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MedKoo Cat#: 525564 | Name: Aticaprant
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aticaprant, also known as JNJ-67953964, LY-2456302 and CERC-501, is a potent, selective, short-acting antagonist of the κ-opioid receptor (KOR) (Ki = 0.81 nM vs. 24.0 nM and 155 nM for the μ-opioid receptor (MOR) and δ-opioid receptor (DOR). Aticaprant is under development for the treatment of major depressive disorder and substance use disorders including alcoholism, nicotine addiction, and illicit drug dependence. Aticaprant has been found to dose-dependently block fentanyl-induced miosis at 25 mg and 60 mg in humans (with minimal to no blockade at doses of 4 to 10 mg), indicating that the drug significantly occupies and antagonizes the MOR at a dose of at least 25 mg but not of 10 mg or less.

Chemical Structure

Aticaprant
Aticaprant
CAS#1174130-61-0

Theoretical Analysis

MedKoo Cat#: 525564

Name: Aticaprant

CAS#: 1174130-61-0

Chemical Formula: C26H27FN2O2

Exact Mass: 418.2057

Molecular Weight: 418.51

Elemental Analysis: C, 74.62; H, 6.50; F, 4.54; N, 6.69; O, 7.65

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Synonym
Aticaprant; JNJ-67953964; JNJ 67953964; JNJ67953964; LY-2456302; LY 2456302; LY2456302; CERC-501; CERC 501; CERC501;
IUPAC/Chemical Name
Benzamide, 4-(4-(((2S)-2-(3,5-dimethylphenyl)-1-pyrrolidinyl)methyl)phenoxy)-3-fluoro-
InChi Key
ZHPMYDSXGRRERG-DEOSSOPVSA-N
InChi Code
InChI=1S/C26H27FN2O2/c1-17-12-18(2)14-21(13-17)24-4-3-11-29(24)16-19-5-8-22(9-6-19)31-25-10-7-20(26(28)30)15-23(25)27/h5-10,12-15,24H,3-4,11,16H2,1-2H3,(H2,28,30)/t24-/m0/s1
SMILES Code
O=C(N)C1=CC=C(OC2=CC=C(CN3[C@H](C4=CC(C)=CC(C)=C4)CCC3)C=C2)C(F)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 418.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zhou Y, Zhou DC, Kreek MJ. Aticaprant (Clinically Developed Kappa-Opioid Receptor Antagonist) Combined With Naltrexone Prevents Alcohol "Relapse" Drinking. J Pharm Pharmacol (Los Angel). 2022 May;9(1):10.13188/2327-204x.1000032. doi: 10.13188/2327-204x.1000032. Epub 2022 May 16. PMID: 35832748; PMCID: PMC9275124. 2: Jacobson ML, Wulf HA, Browne CA, Lucki I. The kappa opioid receptor antagonist aticaprant reverses behavioral effects from unpredictable chronic mild stress in male mice. Psychopharmacology (Berl). 2020 Dec;237(12):3715-3728. doi: 10.1007/s00213-020-05649-y. Epub 2020 Sep 7. PMID: 32894343; PMCID: PMC7686052. 3: Jacobson ML, Wulf HA, Tsuda MC, Browne CA, Lucki I. Sex differences in the modulation of mouse nest building behavior by kappa opioid receptor signaling. Neuropharmacology. 2020 Oct 15;177:108254. doi: 10.1016/j.neuropharm.2020.108254. Epub 2020 Jul 26. PMID: 32726598. 4: Reed B, Butelman ER, Kreek MJ. Kappa Opioid Receptor Antagonists as Potential Therapeutics for Mood and Substance Use Disorders. Handb Exp Pharmacol. 2022;271:473-491. doi: 10.1007/164_2020_401. PMID: 33174064. 5: Chen H, Wu ZZ, Shao DY, Huang PQ. Multicatalysis protocol enables direct and versatile enantioselective reductive transformations of secondary amides. Sci Adv. 2022 Nov 25;8(47):eade3431. doi: 10.1126/sciadv.ade3431. Epub 2022 Nov 23. PMID: 36417504; PMCID: PMC9683713. 6: Liu Y, Diao H, Hong G, Edward J, Zhang T, Yang G, Yang BM, Zhao Y. Iridium- Catalyzed Enantioconvergent Borrowing Hydrogen Annulation of Racemic 1,4-Diols with Amines. J Am Chem Soc. 2023 Mar 8;145(9):5007-5016. doi: 10.1021/jacs.2c09958. Epub 2023 Feb 21. PMID: 36802615. 7: Sato T, Uozumi Y, Yamada YMA. Catalytic Reductive Alkylation of Amines in Batch and Microflow Conditions Using a Silicon-Wafer-Based Palladium Nanocatalyst. ACS Omega. 2020 Oct 9;5(41):26938-26945. doi: 10.1021/acsomega.0c04329. PMID: 33111021; PMCID: PMC7581266. 8: Chavkin C, Koob GF. Dynorphin, Dysphoria, and Dependence: the Stress of Addiction. Neuropsychopharmacology. 2016 Jan;41(1):373-4. doi: 10.1038/npp.2015.258. PMID: 26657953; PMCID: PMC4677142. 9: Page S, Mavrikaki MM, Lintz T, Puttick D, Roberts E, Rosen H, Carroll FI, Carlezon WA, Chartoff EH. Behavioral Pharmacology of Novel Kappa Opioid Receptor Antagonists in Rats. Int J Neuropsychopharmacol. 