Sofalcone | CAS#64506-49-6

MedKoo Cat#: 526345 | Name: Sofalcone

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Description:

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

Sofalcone is an oral gastroprotective, gastrointestinal medication. It is a synthetic analog of sophoradin.

Chemical Structure

Sofalcone

CAS#64506-49-6

Theoretical Analysis

MedKoo Cat#: 526345

Name: Sofalcone

CAS#: 64506-49-6

Chemical Formula: C27H30O6

Exact Mass: 450.2042

Molecular Weight: 450.53

Elemental Analysis: C, 71.98; H, 6.71; O, 21.31

Price and Availability

Size	Price	Availability
100mg	USD 275.00	2 weeks
500mg	USD 450.00	2 weeks
1g	USD 600.00	2 Weeks
5g	USD 1,200.00	2 Weeks

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Related CAS #

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Synonym

Sofalcone; BRN 2191482; Isoprenyl chalcone; Solon; SU-88; RTECS AJ7126000.

IUPAC/Chemical Name

(5-((3-Methyl-2-butenyl)oxy)-2-(p-((3-methyl-2-butenyl)oxy)cinnamoyl)phenoxy)acetic acid

InChi Key

GFWRVVCDTLRWPK-KPKJPENVSA-N

InChi Code

InChI=1S/C27H30O6/c1-19(2)13-15-31-22-8-5-21(6-9-22)7-12-25(28)24-11-10-23(32-16-14-20(3)4)17-26(24)33-18-27(29)30/h5-14,17H,15-16,18H2,1-4H3,(H,29,30)/b12-7+

SMILES Code

O=C(O)COC1=CC(OC/C=C(C)/C)=CC=C1C(/C=C/C2=CC=C(OC/C=C(C)/C)C=C2)=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

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sofalcone induces the expression of Heme oxygenase-1 (HO-1) in gastric epithelium.

In vitro activity:

This study suggests that sofalcone could be a promising therapy for preeclampsia. Sofalcone demonstrated potent activation of the antioxidant pathway (Nrf2/HO-1) in primary trophoblasts and endothelial cells, leading to decreased sFlt-1 secretion from trophoblasts. Sofalcone alleviated endothelial dysfunction by reducing monocyte adhesion and vascular cell adhesion molecule 1 expression in human umbilical vein endothelial cells. Reference: Hypertension. 2015 Apr;65(4):855-62. https://pubmed.ncbi.nlm.nih.gov/25667213/

In vivo activity:

This study suggests that sofalcone can improve ulcer healing. Sofalcone produced a significant improvement in ulcer size as well as a substantial reduction in the number of H. pylori colonies in H. pylori-infected gnotobiotic mice. Reference: Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:223-9. https://pubmed.ncbi.nlm.nih.gov/10807428/

	Solvent	mg/mL	mM
Solubility
	DMF	12.0	26.64
	DMSO	16.0	35.51

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 450.53 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. Onda K, Tong S, Nakahara A, Kondo M, Monchusho H, Hirano T, Kaitu'u-Lino T, Beard S, Binder N, Tuohey L, Brownfoot F, Hannan NJ. Sofalcone upregulates the nuclear factor (erythroid-derived 2)-like 2/heme oxygenase-1 pathway, reduces soluble fms-like tyrosine kinase-1, and quenches endothelial dysfunction: potential therapeutic for preeclampsia. Hypertension. 2015 Apr;65(4):855-62. doi: 10.1161/HYPERTENSIONAHA.114.04781. Epub 2015 Feb 9. PMID: 25667213. 2. Shibuya A, Onda K, Kawahara H, Uchiyama Y, Nakayama H, Omi T, Nagaoka M, Matsui H, Hirano T. Sofalcone, a gastric mucosa protective agent, increases vascular endothelial growth factor via the Nrf2-heme-oxygenase-1 dependent pathway in gastric epithelial cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):581-4. doi: 10.1016/j.bbrc.2010.06.124. Epub 2010 Jul 3. PMID: 20599750. 3. Kim W, Lee H, Kim S, Joo S, Jeong S, Yoo JW, Jung Y. Sofalcone, a gastroprotective drug, covalently binds to KEAP1 to activate Nrf2 resulting in anti-colitic activity. Eur J Pharmacol. 2019 Dec 15;865:172722. doi: 10.1016/j.ejphar.2019.172722. Epub 2019 Oct 12. PMID: 31614142. 4. Kabir AM, Shimizu K, Aiba Y, Igarashi M, Takagi A, Koga Y. The effect of sofalcone on indomethacin-induced gastric ulcers in a Helicobacter pylori-infected gnotobiotic murine model. Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:223-9. doi: 10.1046/j.1365-2036.2000.014s1223.x. PMID: 10807428.

