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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO.C9H10N4O4
Molecular Weight 403.433
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE ACEFYLLINATE

SMILES

C[C@@]([H])([C@@]([H])(c1ccccc1)O)NC.Cn1c2c(c(=O)n(C)c1=O)n(CC(=O)O)cn2

InChI

InChIKey=YSIIKGUQUONBTG-GNAZCLTHSA-N
InChI=1S/C10H15NO.C9H10N4O4/c1-8(11-2)10(12)9-6-4-3-5-7-9;1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h3-8,10-12H,1-2H3;4H,3H2,1-2H3,(H,14,15)/t8-,10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C9H10N4O4
Molecular Weight 238.2005
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H15NO
Molecular Weight 165.2326
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
0.36 µM [EC50]
4.95 null [pKi]
Target ID: P08588
Gene ID: 153.0
Gene Symbol: ADRB1
Target Organism: Homo sapiens (Human)
0.5 µM [EC50]
4.83 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AKOVAZ

Approved Use

AKOVAZ 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 Date

1.46188796E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
79.4 ng/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
6.75 h
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
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

PubMed

TitleDatePubMed
Caffeine and exercise: metabolism, endurance and performance.
2001
Effects of two atypical neuroleptics, olanzapine and risperidone, on the function of the urinary bladder and the external urethral sphincter in anesthetized rats.
2001
Prevention of generalized reactions to contrast media: a consensus report and guidelines.
2001
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
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.
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
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
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
Nutritional supplements as a source for positive doping cases?
2001 Jun
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.
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
Direct resolution of (+/-)-ephedrine and atropine into their enantiomers by impregnated TLC.
2001 May
Determination of ephedrine-type alkaloids in dietary supplements by LC/MS using a stable-isotope labeled internal standard.
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
Patents

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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:15:16 UTC 2021
Edited
by admin
on Fri Jun 25 23:15:16 UTC 2021
Record UNII
69LH6U1N27
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE ACEFYLLINATE
WHO-DD  
Common Name English
EPHEDRINE ACEFYLLINATE [WHO-DD]
Common Name English
BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-, 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXO-7H-PURINE-7-ACETATE (SALT)
Common Name English
7H-PURINE-7-ACETIC ACID, 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXO-, COMPD. WITH (R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL (1:1)
Systematic Name English
EPHEDRINE, 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXOPURINE-7-ACETATE (SALT), (-)-
Common Name English
PURINE-7-ACETIC ACID, 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXO-, COMPD. WITH (-)-EPHEDRINE (1:1)
Common Name English
EPHEDRINE THEOPHYLLINE-7-ACETATE
Common Name English
Code System Code Type Description
FDA UNII
69LH6U1N27
Created by admin on Fri Jun 25 23:15:16 UTC 2021 , Edited by admin on Fri Jun 25 23:15:16 UTC 2021
PRIMARY
PUBCHEM
71289
Created by admin on Fri Jun 25 23:15:16 UTC 2021 , Edited by admin on Fri Jun 25 23:15:16 UTC 2021
PRIMARY
EVMPD
SUB13684MIG
Created by admin on Fri Jun 25 23:15:16 UTC 2021 , Edited by admin on Fri Jun 25 23:15:16 UTC 2021
PRIMARY
CAS
29701-08-4
Created by admin on Fri Jun 25 23:15:16 UTC 2021 , Edited by admin on Fri Jun 25 23:15:16 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY