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Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO4
Molecular Weight 333.422
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOLOMIROLE

SMILES

CNC1CCC2=C(OC(=O)C(C)C)C(OC(=O)C(C)C)=CC=C2C1

InChI

InChIKey=OMMYLOLVPCCZQZ-UHFFFAOYSA-N
InChI=1S/C19H27NO4/c1-11(2)18(21)23-16-9-6-13-10-14(20-5)7-8-15(13)17(16)24-19(22)12(3)4/h6,9,11-12,14,20H,7-8,10H2,1-5H3

HIDE SMILES / InChI
Nolomirole (CHF1035) is an orally active, selective dopamine agonist, primarily activating DA2- and alpha2 receptors, thereby inhibiting norepinephrine release, which may be beneficial in heart failure. Nolomirole is able to attenuate the heart failure signs in the monocrotaline-induced congestive heart failure. CHF1035 is a mixture of two enantiomers, CHF1800 (+) and CHF1810 (-). CHF1035 and its metabolite CHF1024 significantly decreased the IOP in rabbits, and are potential novel IOP lowering agents. Especially, CHF1035 produced a substantial decrease in IOP for a prolonged period of time, and thus may prove useful in glaucoma therapy. Nolomirole is a pre-synaptic stimulator of DA2-dopaminergic and α2-adrenergic receptors in peripheral sympathetic nerve endings. These receptors act as a negative feedback mechanism, inhibiting norepinephrine secretion. In early phase clinical studies lasting 1–3 months, nolomirole reduced peripheral systemic resistance and 24 hour blood pressure and increased cardiac output. In a study of 29 patients with heart failure, followed for 10 days, a reduction in plasma norepinephrine was demonstrated. In spite of the fact that Nolomirole was in clinical trials for the treatment of heart failure, its development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Polymorphism of rac-5,6-diisobutyryloxy-2-methylamino-1,2,3,4-tetrahydro-naphthalene hydrochloride (CHF 1035). I. Thermal, spectroscopic, and X-ray diffraction properties.
2001 Aug
A novel D2-dopaminergic and alpha2-adrenoceptor receptor agonist induces substantial and prolonged IOP decrease in normotensive rabbits.
2003 Jun
Effect of nolomirole on monocrotaline-induced heart failure.
2004 Jan
Patents

Sample Use Guides

5 mg b.i.d. of nolomirole in patients with severe left ventricular systolic dysfunction, recently in New York Heart Association (NYHA) class III/IV. A dose of 5 mg b.i.d. of nolomirole was not beneficial (or harmful) in patients with heart failure.
Route of Administration: Oral
Name Type Language
NOLOMIROLE
INN  
INN  
Official Name English
nolomirole [INN]
Common Name English
PROPANOIC ACID, 2-METHYL-, 1,1'-(5,6,7,8-TETRAHYDRO-6-(METHYLAMINO)-1,2-NAPHTHALENEDIYL) ESTER
Common Name English
PROPANOIC ACID, 2-METHYL-, 5,6,7,8-TETRAHYDRO-6-(METHYLAMINO)-1,2-NAPHTHALENEDIYL ESTER
Common Name English
(±)-5,6,7,8-TETRAHYDRO-6-(METHYLAMINO)-1,2-NAPHTHYLENE DIISOBUTYRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
Code System Code Type Description
PUBCHEM
216238
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
FDA UNII
6EMF80C55F
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
MESH
C457559
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
SMS_ID
300000036955
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105142
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
INN
7554
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
CAS
90060-42-7
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY
NCI_THESAURUS
C75042
Created by admin on Fri Dec 15 16:20:09 GMT 2023 , Edited by admin on Fri Dec 15 16:20:09 GMT 2023
PRIMARY