JNJ-54175446

JNJ-54175446
Legal status
Legal status	Investigational New Drug;
Identifiers
	IUPAC name (R)-(2-chloro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyrimidin-2-yl)-4-methyl-6,7-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone;
CAS Number	1627902-21-9;
PubChem CID	90409366;
Chemical and physical data
Formula	C18H13ClF4N6O
Molar mass	440.79 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1C2=C(CCN1C(=O)C3=C(C(=CC=C3)C(F)(F)F)Cl)N(N=N2)C4=NC=C(C=N4)F;
	InChI InChI=1S/C18H13ClF4N6O/c1-9-15-13(29(27-26-15)17-24-7-10(20)8-25-17)5-6-28(9)16(30)11-3-2-4-12(14(11)19)18(21,22)23/h2-4,7-9H,5-6H2,1H3/t9-/m1/s1; Key:CWFVVQFVGMFTBD-SECBINFHSA-N;

Short description: Chemical compound

JNJ-54175446 is an investigational P2X7 receptor antagonist developed by Janssen Pharmaceuticals. It is hoped that the drug can reduce neuroinflammation and therefore treat psychiatric disorders such as major depressive disorder.^[1]^[2]^[3]^[4]^[5]^[6]

References

↑ Recourt, Kasper; van der Aart, Jasper; Jacobs, Gabriel; de Kam, Marieke; Drevets, Wayne; van Nueten, Luc; Kanhai, Kawita; Siebenga, Pieter et al. (September 2020). "Characterisation of the pharmacodynamic effects of the P2X7 receptor antagonist JNJ-54175446 using an oral dexamphetamine challenge model in healthy males in a randomised, double-blind, placebo-controlled, multiple ascending dose trial". Journal of Psychopharmacology 34 (9): 1030–1042. doi:10.1177/0269881120914206. PMID 32248747.
↑ Timmers, Maarten; Ravenstijn, Paulien; Xi, Liwen; Triana-Baltzer, Gallen; Furey, Maura; Van Hemelryck, Sandy; Biewenga, Jeike; Ceusters, Marc et al. (December 2018). "Clinical pharmacokinetics, pharmacodynamics, safety, and tolerability of JNJ-54175446, a brain permeable P2X7 antagonist, in a randomised single-ascending dose study in healthy participants". Journal of Psychopharmacology 32 (12): 1341–1350. doi:10.1177/0269881118800067. PMID 30260294.
↑ Bhattacharya, Anindya; Ceusters, Marc (January 2020). "Targeting neuroinflammation with brain penetrant P2X7 antagonists as novel therapeutics for neuropsychiatric disorders". Neuropsychopharmacology 45 (1): 234–235. doi:10.1038/s41386-019-0502-9. ISSN 0893-133X. PMID 31477815.
↑ Recourt, Kasper; de Boer, Peter; van der Ark, Peter; Benes, Heike; van Gerven, Joop M. A.; Ceusters, Marc; van Nueten, Luc; Drevets, Wayne C. et al. (24 July 2023). "Characterization of the central nervous system penetrant and selective purine P2X7 receptor antagonist JNJ-54175446 in patients with major depressive disorder" (in en). Translational Psychiatry 13 (1): 1–11. doi:10.1038/s41398-023-02557-5. ISSN 2158-3188. PMID 37482560. PMC 10363543. https://www.nature.com/articles/s41398-023-02557-5.
↑ Koole, Michel; Schmidt, Mark E.; Hijzen, Anja; Ravenstijn, Paulien; Vandermeulen, Corinne; Van Weehaeghe, Donatienne; Serdons, Kim; Celen, Sofie et al. (May 2019). "18 F-JNJ-64413739, a Novel PET Ligand for the P2X7 Ion Channel: Radiation Dosimetry, Kinetic Modeling, Test-Retest Variability, and Occupancy of the P2X7 Antagonist JNJ-54175446". Journal of Nuclear Medicine 60 (5): 683–690. doi:10.2967/jnumed.118.216747. PMID 30262518.
↑ Xu, Yan; Miao, Xin; Ravenstijn, Paulien; Hijzen, Anja; Schmidt, Mark E.; Nandy, Partha; Zhou, Honghui (March 2020). "Translational Model‐Informed Dose Selection for a Human Positron Emission Tomography Imaging Study of JNJ‐54175446, a P2X7 Receptor Antagonist". Clinical and Translational Science 13 (2): 309–317. doi:10.1111/cts.12711. PMID 31642608.