In vitro protocol:

In vivo protocol:

1. Kim W, Lee H, Kim S, Joo S, Jeong S, Yoo JW, Jung Y. Sofalcone, a gastroprotective drug, covalently binds to KEAP1 to activate Nrf2 resulting in anti-colitic activity. Eur J Pharmacol. 2019 Dec 15;865:172722. doi: 10.1016/j.ejphar.2019.172722. Epub 2019 Oct 12. PMID: 31614142. 2. Kabir AM, Shimizu K, Aiba Y, Igarashi M, Takagi A, Koga Y. The effect of sofalcone on indomethacin-induced gastric ulcers in a Helicobacter pylori-infected gnotobiotic murine model. Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:223-9. doi: 10.1046/j.1365-2036.2000.014s1223.x. PMID: 10807428.

1: Onda K, Tong S, Nakahara A, Kondo M, Monchusho H, Hirano T, Kaitu'u-Lino T, Beard S, Binder N, Tuohey L, Brownfoot F, Hannan NJ. Sofalcone upregulates the nuclear factor (erythroid-derived 2)-like 2/heme oxygenase-1 pathway, reduces soluble fms-like tyrosine kinase-1, and quenches endothelial dysfunction: potential therapeutic for preeclampsia. Hypertension. 2015 Apr;65(4):855-62. doi: 10.1161/HYPERTENSIONAHA.114.04781. PubMed PMID: 25667213. 2: Wang L, Song L, Jiang X. Quantification of sofalcone in human plasma and urine by high performance liquid chromatography-mass spectrometry. J Pharm Biomed Anal. 2011 Jul 15;55(5):1179-85. doi: 10.1016/j.jpba.2011.03.040. PubMed PMID: 21530127. 3: Higuchi K, Watanabe T, Tanigawa T, Tominaga K, Fujiwara Y, Arakawa T. Sofalcone, a gastroprotective drug, promotes gastric ulcer healing following eradication therapy for Helicobacter pylori: a randomized controlled comparative trial with cimetidine, an H2-receptor antagonist. J Gastroenterol Hepatol. 2010 May;25 Suppl 1:S155-60. doi: 10.1111/j.1440-1746.2010.06232.x. PubMed PMID: 20586860. 4: Shibuya A, Onda K, Kawahara H, Uchiyama Y, Nakayama H, Omi T, Nagaoka M, Matsui H, Hirano T. Sofalcone, a gastric mucosa protective agent, increases vascular endothelial growth factor via the Nrf2-heme-oxygenase-1 dependent pathway in gastric epithelial cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):581-4. doi: 10.1016/j.bbrc.2010.06.124. PubMed PMID: 20599750. 5: Tanaka H, Nakamura S, Onda K, Tazaki T, Hirano T. Sofalcone, an anti-ulcer chalcone derivative, suppresses inflammatory crosstalk between macrophages and adipocytes and adipocyte differentiation: implication of heme-oxygenase-1 induction. Biochem Biophys Res Commun. 2009 Apr 17;381(4):566-71. doi: 10.1016/j.bbrc.2009.02.086. PubMed PMID: 19239904. 6: Wen A, Wang Z, Hang T, Jia Y, Zhang T, Wu Y, Gao X, Yang Z. Analysis of sofalcone in human plasma by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 1;856(1-2):348-52. PubMed PMID: 17586104. 7: Isomoto H, Furusu H, Ohnita K, Wen CY, Inoue K, Kohno S. Sofalcone, a mucoprotective agent, increases the cure rate of Helicobacter pylori infection when combined with rabeprazole, amoxicillin and clarithromycin. World J Gastroenterol. 2005 Mar 21;11(11):1629-33. PubMed PMID: 15786539; PubMed Central PMCID: PMC4305943. 8: Fukuda Y, Shimoyama T. [Sofalcone]. Nihon Rinsho. 2002 Feb;60 Suppl 2:704-9. Review. Japanese. PubMed PMID: 11979875. 