RIMONABANT HYDROCHLORIDE

Possibly Marketed Outside US

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 Search

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
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trade names Acomplia, Zimulti) was an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects.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
Cannabinoid-mediated inhibition of inducible nitric oxide production by rat microglial cells: evidence for CB1 receptor participation.	2001	11727767
Pharmacological properties of cannabinoid receptors in the avian brain: similarity of rat and chicken cannabinoid1 receptor recognition sites and expression of cannabinoid2 receptor-like immunoreactivity in the embryonic chick brain.	2001 Apr	11322181
Cannabinoid inhibition of capsaicin-sensitive sensory neurotransmission in the rat mesenteric arterial bed.	2001 Apr 20	11334873
Modulation of cytokine responses in Corynebacterium parvum-primed endotoxemic mice by centrally administered cannabinoid ligands.	2001 Aug 3	11672577
The cannabinoid CB(1) receptor antagonist SR141716A increases norepinephrine outflow in the rat anterior hypothalamus.	2001 Aug 31	11527547
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.	2001 Aug 31	11514075
Inhibition of rat C6 glioma cell proliferation by endogenous and synthetic cannabinoids. Relative involvement of cannabinoid and vanilloid receptors.	2001 Dec	11714882
Control by the endogenous cannabinoid system of ras oncogene-dependent tumor growth.	2001 Dec	11687506
Effects of SR141716A on ethanol and sucrose self-administration.	2001 Feb	11236843
Intracerebral self-administration of the cannabinoid receptor agonist CP 55,940 in the rat: interaction with the opioid system.	2001 Feb 16	11226397
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.	2001 Jan 15	11226154
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.	2001 Jul	11553284
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat.	2001 Jul	11454655
Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis.	2001 Jul	11433348
Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology.	2001 Jul	11408519
Functional interaction between opioid and cannabinoid receptors in drug self-administration.	2001 Jul 15	11438610
CB1 receptor mediated analgesia from the Nucleus Reticularis Gigantocellularis pars alpha is activated in an animal model of neuropathic pain.	2001 Jul 20	11457432
Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors.	2001 Jul 6	11448486
The synthetic cannabinoid WIN55,212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain.	2001 Jun	11399676
The central cannabinoid receptor inactivation suppresses endocrine reproductive functions.	2001 Jun 8	11394887
Enhanced acetylcholine release in the hippocampus of cannabinoid CB(1) receptor-deficient mice.	2001 Mar	11250865
Cannabinoidergic and opioidergic inhibition of spinal reflexes in the decerebrated, spinalized rabbit.	2001 Mar	11249966
Cannabinoid inhibition of the capsaicin-induced calcium response in rat dorsal root ganglion neurones.	2001 Mar	11226126
Inhibitory effects of SR141716A on G-protein activation in rat brain.	2001 Mar 2	11239913
Spontaneous and precipitated withdrawal with a synthetic cannabinoid, WIN 55212-2.	2001 Mar 23	11282115
Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study.	2001 May 11	11426837
Cannabinoid receptor agonist-stimulated [35S]guanosine triphosphate gammaS binding in the brain of C57BL/6 and DBA/2 mice.	2001 May 15	11340650
Cannabinoids inhibit the formation of new synapses between hippocampal neurons in culture.	2001 May 15	11319244
Inhibition of peristaltic activity by cannabinoids in the isolated distal colon of mouse.	2001 May 25	11411800
[Antiarrhythmic properties of a cannabinoid (CB) receptor agonist].	2001 May-Jun	11558437
Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice.	2001 May-Jun	11420093
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	11420092
Precipitated cannabinoid withdrawal is reversed by Delta(9)-tetrahydrocannabinol or clonidine.	2001 May-Jun	11420084
Effects of cannabinoids on adrenaline release from adrenal medullary cells.	2001 Nov	11704653
Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats.	2001 Nov	11704633
Anandamide-induced relaxation of sheep coronary arteries: the role of the vascular endothelium, arachidonic acid metabolites and potassium channels.	2001 Nov	11682448
Inhibitory effect of palmitoylethanolamide on gastrointestinal motility in mice.	2001 Nov	11682441
Rapid tolerance to Delta(9)-tetrahydrocannabinol and cross-tolerance between ethanol and Delta(9)-tetrahydrocannabinol in mice.	2001 Nov 16	11728426
The cannabinoid receptor antagonist SR 141716 prevents acquisition of drinking behavior in alcohol-preferring rats.	2001 Nov 2	11711056
Cannabinoid CB(1) receptor expression, activation and detection of endogenous ligand in trabecular meshwork and ciliary process tissues.	2001 Nov 23	11730719
Mechanisms of anandamide-induced vasorelaxation in rat isolated coronary arteries.	2001 Oct	11606334
Cannabinoid receptor agonist WIN 55,212-2 inhibits rat cortical dialysate gamma-aminobutyric acid levels.	2001 Oct 15	11592127
The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2.	2001 Oct 26	11698062
SR141716, a CB1 receptor antagonist, decreases the sensitivity to the reinforcing effects of electrical brain stimulation in rats.	2001 Sep	11605080
Effects of CB1 cannabinoid receptor blockade on ethanol preference after chronic ethanol administration.	2001 Sep	11584151
Differential effects of anandamide on acetylcholine release in the guinea-pig ileum mediated via vanilloid and non-CB1 cannabinoid receptors.	2001 Sep	11522608
A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.	2001 Sep	11522594
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze.	2001 Sep	11522331
Cannabinoids attenuate capsaicin-evoked hyperalgesia through spinal and peripheral mechanisms.	2001 Sep	11514089
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice.	2001 Sep	11504797

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 19:02:35 GMT 2025` Edited by `admin` on `Mon Mar 31 19:02:35 GMT 2025`
Record UNII	HL0V2LQZ09
Record Status	`Validated (UNII)`
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Name

Type

Language

RIMONABANT HYDROCHLORIDE [MI]

Preferred Name

English

RIMONABANT HYDROCHLORIDE

Common Name

English

5-(4-CHLOROPHENYL)-1-(2,4-DICHLOROPHENYL)-4-METHYL-N-1-PIPERIDINYL-1H-PYRAZOLE-3-CARBOXAMIDE MONOHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

HL0V2LQZ09