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MedKoo Cat#: 464654 | Name: FGIN-1-27

Description:

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

FGIN-1-27 is a potent agonist of the 18 kDa translocator protein (TSPO).

Chemical Structure

FGIN-1-27
FGIN-1-27
CAS#142720-24-9

Theoretical Analysis

MedKoo Cat#: 464654

Name: FGIN-1-27

CAS#: 142720-24-9

Chemical Formula: C28H37FN2O

Exact Mass: 436.2890

Molecular Weight: 436.62

Elemental Analysis: C, 77.03; H, 8.54; F, 4.35; N, 6.42; O, 3.66

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
FGIN-1-27; FGIN1-27; FGIN 1-27; FGIN-127; FGIN-1 27; FGIN127; FGIN 1 27;
IUPAC/Chemical Name
2-(2-(4-fluorophenyl)-1H-indol-3-yl)-N,N-dihexylacetamide
InChi Key
VUWXAQFLTSBUDB-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H37FN2O/c1-3-5-7-11-19-31(20-12-8-6-4-2)27(32)21-25-24-13-9-10-14-26(24)30-28(25)22-15-17-23(29)18-16-22/h9-10,13-18,30H,3-8,11-12,19-21H2,1-2H3
SMILES Code
O=C(N(CCCCCC)CCCCCC)CC1=C(C2=CC=C(F)C=C2)NC3=C1C=CC=C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 436.62 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: Lv J, Jiang S, Yang Y, Zhang X, Gao R, Cao Y, Song G. FGIN-1-27 Inhibits Melanogenesis by Regulating Protein Kinase A/cAMP-Responsive Element-Binding, Protein Kinase C-β, and Mitogen-Activated Protein Kinase Pathways. Front Pharmacol. 2020 Dec 3;11:602889. doi: 10.3389/fphar.2020.602889. PMID: 33390991; PMCID: PMC7775666. 2: Musicki B, Karakus S, La Favor JD, Chen H, Silva FH, Sturny M, Zirkin BR, Burnett AL. TSPO ligand FGIN-1-27 controls priapism in sickle cell mice via endogenous testosterone production. J Cell Physiol. 2021 Apr;236(4):3073-3082. doi: 10.1002/jcp.30075. Epub 2020 Sep 24. PMID: 32974910; PMCID: PMC7882022. 3: Singh A, Dashnyam M, Chim B, Escobar TM, Dulcey AE, Hu X, Wilson KM, Koganti PP, Spinner CA, Xu X, Jadhav A, Southall N, Marugan J, Selvaraj V, Lazarevic V, Muljo SA, Ferrer M. Anxiolytic Drug FGIN-1-27 Ameliorates Autoimmunity by Metabolic Reprogramming of Pathogenic Th17 Cells. Sci Rep. 2020 Feb 28;10(1):3766. doi: 10.1038/s41598-020-60610-5. PMID: 32111885; PMCID: PMC7048748. 4: Zhou D, Ji L, Chen Y. TSPO Modulates IL-4-Induced Microglia/Macrophage M2 Polarization via PPAR-γ Pathway. J Mol Neurosci. 2020 Apr;70(4):542-549. doi: 10.1007/s12031-019-01454-1. Epub 2019 Dec 26. Erratum in: J Mol Neurosci. 2020 Jul;70(7):1164. PMID: 31879837. 5: Chung JY, Chen H, Papadopoulos V, Zirkin B. Cholesterol accumulation, lipid droplet formation, and steroid production in Leydig cells: Role of translocator protein (18-kDa). Andrology. 2020 May;8(3):719-730. doi: 10.1111/andr.12733. Epub 2019 Dec 9. PMID: 31738001. 6: Chung JY, Brown S, Chen H, Liu J, Papadopoulos V, Zirkin B. Effects of pharmacologically induced Leydig cell testosterone production on intratesticular testosterone and spermatogenesis†. Biol Reprod. 2020 Feb 14;102(2):489-498. doi: 10.1093/biolre/ioz174. PMID: 31504200; PMCID: PMC7443349. 7: Graeber E, Korkhov VM. Characterisation of the ligand binding sites in the translocator protein TSPO using the chimeric bacterial-mammalian constructs. Protein Expr Purif. 2019 Dec;164:105456. doi: 10.1016/j.pep.2019.105456. Epub 2019 Jul 19. PMID: 31326501. 8: Chen F, Lu H, Chen P, Zhao X, Guan X, Liang Q, Zirkin BR, Ye L, Chen H. Acute effects of the translocator protein drug ligand FGIN-1-27 on serum testosterone and luteinizing hormone levels in male Sprague-Dawley rats†. Biol Reprod. 2019 Mar 1;100(3):824-832. doi: 10.1093/biolre/ioy220. PMID: 30299464; PMCID: PMC6437259. 