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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H38N2O4
Molecular Weight 478.623
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEHYDROEMETINE

SMILES

CCC1=C(C[C@H]2NCCC3=CC(OC)=C(OC)C=C23)C[C@@H]4N(CCC5=C4C=C(OC)C(OC)=C5)C1

InChI

InChIKey=XXLZPUYGHQWHRN-RPBOFIJWSA-N
InChI=1S/C29H38N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,24-25,30H,6-12,17H2,1-5H3/t24-,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H38N2O4
Molecular Weight 478.623
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Oral dehydroemetine dihydrochloride (+/-) (Mebadin) was found useful both as a tissue and contact amoebicide. It is much less toxic and more active than emetine and can be given in larger doses and for longer periods with safety. Owing to the quick excretion, repeat courses can be given at short intervals, as necessary, without danger. No serious side effects were noted particularly with the oral form and it was far better tolerated by children, who received relatively higher dosage than most adults. The only contra-indication is for patients with manifest decompensation of vital organs, or fevers. Mebadin injection and Mebadin tablets are discontinued products.

Approval Year

PubMed

PubMed

TitleDatePubMed
Targeting HSP90 for cancer therapy.
2009-05-19
Development of a pharmacodynamic screening model with Entamoeba histolytica.
2007
[Hepatic fasciolasis diagnosed in state phase].
2006-10-26
In vitro activity of antiamoebic drugs against clinical isolates of Entamoeba histolytica and Entamoeba dispar.
2004-12-21
Histopathology of cutaneous amebiasis.
2004-08
Sonographic findings of hepatic lesions in human fascioliasis.
2003-09
[Fasciola hepatica. study of a series of 37 patients].
2001-10
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992-09
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992-05-29
Psychotrine and its O-methyl ether are selective inhibitors of human immunodeficiency virus-1 reverse transcriptase.
1991-12-15
Ventricular tachycardia in a patient on dehydroemetine and chloroquine for amoebic liver abscess.
1979-05-05
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:23:40 GMT 2025
Edited
by admin
on Mon Mar 31 18:23:40 GMT 2025
Record UNII
7S79QT1T91
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-131546
Preferred Name English
DEHYDROEMETINE
INN   MI   WHO-DD  
INN  
Official Name English
RO-1-9334/19
Code English
(11BS)-3-ETHYL-1,6,7,11B-TETRAHYDRO-9,10-DIMETHOXY-2-(((1R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-4H-BENZO(A)QUINOLIZINE
Common Name English
RO 1-9334/19
Code English
Dehydroemetine [WHO-DD]
Common Name English
4H-BENZO(A)QUINOLIZINE, 3-ETHYL-1,6,7,11B-TETRAHYDRO-9,10-DIMETHOXY-2-(((1R)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-ISOQUINOLINYL)METHYL)-, (11BS)-
Common Name English
RO-1933419
Code English
dehydroemetine [INN]
Common Name English
DEHYDROEMETINE [MI]
Common Name English
(-)-2,3-DEHYDROEMETINE
Common Name English
3-ETHYL-9,10-DIMETHOXY-1,6,7,11B-TETRAHYDRO-2-((1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-ISOQUINOLYL)METHYL)-4H-BENZO(A)QUINOLIZINE
Common Name English
Classification Tree Code System Code
WHO-ATC P01AX09
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
Code System Code Type Description
FDA UNII
7S79QT1T91
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
DRUG CENTRAL
3129
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
CAS
4914-30-1
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
PUBCHEM
21022
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
INN
1796
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
NSC
131546
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
RXCUI
3142
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
DEHYDROEMETINE
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
MESH
C086742
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID901023600
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL1697741
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
DRUG BANK
DB13865
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
SMS_ID
100000083497
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
NCI_THESAURUS
C418
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
MERCK INDEX
m4144
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
225-542-7
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
CHEBI
149634
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
EVMPD
SUB06946MIG
Created by admin on Mon Mar 31 18:23:40 GMT 2025 , Edited by admin on Mon Mar 31 18:23:40 GMT 2025
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY