JNJ-42165279 | CAS# 1346528-50-4 | FAAH inhibitor

JNJ-42165279
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522477

CAS#: 1346528-50-4 (free base)

Description: JNJ-42165279 is a potent and selective fatty acid amide hydrolase (FAAH) inhibitor. JNJ-42165279 covalently inactivates the FAAH enzyme, but is highly selective with regard to other enzymes, ion channels, transporters, and receptors. JNJ-42165279 exhibited excellent ADME and pharmacodynamic properties as evidenced by its ability to block FAAH in the brain and periphery of rats and thereby cause an elevation of the concentrations of anandamide (AEA), oleoylethanolamide (OEA), and palmitoyl ethanolamide (PEA). JNJ-42165279 was also efficacious in the spinal nerve ligation (SNL) model of neuropathic pain. JNJ-42165279 is currently under clinical trials.

Chemical Structure

JNJ-42165279

CAS# 1346528-50-4 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522477
Name: JNJ-42165279
CAS#: 1346528-50-4 (free base)
Chemical Formula: C18H17ClF2N4O3
Exact Mass: 410.10
Molecular Weight: 410.806
Elemental Analysis: C, 52.63; H, 4.17; Cl, 8.63; F, 9.25; N, 13.64; O, 11.68

Price and Availability

Size	Price	Availability
100mg	USD 1350
200mg	USD 2250	2 Weeks
500mg	USD 2950	2 Weeks
1g	USD 4950	2 Weeks
2g	USD 7950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: JNJ-42165279; JNJ 42165279; JNJ42165279.

IUPAC/Chemical Name: N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine-1-carboxamide

InChi Key: YWGYNGCRVZLMCS-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H17ClF2N4O3/c19-13-3-4-22-10-14(13)23-17(26)25-7-5-24(6-8-25)11-12-1-2-15-16(9-12)28-18(20,21)27-15/h1-4,9-10H,5-8,11H2,(H,23,26)

SMILES Code: O=C(N1CCN(CC2=CC=C(OC(F)(F)O3)C3=C2)CC1)NC4=C(Cl)C=CN=C4

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, not in water

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:

Product Data:

Product Data

Instruction:

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Biological target:	JNJ-42165279 is a FAAH inhibitor with IC50 of 70 ± 8 nM and 313 ± 28 nM for hFAAH and rFAAH, respectively.
In vitro activity:	BIA 10‐2474, PF‐04457845 and JNJ‐42165279 concentration‐dependently inhibited human recombinant fatty acid amide hydrolase in COS‐human fatty acid amide hydrolase cells at all tested pre‐incubation periods (IC50 values are in Table 2). The IC50 values for PF‐04457845 were similar to those observed in vitro, in contrast to BIA 10‐2474 and JNJ‐42165279, which inhibited more potently fatty acid amide hydrolase in cells than in vitro. Reference: Br J Pharmacol. 2020 May;177(9):2123-2142. doi: 10.1111/bph.14973. https://pubmed.ncbi.nlm.nih.gov/31901141/
In vivo activity:	JNJ-42165279 exhibited excellent ADME and pharmacodynamic properties as evidenced by its ability to block FAAH in the brain and periphery of rats and thereby cause an elevation of the concentrations of anandamide (AEA), oleoyl ethanolamide (OEA), and palmitoyl ethanolamide (PEA). Reference: ACS Med Chem Lett. 2015 Nov 2;6(12):1204-8. https://pubmed.ncbi.nlm.nih.gov/26713105/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	73.03
	DMSO	65.0	158.23
	Ethanol	30.0	73.03

Preparing Stock Solutions

The following data is based on the product molecular weight 410.81 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.

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

Formulation protocol:	1. Bonifácio MJ, Sousa F, Aires C, Loureiro AI, Fernandes-Lopes C, Pires NM, Palma PN, Moser P, Soares-da-Silva P. Preclinical pharmacological evaluation of the fatty acid amide hydrolase inhibitor BIA 10-2474. Br J Pharmacol. 2020 May;177(9):2123-2142. doi: 10.1111/bph.14973. Epub 2020 Feb 12. PMID: 31901141; PMCID: PMC7161550. 2. Keith JM, Jones WM, Tichenor M, Liu J, Seierstad M, Palmer JA, Webb M, Karbarz M, Scott BP, Wilson SJ, Luo L, Wennerholm ML, Chang L, Rizzolio M, Rynberg R, Chaplan SR, Breitenbucher JG. Preclinical Characterization of the FAAH Inhibitor JNJ-42165279. ACS Med Chem Lett. 2015 Nov 2;6(12):1204-8. doi: 10.1021/acsmedchemlett.5b00353. PMID: 26713105; PMCID: PMC4677372.
In vitro protocol:	1. Bonifácio MJ, Sousa F, Aires C, Loureiro AI, Fernandes-Lopes C, Pires NM, Palma PN, Moser P, Soares-da-Silva P. Preclinical pharmacological evaluation of the fatty acid amide hydrolase inhibitor BIA 10-2474. Br J Pharmacol. 2020 May;177(9):2123-2142. doi: 10.1111/bph.14973. Epub 2020 Feb 12. PMID: 31901141; PMCID: PMC7161550.
In vivo protocol:	1. Bonifácio MJ, Sousa F, Aires C, Loureiro AI, Fernandes-Lopes C, Pires NM, Palma PN, Moser P, Soares-da-Silva P. Preclinical pharmacological evaluation of the fatty acid amide hydrolase inhibitor BIA 10-2474. Br J Pharmacol. 2020 May;177(9):2123-2142. doi: 10.1111/bph.14973. Epub 2020 Feb 12. PMID: 31901141; PMCID: PMC7161550. 2. Keith JM, Jones WM, Tichenor M, Liu J, Seierstad M, Palmer JA, Webb M, Karbarz M, Scott BP, Wilson SJ, Luo L, Wennerholm ML, Chang L, Rizzolio M, Rynberg R, Chaplan SR, Breitenbucher JG. Preclinical Characterization of the FAAH Inhibitor JNJ-42165279. ACS Med Chem Lett. 2015 Nov 2;6(12):1204-8. doi: 10.1021/acsmedchemlett.5b00353. PMID: 26713105; PMCID: PMC4677372.

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John M. Keith,* William M. Jones, Mark Tichenor, Jing Liu, Mark Seierstad, James A. Palmer, Michael Webb, Mark Karbarz, Brian P. Scott, Sandy J. Wilson, Lin Luo, Michelle L. Wennerholm, Leon Chang, Michele Rizzolio, Raymond Rynberg, Sandra R. Chaplan, and J. Guy Breitenbucher. Preclinical Characterization of the FAAH Inhibitor JNJ-42165279, ACS Med. Chem. Lett. Articles ASAP (As Soon As Publishable), Publication Date (Web): November 2, 2015 (Letter), DOI: 10.1021/acsmedchemlett.5b00353

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