Monlunabant

Chemical compound

Investigational

Identifiers

IUPAC name

N-[(E)-N′-[(Z)-C-[(4S)-5-(4-Chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]-N-[4-(trifluoromethyl)phenyl]sulfonylcarbonimidoyl]carbamimidoyl]acetamide

PubChem CID

164888943

UNII

4G8X27X87A

Chemical and physical dataFormulaC₂₆H₂₂ClF₃N₆O₃SMolar mass591.01 g·mol⁻¹

Monlunabant (INV-202, MRI-1891, or S-MRI-1891) is a peripherally selective cannabinoid receptor 1 inverse agonist, discovered as a β-arrestin-2-biased cannabinoid receptor 1 antagonist by the National Institutes of Health.^[1] It was developed as a weight loss drug by Inversago Pharma.^[2]^[3]^[4]

References

^ Liu, Ziyi; Iyer, Malliga R.; Godlewski, Grzegorz; Jourdan, Tony; Liu, Jie; Coffey, Nathan J.; Zawatsky, Charles N.; Puhl, Henry L.; Wess, Jürgen; Meister, Jaroslawna; Liow, Jeih-San; Innis, Robert B.; Hassan, Sergio A.; Lee, Yong Sok; Kunos, George; Cinar, Resat (11 June 2021). "Functional Selectivity of a Biased Cannabinoid-1 Receptor (CB 1 R) Antagonist". ACS Pharmacology & Translational Science. 4 (3): 1175–1187. doi:10.1021/acsptsci.1c00048. PMC 8204328.</
^ Crater, Glenn D.; Ravenelle, Francois; Lalonde, Karine; DespréS, Jean-Pierre (20 June 2023). "431-P: Effects of CB1 Antagonist INV-202 in Patients with Metabolic Syndrome—A Randomized, Placebo-Controlled, Double-Blind Phase 1B Study". Diabetes. 72 (Supplement_1). doi:10.2337/db23-431-P. S2CID 259384475.
^ Morris, C.R.; Chandrasekaran, R.; Butzirius, I.; Daphtary, N.; Aliyeva, M.; Bates, J.H.T.; Anathy, V.; Crater, G.D.; Gaucher, G.; Dixon, A.E. (May 2023). "Cannabinoid Receptor 1 Inverse Agonist, INV-202, Induces Weight Loss and Reduces Airway Hyperreactivity in a Mouse Model of Obese Asthma". B15. Asthma: Hot off the Press from the Bench to the Clinic. pp. A2759. doi:10.1164/ajrccm-conference.2023.207.1_MeetingAbstracts.A2759. S2CID 258446002.
^ Crater, Glenn D.; Lalonde, Karine; Ravenelle, François; Harvey, Michael; Després, Jean-Pierre (8 November 2023). "Effects of CB1R inverse agonist, INV -202, in patients with features of metabolic syndrome. A randomized, placebo-controlled, double-blind phase 1b study". Diabetes, Obesity and Metabolism. doi:10.1111/dom.15353. PMID 37941317.

Cannabinoid receptor modulators

Receptor
(ligands)

CB₁Tooltip Cannabinoid receptor type 1

Agonists (abridged, full list)	2-AG 2-AGE (noladin ether) 11-Hydroxy-THC α-Amyrin · β-Amyrin AB-CHMINACA AM-1172 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide Arvanil AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol (gallocatechin) Honokiol HU-210 JWH-007 JWH-015 JWH-018 JWH-073 Kavain L-759,633 Levonantradol Menabitan Nabilone Nabitan NADA O-1812 Oleamide Pravadoline Serinolamide A THC (dronabinol) UR-144 WIN 55,212-2 Yangonin
Inverse agonists	AM-251 INV-202 Monlunabant Rimonabant Surinabant Taranabant TM-38837 Zevaquenabant
Antagonists	AM-6545 Cannabidiol Cannabigerol Drinabant Falcarinol (carotatoxin) Hemopressin Ibipinabant LY-320,135 MK-9470 NESS-0327 O-2050 Otenabant PF-514273 PipISB Rosonabant Selonabant THCV VCHSR Virodhamine

CB₂Tooltip Cannabinoid receptor type 2

Agonists

Antagonists

NAGly
(GPR18)

Agonists	Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602
Antagonists	PSB-CB5 O-1918

GPR55

Agonists	2-AGE (noladin ether) 2-ALPI Abnormal cannabidiol AM-251 CID1011163 CID1252842 CID1792579 CP 55,940 GSK-494581A Lysophosphatidylinositol ML-184 ML-185 ML-186 O-1602 Oleoylethanolamide Palmitoylethanolamide THC (dronabinol)
Antagonists	Cannabidiol CID-16020046 ML-191 ML-192 ML-193 O-1918 PSB-SB-487 PSB-SB-1202 PSB-SB-1203 Tetrahydromagnolol

GPR119

Agonists	2-Oleoylglycerol Anandamide APD668 AR-231,453 AS-1269574 MBX-2982 N-Oleoyldopamine Oleoylethanolamide Olvanil PSN-375,963 PSN-632,408

Transporter
(modulators)

eCBTsTooltip Endocannabinoid transporter	Inhibitors: 5'-DMH-CBD AM-404 AM-1172 Arachidonoyl serotonin Arvanil Cannabidiol Guineensine LY-2183240 O-2093 OMDM-2 Paracetamol (acetaminophen) SB-FI-26 UCM-707 URB-597 VDM-11 WOBE490 WOBE491 WOBE492

Enzyme
(modulators)

FAAHTooltip Fatty acid amide hydrolase	Inhibitors: 4-Nonylphenylboronic acid AACOCF₃ AM-404 Arachidonoyl serotonin BIA 10-2474 Biochanin A Genistein IDFP JNJ-1661010 JNJ-42165279 JZL-195 Kaempferol LY-2183240 MAFP Palmitoylisopropylamide Paracetamol (acetaminophen) PF-3845 PF-750 Redafamdastat (JZP-150, PF-04457845) SA-47 SA-57 TAK 21d TC-F 2 UCM710 URB-597 Activators: PDP-EA
MAGL	Inhibitors: ABX-1431 IDFP JJKK 048 JW 642 JZL-184 JZL-195 JZP-361 KML 29 MAFP MJN110 NAM Pristimerin URB-602
ABHD6	Inhibitors: JZP-169 JZP-430 KT182 KT185 KT195 KT203 LEI-106 ML294 ML295 ML296 UCM710 WWL-70
ABHD12	Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat (tetrahydrolipstatin) Ursolic acid