9: Fujiwara Y, Higuchi K, Fukuda T, Watanabe T, Tominaga K, Arakawa T. Inhibitory effect of sofalcone on tumor necrosis factor-alpha and interleukin-1 beta production in human monocytes stimulated by Helicobacter pylori water extract. Drugs Exp Clin Res. 2001;27(3):103-6. PubMed PMID: 11447767. 10: Yoshiyama H, Nakamura H, Okamoto T, Okita K, Nakazawa T. A novel in vitro effect of the mucosal protective agent sofalcone--inhibition of chemotactic motility in Helicobacter pylori. Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:230-6. PubMed PMID: 10807429. 11: Kabir AM, Shimizu K, Aiba Y, Igarashi M, Takagi A, Koga Y. The effect of sofalcone on indomethacin-induced gastric ulcers in a Helicobacter pylori-infected gnotobiotic murine model. Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:223-9. PubMed PMID: 10807428. 12: Nakamura M, Kishikawa H, Ishii H, Kumagai N, Tsuchimoto K. Autonomic nervous regeneration in acetic acid-induced ulcer from the viewpoint of synapse formation--effect of basic fibroblast growth factor and sofalcone in the rat. Aliment Pharmacol Ther. 2000 Apr;14 Suppl 1:50-7. PubMed PMID: 10807403. 13: Sakaki N, Arakawa T, Kozawa H, Yamada Y, Kato H, Kamisawa T, Momma K. Preliminary study on a novel quadruple eradication therapy with a mucoprotective drug, sofalcone, for Helicobacter pylori infection. J Clin Gastroenterol. 1998;27 Suppl 1:S187-91. PubMed PMID: 9872520. 14: Suzuki M, Kitahora T, Nagahashi S, Suzuki H, Mori M, Hibi T, Ishii H. Gastric urease activity is inversely associated with the success of treatment for Helicobacter pylori: effect of sofalcone. J Clin Gastroenterol. 1998;27 Suppl 1:S183-6. PubMed PMID: 9872519. 15: Takahashi M, Maeda S, Ogura K, Terano A, Omata M. The possible role of vascular endothelial growth factor (VEGF) in gastric ulcer healing: effect of sofalcone on VEGF release in vitro. J Clin Gastroenterol. 1998;27 Suppl 1:S178-82. Review. PubMed PMID: 9872518. 16: Nakamura M, Akiba Y, Kishikawa H, Oda M, Ishii H. Effect of combined administration of lansoprazole and sofalcone on microvascular and connective tissue regeneration after ethanol-induced gastric mucosal damage. J Clin Gastroenterol. 1998;27 Suppl 1:S170-7. PubMed PMID: 9872517. 17: Kamiya S, Osaki T, Kumada J, Yamaguchi H, Taguchi H. Effect of sofalcone on adherence, production of vacuolating toxin, and induction of interleukin-8 secretion by Helicobacter pylori. J Clin Gastroenterol. 1997;25 Suppl 1:S172-8. PubMed PMID: 9479645. 18: Takahashi M, Hata Y, Terano A. Effect of sofalcone on the expression of hepatocyte growth factor (HGF) and a brief review of HGF in the stomach. J Clin Gastroenterol. 1997;25 Suppl 1:S21-7. PubMed PMID: 9479623. 19: Nakamura M, Akiba Y, Oda M, Ishii H. Alteration of basic fibroblast growth factor concentration and immunoreactivity in healing of ethanol-induced gastric mucosal damage: effect of sofalcone. J Clin Gastroenterol. 1997;25 Suppl 1:S13-20. PubMed PMID: 9479622. 20: Fujioka T, Murakami K, Kubota T, Kodama R, Honda S, Nasu M. Sofalcone for treatment of Helicobacter pylori infection. J Gastroenterol. 1996 Nov;31 Suppl 9:56-8. PubMed PMID: 8959521.