MedKoo Cat#: 465972 | Name: Zevaquenabant

Description:

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

Zevaquenabant , also known as MRI-1867, is a cannabinoid 1 (CB1) receptor antagonist. MRI-1867 is a hybrid molecule that acts both as an inverse agonist of peripheral cannabinoid receptor 1 (CB1) and as an inhibitor of inducible nitric oxide synthase (iNOS). MRI-1867 was initially shown to exhibit anti-fibrotic activity in mouse models of liver fibrosis and it has subsequently been demonstrated to reduce signs of inflammation, fibrosis, oxidative stress and overall renal injury in a mouse model of obesity-induced chronic kidney disease. The therapeutic effect of MRI-1867 is two-fold; it both reduces fibrotic progression and is able to attenuate established fibrosis. Activities at both of its molecular targets are involved in mediating its in vivo efficacy.

Chemical Structure

Zevaquenabant
Zevaquenabant
CAS#1998760-00-1

Theoretical Analysis

MedKoo Cat#: 465972

Name: Zevaquenabant

CAS#: 1998760-00-1

Chemical Formula: C25H21ClF3N5O2S

Exact Mass: 547.1057

Molecular Weight: 547.98

Elemental Analysis: C, 54.80; H, 3.86; Cl, 6.47; F, 10.40; N, 12.78; O, 5.84; S, 5.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Zevaquenabant; MRI-1867; MRI 1867; MRI1867;
IUPAC/Chemical Name
(R,Z)-N-((Z)-1-aminoethylidene)-3-(4-chlorophenyl)-4-phenyl-N'-((4-(trifluoromethyl)phenyl)sulfonyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide
InChi Key
NLXIJZHFEOSWPU-QFIPXVFZSA-N
InChi Code
InChI=1S/C25H21ClF3N5O2S/c1-16(30)31-24(33-37(35,36)21-13-9-19(10-14-21)25(27,28)29)34-15-22(17-5-3-2-4-6-17)23(32-34)18-7-11-20(26)12-8-18/h2-14,22H,15H2,1H3,(H2,30,31,33)/t22-/m0/s1
SMILES Code
N/C(C)=N\C(N1C[C@H](C(C2=CC=C(C=C2)Cl)=N1)C3=CC=CC=C3)=N\S(C4=CC=C(C=C4)C(F)(F)F)(=O)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Scleroderma, or systemic sclerosis, is a multi-organ connective tissue disease resulting in fibrosis of the skin, heart, and lungs with no effective treatment. Endocannabinoids acting via cannabinoid-1 receptors (CB1R) and increased activity of inducible NO synthase (iNOS) promote tissue fibrosis including skin fibrosis, and joint targeting of these pathways may improve therapeutic efficacy.

Preparing Stock Solutions

The following data is based on the product molecular weight 547.98 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: Zawatsky CN, Park JK, Abdalla J, Kunos G, Iyer MR, Cinar R. Peripheral Hybrid CB1R and iNOS Antagonist MRI-1867 Displays Anti-Fibrotic Efficacy in Bleomycin-Induced Skin Fibrosis. Front Endocrinol (Lausanne). 2021 Sep 28;12:744857. doi: 10.3389/fendo.2021.744857. PMID: 34650521; PMCID: PMC8505776. 2: Santos-Molina L, Herrerias A, Zawatsky CN, Gunduz-Cinar O, Cinar R, Iyer MR, Wood CM, Lin Y, Gao B, Kunos G, Godlewski G. Effects of a Peripherally Restricted Hybrid Inhibitor of CB1 Receptors and iNOS on Alcohol Drinking Behavior and Alcohol-Induced Endotoxemia. Molecules. 2021 Aug 22;26(16):5089. doi: 10.3390/molecules26165089. PMID: 34443679; PMCID: PMC8399901. 3: Cinar R, Park JK, Zawatsky CN, Coffey NJ, Bodine SP, Abdalla J, Yokoyama T, Jourdan T, Jay L, Zuo MXG, O'Brien KJ, Huang J, Mackie K, Alimardanov A, Iyer MR, Gahl WA, Kunos G, Gochuico BR, Malicdan MCV. CB1 R and iNOS are distinct players promoting pulmonary fibrosis in Hermansky-Pudlak syndrome. Clin Transl Med. 2021 Jul;11(7):e471. doi: 10.1002/ctm2.471. PMID: 34323400; PMCID: PMC8255071. 4: Roger C, Buch C, Muller T, Leemput J, Demizieux L, Passilly-Degrace P, Cinar R, Iyer MR, Kunos G, Vergès B, Degrace P, Jourdan T. Simultaneous Inhibition of Peripheral CB1R and iNOS Mitigates Obesity-Related Dyslipidemia Through Distinct Mechanisms. Diabetes. 2020 Oct;69(10):2120-2132. doi: 10.2337/db20-0078. Epub 2020 Jul 17. PMID: 32680936; PMCID: PMC7506827. 5: Cinar R, Iyer MR, Kunos G. The therapeutic potential of second and third generation CB1R antagonists. Pharmacol Ther. 2020 Apr;208:107477. doi: 10.1016/j.pharmthera.2020.107477. Epub 2020 Jan 9. PMID: 31926199; PMCID: PMC8605822. 6: Udi S, Hinden L, Ahmad M, Drori A, Iyer MR, Cinar R, Herman-Edelstein M, Tam J. Dual inhibition of cannabinoid CB1 receptor and inducible NOS attenuates obesity-induced chronic kidney disease. Br J Pharmacol. 2020 Jan;177(1):110-127. doi: 10.1111/bph.14849. Epub 2019 Dec 27. Erratum in: Br J Pharmacol. 2021 Mar;178(5):1250. PMID: 31454063; PMCID: PMC6976880. 7: Iyer MR, Cinar R, Coffey NJ, Kunos G. Synthesis of 13 C6 -labeled, dual-target inhibitor of cannabinoid-1 receptor (CB1 R) and inducible nitric oxide synthase (iNOS). J Labelled Comp Radiopharm. 2018 May 23. doi: 10.1002/jlcr.3639. Epub ahead of print. PMID: 29790591. 8: Cinar R, Gochuico BR, Iyer MR, Jourdan T, Yokoyama T, Park JK, Coffey NJ, Pri-Chen H, Szanda G, Liu Z, Mackie K, Gahl WA, Kunos G. Cannabinoid CB1 receptor overactivity contributes to the pathogenesis of idiopathic pulmonary fibrosis. JCI Insight. 2017 Apr 20;2(8):e92281. doi: 10.1172/jci.insight.92281. PMID: 28422760; PMCID: PMC5396529.