Acifran | CAS# 72420-38-3 | Hypolipidemic

MedKoo Cat#: 571521 | Name: Acifran

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Description:

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

Acifran is a hypolipidaemic agent more potent than nicotinic acid and clofibrate. Acifran is an agonist of human orphan GPCR HM74A/GPR109A and HM74B (GPR109B) and has been shown to reduce serum triglycerides and circulating LDL-cholesterol in vivo, without having an effect on liver weight or liver enzymes.

Chemical Structure

Acifran

CAS#72420-38-3

Theoretical Analysis

MedKoo Cat#: 571521

Name: Acifran

CAS#: 72420-38-3

Chemical Formula: C12H10O4

Exact Mass: 218.0579

Molecular Weight: 218.21

Elemental Analysis: C, 66.05; H, 4.62; O, 29.33

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,450.00	2 Weeks
500mg	USD 2,850.00	2 Weeks
1g	USD 4,250.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

72420-38-3

Synonym

Acifran; Reductol

IUPAC/Chemical Name

4,5-Dihydro-5-methyl-4-oxo-5-phenyl-2-furancarboxylic acid

InChi Key

DFDGRKNOFOJBAJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)

SMILES Code

O=C(C(OC1(C)C2=CC=CC=C2)=CC1=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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 218.21 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

