Details of the Drug

General Information of Drug (ID: DMCO5JZ)

Drug Name
SR141716A
Synonyms
Riobant; Slimona; [3H]SR141716A; Acomplia (TN); Bethin (TN); Monaslim (TN); Remonabent (TN); Rimonabant [USAN:INN]; Rimoslim (TN); Riobant (TN); Riomont (TN); Slimona (TN); Zimulti (TN); Rimonabant (JAN/USAN/INN); 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide; 5-(p-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidinopyrazole-3-carboxamide
Indication
Disease Entry ICD 11 Status REF
Obesity 5B81 Approved [1]
Therapeutic Class
Antiobesity Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 463.8
Logarithm of the Partition Coefficient (xlogp) 6.5
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 6 - 9 days [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C22H21Cl3N4O
IUPAC Name
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
Canonical SMILES
CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl
InChI
InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
InChIKey
JZCPYUJPEARBJL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
104850
ChEBI ID
CHEBI:34967
CAS Number
168273-06-1
DrugBank ID
DB06155
TTD ID
D0O3OS
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Antagonist [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alanine aminotransferase 1 (GPT) OTOXOA0Q ALAT1_HUMAN Gene/Protein Processing [4]
Aurora kinase B (AURKB) OTIY4VHU AURKB_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [6]
G1/S-specific cyclin-D1 (CCND1) OT8HPTKJ CCND1_HUMAN Gene/Protein Processing [6]
G2/mitotic-specific cyclin-B1 (CCNB1) OT19S7E5 CCNB1_HUMAN Gene/Protein Processing [5]
Hepatocyte nuclear factor 4-alpha (HNF4A) OTY1TOAB HNF4A_HUMAN Gene/Protein Processing [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Protein Interaction/Cellular Processes [6]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Protein Interaction/Cellular Processes [6]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [5]
Serine/threonine-protein kinase Chk1 (CHEK1) OTTTI622 CHK1_HUMAN Post-Translational Modifications [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Obesity
ICD Disease Classification 5B81
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cannabinoid receptor 1 (CB1) DTT CNR1 5.59E-02 -0.22 -0.45
Cannabinoid receptor 1 (CB1) DTT CNR1 7.68E-01 -0.06 -0.46
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
4 Endocannabinoid receptor blockade reduces alanine aminotransferase in polycystic ovary syndrome independent of weight loss. BMC Endocr Disord. 2017 Jul 14;17(1):41. doi: 10.1186/s12902-017-0194-2.
5 Rimonabant inhibits human colon cancer cell growth and reduces the formation of precancerous lesions in the mouse colon. Int J Cancer. 2009 Sep 1;125(5):996-1003. doi: 10.1002/ijc.24483.
6 The cannabinoid CB1 receptor antagonist rimonabant (SR141716) inhibits human breast cancer cell proliferation through a lipid raft-mediated mechanism. Mol Pharmacol. 2006 Oct;70(4):1298-306. doi: 10.1124/mol.106.025601. Epub 2006 Jul 5.
7 Rimonabant suppresses RNA transcription of hepatitis B virus by inhibiting hepatocyte nuclear factor 4. Microbiol Immunol. 2020 May;64(5):345-355. doi: 10.1111/1348-0421.12777. Epub 2020 Feb 25.