Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C10H15NO.H2O4S |
| Molecular Weight | 428.543 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C2=CC=CC=C2
InChI
InChIKey=CAVQBDOACNULDN-KHFUBBAMSA-N
InChI=1S/2C10H15NO.H2O4S/c2*1-8(11-2)10(12)9-6-4-3-5-7-9;1-5(2,3)4/h2*3-8,10-12H,1-2H3;(H2,1,2,3,4)/t2*8-,10-;/m00./s1
Ephedrine (l-form) is an alkaloid, which was initially purified from Ephedra plant. The extract form Ephedra has been used in China for medicinal purposes for several thousand years. Ephedrine acts as an agonist at alpha- and beta-adrenergic receptors and indirectly causes the release of norepinephrine from sympathetic neurons. The drug crosses the blood brain barrier and stimulates the central nervous system. Ephedrine products are now banned in many countries, as they are a major source for the production of the addictive compound methamphetamine. FDA has approved ephedrine only for the treatment of clinically important hypotension occurring in the setting of anesthesia.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P07550|||Q53GA6|||Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) |
0.36 µM [EC50] | ||
Target ID: CHEMBL2094251 |
4.95 null [pKi] | ||
Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) |
0.5 µM [EC50] | ||
Target ID: CHEMBL2095158 |
4.83 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | AKOVAZ Approved UseAKOVAZ injection is an alpha- and beta- adrenergic agonist and a norepinephrine-releasing agent that is indicated for the treatment of clinically important hypotension occurring in the setting of anesthesia. Launch Date2016 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
79.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
22 mg single, oral dose: 22 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPHEDRINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
87.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
11 mg 3 times / day multiple, oral dose: 11 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EPHEDRINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
22 mg single, oral dose: 22 mg route of administration: Oral experiment type: SINGLE co-administered: |
EPHEDRINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.69 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/973934/ |
11 mg 3 times / day multiple, oral dose: 11 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
EPHEDRINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Caffeine and exercise: metabolism, endurance and performance. | 2001 |
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| Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats. | 2001 |
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| Prevention of generalized reactions to contrast media: a consensus report and guidelines. | 2001 |
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| Recurrent ischaemic colitis associated with pseudoephedrine use. | 2001 Apr |
|
| Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats. | 2001 Apr 12 |
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| Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort. | 2001 Aug |
|
| Role of the atrial natriuretic factor in obstetric spinal hypotension. | 2001 Aug |
|
| Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section. | 2001 Aug |
|
| Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section. | 2001 Aug |
|
| Prevention and management of hypotension during spinal anaesthesia for elective Caesarean section: a survey of practice. | 2001 Aug |
|
| Hypokalemic metabolic acidosis attributed to cough mixture abuse. | 2001 Aug |
|
| Effect of caffeine and ephedrine ingestion on anaerobic exercise performance. | 2001 Aug |
|
| Asymmetric synthesis of chiral organofluorine compounds: use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors. | 2001 Aug 1 |
|
| Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters. | 2001 Aug 17 |
|
| Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis. | 2001 Aug 20 |
|
| Use of nonprescription weight loss products: results from a multistate survey. | 2001 Aug 22-29 |
|
| The trouble with fat-burner pills. | 2001 Aug 27 |
|
| Comparison of effects of remifentanil and alfentanil on cardiovascular response to tracheal intubation in hypertensive patients. | 2001 Jan |
|
| The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001 Jul |
|
| Pre-filled ephedrine syringes. | 2001 Jul |
|
| The olfactory G protein G(alphaolf) possesses a lower GDP-affinity and deactivates more rapidly than G(salphashort): consequences for receptor-coupling and adenylyl cyclase activation. | 2001 Jul |
|
| A stable gas chromatography-mass spectrometry analysis system to characterize Ma Huang products found in health foods and supplements. | 2001 Jul |
|
| New observations on the secondary chemistry of world Ephedra (Ephedraceae). | 2001 Jul |
|
| Reappearance of cardiac presynaptic sympathetic nerve terminals in the transplanted heart: correlation between PET using (11)C-hydroxyephedrine and invasively measured norepinephrine release. | 2001 Jul |
|
| Determination of ephedrines in urine by gas chromatography-mass spectrometry. | 2001 Jul 15 |
|
