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Details

Stereochemistry ABSOLUTE
Molecular Formula C76H52O46.C10H15NO
Molecular Weight 1866.4341
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPHEDRINE TANNATE

SMILES

c1c(cc(c(c1O)O)O)C(=O)Oc2cc(cc(c2O)O)C(=O)OC[C@]3([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O3)OC(=O)c4cc(c(c(c4)OC(=O)c5cc(c(c(c5)O)O)O)O)O)OC(=O)c6cc(c(c(c6)OC(=O)c7cc(c(c(c7)O)O)O)O)O)OC(=O)c8cc(c(c(c8)OC(=O)c9cc(c(c(c9)O)O)O)O)O)OC(=O)c%10cc(c(c(c%10)OC(=O)c%11cc(c(c(c%11)O)O)O)O)O.C[C@@]([H])([C@@]([H])(c1ccccc1)O)NC

InChI

InChIKey=FGPQMDDYPJHDFD-RDVHWUOCSA-N
InChI=1S/C76H52O46.C10H15NO/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-8(11-2)10(12)9-6-4-3-5-7-9/h1-20,52,63-65,76-101H,21H2;3-8,10-12H,1-2H3/t52-,63-,64+,65-,76+;8-,10-/m10/s1

HIDE SMILES / InChI

Molecular Formula C76H52O46
Molecular Weight 1701.2015
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.
1999 Mar
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.
1999 May
Guaifenesin- and ephedrine-induced stones.
1999 Nov
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
l-Ephedrine is a major constituent of Mao-Bushi-Saishin-To, one of the formulas of Chinese medicine, which shows immediate inhibition after oral administration of passive cutaneous anaphylaxis in rats.
2000 Aug
Olanzapine-induced urinary incontinence: treatment with ephedrine.
2000 Aug
Minidose bupivacaine-fentanyl spinal anesthesia for surgical repair of hip fracture in the aged.
2000 Jan
[Misuse of drugs in recreational sports].
2001 Apr
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.
2001 Apr 12
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
Study on the chiral recognition of the enantiomers of ephedrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-beta-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry.
2001 Apr 20
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.
2001 Apr-Jun
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
Hypokalemic metabolic acidosis attributed to cough mixture abuse.
2001 Aug
Application of carboxymethyl-beta-cyclodextrin as a chiral selector in capillary electrophoresis for enantiomer separation of selected neurotransmitters.
2001 Aug 17
Use of nonprescription weight loss products: results from a multistate survey.
2001 Aug 22-29
The trouble with fat-burner pills.
2001 Aug 27
Ephedra is linked to CNS, cardiovascular risks.
2001 Feb
Successful management of venous air embolism with inotropic support.
2001 Feb
Natural hazards. Tonic or toxic? Americans are gobbling up nature's remedies for everything from obesity to depression.
2001 Feb 12
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors].
2001 Jan
NCAA study of substance use and abuse habits of college student-athletes.
2001 Jan
Should the angiotensin II antagonists be discontinued before surgery?
2001 Jan
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
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
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
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.
2001 Mar
[Generalized edema following insulin treatment of newly diagnosed diabetes mellitus].
2001 Mar 20
Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters by Mannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines.
2001 Mar 8
Factitious hypertension by pseudoephedrine.
2001 Mar-Apr
Acute myocardial ischemia associated with ingestion of bupropion and pseudoephedrine in a 21-year-old man.
2001 May
Pharmacologic options available to treat symptomatic intradialytic hypotension.
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
Separation and determination of ephedrine alkaloids and tetramethylpyrazine in Ephedra sinica Stapf by gas chromatography-mass spectrometry.
2001 Sep
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
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 Sat Jun 26 13:37:06 UTC 2021
Edited
by admin
on Sat Jun 26 13:37:06 UTC 2021
Record UNII
1M92VL7U3I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPHEDRINE TANNATE
VANDF   WHO-DD  
Common Name English
EPHEDRINE TANNATE [VANDF]
Common Name English
EPHEDRINE TANNATE [WHO-DD]
Common Name English
Code System Code Type Description
CAS
1405-94-3
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY
DRUG BANK
DBSALT002746
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY
PUBCHEM
72941444
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY
FDA UNII
1M92VL7U3I
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY
RXCUI
221096
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY RxNorm
EVMPD
SUB128907
Created by admin on Sat Jun 26 13:37:06 UTC 2021 , Edited by admin on Sat Jun 26 13:37:06 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY