U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO.C9H10N4O4
Molecular Weight 403.4323
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE ACEFYLLINATE

SMILES

CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN2C3=C(N(CC(O)=O)C=N3)C(=O)N(C)C2=O

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 238.2001
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H15NO
Molecular Weight 165.2322
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
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.
1999 Mar
Pharmaceutical cost savings of treating obesity with weight loss medications.
1999 Nov
The haemodynamic effects of propofol in combination with ephedrine in elderly patients (ASA groups 3 and 4).
1999 Oct
Olanzapine-induced urinary incontinence: treatment with ephedrine.
2000 Aug
Caffeine and exercise: metabolism, endurance and performance.
2001
Prevention of generalized reactions to contrast media: a consensus report and guidelines.
2001
Recurrent ischaemic colitis associated with pseudoephedrine use.
2001 Apr
The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy.
2001 Apr
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
The many faces of ecstasy.
2001 Apr
The effects of an increase of central blood volume before spinal anesthesia for cesarean delivery: a qualitative systematic review.
2001 Apr
Mass spectrometric quantitation of chiral drugs by the kinetic method.
2001 Apr 15
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.
2001 Apr 15
Dietary supplements containing ephedra alkaloids.
2001 Apr 5
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective 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
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.
2001 Aug 17
Ephedra is linked to CNS, cardiovascular risks.
2001 Feb
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.
2001 Jan
Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999).
2001 Jan 15
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.
2001 Jan-Feb
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.
2001 Jan-Feb
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
Cold-syrup induced movement disorder.
2001 Jun
It's a rave new world: rave culture and illicit drug use in the young.
2001 Jun
[A case of pulmonary embolism associated with pneumatic tourniquet deflation].
2001 Mar
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.
2001 Mar
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.
2001 Mar
Ergogenic aids: counseling the athlete.
2001 Mar 1
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].
2001 Mar 20
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
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.
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
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
Effect of sympathetic reinnervation on cardiac performance after heart transplantation.
2001 Sep 6
A history of nebulization.
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 Thu Jul 06 13:32:42 UTC 2023
Edited
by admin
on Thu Jul 06 13:32:42 UTC 2023
Record UNII
69LH6U1N27
Record Status Validated (UNII)
Record Version
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Name Type Language
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 acefyllinate [WHO-DD]
Common Name English
EPHEDRINE THEOPHYLLINE-7-ACETATE
Common Name English
Code System Code Type Description
FDA UNII
69LH6U1N27
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
PUBCHEM
71289
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
SMS_ID
100000078945
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID00952151
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
EVMPD
SUB13684MIG
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
CAS
29701-08-4
Created by admin on Thu Jul 06 13:32:42 UTC 2023 , Edited by admin on Thu Jul 06 13:32:42 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY