Nolomirole

Pharmaceutical compound From Wikipedia, the free encyclopedia

Nolomirole (INNTooltip International Nonproprietary Name; developmental code name CHF-1035), also known as 5,6-diisobutyryloxy-N-methyl-2-aminotetralin, is a dual dopamine D2 and α2-adrenergic receptor agonist which was under development for the treatment of heart failure but was never marketed.[1][2][3][4] It is taken orally.[1][2]

Other namesCHF-1035; CHF1035; 5,6-Diisobutyryloxy-N-methyl-2-aminotetralin; 5,6-Diisobutyryloxy-2-(methylamino)-1,2,3,4-tetrahydronaphthalene; 5,6,7,8-Tetrahydro-6-(methylamino)-1,2-naphthylene diisobutyrate; N-Methyl-2-aminotetralin
Routes of
administrationOral[1][2]
Drug classDopamine D2 receptor agonist; α2-Adrenergic receptor agonist
ATC code
  • None
Quick facts Clinical data, Other names ...
Nolomirole
Clinical data
Other namesCHF-1035; CHF1035; 5,6-Diisobutyryloxy-N-methyl-2-aminotetralin; 5,6-Diisobutyryloxy-2-(methylamino)-1,2,3,4-tetrahydronaphthalene; 5,6,7,8-Tetrahydro-6-(methylamino)-1,2-naphthylene diisobutyrate; N-Methyl-2-aminotetralin
Routes of
administration		Oral[1][2]
Drug classDopamine D2 receptor agonist; α2-Adrenergic receptor agonist
ATC code
  • None
Identifiers
  • [6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H27NO4
Molar mass333.428 g·mol−1
3D model (JSmol)
  • CC(C)C(=O)OC1=C(C2=C(CC(CC2)NC)C=C1)OC(=O)C(C)C
  • 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
  • Key:OMMYLOLVPCCZQZ-UHFFFAOYSA-N
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Pharmacology

The drug acts as an agonist of the dopamine D2 receptor, with an affinity (Ki) of 120 nM for the (–)- enantiomer and 2,400 nM for the (+)- enantiomer, and as an agonist of the α2-adrenergic receptor, with an affinity (Ki) of 130 nM for the (–)- enantiomer and 1,600 nM for the (+)- enantiomer.[1][2] It is a prodrug of CHF-1024 (5,6-dihydroxy-N-methyl-2-aminotetralin), to which it is rapidly hydrolyzed by circulating esterase enzymes.[1] The elimination half-life of nolomirole is said to be 3 hours and its log P is 1.97.[3]

Chemistry

Nolomirole and its active form CHF-1024 are cyclized phenethylamines and 2-aminotetralin analogues of the catecholamine neurotransmitter dopamine and its N-methyl derivative epinine (deoxyepinephrine, N-methyldopamine).[1][2]

History

Nolomirole was first described in the scientific literature by 1992.[1][5] It was being developed by the pharmaceutical company Chiesi Farmaceutici in the 1990s and 2000s.[1][4] Nolomirole reached phase 3 clinical trials prior to the discontinuation of its development.[1][4]

See also

References

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