RIMONABANT

Possibly Marketed Outside US

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 Search

SMILES

CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=CC=C(Cl)C=C3Cl)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

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

Description
Sources: https://www.drugbank.ca/drugs/DB06155
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trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects.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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21334892	Inverse Agonist 85		11.22 nM [IC50]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18712856	Inverse Agonist 85		1939.8 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Obesity 206 Sources: https://clinicaltrials.gov/ct2/show/NCT00584389	Primary	Approved 8583	Zimulti Approved Use Unknown
Fatty liver disease 10 Sources: https://clinicaltrials.gov/ct2/show/NCT00576667	Primary	Phase III 665	Zimulti Approved Use Unknown
Arteriosclerosis 3 Sources: https://clinicaltrials.gov/ct2/show/NCT00228176	Primary	Phase III 665	Zimulti Approved Use Unknown

C_max

Value	Dose	Analyte	Population
57.9 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	3 mg 1 times / day steady-state, oral dose: 3 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
118 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
196 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
326 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
416 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
188 ng/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
28.1 ng/mL DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/acomplia-epar-product-information_en.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
665 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	3 mg 1 times / day steady-state, oral dose: 3 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1480 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2960 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4830 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6760 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2480 ng × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2959.98 ng × h/mL DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/acomplia-epar-product-information_en.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
210 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	3 mg 1 times / day steady-state, oral dose: 3 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
180 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
216 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
193 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
151 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
376 h EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/j.clpt.2005.12.177	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9 day DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/acomplia-epar-product-information_en.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.1% DRUG LABEL https://www.ema.europa.eu/en/documents/product-information/acomplia-epar-product-information_en.pdf	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIMONABANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17098084/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17098084/	Disc. AE: Depressed mood disorders and disturbances, Anxiety... AEs leading to discontinuation/dose reduction: Depressed mood disorders and disturbances (3%) Anxiety (0.6%) Headache (0.6%) Dizziness (0.9%) Paraesthesia (0.6%) Nausea (1.5%) Vomiting (0.6%) Chest pain (0.6%) Asthenia (0.3%) Fatigue (0.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/17098084/
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18678611/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18678611/	Disc. AE: Psychiatric and behavioural symptoms NEC, Depressed mood... AEs leading to discontinuation/dose reduction: Psychiatric and behavioural symptoms NEC (5.1%) Depressed mood (2.2%) Nervous system disorder (3.6%) Paresthesia (2.2%) Dizziness (1.4%) Hyposmia (1.4%) Gastrointestinal disorder (2.9%) Anorexia (1.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/18678611/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inducer 1087	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 MRP2 499 MRP4 290 MRP3 246 BSEP 550 MRP1 116 CYP19A1 429 CYP2C19 2057	P-gp 2052 CYP2C19 1119	CYP3A 142 CYP1A1 151 CYP1A2 832 CYP2A 2

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	no [IC50 >0.02 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTExIn19	no [IC50 >0.02 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	no [IC50 >133 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/104850#section=Biological-Test-Results Page: 212.0	no
CYP1A1 272	inducer 1966 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 6.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 6.0	no
CYP2A 2	inducer 1966 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 6.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/104850#section=Biological-Test-Results Page: 274.0	no
CYP3A 317	inducer 1966 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 6.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/104850#section=Biological-Test-Results Page: 260.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf \| https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ== Page: 13.0	yes [IC50 0.0053 uM]	no (co-administration study) Comment: No effect of rimonabant (40 mg o.d. for 8 days and 6 days continued after warfarin administration) on the pharmacokinetics of warfarin (30 mg single dose), a narrow therapeutic index drug and a CYP2C9 substrate, was observed. Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf \| https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ== Page: 13.0
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	yes [IC50 <10 uM]
MRP1 232	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMDA0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	yes [Ki 1.4 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 12 \| 13	major	yes (co-administration study) Comment: Seven days of treatment with a daily oral dose of 200 mg ketoconazole increased Cmax, AUC0-24h, and AUCinf of rimonabant by 1.42 (90% C.I.: 1.18, 1.70), 1.55 (90% C.I.: 1.43, 1.68), and 2.04 (90% C.I.: 1.89, 2.23)-fold, respectively. Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 12 \| 13
CYP2C19 1119	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 12.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 12.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf Page: 12.0	no
P-gp 2052	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMSJ9fQ==	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTExIn19 \| https://www.ema.europa.eu/en/documents/scientific-discussion/acomplia-epar-scientific-discussion_en.pdf#page=5