2019 Nov 1;22(11):735-745. doi: 10.1093/ijnp/pyz054. PMID: 31613314; PMCID: PMC7145521. 10: Wang J, Song Q, Xu A, Bao Y, Xu Y, Zhu Q. Design, synthesis and biological evaluation of aminobenzyloxyarylamide derivatives as selective κ opioid receptor antagonists. Eur J Med Chem. 2017 Apr 21;130:15-25. doi: 10.1016/j.ejmech.2017.02.029. Epub 2017 Feb 16. PMID: 28237793. 11: Fava M, Mazzone E, Freeman M, Flynn M, Judge H, Hoeppner B, Hock RS, Shui A, Macaluso M, Morrison MF, Carpenter LL, Shelton R, Zajecka J, Papakostas GI. Double-blind, placebo-controlled, proof-of-concept trial of a kappa-selective opioid receptor antagonist augmentation in treatment-resistant depression. Ann Clin Psychiatry. 2020 Feb;32(4):18-26. doi: 10.12788/acp.0003. PMID: 33125454. 12: Custodio-Patsey L, Donahue RR, Fu W, Lambert J, Smith BN, Taylor BK. Sex differences in kappa opioid receptor inhibition of latent postoperative pain sensitization in dorsal horn. Neuropharmacology. 2020 Feb;163:107726. doi: 10.1016/j.neuropharm.2019.107726. Epub 2019 Jul 25. PMID: 31351975; PMCID: PMC6979801. 13: Margolis EB, Wallace TL, Van Orden LJ, Martin WJ. Differential effects of novel kappa opioid receptor antagonists on dopamine neurons using acute brain slice electrophysiology. PLoS One. 2020 Dec 29;15(12):e0232864. doi: 10.1371/journal.pone.0232864. PMID: 33373369; PMCID: PMC7771853. 14: Krystal AD, Pizzagalli DA, Smoski M, Mathew SJ, Nurnberger J Jr, Lisanby SH, Iosifescu D, Murrough JW, Yang H, Weiner RD, Calabrese JR, Sanacora G, Hermes G, Keefe RSE, Song A, Goodman W, Szabo ST, Whitton AE, Gao K, Potter WZ. A randomized proof-of-mechanism trial applying the 'fast-fail' approach to evaluating κ-opioid antagonism as a treatment for anhedonia. Nat Med. 2020 May;26(5):760-768. doi: 10.1038/s41591-020-0806-7. Epub 2020 Mar 30. PMID: 32231295; PMCID: PMC9949770. 15: Jackson KJ, Jackson A, Carroll FI, Damaj MI. Effects of orally-bioavailable short-acting kappa opioid receptor-selective antagonist LY2456302 on nicotine withdrawal in mice. Neuropharmacology. 2015 Oct;97:270-4. doi: 10.1016/j.neuropharm.2015.05.023. Epub 2015 Jun 1. PMID: 26044637; PMCID: PMC4537361. 16: Domi E, Barbier E, Augier E, Augier G, Gehlert D, Barchiesi R, Thorsell A, Holm L, Heilig M. Preclinical evaluation of the kappa-opioid receptor antagonist CERC-501 as a candidate therapeutic for alcohol use disorders. Neuropsychopharmacology. 2018 Aug;43(9):1805-1812. doi: 10.1038/s41386-018-0015-y. Epub 2018 Feb 5. PMID: 29463912; PMCID: PMC6046052. 17: Jones JD, Babalonis S, Marcus R, Vince B, Kelsh D, Lofwall MR, Fraser H, Paterson B, Martinez S, Martinez DM, Nunes EV, Walsh SL, Comer SD. A randomized, double-blind, placebo-controlled study of the kappa opioid receptor antagonist, CERC-501, in a human laboratory model of smoking behavior. Addict Biol. 2020 Jul;25(4):e12799. doi: 10.1111/adb.12799. Epub 2019 Jun 26. PMID: 31240842; PMCID: PMC9148540. 18: Rorick-Kehn LM, Witcher JW, Lowe SL, Gonzales CR, Weller MA, Bell RL, Hart JC, Need AB, McKinzie JH, Statnick MA, Suico JG, McKinzie DL, Tauscher- Wisniewski S, Mitch CH, Stoltz RR, Wong CJ. Determining pharmacological selectivity of the kappa opioid receptor antagonist LY2456302 using pupillometry as a translational biomarker in rat and human. Int J Neuropsychopharmacol. 2014 Oct 31;18(2):pyu036. doi: 10.1093/ijnp/pyu036. PMID: 25637376; PMCID: PMC4368892. 19: Lowe SL, Wong CJ, Witcher J, Gonzales CR, Dickinson GL, Bell RL, Rorick-Kehn L, Weller M, Stoltz RR, Royalty J, Tauscher-Wisniewski S. Safety, tolerability, and pharmacokinetic evaluation of single- and multiple-ascending doses of a novel kappa opioid receptor antagonist LY2456302 and drug interaction with ethanol in healthy subjects. J Clin Pharmacol. 2014 Sep;54(9):968-78. doi: 10.1002/jcph.286. Epub 2014 Mar 26. PMID: 24619932. 20: Reed B, Butelman ER, Fry RS, Kimani R, Kreek MJ. Repeated Administration of Opra Kappa (LY2456302), a Novel, Short-Acting, Selective KOP-r Antagonist, in Persons with and without Cocaine Dependence. Neuropsychopharmacology. 2018 Mar;43(4):739-750. doi: 10.1038/npp.2017.205. Epub 2017 Aug 31. Erratum in: Neuropsychopharmacology. 2018 Mar;43(4):928. PMID: 28857070; PMCID: PMC5809790.