EPHEDRINE SULFATE

US Approved OTC

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf | https://www.rcpe.ac.uk/sites/default/files/lee_0.pdf

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	Potency
Beta-2 adrenergic receptor 203 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	0.36 µM [EC50]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	4.95 null [pKi]
Beta-1 adrenergic receptor 158 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	0.5 µM [EC50]
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Agonist 2662	4.83 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anesthesia-induced hypotension 10 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208289s000lbl.pdf	Primary		Approved 8360	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

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
Achemtek	0104-020654	http://www.achemtek.com/299-42-3
Acorn PharmaTech	ACN-037777	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	A17.887.833	http://online.aurorafinechemicals.com/info?ID=A17.887.833
BioSynth	J-500280	https://www.biosynth.com/en/products/all-products/products/J-500280.html
Capot Chemical	PubChem5778	http://www.capotchem.com/en/5778.htm
Chem Scene	CS-4802	http://www.chemscene.com/Ephedrine.html
ChemMol	99067321	http://www.chemmol.com/chemmol/99067321.html
MedChem Express	HY-B1195	http://www.medchemexpress.com/Ephedrine.html
OChem	2694	http://www.ocheminc.com/index.php?act=psearch&pid=299E423
Parchem	26857	http://www.parchem.com/chemical-supplier-distributor/Ephedrine-016857.aspx
Sigma-Aldrich	134910_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/134910?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S007941	http://www.smolecule.com/products/s007941
Smolecule	S527246	http://www.smolecule.com/products/s527246
THE BioTek	bt-255443	https://www.thebiotek.com/product/inhibitors/bt-255443
THE BioTek	bt-267449	https://www.thebiotek.com/product/inhibitors/bt-267449
iChemical	EBD2203043	http://www.ichemical.com/products/299-42-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1217859840	https://mcule.com/MCULE-1217859840/

PubMed

Title	Date	PubMed
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.	1999 Mar	10407528
Guaifenesin- and ephedrine-induced stones.	1999 Nov	10608519
The haemodynamic effects of propofol in combination with ephedrine in elderly patients (ASA groups 3 and 4).	1999 Oct	10520387
An evaluation of l-ephedrine neurotoxicity with respect to hyperthermia and caudate/putamen microdialysate levels of ephedrine, dopamine, serotonin, and glutamate.	2000 May	10788568
Recurrent ischaemic colitis associated with pseudoephedrine use.	2001 Apr	11478350
The effects of ginseng, ephedrine, and caffeine on cognitive performance, mood and energy.	2001 Apr	11368507
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Stimulatory effect of D-ephedrine on beta3-adrenoceptors in adipose tissue of rats.	2001 Apr 12	11474539
Mass spectrometric quantitation of chiral drugs by the kinetic method.	2001 Apr 15	11338581
Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions.	2001 Apr 15	11338580
Dietary supplements containing ephedra alkaloids.	2001 Apr 5	11291668
Intrathecal anaesthesia for the elderly patient: the influence of the induction position on perioperative haemodynamic stability and patient comfort.	2001 Aug	11512648
Role of the atrial natriuretic factor in obstetric spinal hypotension.	2001 Aug	11506108
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.	2001 Aug	11506099
Dose of prophylactic intravenous ephedrine during spinal anesthesia for cesarean section.	2001 Aug	11498318
Hypokalemic metabolic acidosis attributed to cough mixture abuse.	2001 Aug	11479167
Effect of caffeine and ephedrine ingestion on anaerobic exercise performance.	2001 Aug	11474345
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	11472148
Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase from Zymomonas mobilis.	2001 Aug 20	11410856
The trouble with fat-burner pills.	2001 Aug 27	11534484
[Refractory hypotension sustained during general anesthesia due to chronic treatment with angiotensin-converting enzyme inhibitors].	2001 Jan	11234604
Should the angiotensin II antagonists be discontinued before surgery?	2001 Jan	11133595
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.	2001 Jan-Feb	11172511
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.	2001 Jan-Feb	11153535
Pre-filled ephedrine syringes.	2001 Jul	11463045
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	11461968
Determination of ephedrines in urine by gas chromatography-mass spectrometry.	2001 Jul 15	11486842
Hypotension in spinal anesthesia for cesarean section: a comparison of 0.5% hyperbaric bupivacaine and 5% hyperbaric lidocaine.	2001 Jun	11529341
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.	2001 Jun	11377047
Evaluation of pre-emptive intramuscular phenylephrine and ephedrine for reduction of spinal anaesthesia-induced hypotension during Caesarean section.	2001 Mar	11573527
Venlafaxine occupation at the noradrenaline reuptake site: in-vivo determination in healthy volunteers.	2001 Mar	11277612
High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.	2001 Mar	11277256
Induction with propofol target-concentration infusion vs. 8% sevoflurane inhalation and alfentanil in hypertensive patients.	2001 Mar	11251433
Ergogenic aids: counseling the athlete.	2001 Mar 1	11261867
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	11259059
Fulminant exacerbation of autoimmune hepatitis after the use of ma huang.	2001 May	11374728
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.	2001 May	11361053
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.	2001 May-Jun	11386016
Over-the-counter drug use in gymnasiums: an underrecognized substance abuse problem?	2001 May-Jun	11340414
Pharmacologic options available to treat symptomatic intradialytic hypotension.	2001 Oct	11602458
The anesthetic management of triplet cesarean delivery: a retrospective case series of maternal outcomes.	2001 Oct	11574371
Time-controlled release pseudoephedrine tablets: bioavailability and in vitro/in vivo correlations.	2001 Sep	11593992
Phenylephrine added to prophylactic ephedrine infusion during spinal anesthesia for elective cesarean section.	2001 Sep	11575540
What constitutes an effective but safe initial dose of lidocaine to test a thoracic epidural catheter?	2001 Sep	11524351
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	11492981
Kinetic spectrophotometric methods for the quantitation of triprolidine in bulk and in drug formulations.	2001 Sep	11470203
[Risk management by reporting critical incidents. Vitamin K and ephedrine mix-up at a birthing unit].	2001 Sep 24	11590951
Simultaneous quantitation of ephedrines in urine by gas chromatography-nitrogen-phosphorus detection for doping control purposes.	2001 Sep 5	11530984
Effect of sympathetic reinnervation on cardiac performance after heart transplantation.	2001 Sep 6	11547742
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart.	2001 Spring	11469712

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Jul 05 22:50:17 UTC 2023` Edited by `admin` on `Wed Jul 05 22:50:17 UTC 2023`
Record UNII	U6X61U5ZEG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPHEDRINE SULFATE

Common Name

English

Ephedrine sulfate [WHO-DD]

Common Name

English

EPHEDRINE SULFATE [WHO-IP]

Common Name

English

EPHEDRINI SULFAS [WHO-IP LATIN]

Common Name

English

EPHEDRINE SULFATE [MI]

Common Name

English

(-)-EPHEDRINE SULFATE (2:1) (SALT)

Common Name

English

EPHEDRINE SULFATE [VANDF]

Common Name

English

AKOVAZ

Common Name

English

(R-(R*,S*))-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZENEMETHANOL SULFATE (2:1) (SALT) [WHO-IP]

Systematic Name

English

EPHEDRINE SULFATE [USP-RS]

Common Name

English

EPHEDRINE SULFATE [USP MONOGRAPH]

Common Name

English

EPHEDRINE SULPHATE

Common Name

English

CORPHEDRA

Brand Name

English

EPHEDRINE SULFATE [ORANGE BOOK]

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (R-(R*,S*))-, SULFATE (2:1) (SALT)

Common Name

English

EPHEDRINE SULFATE [MART.]

Common Name

English

ISOFEDROL

Brand Name

English

EMERPHED

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319