Acipimox | Olbemox | K-9321 | CAS#51037-30-0 | Hormone-Sensitive Lipase Inhibitor

MedKoo Cat#: 329406 | Name: Acipimox

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Description:

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

Acipimox, also known as Olbemox and K-9321, is hormone-sensitive lipase inhibitor. Acipimox treatment resulted in a robust elevation in expression of nuclear-encoded mitochondrial gene sets and a mitonuclear protein imbalance, which may indicate activation of the mitochondrial unfolded protein response. Further studies in C2C12 myotubes confirmed a direct effect of acipimox on NAD(+) levels, mitonuclear protein imbalance, and mitochondrial oxidative capacity.

Chemical Structure

Acipimox

CAS#51037-30-0

Theoretical Analysis

MedKoo Cat#: 329406

Name: Acipimox

CAS#: 51037-30-0

Chemical Formula: C6H6N2O3

Exact Mass: 154.0378

Molecular Weight: 154.13

Elemental Analysis: C, 46.76; H, 3.92; N, 18.18; O, 31.14

Price and Availability

Size	Price	Availability
250mg	USD 350.00	2 Weeks
1g	USD 550.00	2 Weeks
2g	USD 750.00	2 Weeks
5g	USD 1,050.00	2 Weeks

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Synonym

Acipimox; K-9321; K9321; K 9321; Olbemox; Olbetam; 2-Carboxy-5-methylpyrazine 4-oxide; 5-Methylpyrazinecarboxylic acid 4-oxide; 5-methylpyrazine-2-carboxylic acid 4-oxide

IUPAC/Chemical Name

5-carboxy-2-methylpyrazine 1-oxide

InChi Key

DJQOOSBJCLSSEY-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H6N2O3/c1-4-2-7-5(6(9)10)3-8(4)11/h2-3H,1H3,(H,9,10)

SMILES Code

O=C(C1=C[N+]([O-])=C(C)C=N1)O

Appearance

Solid powder

Purity

>97% (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 154.13 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: Mori M, Supuran CT. Acipimox inhibits human carbonic anhydrases. J Enzyme Inhib Med Chem. 2022 Dec;37(1):672-679. doi: 10.1080/14756366.2022.2037579. PMID: 35139721; PMCID: PMC8843171. 2: Acipimox--a nicotinic acid analogue for hyperlipidaemia. Drug Ther Bull. 1991 Jul 22;29(15):57-9. PMID: 1914867. 3: Castaño C, Kalko S, Novials A, Párrizas M. Obesity-associated exosomal miRNAs modulate glucose and lipid metabolism in mice. Proc Natl Acad Sci U S A. 2018 Nov 27;115(48):12158-12163. doi: 10.1073/pnas.1808855115. Epub 2018 Nov 14. PMID: 30429322; PMCID: PMC6275521. 4: Vestergaard ET, Hjelholt AJ, Kuhre RE, Møller N, Larraufie P, Gribble FM, Reimann F, Jessen N, Holst JJ, Jørgensen JOL. Acipimox Acutely Increases GLP-1 Concentrations in Overweight Subjects and Hypopituitary Patients. J Clin Endocrinol Metab. 2019 Jul 1;104(7):2581-2592. doi: 10.1210/jc.2018-02503. PMID: 30726969; PMCID: PMC7212086. 5: Shen X, Li G, Wang L, Yu H, Zhou L, Deng H, Wang N, Lai C, Zhou W, Gao Y. Quantification of Acipimox in Plasma and Tissues by LC-MS/MS: Application to Pharmacokinetic Comparison between Normoxia and Hypoxia. Molecules. 2022 Sep 28;27(19):6413. doi: 10.3390/molecules27196413. PMID: 36234950; PMCID: PMC9573116. 6: Lanes R, Lunar L, Carrillo E, Villaroel O, Gunczler P, Palacios A. Acipimox, a nicotinic acid analog, stimulates growth hormone secretion in short healthy prepubertal children. J Pediatr Endocrinol Metab. 2000 Sep-Oct;13(8):1115-20. doi: 10.1515/jpem.2000.13.8.1115. PMID: 11085190. 7: Vestergaard ET, Cichosz SL, Møller N, Jørgensen JOL, Fleischer J. Short-term acipimox treatment is associated with decreased cardiac parasympathetic modulation. Br J Clin Pharmacol. 2017 Dec;83(12):2671-2677. doi: 10.1111/bcp.13384. Epub 2017 Aug 24. PMID: 28736944; PMCID: PMC5698577. 8: Jin F, Jiang S, Yang D, Zhang X, Yang Y, Zhang Y, Li K, Yang Y, Ma S. Acipimox attenuates atherosclerosis and enhances plaque stability in ApoE- deficient mice fed a palmitate-rich diet. Biochem Biophys Res Commun. 2012 Nov 9;428(1):86-92. doi: 10.1016/j.bbrc.2012.10.011. Epub 2012 Oct 8. PMID: 23058919. 9: Peino R, Cordido F, Peñalva A, Alvarez CV, Dieguez C, Casanueva FF. Acipimox- mediated plasma free fatty acid depression per se stimulates growth hormone (GH) secretion in normal subjects and potentiates the response to other GH-releasing stimuli. J Clin Endocrinol Metab. 1996 Mar;81(3):909-13. doi: 10.1210/jcem.81.3.8772549. PMID: 8772549. 10: Sánchez-Vera I, Bonet B, Viana M, Herrera E, Indart A. Effect of acipimox on plasma lipids and glucose/insulin in pregnant rats. Int J Exp Diabetes Res. 2002 Oct-Dec;3(4):233-9. doi: 10.1080/15604280214938. PMID: 12546276; PMCID: PMC2478592. 11: Maggi P, Di Biagio A, Rusconi S, Cicalini S, D'Abbraccio M, d'Ettorre G, Martinelli C, Nunnari G, Sighinolfi L, Spagnuolo V, Squillace N. Cardiovascular risk and dyslipidemia among persons living with HIV: a review. BMC Infect Dis. 2017 Aug 9;17(1):551. doi: 10.1186/s12879-017-2626-z. PMID: 28793863; PMCID: PMC5550957. 12: Wu L, Huang W, Liu X, Yang B. Investigation of the clinical effects of acipimox in patients with vulnerable carotid atherosclerosis. Vascular. 2022 Jul 20:17085381221112551. doi: 10.1177/17085381221112551. Epub ahead of print. PMID: 35857037. 13: Barayan D, Vinaik R, Auger C, Knuth CM, Abdullahi A, Jeschke MG. Inhibition of Lipolysis With Acipimox Attenuates Postburn White Adipose Tissue Browning and Hepatic Fat Infiltration. Shock. 2020 Feb;53(2):137-145. doi: 10.1097/SHK.0000000000001439. PMID: 31425403. 14: Montecucco F, Bertolotto M, Vuilleumier N, Franciosi U, Puddu A, Minetti S, Delrio A, Quercioli A, Bergamini E, Ottonello L, Pende A, Lenglet S, Pelli G, Mach F, Dallegri F, Viviani GL. Acipimox reduces circulating levels of insulin and associated neutrophilic inflammation in metabolic syndrome. Am J Physiol Endocrinol Metab. 2011 Apr;300(4):E681-90. doi: 10.1152/ajpendo.00527.2010. Epub 2011 Jan 25. PMID: 21266669. 15: Paragh G, Balogh Z, Boda J, Mohácsi A, Juhász A, Leövey A. Acipimox hatása a diabetes mellitushoz társult hyperlipoproteinaemiákra [Effect of acipimox on diabetes mellitus-associated hyperlipoproteinemia]. Orv Hetil. 1993 Jan 17;134(3):121-4. Hungarian. PMID: 8421622. 16: AIMM Trial Group:; Abouhajar A, Alcock L, Bigirumurame T, Bradley P, Brown L, Campbell I, Del Din S, Faitg J, Falkous G, Gorman GS, Lakey R, McFarland R, Newman J, Rochester L, Ryan V, Smith H, Steel A, Stefanetti RJ, Su H, Taylor RW, Thomas NJP, Tuppen H, Vincent AE, Warren C, Watson G. Acipimox in Mitochondrial Myopathy (AIMM): study protocol for a randomised, double-blinded, placebo- controlled, adaptive design trial of the efficacy of acipimox in adult patients with mitochondrial myopathy. Trials. 2022 Sep 20;23(1):789. doi: 10.1186/s13063-022-06544-x. Erratum in: Trials. 2022 Oct 5;23(1):852. PMID: 36127727; PMCID: PMC9486776. 17: Bain SC, Jones AF, Barnett AH. Acipimox and hypertriglyceridaemia. Br J Hosp Med. 1990 Mar;43(3):182. PMID: 2317609. 18: Ball MJ, Vella M, Rechlass JP, Jones DB, Stirling C, Mann JI, Galton D. Acipimox in the treatment of patients with hyperlipidaemia: a double blind trial. Eur J Clin Pharmacol. 1986;31(2):201-4. doi: 10.1007/BF00606659. PMID: 3803417. 19: AIMM Trial Group:; Abouhajar A, Alcock L, Bigirumurame T, Bradley P, Brown L, Campbell I, Del Din S, Faitg J, Falkous G, Gorman GS, Lakey R, McFarland R, Newman J, Rochester L, Ryan V, Smith H, Steel A, Stefanetti RJ, Su H, Taylor RW, Thomas NJP, Tuppen H, Vincent AE, Warren C, Watson G. Correction: Acipimox in Mitochondrial Myopathy (AIMM): study protocol for a randomised, double-blinded, placebo-controlled, adaptive design trial of the efficacy of acipimox in adult patients with mitochondrial myopathy. Trials. 2022 Oct 5;23(1):852. doi: 10.1186/s13063-022-06814-8. Erratum for: Trials. 2022 Sep 20;23(1):789. PMID: 36199067; PMCID: PMC9533513. 20: Nellemann B, Søndergaard E, Jensen J, Pedersen SB, Jessen N, Jørgensen JO, Nielsen S. Kinetics and utilization of lipid sources during acute exercise and acipimox. Am J Physiol Endocrinol Metab. 2014 Jul 15;307(2):E199-208. doi: 10.1152/ajpendo.00043.2014. Epub 2014 Jun 3. PMID: 24895285.