| Perioperative bradycardia and asystole: relationship to vasovagal syncope and the Bezold-Jarisch reflex. | 2001 Jun |
|
| Spinal anaesthesia for Caesarean section with bupivacaine 5 mg ml(-1) in glucose 8 or 80 mg ml(-1). | 2001 Jun |
|
| Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine. | 2001 Jun |
|
| Cold-syrup induced movement disorder. | 2001 Jun |
|
| Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section. | 2001 Mar |
|
| Extra-strong graduated compression stocking reduces usage of vasopressor agents during spinal anesthesia for cesarean section. | 2001 May |
|
| Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man. | 2001 May |
|
| Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard. | 2001 May-Jun |
|
| Neuropeptide Y in obese women during treatment with adrenergic modulation drugs. | 2001 May-Jun |
|
| Pharmacologic options available to treat symptomatic intradialytic hypotension. | 2001 Oct |
|
| The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes. | 2001 Oct |
|
| High performance liquid chromatography with UV detection for the simultaneous determination of sympathomimetic amines using 4-(4,5-diphenyl-1H-imidazole-2-yl)benzoyl chloride as a label. | 2001 Oct |
|
| Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations. | 2001 Sep |
|
| Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section. | 2001 Sep |
|
| Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry. | 2001 Sep |
|
| What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter? | 2001 Sep |
|
| Treatment of erectile dysfunction with sildenafil citrate (Viagra) in parkinsonism due to Parkinson's disease or multiple system atrophy with observations on orthostatic hypotension. | 2001 Sep |
|
| Studying the neuronal side of the synaptic cleft. A tool for investigating the paradox of sympathetic nervous system and heart failure in dilated cardiomyopathy. | 2001 Sep |
|
| Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations. | 2001 Sep |
|
| Rapid chiral on-chip separation with simplified amperometric detection. | 2001 Sep 14 |
|
| [Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit]. | 2001 Sep 24 |
|
| Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes. | 2001 Sep 5 |
|
| Effect of sympathetic reinnervation on cardiac performance after heart transplantation. | 2001 Sep 6 |
|
| A history of nebulization. | 2001 Spring |
|
| New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart. | 2001 Spring |
Sample Use Guides
The recommended dosages for the treatment of clinically important hypotension in the setting of
anesthesia is an initial dose of 5 to 10 mg administered by intravenous bolus. Administer additional boluses as needed, not to exceed a total dosage of 50 mg.
Route of Administration:
Intravenous
Segments of guinea-pig ileum were treated with 10(-6)-10(-3) M ephedrine. Ephedrine inhibited the ileal responses to transmural stimulation in the terminal and the proximal ileum with EC50 values of 57.2 and 85.5 uM, respectively. In the proximal part of the ileum, more than 70% of preparations were relaxed by ephedrine.
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C319
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CFR |
21 CFR 346.12
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21 CFR 341.16
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CFR |
21 CFR 341.20
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NCI_THESAURUS |
C87053
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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SUB13688MIG
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EPHEDRINE SULFATE
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless.Solubility: Freely soluble in water; sparingly soluble in ethanol (~750 g/l) TS.Category: Antiasthmatic drug.Storage: Ephedrine sulfate should be kept in a well-closed container, protected from light.Additional information: Ephedrine sulfate darkens on exposure to light. Even in the absence of light, it is gradually degraded onexposure to a humid atmosphere, the decomposition being faster at higher temperatures.RequirementsDefinition: Ephedrine sulfate contains not less than 98.0% and not more than 101.0% of (C10H15NO)2,H2SO4, calculated withreference to the dried substance. | ||
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100000078927
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91166
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DTXSID6020565
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U6X61U5ZEG
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DBSALT001503
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CHEMBL211456
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134-72-5
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C72765
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1236007
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m4933
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205-154-4
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U6X61U5ZEG
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5359318
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ACTIVE MOIETY
SUBSTANCE RECORD