1: Adepu KK, Kachhap S, Bhandari D, Anishkin A, Chintapalli SV. Computational insights on molecular interactions of acifran with GPR109A and GPR109B. J Mol Model. 2022 Jul 28;28(8):237. doi: 10.1007/s00894-022-05233-5. PMID: 35900600. 2: Cayen MN, Gonzalez R, Ferdinandi ES, Greselin E, Hicks DR, Kraml M, Dvornik D. The metabolic disposition of acifran, a new antihyperlipidemic agent, in rats and dogs. Xenobiotica. 1986 Mar;16(3):251-63. doi: 10.3109/00498258609043528. PMID: 3705621. 3: Hunninghake DB, Edwards KD, Sopko GS, Tosiello RL. Controlled trial of acifran in type II hyperlipoproteinemia. Clin Pharmacol Ther. 1985 Sep;38(3):313-7. doi: 10.1038/clpt.1985.177. PMID: 4028627. 4: Mahboubi K, Witman-Jones T, Adamus JE, Letsinger JT, Whitehouse D, Moorman AR, Sawicki D, Bergenhem N, Ross SA. Triglyceride modulation by acifran analogs: activity towards the niacin high and low affinity G protein-coupled receptors HM74A and HM74. Biochem Biophys Res Commun. 2006 Feb 10;340(2):482-90. doi: 10.1016/j.bbrc.2005.12.022. Epub 2005 Dec 19. PMID: 16389067. 5: Jung JK, Johnson BR, Duong T, Decaire M, Uy J, Gharbaoui T, Boatman PD, Sage CR, Chen R, Richman JG, Connolly DT, Semple G. Analogues of acifran: agonists of the high and low affinity niacin receptors, GPR109a and GPR109b. J Med Chem. 2007 Apr 5;50(7):1445-8. doi: 10.1021/jm070022x. Epub 2007 Mar 15. PMID: 17358052. 6: LaRosa JC, Miller VT, Edwards KD, DeBovis MR, Stoy DB. Acifran: a double- blind, randomized, placebo-controlled efficacy study in type IIa hyperlipoproteinemic patients. Artery. 1987;14(6):338-50. PMID: 3314798. 7: Cayen MN, Ferdinandi ES, Hicks DR, Gonzalez R, Cosyns L, Dubuc J, Kraml M, Edwards KD. Pharmacokinetics and disposition of the lipid-lowering drug acifran in normal subjects and in patients with renal failure. Clin Pharmacol Ther. 1990 Jan;47(1):50-6. doi: 10.1038/clpt.1990.7. PMID: 2295219. 8: Hughes-Large JM, Pang DK, Robson DL, Chan P, Toma J, Borradaile NM. Niacin receptor activation improves human microvascular endothelial cell angiogenic function during lipotoxicity. Atherosclerosis. 2014 Dec;237(2):696-704. doi: 10.1016/j.atherosclerosis.2014.10.090. Epub 2014 Oct 28. PMID: 25463108. 9: Maciejewski-Lenoir D, Richman JG, Hakak Y, Gaidarov I, Behan DP, Connolly DT. Langerhans cells release prostaglandin D2 in response to nicotinic acid. J Invest Dermatol. 2006 Dec;126(12):2637-46. doi: 10.1038/sj.jid.5700586. Epub 2006 Sep 28. PMID: 17008871. 10: Knowles HJ, te Poele RH, Workman P, Harris AL. Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. Biochem Pharmacol. 2006 Feb 28;71(5):646-56. doi: 10.1016/j.bcp.2005.11.019. Epub 2006 Jan 18. Erratum in: Biochem Pharmacol. 2006 May 28;71(11):1662. Te Poole, Robert [corrected to te Poele, Robert H]. PMID: 16386710. 11: Bhandari D, Kachhap S, Madhukar G, Adepu KK, Anishkin A, Chen JR, Chintapalli SV. Exploring GPR109A Receptor Interaction with Hippuric Acid Using MD Simulations and CD Spectroscopy. Int J Mol Sci. 2022 Nov 26;23(23):14778. doi: 10.3390/ijms232314778. PMID: 36499106; PMCID: PMC9741133. 12: Pike NB, Wise A. Identification of a nicotinic acid receptor: is this the molecular target for the oldest lipid-lowering drug? Curr Opin Investig Drugs. 2004 Mar;5(3):271-5. PMID: 15083592. 13: Cayen MN, Kallai-Sanfacon MA, Dubuc J, Greselin E, Dvornik D. Evaluation of the lipid-lowering activity of AY-25,712 in rats. Atherosclerosis. 1982 Dec;45(3):267-79. doi: 10.1016/0021-9150(82)90228-3. PMID: 6818976. 14: Cayen MN, Kallai-Sanfacon MA, Dubuc J, Greselin E, Dvornik D. Effect of AY-25,712 on fatty acid metabolism in rats. Atherosclerosis. 1982 Dec;45(3):281-90. doi: 10.1016/0021-9150(82)90229-5. PMID: 7159499. 15: Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A, Brown AJ, Dowell SJ, Szekeres PG, Hassall DG, Marshall FH, Wilson S, Pike NB. Molecular identification of high and low affinity receptors for nicotinic acid. J Biol Chem. 2003 Mar 14;278(11):9869-74. doi: 10.1074/jbc.M210695200. Epub 2003 Jan 9. PMID: 12522134. 16: Liu R, van Veldhoven JP, IJzerman AP. The role of the C-terminus of the human hydroxycarboxylic acid receptors 2 and 3 in G protein activation using Gα- engineered yeast cells. Eur J Pharmacol. 2016 Jan 5;770:70-7. doi: 10.1016/j.ejphar.2015.11.052. Epub 2015 Dec 4. PMID: 26656756. 17: Cercós-del-Pozo RA, Pérez-Giménez F, Gálvez-Alvarez J, Salabert-Salvador MT, Garcia-March FJ, Antón-Fos GM. Correlation of pharmacological properties of a group of hypolipaemic drugs by molecular topology. J Pharm Pharmacol. 1996 Mar;48(3):240-4. doi: 10.1111/j.2042-7158.1996.tb05909.x. PMID: 8737046. 18: Gonzalez R, Thibeault D. A liquid chromatographic method for the determination of AY-25,712, a lipid-lowering agent, in serum. Clin Biochem. 1983 Aug;16(4):244-8. doi: 10.1016/s0009-9120(83)90112-1. PMID: 6616810. 19: Kallai-Sanfacon MA, Cayen MN, Dubuc J, Greselin E, Dvornik D. Effect of AY-25,712 and other lipid-lowering agents on liver catalase and liver carnitine acetyltransferase in rats. Proc Soc Exp Biol Med. 1983 Jul;173(3):367-71. doi: 10.3181/00379727-173-41658. PMID: 6867010.