , Edited by admin on Fri Jun 25 20:52:21 UTC 2021
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M4944
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C73826
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329-63-5
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206-346-0
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329-63-5
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CHEMBL1740
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1598097
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336096P2WE
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DBSALT001518
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5924
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314610
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SUB33967
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |