Details of the Drug

General Information of Drug (ID: DMWHEV8)

Drug Name
[3H]spiperone
Synonyms
Spiperone; spiperone; Spiroperidol; Spiropitan; 749-02-0; Espiperona; Spiperonum; [3H]-spiperone; R 5147; Spiperonum [INN-Latin]; Espiperona [INN-Spanish]; E 525; UNII-4X6E73CJ0Q; NSC 170983; MLS000028615; Spiperone [USAN:INN:BAN:JAN]; 8-(3-(p-Fluorobenzoyl)propyl)-1-phenyl-1,3,8-triazaspiro(45)decan-4-one; 8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[45]decan-4-one; 8-(3-p-Fluorobenzoyl-1-propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decane; EINECS 212-024-0; BRN 0632204; SMR000058674; [3H]-spiperone; SPIPERONE
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 395.5
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C23H26FN3O2
IUPAC Name
8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Canonical SMILES
C1CN(CCC12C(=O)NCN2C3=CC=CC=C3)CCCC(=O)C4=CC=C(C=C4)F
InChI
InChI=1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)
InChIKey
DKGZKTPJOSAWFA-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5265
ChEBI ID
CHEBI:9233
CAS Number
749-02-0
UNII
4X6E73CJ0Q
DrugBank ID
DB17056
TTD ID
D05EQG
VARIDT ID
DR01493

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1A receptor (HTR1A) TTSQIFT 5HT1A_HUMAN Inhibitor [2]
5-HT 2A receptor (HTR2A) TTJQOD7 5HT2A_HUMAN Inhibitor [3]
5-HT 6 receptor (HTR6) TTJS8PY 5HT6R_HUMAN Inhibitor [4]
5-HT 7 receptor (HTR7) TTO9X1H 5HT7R_HUMAN Inhibitor [4]
Adrenergic receptor alpha-1A (ADRA1A) TTNGILX ADA1A_HUMAN Inhibitor [5]
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Antagonist [6]
Dopamine D3 receptor (D3R) TT4C8EA DRD3_HUMAN Antagonist [6]
Dopamine D4 receptor (D4R) TTE0A2F DRD4_HUMAN Antagonist [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
D(2) dopamine receptor (DRD2) OTBLXKEG DRD2_HUMAN Protein Interaction/Cellular Processes [9]
D(3) dopamine receptor (DRD3) OT0OFFKB DRD3_HUMAN Protein Interaction/Cellular Processes [10]
D(4) dopamine receptor (DRD4) OTAJTO7N DRD4_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 1A receptor (HTR1A) DTT HTR1A 1.49E-05 -0.22 -0.58
5-HT 6 receptor (HTR6) DTT HTR6 1.23E-05 -0.12 -0.71
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3300).
2 Synthesis of (R,S)-trans-8-hydroxy-2-[N-n-propyl-N-(3'-iodo-2'-propenyl)amino]tetral in (trans-8-OH-PIPAT): a new 5-HT1A receptor ligand. J Med Chem. 1993 Oct 15;36(21):3161-5.
3 Activity of Parthenolide at 5HT2A receptors. J Nat Prod. 1997 Jun;60(6):651-3.
4 Higher-end serotonin receptors: 5-HT(5), 5-HT(6), and 5-HT(7). J Med Chem. 2003 Jul 3;46(14):2795-812.
5 Pharmacophore identification of alpha(1A)-adrenoceptor antagonists. Bioorg Med Chem Lett. 2005 Feb 1;15(3):657-64.
6 Regulation of human D(1), d(2(long)), d(2(short)), D(3) and D(4) dopamine receptors by amiloride and amiloride analogues. Br J Pharmacol. 2000 Jul;130(5):1045-59.
7 Differential effects of [3H]nemonapride and [3H]spiperone binding on human dopamine D4 receptors. Neurosci Lett. 1995 Feb 17;186(2-3):145-8.
8 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
9 Melittin stimulates fatty acid release through non-phospholipase-mediated mechanisms and interacts with the dopamine transporter and other membrane-spanning proteins. Eur J Pharmacol. 2011 Jan 15;650(2-3):501-10. doi: 10.1016/j.ejphar.2010.10.023. Epub 2010 Oct 20.
10 Development of a bivalent dopamine D? receptor agonist. J Med Chem. 2011 Nov 24;54(22):7911-9. doi: 10.1021/jm2009919. Epub 2011 Oct 31.