PubMed

Title	Date	PubMed
Inhibition of rat C6 glioma cell proliferation by endogenous and synthetic cannabinoids. Relative involvement of cannabinoid and vanilloid receptors.	2001-12	11714882
Control by the endogenous cannabinoid system of ras oncogene-dependent tumor growth.	2001-12	11687506
Cannabinoid CB(1) receptor expression, activation and detection of endogenous ligand in trabecular meshwork and ciliary process tissues.	2001-11-23	11730719
Rapid tolerance to Delta(9)-tetrahydrocannabinol and cross-tolerance between ethanol and Delta(9)-tetrahydrocannabinol in mice.	2001-11-16	11728426
The cannabinoid receptor antagonist SR 141716 prevents acquisition of drinking behavior in alcohol-preferring rats.	2001-11-02	11711056
Effects of cannabinoids on adrenaline release from adrenal medullary cells.	2001-11	11704653
Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.	2001-11	11704633
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.	2001-11	11682448
Inhibitory effect of palmitoylethanolamide on gastrointestinal motility in mice.	2001-11	11682441
The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2.	2001-10-26	11698062
Cannabinoid receptor agonist WIN 55,212-2 inhibits rat cortical dialysate gamma-aminobutyric acid levels.	2001-10-15	11592127
Interaction of anandamide with the M(1) and M(4) muscarinic acetylcholine receptors.	2001-10-05	11578621
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.	2001-10	11606334
A cannabinoid mechanism in relapse to cocaine seeking.	2001-10	11590440
Cannabinoid activity curtails cocaine craving.	2001-10	11590424
Cannabinoid CB1-receptor mediated regulation of gastrointestinal motility in mice in a model of intestinal inflammation.	2001-10	11588110
Cannabinoids inhibit nitric oxide production in bone marrow derived feline macrophages.	2001-10	11587735
[Antiarrhythmic properties of a cannabinoid (CB) receptor agonist].	2001-09-18	11558437
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.	2001-09-01	11517236
SR141716, a CB1 receptor antagonist, decreases the sensitivity to the reinforcing effects of electrical brain stimulation in rats.	2001-09	11605080
Effects of CB1 cannabinoid receptor blockade on ethanol preference after chronic ethanol administration.	2001-09	11584151
Cannabinoid effects on anxiety-related behaviours and hypothalamic neurotransmitters.	2001-09	11566149
Differential effects of anandamide on acetylcholine release in the guinea-pig ileum mediated via vanilloid and non-CB1 cannabinoid receptors.	2001-09	11522608
A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.	2001-09	11522594
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze.	2001-09	11522331
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.	2001-09	11514089
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice.	2001-09	11504797
The cannabinoid CB(1) receptor antagonist SR141716A increases norepinephrine outflow in the rat anterior hypothalamus.	2001-08-31	11527547
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.	2001-08-31	11514075
Modulation of cytokine responses in Corynebacterium parvum-primed endotoxemic mice by centrally administered cannabinoid ligands.	2001-08-03	11672577
Inhibition of glioma growth in vivo by selective activation of the CB(2) cannabinoid receptor.	2001-08-01	11479216
Intravenous self-administration of the cannabinoid CB1 receptor agonist WIN 55,212-2 in rats.	2001-08	11498718
(R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide.	2001-08	11498713
The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: an in vivo and in vitro study.	2001-08	11459762
CB1 receptor mediated analgesia from the Nucleus Reticularis Gigantocellularis pars alpha is activated in an animal model of neuropathic pain.	2001-07-20	11457432
Anandamide-induced sleep is blocked by SR141716A, a CB1 receptor antagonist and by U73122, a phospholipase C inhibitor.	2001-07-20	11447321
Functional interaction between opioid and cannabinoid receptors in drug self-administration.	2001-07-15	11438610
Endogenously produced cannabinoids and liver cirrhosis.	2001-07-07	11454385
Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors.	2001-07-06	11448486
Comparative characterization in the rat of the interaction between cannabinoids and opiates for their immunosuppressive and analgesic effects.	2001-07-02	11431011
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.	2001-07	11553284
Effects of cannabinoids on prefrontal neuronal responses to ventral tegmental area stimulation.	2001-07	11488953
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat.	2001-07	11454655
Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis.	2001-07	11433348
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.	2001-06	11465637
Cannabinoids and pain.	2001-03	11575713
Endogenous cannabinoid anandamide increases heart resistance to arrhythmogenic effects of epinephrine: role of CB(1) and CB(2) receptors.	2001-03	11427912
Cannabinoid-mediated inhibition of inducible nitric oxide production by rat microglial cells: evidence for CB1 receptor participation.	2001	11727767
Novel cannabinoid-sensitive receptor mediates inhibition of glutamatergic synaptic transmission in the hippocampus.	2001	11564411
Conditioned place preference induced by the cannabinoid agonist CP 55,940: interaction with the opioid system.	2001	11457579

Patents

Sample Use Guides

In Vivo Use Guide

20-mg once daily

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 21:32:31 GMT 2025` Edited by `admin` on `Mon Mar 31 21:32:31 GMT 2025`
Record UNII	RML78EN3XE
Record Status	`Validated (UNII)`
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Name

Type

Language

ZIMULTI

Preferred Name

English

RIMONABANT

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

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