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Details

Stereochemistry ACHIRAL
Molecular Formula C22H21Cl3N4O.ClH
Molecular Weight 500.248
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIMONABANT HYDROCHLORIDE

SMILES

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

InChI

InChIKey=REOYOKXLUFHOBV-UHFFFAOYSA-N
InChI=1S/C22H21Cl3N4O.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula C22H21Cl3N4O
Molecular Weight 463.787
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
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trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects.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
Inhibition of glioma growth in vivo by selective activation of the CB(2) cannabinoid receptor.
2001 Aug 1
Effects of SR141716A on ethanol and sucrose self-administration.
2001 Feb
Involvement of cannabinoids in the cardioprotection induced by lipopolysaccharide.
2001 Feb
Endocannabinoids control spasticity in a multiple sclerosis model.
2001 Feb
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
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
Endogenous cannabinoid anandamide increases heart resistance to arrhythmogenic effects of epinephrine: role of CB(1) and CB(2) receptors.
2001 Mar
Cannabinoidergic and opioidergic inhibition of spinal reflexes in the decerebrated, spinalized rabbit.
2001 Mar
Novel pyrazole cannabinoids: insights into CB(1) receptor recognition and activation.
2001 Mar
Inhibitory effects of SR141716A on G-protein activation in rat brain.
2001 Mar 2
Spontaneous and precipitated withdrawal with a synthetic cannabinoid, WIN 55212-2.
2001 Mar 23
Endogenous cannabinoids mediate retrograde signalling at hippocampal synapses.
2001 Mar 29
Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.
2001 Nov
Cannabinoid activity curtails cocaine craving.
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
Interaction of anandamide with the M(1) and M(4) muscarinic acetylcholine receptors.
2001 Oct 5
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 Fri Dec 15 18:06:50 GMT 2023
Edited
by admin
on Fri Dec 15 18:06:50 GMT 2023
Record UNII
HL0V2LQZ09
Record Status Validated (UNII)
Record Version
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Name Type Language
RIMONABANT HYDROCHLORIDE
MI  
Common Name English
5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYL-N-1-PIPERIDINYL-1H-PYRAZOLE-3-CARBOXAMIDE MONOHYDROCHLORIDE
Systematic Name English
RIMONABANT HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
FDA UNII
HL0V2LQZ09
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
PRIMARY
CAS
158681-13-1
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
PRIMARY
MERCK INDEX
m9625
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID20166495
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
PRIMARY
DRUG BANK
DB06155
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
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PUBCHEM
104849
Created by admin on Fri Dec 15 18:06:50 GMT 2023 , Edited by admin on Fri Dec 15 18:06:50 GMT 2023
PRIMARY
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