Details of the Drug

General Information of Drug (ID: DMS8JIU)

Drug Name
ADROGOLIDE HYDROCHLORIDE
Synonyms ABT-431; Adrogolide hydrochloride < USAN; DAS-431; A-93431.1; 9,10-Diacetoxy-2-propyl-4,5,5a(R),6,7,11b(S)-hexahydrobenzo[f]thieno[2,3-c]quinoline hydrochloride
Indication
Disease Entry ICD 11 Status REF
Cognitive impairment 6D71 Discontinued in Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
0		 Molecular Weight 436
Topological Polar Surface Area Not Available
Rotatable Bond Count 6
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 6
Chemical Identifiers
Formula
C22H26ClNO4S
IUPAC Name
[(1S,10R)-4-acetyloxy-15-propyl-14-thia-11-azatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17),15-pentaen-5-yl] acetate;hydrochloride
Canonical SMILES
CCCC1=CC2=C(S1)CN[C@H]3[C@H]2C4=CC(=C(C=C4CC3)OC(=O)C)OC(=O)C.Cl
InChI
InChI=1S/C22H25NO4S.ClH/c1-4-5-15-9-17-21(28-15)11-23-18-7-6-14-8-19(26-12(2)24)20(27-13(3)25)10-16(14)22(17)18;/h8-10,18,22-23H,4-7,11H2,1-3H3;1H/t18-,22+;/m1./s1
InChIKey
NPEZSCRKHFTLPE-MYXGOWFTSA-N
Cross-matching ID
PubChem CID
6918298
CAS Number
166591-11-3
TTD ID
D0N5JJ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dopamine D1 receptor (D1R) TTZFYLI DRD1_HUMAN Agonist [2], [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cognitive impairment
ICD Disease Classification 6D71
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Dopamine D1 receptor (D1R) DTT DRD1 8.99E-01 -0.06 -0.3
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800006590)
2 Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data. CNS Drug Rev. 2001 Fall;7(3):305-16.
3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4 Dopamine/serotonin receptor ligands. 9. Oxygen-containing midsized heterocyclic ring systems and nonrigidized analogues. A step toward dopamine D5 ... J Med Chem. 2004 Aug 12;47(17):4155-8.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20.
7 Etiology of iodinated radiocontrast nephrotoxicity and its attenuation by beraprost. Yakugaku Zasshi. 2008 Jul;128(7):1023-9.
8 Clinical pipeline report, company report or official report of Lundbeck.
9 A D1 receptor antagonist, ecopipam, for treatment of tics in Tourette syndrome.Clin Neuropharmacol.2014 Jan-Feb;37(1):26-30.
10 trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization o... J Med Chem. 2006 Nov 16;49(23):6848-57.
11 Therapeutic effects of dopamine D1/D2 receptor agonists on detrusor hyperreflexia in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned parkinso... J Pharmacol Exp Ther. 1998 Jul;286(1):228-33.
12 The D-1 dopamine receptor partial agonist, CY 208-243, exhibits antiparkinsonian activity in the MPTP-treated marmoset. Eur J Pharmacol. 1988 Nov 1;156(2):197-206.