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Details

Stereochemistry ACHIRAL
Molecular Formula C22H21Cl3N4O
Molecular Weight 463.787
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIMONABANT

SMILES

CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(Cl)C=C(Cl)C=C3)C4=CC=C(Cl)C=C4

InChI

InChIKey=JZCPYUJPEARBJL-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21334892 | https://www.ncbi.nlm.nih.gov/pubmed/18712856 | https://www.ncbi.nlm.nih.gov/pubmed/21951309 | https://clinicaltrials.gov/ct2/show/record/NCT00228176 | https://clinicaltrials.gov/ct2/show/NCT00584389 | https://clinicaltrials.gov/ct2/show/NCT00576667 | https://www.ncbi.nlm.nih.gov/pubmed/7776817 | https://www.ncbi.nlm.nih.gov/pubmed/28315677

Rimonabant (also known as SR141716; trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects. Rimonabant is an inverse agonist for the cannabinoid receptor CB1 and was the first drug approved in that class. There is considerable evidence that the endocannabinoid (endogenous cannabinoid) system plays a significant role in appetitive drive and associated behaviors. It is, therefore, reasonable to hypothesize that the attenuation of the activity of this system would have therapeutic benefit in treating disorders that might have a component of excess appetitive drive or over-activity of the endocannabinoid system, such as obesity, ethanol and other drug abuse, and a variety of central nervous system and other disorders. Data from clinical trials submitted to regulatory authorities showed that rimonabant caused depressive disorders or mood alterations in up to 10% of subjects and suicidal ideation in around 1%, and in Europe, it was contraindicated for people with any psychiatric disorder, including depressed or suicidal people. Additionally, nausea and upper respiratory tract infections were very common (occurring in more than 10% of people) adverse effects; common adverse effects (occurring in between 1% and 10% of people) included gastroenteritis, anxiety, irritability, insomnia and other sleep disorders, hot flushes, diarrhea, vomiting, dry or itchy skin, tendonitis, muscle cramps and spasms, fatigue, flu-like symptoms, and increased risk of falling.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
11.22 nM [IC50]
1939.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Zimulti

Approved Use

Unknown
Primary
Zimulti

Approved Use

Unknown
Primary
Zimulti

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cannabinoid CB(1) receptors colocalize with tyrosine hydroxylase in cultured fetal mesencephalic neurons and their activation increases the levels of this enzyme.
2000 Feb 28
Cannabinoid-mediated inhibition of inducible nitric oxide production by rat microglial cells: evidence for CB1 receptor participation.
2001
Novel cannabinoid-sensitive receptor mediates inhibition of glutamatergic synaptic transmission in the hippocampus.
2001
Reduction of opioid dependence by the CB(1) antagonist SR141716A in mice: evaluation of the interest in pharmacotherapy of opioid addiction.
2001 Apr
Effect of vanilloid drugs on gastrointestinal transit in mice.
2001 Apr
The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism.
2001 Apr 20
CB1 cannabinoid receptor inhibits synaptic release of glutamate in rat dorsolateral striatum.
2001 Jan
Synergistic efects of opioid and cannabinoid antagonists on food intake.
2001 Jan 1
Effects of cannabinoids on prefrontal neuronal responses to ventral tegmental area stimulation.
2001 Jul
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat.
2001 Jul
Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis.
2001 Jul
Functional interaction between opioid and cannabinoid receptors in drug self-administration.
2001 Jul 15
Anandamide-induced sleep is blocked by SR141716A, a CB1 receptor antagonist and by U73122, a phospholipase C inhibitor.
2001 Jul 20
The synthetic cannabinoid WIN55,212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain.
2001 Jun
Endogenous cannabinoid anandamide increases heart resistance to arrhythmogenic effects of epinephrine: role of CB(1) and CB(2) receptors.
2001 Mar
2-Arachidonoylglycerol, a candidate of endothelium-derived hyperpolarizing factor.
2001 Mar
Pharmacological analysis of cannabinoid receptor activity in the rat vas deferens.
2001 Mar
Endogenous cannabinoids mediate retrograde signalling at hippocampal synapses.
2001 Mar 29
Presynaptic mechanisms underlying cannabinoid inhibition of excitatory synaptic transmission in rat striatal neurons.
2001 May 1
Effects of cannabinoids on adrenaline release from adrenal medullary cells.
2001 Nov
Rapid tolerance to Delta(9)-tetrahydrocannabinol and cross-tolerance between ethanol and Delta(9)-tetrahydrocannabinol in mice.
2001 Nov 16
The cannabinoid receptor antagonist SR 141716 prevents acquisition of drinking behavior in alcohol-preferring rats.
2001 Nov 2
Cannabinoid CB(1) receptor expression, activation and detection of endogenous ligand in trabecular meshwork and ciliary process tissues.
2001 Nov 23
Interaction of anandamide with the M(1) and M(4) muscarinic acetylcholine receptors.
2001 Oct 5
Effects of CB1 cannabinoid receptor blockade on ethanol preference after chronic ethanol administration.
2001 Sep
Cannabinoid effects on anxiety-related behaviours and hypothalamic neurotransmitters.
2001 Sep
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.
2001 Sep
Patents

Sample Use Guides

20-mg once daily
Route of Administration: Oral
The 661 W cells were seeded at 3×103 cells per well in 96-well plates and then incubated for 24 h. The entire medium was then replaced with fresh medium containing 1% fetal bovine serum. Rimonabant (Cayman Chemical, Ann Arbor, MI, USA) at 1–100 nM and trolox (Wako, Osaka, Japan) at 100 nM were added and, 1 h following treatment, the cells were exposed to 2500 lx of white fluorescent light (C-FPS115D; Nikon, Tokyo, Japan) for 24 h at 37 °C. The luminance was measured using a light meter, LM-332 (As One, Osaka, Japan). Nuclear staining assays were performed after an additional 24 h of incubation.
Name Type Language
RIMONABANT
EMA EPAR   INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
RIMONABANT [EMA EPAR]
Common Name English
Rimonabant [WHO-DD]
Common Name English
rimonabant [INN]
Common Name English
RIMONABANT [MART.]
Common Name English
ZIMULTI
Brand Name English
RIMONABANT [JAN]
Common Name English
RIMONABANT [MI]
Common Name English
SR-14171
Code English
SR-141716A
Code English
SR-141716
Code English
SR141716
Code English
RIMONABANT [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
EMA ASSESSMENT REPORTS ZIMULTI (WITHDRAWN: OBESITY)
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
EMA ASSESSMENT REPORTS ACOMPLIA (WITHDRAWN: OBESITY)
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
WHO-VATC QA08AX01
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
WHO-ATC A08AX01
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
Code System Code Type Description
INN
8029
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY
MESH
C089032
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY
WIKIPEDIA
RIMONABANT
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY
EVMPD
SUB21719
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PRIMARY
USAN
RR-26
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PRIMARY
SMS_ID
100000089586
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CHEBI
34967
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DRUG BANK
DB06155
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MERCK INDEX
m9625
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PRIMARY Merck Index
IUPHAR
743
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PRIMARY
NCI_THESAURUS
C73244
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
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FDA UNII
RML78EN3XE
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
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ChEMBL
CHEMBL111
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PRIMARY
EPA CompTox
DTXSID3046453
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PRIMARY
CAS
168273-06-1
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY
PUBCHEM
104850
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY
DRUG CENTRAL
4150
Created by admin on Sat Dec 16 05:43:01 GMT 2023 , Edited by admin on Sat Dec 16 05:43:01 GMT 2023
PRIMARY