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[1] Recourt, Kasper; van der Aart, Jasper; Jacobs, Gabriel; de Kam, Marieke; Drevets, Wayne; van Nueten, Luc; Kanhai, Kawita; Siebenga, Pieter et al. (September 2020). "Characterisation of the pharmacodynamic effects of the P2X7 receptor antagonist JNJ-54175446 using an oral dexamphetamine challenge model in healthy males in a randomised, double-blind, placebo-controlled, multiple ascending dose trial". Journal of Psychopharmacology 34 (9): 1030–1042. doi:10.1177/0269881120914206. PMID 32248747.

[2] Timmers, Maarten; Ravenstijn, Paulien; Xi, Liwen; Triana-Baltzer, Gallen; Furey, Maura; Van Hemelryck, Sandy; Biewenga, Jeike; Ceusters, Marc et al. (December 2018). "Clinical pharmacokinetics, pharmacodynamics, safety, and tolerability of JNJ-54175446, a brain permeable P2X7 antagonist, in a randomised single-ascending dose study in healthy participants". Journal of Psychopharmacology 32 (12): 1341–1350. doi:10.1177/0269881118800067. PMID 30260294.

[3] Bhattacharya, Anindya; Ceusters, Marc (January 2020). "Targeting neuroinflammation with brain penetrant P2X7 antagonists as novel therapeutics for neuropsychiatric disorders". Neuropsychopharmacology 45 (1): 234–235. doi:10.1038/s41386-019-0502-9. ISSN 0893-133X. PMID 31477815.

[4] Recourt, Kasper; de Boer, Peter; van der Ark, Peter; Benes, Heike; van Gerven, Joop M. A.; Ceusters, Marc; van Nueten, Luc; Drevets, Wayne C. et al. (24 July 2023). "Characterization of the central nervous system penetrant and selective purine P2X7 receptor antagonist JNJ-54175446 in patients with major depressive disorder" (in en). Translational Psychiatry 13 (1): 1–11. doi:10.1038/s41398-023-02557-5. ISSN 2158-3188. PMID 37482560. PMC 10363543. https://www.nature.com/articles/s41398-023-02557-5.

[5] Koole, Michel; Schmidt, Mark E.; Hijzen, Anja; Ravenstijn, Paulien; Vandermeulen, Corinne; Van Weehaeghe, Donatienne; Serdons, Kim; Celen, Sofie et al. (May 2019). "18 F-JNJ-64413739, a Novel PET Ligand for the P2X7 Ion Channel: Radiation Dosimetry, Kinetic Modeling, Test-Retest Variability, and Occupancy of the P2X7 Antagonist JNJ-54175446". Journal of Nuclear Medicine 60 (5): 683–690. doi:10.2967/jnumed.118.216747. PMID 30262518.

[6] Xu, Yan; Miao, Xin; Ravenstijn, Paulien; Hijzen, Anja; Schmidt, Mark E.; Nandy, Partha; Zhou, Honghui (March 2020). "Translational Model‐Informed Dose Selection for a Human Positron Emission Tomography Imaging Study of JNJ‐54175446, a P2X7 Receptor Antagonist". Clinical and Translational Science 13 (2): 309–317. doi:10.1111/cts.12711. PMID 31642608.

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JNJ-54175446

Topic: Chemistry

See also

References

Legal status

Legal status	Investigational New Drug
Identifiers
IUPAC name (R)-(2-chloro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyrimidin-2-yl)-4-methyl-6,7-dihydro-1H-[1,2,3]triazolo[4,5-c]pyridin-5(4H)-yl)methanone
CAS Number	1627902-21-9
PubChem CID	90409366
Chemical and physical data
Formula	C₁₈H₁₃ClF₄N₆O
Molar mass	440.79 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H]1C2=C(CCN1C(=O)C3=C(C(=CC=C3)C(F)(F)F)Cl)N(N=N2)C4=NC=C(C=N4)F
InChI InChI=1S/C18H13ClF4N6O/c1-9-15-13(29(27-26-15)17-24-7-10(20)8-25-17)5-6-28(9)16(30)11-3-2-4-12(14(11)19)18(21,22)23/h2-4,7-9H,5-6H2,1H3/t9-/m1/s1 Key:CWFVVQFVGMFTBD-SECBINFHSA-N