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

[H][C@@]12CC(C[C@H]3NCCC4=CC(OC)=C(OC)C=C34)=C(CC)CN1CCC5=CC(OC)=C(OC)C=C25

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
Ventricular tachycardia in a patient on dehydroemetine and chloroquine for amoebic liver abscess.
1979 May 5
Psychotrine and its O-methyl ether are selective inhibitors of human immunodeficiency virus-1 reverse transcriptase.
1991 Dec 15
Sonographic findings of hepatic lesions in human fascioliasis.
2003 Sep
In vitro activity of antiamoebic drugs against clinical isolates of Entamoeba histolytica and Entamoeba dispar.
2004 Dec 21
Development of a pharmacodynamic screening model with Entamoeba histolytica.
2007
Targeting HSP90 for cancer therapy.
2009 May 19
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:16:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:16:23 GMT 2023
Record UNII
7S79QT1T91
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
NSC-131546
Code 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 Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
Code System Code Type Description
FDA UNII
7S79QT1T91
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
DRUG CENTRAL
3129
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
CAS
4914-30-1
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
PUBCHEM
21022
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
INN
1796
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
NSC
131546
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
RXCUI
3142
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
DEHYDROEMETINE
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
MESH
C086742
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID901023600
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL1697741
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
DRUG BANK
DB13865
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
SMS_ID
100000083497
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
NCI_THESAURUS
C418
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
MERCK INDEX
m4144
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
225-542-7
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
CHEBI
149634
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
EVMPD
SUB06946MIG
Created by admin on Fri Dec 15 16:16:23 GMT 2023 , Edited by admin on Fri Dec 15 16:16:23 GMT 2023
PRIMARY
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