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

Details

Stereochemistry ACHIRAL
Molecular Formula C24H29NO4
Molecular Weight 395.4914
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHAVERINE

SMILES

CCOC1=CC=C(CC2=NC=CC3=C2C=C(OCC)C(OCC)=C3)C=C1OCC

InChI

InChIKey=ZOWYFYXTIWQBEP-UHFFFAOYSA-N
InChI=1S/C24H29NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-12,14-16H,5-8,13H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C24H29NO4
Molecular Weight 395.4914
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

In the US, Ethaverine is a member of the drug class peripheral vasodilators. It’s an alkaloid prepared synthetically from opium with no narcotic properties. Directly relaxes all smooth muscles, especially when they have been spasmodically contracted. Action is especially pronounced when spasm is present on coronary, cerebral, pulmonary, and peripheral arteries. Acts directly on myocardium like quinidine; depresses conduction and irritability, and prolongs refractory period. Primarily for peripheral and cerebral vascular insufficiency associated with arterial spasm; also a smooth muscle spasmolytic in spastic conditions of the GI and GU tracts. Adverse Effects ( 1%) CNS: Vertigo, headache, drowsiness. CV: Hypotension, arrhythmias. GI: Nausea, anorexia, abdominal distress, dry throat. Other: Malaise, flushing, sweating, lassitude, respiratory depression. Ethaverine may decrease levodopa effectiveness; morphine may antagonize smooth muscle relaxation effect of ethaverine.

CNS Activity

Curator's Comment: Adverse effect: Vertigo, headache, drowsiness

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Tumor- and drug-induced cutaneous neuro-phospholipidosis.
1975
Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents.
2001 Nov
Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensin.
2008 Jan 4
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation.
2009 Jun 25
Patents

Sample Use Guides

for adult: 100 mg t.i.d., may increase up to 200 mg t.i.d.
Route of Administration: Oral
In Vitro Use Guide
0.3-30 microM ethaverine on either side of the dihydropyridine-sensitive, L-type calcium channel from porcine cardiac muscle caused a reduction in the channel open probability (EC50 approximately 1 microM), with the higher concentrations inhibiting channel activity almost completely
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:58 GMT 2023
Record UNII
2H2HC19DYZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHAVERINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ethaverine [INN]
Common Name English
ETHQUINOL
Brand Name English
Ethaverine [WHO-DD]
Common Name English
1-(3,4-DIETHOXYBENZYL)-6,7-DIETHOXYISOQUINOLINE
Systematic Name English
ETHAVERINE [MI]
Common Name English
ETHAVERINE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
NCI_THESAURUS C333
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
Code System Code Type Description
PUBCHEM
3280
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
NCI_THESAURUS
C73332
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL1555736
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
DRUG CENTRAL
1077
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
SMS_ID
100000082615
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-633-3
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
INN
299
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023009
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
FDA UNII
2H2HC19DYZ
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
CAS
486-47-5
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
RXCUI
24464
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY RxNorm
EVMPD
SUB07272MIG
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY
MERCK INDEX
m5053
Created by admin on Fri Dec 15 15:19:58 GMT 2023 , Edited by admin on Fri Dec 15 15:19:58 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY