TOBORINONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H24N2O5
Molecular Weight	384.4257
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CNCC(O)COC2=CC3=C(NC(=O)C=C3)C=C2)C=C1OC

InChI

InChIKey=BYKYPZBCMBEEGU-UHFFFAOYSA-N

InChI=1S/C21H24N2O5/c1-26-19-7-3-14(9-20(19)27-2)11-22-12-16(24)13-28-17-5-6-18-15(10-17)4-8-21(25)23-18/h3-10,16,22,24H,11-13H2,1-2H3,(H,23,25)

HIDE SMILES / InChI

Molecular Formula	C21H24N2O5
Molecular Weight	384.4257
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11060731
Curator's Comment: description was created based on several sources, including: DOI: 10.1111/j.1527-3466.1995.tb00306.x http://www.ncbi.nlm.nih.gov/pubmed/18465598

Toborinone is an inotropic agent. Positive inotropic effects are produced by Phosphodiesterase inhibition with resulting increase in cAMP and intracellular calcium levels. There is also marked venous and arterial vasodilating properties. With regards to human administration, toborinone is generally well-tolerated, though there are no available data regarding long-term tolerability and side effects. Toborinone can be combined with angiotensin-converting-enzyme inhibitors, nitrates and diuretics for the treatment of heart failure.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 3 61 Target ID: CHEMBL2094125 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11060731	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 106 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18465598 http://adisinsight.springer.com/drugs/800002217	Primary		Approved 8583	Toborinone Approved Use Toborinone is used to treat heart failure.

C_max

Value	Dose	Analyte	Population
102 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12017343/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
108 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12017343/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
244.26 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.05 mg/kg bw single, intravenous dose: 0.05 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
447.32 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.1 mg/kg bw single, intravenous dose: 0.1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1093.56 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.2 mg/kg bw single, intravenous dose: 0.2 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2334.14 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.4 mg/kg bw single, intravenous dose: 0.4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
33.57 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.5 mg/kg bw single, intravenous dose: 0.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
91.77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	1 mg/kg bw single, intravenous dose: 1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
205.97 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	2.5 mg/kg bw single, intravenous dose: 2.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
435.43 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	5 mg/kg bw single, intravenous dose: 5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
851.17 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1206.26 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
104 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
102 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
125 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
130 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
180.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(S)-(-)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
211.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(R)-(PLUS)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
483 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12017343/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
488 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12017343/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
52.38 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.05 mg/kg bw single, intravenous dose: 0.05 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
189.57 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.1 mg/kg bw single, intravenous dose: 0.1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
445.44 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.2 mg/kg bw single, intravenous dose: 0.2 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
835.86 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.4 mg/kg bw single, intravenous dose: 0.4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
42.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.5 mg/kg bw single, intravenous dose: 0.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
136.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	1 mg/kg bw single, intravenous dose: 1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
336.87 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	2.5 mg/kg bw single, intravenous dose: 2.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
752.33 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	5 mg/kg bw single, intravenous dose: 5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1399.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2044.13 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
498 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
623 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
735 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
694 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
261 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(S)-(-)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
297.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(R)-(PLUS)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.22 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.05 mg/kg bw single, intravenous dose: 0.05 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.1 mg/kg bw single, intravenous dose: 0.1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.2 mg/kg bw single, intravenous dose: 0.2 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.4 mg/kg bw single, intravenous dose: 0.4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	0.5 mg/kg bw single, intravenous dose: 0.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	1 mg/kg bw single, intravenous dose: 1 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	2.5 mg/kg bw single, intravenous dose: 2.5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	5 mg/kg bw single, intravenous dose: 5 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8163718/	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.74 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.78 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(S)-(-)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8106598/	5 μg/kg/min single, intravenous dose: 5 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	(R)-(PLUS)-TOBORINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
19.59% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
22.32% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
25.61% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
23.57% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12463726/	1 μg/kg/min single, intravenous dose: 1 μg/kg/min route of administration: Intravenous experiment type: SINGLE co-administered:	TOBORINONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 ug/kg/min single, intravenous Highest studied dose Dose: 15 ug/kg/min Route: intravenous Route: single Dose: 15 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/8163718/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8163718/	Sources: https://pubmed.ncbi.nlm.nih.gov/8163718/

PubMed

Title	Date	PubMed
Toborinone and olprinone, phosphodiesterase III inhibitors, inhibit human platelet aggregation due to the inhibition of both calcium release from intracellular stores and calcium entry.	2004	15127258
Clinical overview of the novel inotropic agent toborinone.	2000-05	11060731
Toborinone Otsuka Pharmaceutical Co Ltd.	1998-09	18465598

Patents

Sample Use Guides

In Vivo Use Guide

Patients received 1.25, 2.5, 5 or 10 ug/kg/min toborinone via a 6-h infusion.

Route of Administration: Other

In Vitro Use Guide

9.7 uM of Toborinone inhibits human platelet aggregation.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:19:14 GMT 2025` Edited by `admin` on `Mon Mar 31 19:19:14 GMT 2025`
Record UNII	1U1N0YXM99
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OPC-18790

Preferred Name

English

TOBORINONE

Official Name

English

Toborinone [WHO-DD]

Common Name

English

TOBORINONE [USAN]

Common Name

English

TOBORINONE [JAN]

Common Name

English

toborinone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744