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Details

Stereochemistry ACHIRAL
Molecular Formula C22H21Cl3N4O
Molecular Weight 463.788
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIMONABANT

SMILES

Cc1c(C(=NN2CCCCC2)O)nn(-c3ccc(cc3Cl)Cl)c1-c4ccc(cc4)Cl

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

Molecular Formula C22H21Cl3N4O
Molecular Weight 463.788
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects.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-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
Conditioned place preference induced by the cannabinoid agonist CP 55,940: interaction with the opioid system.
2001
Intravenous self-administration of the cannabinoid CB1 receptor agonist WIN 55,212-2 in rats.
2001 Aug
(R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide.
2001 Aug
The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: an in vivo and in vitro study.
2001 Aug
Inhibition of glioma growth in vivo by selective activation of the CB(2) cannabinoid receptor.
2001 Aug 1
Modulation of cytokine responses in Corynebacterium parvum-primed endotoxemic mice by centrally administered cannabinoid ligands.
2001 Aug 3
The cannabinoid CB(1) receptor antagonist SR141716A increases norepinephrine outflow in the rat anterior hypothalamus.
2001 Aug 31
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.
2001 Aug 31
Inhibition of rat C6 glioma cell proliferation by endogenous and synthetic cannabinoids. Relative involvement of cannabinoid and vanilloid receptors.
2001 Dec
Control by the endogenous cannabinoid system of ras oncogene-dependent tumor growth.
2001 Dec
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.
2001 Jul
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
Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology.
2001 Jul
Functional interaction between opioid and cannabinoid receptors in drug self-administration.
2001 Jul 15
Comparative characterization in the rat of the interaction between cannabinoids and opiates for their immunosuppressive and analgesic effects.
2001 Jul 2
CB1 receptor mediated analgesia from the Nucleus Reticularis Gigantocellularis pars alpha is activated in an animal model of neuropathic pain.
2001 Jul 20
Anandamide-induced sleep is blocked by SR141716A, a CB1 receptor antagonist and by U73122, a phospholipase C inhibitor.
2001 Jul 20
Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors.
2001 Jul 6
Endogenously produced cannabinoids and liver cirrhosis.
2001 Jul 7
Cannabinoid receptor agonist and antagonist effects on motor function in normal and 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP)-treated non-human primates.
2001 Jun
Cannabinoids and pain.
2001 Mar
Endogenous cannabinoid anandamide increases heart resistance to arrhythmogenic effects of epinephrine: role of CB(1) and CB(2) receptors.
2001 Mar
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth.
2001 May 11
Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study.
2001 May 11
[Antiarrhythmic properties of a cannabinoid (CB) receptor agonist].
2001 May-Jun
Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice.
2001 May-Jun
Delta-9-tetrahydrocannabinol differentially suppresses cisplatin-induced emesis and indices of motor function via cannabinoid CB(1) receptors in the least shrew.
2001 May-Jun
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.
2001 Nov
Inhibitory effect of palmitoylethanolamide on gastrointestinal motility in mice.
2001 Nov
Rapid tolerance to Delta(9)-tetrahydrocannabinol and cross-tolerance between ethanol and Delta(9)-tetrahydrocannabinol in mice.
2001 Nov 16
Cannabinoid CB(1) receptor expression, activation and detection of endogenous ligand in trabecular meshwork and ciliary process tissues.
2001 Nov 23
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.
2001 Oct
A cannabinoid mechanism in relapse to cocaine seeking.
2001 Oct
Cannabinoid CB1-receptor mediated regulation of gastrointestinal motility in mice in a model of intestinal inflammation.
2001 Oct
Cannabinoids inhibit nitric oxide production in bone marrow derived feline macrophages.
2001 Oct
Cannabinoid receptor agonist WIN 55,212-2 inhibits rat cortical dialysate gamma-aminobutyric acid levels.
2001 Oct 15
The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2.
2001 Oct 26
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
Differential effects of anandamide on acetylcholine release in the guinea-pig ileum mediated via vanilloid and non-CB1 cannabinoid receptors.
2001 Sep
A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.
2001 Sep
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze.
2001 Sep
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.
2001 Sep
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice.
2001 Sep
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.
2001 Sep 1
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:57:46 UTC 2021
Edited
by admin
on Sat Jun 26 09:57:46 UTC 2021
Record UNII
RML78EN3XE
Record Status Validated (UNII)
Record Version
  • Download
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 [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
RIMONABANT [WHO-DD]
Common Name 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 Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
EMA ASSESSMENT REPORTS ZIMULTI (WITHDRAWN: OBESITY)
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
EMA ASSESSMENT REPORTS ACOMPLIA (WITHDRAWN: OBESITY)
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
WHO-VATC QA08AX01
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
WHO-ATC A08AX01
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
Code System Code Type Description
INN
8029
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
MESH
C089032
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
WIKIPEDIA
RIMONABANT
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
EVMPD
SUB21719
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
DRUG BANK
DB06155
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
MERCK INDEX
M9625
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY Merck Index
IUPHAR
743
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
NCI_THESAURUS
C73244
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
FDA UNII
RML78EN3XE
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL111
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
EPA CompTox
168273-06-1
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
CAS
168273-06-1
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
PUBCHEM
104850
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
DRUG CENTRAL
4150
Created by admin on Sat Jun 26 09:57:46 UTC 2021 , Edited by admin on Sat Jun 26 09:57:46 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Rimonabant was the first CB1r antagonist to be approved for the treatment of obesity in Europe (Van Gaal et al., 2005; Henness et al., 2006). It was withdrawn from the market in 2008 because it was found to cause a significant drug-related risk of serious psychiatric disorders including anxiety and depression (Christensen et al., 2007).
Ki
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
Related Record Type Details
ACTIVE MOIETY