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 106 Target ID: CHEMBL2056 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11996645	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic heart failure 21 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23676366	Primary		Approved 8583	TANADOPA Approved Use Unknown

C_max

Value	Dose	Analyte	Population
63 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2119007D1031_1_08A_1F.pdf#page=20	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
53.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
62.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg 3 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
76.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
97 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2119007D1031_1_08A_1F.pdf#page=20	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
100.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
100 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg 3 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
97.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
0.7 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2119007D1031_1_08A_1F.pdf#page=20	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg 3 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DOPAMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10484011/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	DOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
59.5% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400315_2119007D1031_1_08A_1F.pdf#page=21 \| https://www.jstage.jst.go.jp/article/dmpk1986/6/2/6_2_277/_article/-char/en			DOCARPAMINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status:

Doses

Dose	Population	Adverse events
1500 mg single, oral Highest studied dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1971575/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1971575/	Sources: https://pubmed.ncbi.nlm.nih.gov/1971575/
750 mg 4 times / day multiple, oral Highest studied dose Dose: 750 mg, 4 times / day Route: oral Route: multiple Dose: 750 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14503971/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14503971/	Sources: https://pubmed.ncbi.nlm.nih.gov/14503971/

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 `Mon Mar 31 17:58:21 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:21 GMT 2025`
Record UNII	RPQ57D8S72
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOCARPAMINE

Official Name

English

TANADOPA

Preferred Name

English

DOCARPAMINE [JAN]

Common Name

English

DOCARPAMINE [MART.]

Common 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