DOCARPAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H30N2O8S
Molecular Weight	470.537
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)OC1=C(OC(=O)OCC)C=C(CCNC(=O)[C@H](CCSC)NC(C)=O)C=C1

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	470.537
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3466.1992.tb00239.x/abstract
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11996645	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic heart failure 21 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23676366	Primary		Approved 8429	TANADOPA Approved Use Unknown

PubMed

Title	Date	PubMed
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	2906602
A novel orally active dopamine prodrug TA-870. II. Evidence that TA-870 is a dopamine prodrug.	1989 Aug	2476589
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	2484082
A novel orally active dopamine prodrug TA-870. III. Positive inotropic effect and cardiorenal selectivity in anesthetized dogs.	1990 Feb	1689425
Metabolism of dopamine prodrug, docarpamine.	1995 Jun	8529066

Patents

Sample Use Guides

In Vivo Use Guide

2250 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:28:30 GMT 2023` Edited by `admin` on `Fri Dec 15 15:28:30 GMT 2023`
Record UNII	RPQ57D8S72
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOCARPAMINE

Official Name

English

DOCARPAMINE [JAN]

Common Name

English

DOCARPAMINE [MART.]

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

Docarpamine [WHO-DD]

Common Name

English

TA-870

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

701519