9: Lima-Maximino MG, Cueto-Escobedo J, Rodríguez-Landa JF, Maximino C. FGIN-1-27, an agonist at translocator protein 18 kDa (TSPO), produces anti- anxiety and anti-panic effects in non-mammalian models. Pharmacol Biochem Behav. 2018 Aug;171:66-73. doi: 10.1016/j.pbb.2018.04.007. Epub 2018 Apr 24. PMID: 29698632. 10: Biswas L, Zhou X, Dhillon B, Graham A, Shu X. Retinal pigment epithelium cholesterol efflux mediated by the 18 kDa translocator protein, TSPO, a potential target for treating age-related macular degeneration. Hum Mol Genet. 2017 Nov 15;26(22):4327-4339. doi: 10.1093/hmg/ddx319. PMID: 28973423. 11: Rosenberg N, Rosenberg O, Weizman A, Veenman L, Gavish M. In vitro Effects of the Specific Mitochondrial TSPO Ligand Ro5 4864 in Cultured Human Osteoblasts. Exp Clin Endocrinol Diabetes. 2018 Feb;126(2):77-84. doi: 10.1055/s-0043-103282. Epub 2017 Sep 27. PMID: 28954307. 12: Zhang Y, Yu S, Li X, Yang B, Wu C. The ligands of translocator protein inhibit human Th1 responses and the rejection of murine skin allografts. Clin Sci (Lond). 2017 Feb 1;131(4):297-308. doi: 10.1042/CS20160547. Epub 2016 Dec 6. PMID: 27923881. 13: Kim T, Pae AN. Translocator protein (TSPO) ligands for the diagnosis or treatment of neurodegenerative diseases: a patent review (2010 - 2015; part 2). Expert Opin Ther Pat. 2016 Nov;26(11):1353-1366. doi: 10.1080/13543776.2016.1230605. Epub 2016 Sep 16. PMID: 27599163. 14: Li J, Papadopoulos V. Translocator protein (18 kDa) as a pharmacological target in adipocytes to regulate glucose homeostasis. Biochem Pharmacol. 2015 Sep 1;97(1):99-110. doi: 10.1016/j.bcp.2015.06.020. Epub 2015 Jun 26. PMID: 26123521. 15: Midzak A, Denora N, Laquintana V, Cutrignelli A, Lopedota A, Franco M, Altomare CD, Papadopoulos V. 2-Phenylimidazo[1,2-a]pyridine-containing ligands of the 18-kDa translocator protein (TSPO) behave as agonists and antagonists of steroidogenesis in a mouse leydig tumor cell line. Eur J Pharm Sci. 2015 Aug 30;76:231-7. doi: 10.1016/j.ejps.2015.05.021. Epub 2015 May 19. PMID: 26002041. 16: Wu Y, Kazumura K, Maruyama W, Osawa T, Naoi M. Rasagiline and selegiline suppress calcium efflux from mitochondria by PK11195-induced opening of mitochondrial permeability transition pore: a novel anti-apoptotic function for neuroprotection. J Neural Transm (Vienna). 2015 Oct;122(10):1399-407. doi: 10.1007/s00702-015-1398-0. Epub 2015 Apr 12. PMID: 25863936. 17: Taylor JM, Allen AM, Graham A. Targeting mitochondrial 18 kDa translocator protein (TSPO) regulates macrophage cholesterol efflux and lipid phenotype. Clin Sci (Lond). 2014 Nov;127(10):603-13. doi: 10.1042/CS20140047. PMID: 24814875. 18: Frye CA, Koonce CJ, Walf AA. The pregnane xenobiotic receptor, a prominent liver factor, has actions in the midbrain for neurosteroid synthesis and behavioral/neural plasticity of female rats. Front Syst Neurosci. 2014 Apr 21;8:60. doi: 10.3389/fnsys.2014.00060. PMID: 24795576; PMCID: PMC4001026. 19: Rosenberg N, Rosenberg O, Weizman A, Veenman L, Gavish M. In vitro effect of FGIN-1-27, a ligand to 18 kDa mitochondrial translocator protein, in human osteoblast-like cells. J Bioenerg Biomembr. 2014 Jun;46(3):197-204. doi: 10.1007/s10863-014-9542-3. Epub 2014 Feb 18. PMID: 24532136. 20: Fang J, Sun L, Peng G, Xu J, Zhou R, Cao S, Chen H, Song Y. Identification of three antiviral inhibitors against Japanese encephalitis virus from library of pharmacologically active compounds 1280. PLoS One. 2013 Nov 4;8(11):e78425. doi: 10.1371/journal.pone.0078425. PMID: 24348901; PMCID: PMC3857149.

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