Details of the Drug

General Information of Drug (ID: DMDOQCV)

Drug Name
ABANOQUIL
Synonyms
TCMDC-131968; UNII-MAX6HQS78D; MAX6HQS78D; UK 52046; UK 52046 mesylate; UK-52,046; UK 52046-27; Abanoquil mesilate; 118931-00-3; AC1Q6WCW; 4-Amino-6,7-dimethoxy-2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)quinoline methanesulfonate; CHEMBL527515; AC1L4U62; SCHEMBL3672975; UK-52046-27; A807482; 4-Quinolinamine, 2-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)-6,7-dimethoxy-, monomethanesulfonate; 2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxy-quinolin-4-amine
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 395.5
Topological Polar Surface Area (xlogp) 3.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C22H25N3O4
IUPAC Name
2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-6,7-dimethoxyquinolin-4-amine
Canonical SMILES
COC1=C(C=C2CN(CCC2=C1)C3=NC4=CC(=C(C=C4C(=C3)N)OC)OC)OC
InChI
InChI=1S/C22H25N3O4/c1-26-18-7-13-5-6-25(12-14(13)8-19(18)27-2)22-10-16(23)15-9-20(28-3)21(29-4)11-17(15)24-22/h7-11H,5-6,12H2,1-4H3,(H2,23,24)
InChIKey
ANZIISNSHPKVRV-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
164089
CAS Number
90402-40-7
TTD ID
D0U3HP

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor alpha-1A (ADRA1A) TTNGILX ADA1A_HUMAN Inhibitor [1]
Adrenergic receptor alpha-1B (ADRA1B) TTBRKXS ADA1B_HUMAN Inhibitor [1]
Adrenergic receptor alpha-1D (ADRA1D) TT34BHT ADA1D_HUMAN Inhibitor [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Adrenergic receptor alpha-1A (ADRA1A) DTT ADRA1A 9.43E-01 -0.03 -0.25
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Alpha- and beta-adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification. J Med Chem. 1995 Sep 1;38(18):3415-44.
2 Mirtazapine treatment after conditioning with methamphetamine alters subsequent expression of place preference. Drug Alcohol Depend. 2009 Jan 1;99(1-3):231-9.
3 Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91.
4 Activation of alpha1-adrenoceptors inhibits growth hormone secretion in humans. Exp Clin Endocrinol Diabetes. 2009 Oct;117(9):460-2.
5 Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
6 A structure-activity relationship study of benzylic modifications of 4-[1-(1-naphthyl)ethyl]-1H-imidazoles on alpha 1- and alpha 2-adrenergic recep... J Med Chem. 1994 Jul 22;37(15):2328-33.
7 3-Benzisothiazolylpiperazine derivatives as potential atypical antipsychotic agents. J Med Chem. 1996 Jan 5;39(1):143-8.
8 An integrated in silico 3D model-driven discovery of a novel, potent, and selective amidosulfonamide 5-HT1A agonist (PRX-00023) for the treatment o... J Med Chem. 2006 Jun 1;49(11):3116-35.
9 A new arylpiperazine antipsychotic with high D2/D3/5-HT1A/alpha 1A-adrenergic affinity and a low potential for extrapyramidal effects. J Med Chem. 1994 Apr 15;37(8):1060-2.
10 Drug repositioning: identifying and developing new uses for existing drugs. Nat Rev Drug Discov. 2004 Aug;3(8):673-83.
11 Alpha- and beta-adrenoceptors: from the gene to the clinic. 2. Structure-activity relationships and therapeutic applications. J Med Chem. 1995 Sep 15;38(19):3681-716.
12 The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43.
13 Mechanisms of modafinil: A review of current research. Neuropsychiatr Dis Treat. 2007 June; 3(3): 349-364.
14 Alfuzosin: a review of the therapeutic use of the prolonged-release formulation given once daily in the management of benign prostatic hyperplasia. Drugs. 2002;62(4):633-53.
15 Pharmacokinetics of moxisylyte in healthy volunteers after intracavernous injection of increasing doses. Eur J Clin Pharmacol. 1996;49(5):411-5.
16 Induction of prostate apoptosis by alpha1-adrenoceptor antagonists: mechanistic significance of the quinazoline component. Prostate Cancer Prostatic Dis. 2002;5(2):88-95.
17 Bunazosin, a selective alpha1-adrenoceptor antagonist, as an anti-glaucoma drug: effects on ocular circulation and retinal neuronal damage. Cardiovasc Drug Rev. 2005 Spring;23(1):43-56.
18 The hypotensive effect of trimazosin is not caused solely by alpha 1-adrenoceptor blockade. J Cardiovasc Pharmacol. 1984 Jan-Feb;6(1):142-50.
19 Antihypertensive action and blockade of alpha1-adrenoceptors by DL-017, a quinazoline derivative. J Cardiovasc Pharmacol. 2001 Dec;38(6):893-9.
20 5-HT1A receptor ligands and their therapeutic applications: review of new patents.Expert Opin Ther Pat. 2018 Sep;28(9):679-689.
21 Pharmacophore identification of alpha(1A)-adrenoceptor antagonists. Bioorg Med Chem Lett. 2005 Feb 1;15(3):657-64.
22 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
23 Pharma & Vaccines. Product Development Pipeline. April 29 2009.
24 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
25 Alpha-Adrenergic activity and cardiovascular effects of besipirdine HCl (HP 749) and metabolite P7480 in vitro and in the conscious rat and dog. J Pharmacol Exp Ther. 1997 Apr;281(1):337-46.