DENOPAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23NO4
Molecular Weight	317.3795
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C=C(CCNC[C@H](O)C2=CC=C(O)C=C2)C=C1

InChI

InChIKey=VHSBBVZJABQOSG-INIZCTEOSA-N

InChI=1S/C18H23NO4/c1-22-17-8-3-13(11-18(17)23-2)9-10-19-12-16(21)14-4-6-15(20)7-5-14/h3-8,11,16,19-21H,9-10,12H2,1-2H3/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H23NO4
Molecular Weight	317.3795
Charge	0
Count

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

Description
Sources: https://medical.mt-pharma.co.jp/di/file/dc/kal.pdf

Denopamine is a selective agonist of beta-1 adrenergic receptor. The drug was approved in Japan under the name Kalgut for the treatment of chronic heart failure.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 163 Target ID: P08588 Gene ID: 153.0 Gene Symbol: ADRB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12487507	Agonist 2752		7.73 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic heart failure 21 Sources: https://medical.mt-pharma.co.jp/di/file/dc/kal.pdf	Primary		Approved 8583	KALGUT Approved Use Chronic heart failure. Launch Date 1988

C_max

Value	Dose	Analyte	Population
19.2 ng/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15.5 ng/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
16.9 ng/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
12.3 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
14.2 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
11.6 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
7.8 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10.7 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10.7 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
22.4 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
68.3 ng × h/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
57.2 ng × h/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
59.3 ng × h/mL DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
43.6 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
80.8 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
72.2 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
55.6 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
65.3 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
65.3 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
137 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
4.02 h DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4 h DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.67 h DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2 \| https://pubmed.ncbi.nlm.nih.gov/2229268/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.6 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.4 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.5 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.5 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.8 h EXPERIMENT https://www.jstage.jst.go.jp/article/jsdt1985/24/3/24_3_322/_article/-char/en	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DENOPAMINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
57% DRUG LABEL https://www.pmda.go.jp/PmdaSearch/iyakuDetail/ResultDataSetPDF/400315_2119004C1032_1_06#page=2			DENOPAMINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
10 mg 4 times / day multiple, oral Studied dose Dose: 10 mg, 4 times / day Route: oral Route: multiple Dose: 10 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8096549/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8096549/	Sources: https://pubmed.ncbi.nlm.nih.gov/8096549/

PubMed

Title	Date	PubMed
Binding pockets of the beta(1)- and beta(2)-adrenergic receptors for subtype-selective agonists.	1999-11	10531390
Cellular characterization of the pharmacological selectivity and tachyphylactic properties of denopamine for the human beta adrenergic receptors.	1993-11	7902433
Beta 1-adrenergic selectivity of the new cardiotonic agent denopamine in its stimulating effects on adenylate cyclase.	1987-06-15	3036156
Cardiovascular effects of the new positive inotropic agent denopamine with special reference to species difference and the effect on failing heart.	1986-07	3768073
Metabolic fate of the new cardiotonic denopamine in animals. 4th communication: effects of coadministered drugs on the plasma concentration and metabolism of denopamine in dogs.	1986-04	3718591
Metabolic fate of the new cardiotonic denopamine in animals. 2nd communication: tissue accumulation in the rat after consecutive oral administration of 14C-denopamine.	1986-04	3718589
In vitro metabolism of the new cardiotonic agent denopamine (TA-064) by rat and rabbit liver preparations. Oxidation, methylation, and glucuronidation.	1985-03-01	2859176
Relationship between positive inotropic action and blood levels of denopamine in cats.	1985	4026907
Cardiovascular effects of a new positive inotropic agent, (-)-(R)-1-(p-hydroxyphenyl)-2-[(3,4-dimethoxyphenethyl)amino]-ethanol (TA-064) in the anesthetized dog and isolated guinea pig heart.	1984-08	6150129

Patents

Sample Use Guides

In Vivo Use Guide

15-30 mg are administered orally in three divided doses.

Route of Administration: Oral

In Vitro Use Guide

The effects of denopamine on the L-type Ca2+ current (ICa) were examined in rabbit ventricular cells. Denopamine stimulated basal ICa with a maximum response of +33.2% and a concentration for half-maximal response (EC50) of 0.039 uM. The maximun response of ICa was only a quarter of that induced by isoprenaline (ISO), while 10 uM denopamine elicited 70–75% of the maximum inotropic response in the papillary muscle preparations.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:00 GMT 2025`
Record UNII	V5F60UPD8P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DENOPAMINE

Official Name

English

KALGUT

Preferred Name

English

TA-064

Code

English

DENOPAMINE [JAN]

Common Name

English

Denopamine [WHO-DD]

Common Name

English

(-)-(R)-.ALPHA.-(((3,4-DIMETHOXYPHENETHYL)AMINO)METHYL)-P-HYDROXYBENZYL ALCOHOL

Common Name

English

TA 064

Code

English

denopamine [INN]

Common Name

English

DENOPAMINE [MART.]

Common Name

English

DENOPAMINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149