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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30N2O8S
Molecular Weight 470.5384
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOCARPAMINE

SMILES

CCOC(=O)Oc1ccc(CCN=C([C@]([H])(CCSC)N=C(C)O)O)cc1OC(=O)OCC

InChI

InChIKey=ZLVMAMIPILWYHQ-INIZCTEOSA-N
InChI=1S/C21H30N2O8S/c1-5-28-20(26)30-17-8-7-15(13-18(17)31-21(27)29-6-2)9-11-22-19(25)16(10-12-32-4)23-14(3)24/h7-8,13,16H,5-6,9-12H2,1-4H3,(H,22,25)(H,23,24)/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H30N2O8S
Molecular Weight 470.5384
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/8529066

Docarpamine (marketed under the tradename Tanadopa) is a dopamine prodrug developed in Japan for the treatment of chronic heart failure. The drug does not cross the blood-brain barrier and shows no effect on CNS activity. It is supposed that the drug exerts its action by activating dopamine receptor D1.

CNS Activity

Curator's Comment:: Docarpamine itself does not cross the blood-brain barrier and shows no effect on CNS even at high dose. However, its active metabolite, dopamine, functions as a neurotransmitter in brain.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TANADOPA
PubMed

PubMed

TitleDatePubMed
Comparative study on the disposition of a new orally active dopamine prodrug, N-(N-acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine (TA-870) and dopamine hydrochloride in rats and dogs.
1988 Sep-Oct
A novel orally active dopamine prodrug TA-870. II. Evidence that TA-870 is a dopamine prodrug.
1989 Aug
A novel orally active dopamine prodrug TA-870. I. Renal and cardiovascular effects and plasma levels of free dopamine in dogs and rats.
1989 Jun
A novel orally active dopamine prodrug TA-870. III. Positive inotropic effect and cardiorenal selectivity in anesthetized dogs.
1990 Feb
Metabolism of dopamine prodrug, docarpamine.
1995 Jun
Patents

Sample Use Guides

2250 mg/day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:43:37 UTC 2021
Edited
by admin
on Fri Jun 25 22:43:37 UTC 2021
Record UNII
RPQ57D8S72
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOCARPAMINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
DOCARPAMINE [JAN]
Common Name English
DOCARPAMINE [MART.]
Common Name English
DOCARPAMINE [WHO-DD]
Common Name English
TANADOPA
Brand Name English
(-)-(S)-2-ACETAMIDO-N-(3,4-DIHYDROXYPHENETHYL)-4-(METHYLTHIO)BUTYRAMIDE BIS(ETHYL CARBONATE) (ESTER)
Common Name English
DOCARPAMINE [MI]
Common Name English
DOCARPAMINE [INN]
Common Name English
TA-870
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 701519
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
NCI_THESAURUS C66884
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
Code System Code Type Description
MESH
C052143
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
CAS
74639-40-0
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
DRUG CENTRAL
938
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL2106351
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
MERCK INDEX
M4711
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY Merck Index
EPA CompTox
74639-40-0
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
EVMPD
SUB06344MIG
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
FDA UNII
RPQ57D8S72
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
PUBCHEM
71137
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
INN
6258
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
NCI_THESAURUS
C65453
Created by admin on Fri Jun 25 22:43:37 UTC 2021 , Edited by admin on Fri Jun 25 22:43:37 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE ACTIVE -> PRODRUG
PLASMA; URINE
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE -> PARENT
PLASMA; URINE
Related Record Type Details
ACTIVE MOIETY