Synonym
JNJ-1661010; JNJ 1661010; JNJ1661010.
IUPAC/Chemical Name
1-Piperazinecarboxamide, N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)-
InChi Key
BHBOSTKQCZEAJM-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H19N5OS/c25-18(20-16-9-5-2-6-10-16)23-11-13-24(14-12-23)19-21-17(22-26-19)15-7-3-1-4-8-15/h1-10H,11-14H2,(H,20,25)
SMILES Code
O=C(N1CCN(C2=NC(C3=CC=CC=C3)=NS2)CC1)NC4=CC=CC=C4
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
Biological target:
JNJ-1661010 (Takeda-25) a potent and selective fatty acid amide hydrolase (FAAH) inhibitor with IC50s of 34 and 33 nM for rat FAAH and human FAAH, respectively.
In vitro activity:
Under these conditions, AEA (at 10−6 M and 10−8 M) and concomitant FAAH inhibition with JNJ1661010 (1 μM) reduced the production of IL-6 and IL-8 by RA but not OA mixed synoviocytes (Fig. 1b, d).
Reference: Arthritis Res Ther. 2015 Nov 14;17:321. https://pubmed.ncbi.nlm.nih.gov/26567045/
In vivo activity:
JNJ-1661010 dose-dependently increases arachidonoyl ethanolamide, oleoyl ethanolamide, and palmitoyl ethanolamide in the rat brain. The compound attenuates tactile allodynia in the rat mild thermal injury model of acute tissue damage and in the rat spinal nerve ligation (Chung) model of neuropathic pain. JNJ-1661010 also diminishes thermal hyperalgesia in the inflammatory rat carrageenan paw model. These data suggest that FAAH inhibitors with modes of action similar to JNJ-1661010 may be useful clinically as broad-spectrum analgesics.
Reference: Anesth Analg. 2009 Jan;108(1):316-29. https://pubmed.ncbi.nlm.nih.gov/19095868/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
25.0 |
68.41 |
|
| DMF:PBS (pH 7.2) (1:5) |
0.2 |
0.44 |
|
| DMSO |
48.1 |
131.72 |
|
| Ethanol |
2.6 |
7.05 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
365.46
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. Lowin T, Apitz M, Anders S, Straub RH. Anti-inflammatory effects of N-acylethanolamines in rheumatoid arthritis synovial cells are mediated by TRPV1 and TRPA1 in a COX-2 dependent manner. Arthritis Res Ther. 2015 Nov 14;17:321. doi: 10.1186/s13075-015-0845-5. PMID: 26567045; PMCID: PMC4644337.
2. Karbarz MJ, Luo L, Chang L, Tham CS, Palmer JA, Wilson SJ, Wennerholm ML, Brown SM, Scott BP, Apodaca RL, Keith JM, Wu J, Breitenbucher JG, Chaplan SR, Webb M. Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase. Anesth Analg. 2009 Jan;108(1):316-29. doi: 10.1213/ane.0b013e31818c7cbd. PMID: 19095868.
In vitro protocol:
1. Lowin T, Apitz M, Anders S, Straub RH. Anti-inflammatory effects of N-acylethanolamines in rheumatoid arthritis synovial cells are mediated by TRPV1 and TRPA1 in a COX-2 dependent manner. Arthritis Res Ther. 2015 Nov 14;17:321. doi: 10.1186/s13075-015-0845-5. PMID: 26567045; PMCID: PMC4644337.
2. Karbarz MJ, Luo L, Chang L, Tham CS, Palmer JA, Wilson SJ, Wennerholm ML, Brown SM, Scott BP, Apodaca RL, Keith JM, Wu J, Breitenbucher JG, Chaplan SR, Webb M. Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase. Anesth Analg. 2009 Jan;108(1):316-29. doi: 10.1213/ane.0b013e31818c7cbd. PMID: 19095868.
In vivo protocol:
1. Lowin T, Apitz M, Anders S, Straub RH. Anti-inflammatory effects of N-acylethanolamines in rheumatoid arthritis synovial cells are mediated by TRPV1 and TRPA1 in a COX-2 dependent manner. Arthritis Res Ther. 2015 Nov 14;17:321. doi: 10.1186/s13075-015-0845-5. PMID: 26567045; PMCID: PMC4644337.
2. Karbarz MJ, Luo L, Chang L, Tham CS, Palmer JA, Wilson SJ, Wennerholm ML, Brown SM, Scott BP, Apodaca RL, Keith JM, Wu J, Breitenbucher JG, Chaplan SR, Webb M. Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase. Anesth Analg. 2009 Jan;108(1):316-29. doi: 10.1213/ane.0b013e31818c7cbd. PMID: 19095868.
1: Karbarz MJ, Luo L, Chang L, Tham CS, Palmer JA, Wilson SJ, Wennerholm ML, Brown SM, Scott BP, Apodaca RL, Keith JM, Wu J, Breitenbucher JG, Chaplan SR, Webb M. Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase. Anesth Analg. 2009 Jan;108(1):316-29. doi: 10.1213/ane.0b013e31818c7cbd. PubMed PMID: 19095868.
