Details of the Drug

General Information of Drug (ID: DMH7IPW)

Drug Name
Sarizotan
Synonyms
Sarizotan [INN]; EMD 128130; N-((3,4-Dihydro-2H-1-benzopyran-2-yl)methyl)-5-(4-fluorophenyl)-3-pyridinemethanamine; (-)-3-((((R)-2-Chromanylmethyl)amino)methyl)-5-(p-fluorophenyl)pyridine; 1-(3,4-dihydro-2H-chromen-2-yl)-N-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]methanamine
Indication
Disease Entry ICD 11 Status REF
Rett syndrome LD90.4 Phase 2/3 [1]
Parkinson disease 8A00.0 Discontinued in Phase 2 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 348.4
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C22H21FN2O
IUPAC Name
1-[(2R)-3,4-dihydro-2H-chromen-2-yl]-N-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]methanamine
Canonical SMILES
C1CC2=CC=CC=C2O[C@H]1CNCC3=CC(=CN=C3)C4=CC=C(C=C4)F
InChI
InChI=1S/C22H21FN2O/c23-20-8-5-17(6-9-20)19-11-16(12-24-14-19)13-25-15-21-10-7-18-3-1-2-4-22(18)26-21/h1-6,8-9,11-12,14,21,25H,7,10,13,15H2/t21-/m1/s1
InChIKey
HKFMQJUJWSFOLY-OAQYLSRUSA-N
Cross-matching ID
PubChem CID
6918388
ChEBI ID
CHEMBL220808
CAS Number
351862-32-3
UNII
467LU0UCUW
DrugBank ID
DB06454
TTD ID
D0W5EH
INTEDE ID
DR1872
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 Modulator [3]
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Modulator [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
D(2) dopamine receptor (DRD2) OTBLXKEG DRD2_HUMAN Protein Interaction/Cellular Processes [5]
D(3) dopamine receptor (DRD3) OT0OFFKB DRD3_HUMAN Protein Interaction/Cellular Processes [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Rett syndrome
ICD Disease Classification LD90.4
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
Dopamine D2 receptor (D2R) DTT DRD2 2.50E-02 -0.08 -0.49
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 1.82E-04 -1.35E-01 -5.84E-01
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 7.36E-01 1.62E-02 1.08E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 1.90E-01 -9.81E-03 -5.96E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Drugs used to treat Parkinson's disease, present status and future directions. CNS Neurol Disord Drug Targets. 2008 Oct;7(4):321-42.
3 Dual ligands targeting dopamine D2 and serotonin 5-HT1A receptors as new antipsychotical or anti-Parkinsonian agents.Curr Med Chem.2014;21(4):437-57.
4 In vitro characterization of sarizotan metabolism: hepatic clearance, identification and characterization of metabolites, drug-metabolizing enzyme identification, and evaluation of cytochrome p450 inhibition. Drug Metab Dispos. 2010 Jun;38(6):905-16.
5 Sarizotan, a serotonin 5-HT1A receptor agonist and dopamine receptor ligand. 1. Neurochemical profile. J Neural Transm (Vienna). 2004 Feb;111(2):113-26. doi: 10.1007/s00702-003-0094-7. Epub 2003 Dec 31.