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MedKoo Cat#: 584657 | Name: Diacetolol

Description:

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

Diacetolol is the major metabolite of acebutolol in man.

Chemical Structure

Diacetolol
CAS#22568-64-5 (free base)

Theoretical Analysis

MedKoo Cat#: 584657

Name: Diacetolol

CAS#: 22568-64-5 (free base)

Chemical Formula: C16H24N2O4

Exact Mass: 308.1736

Molecular Weight: 308.38

Elemental Analysis: C, 62.32; H, 7.84; N, 9.08; O, 20.75

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 #
69796-04-9 (HCl) 22568-64-5 (free base)
Synonym
Diacetolol; Acetylacebutolol; M and B 16942; (+-)-Diacetolol
IUPAC/Chemical Name
(1)-N-(3-Acetyl-4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamide
InChi Key
AWOGXJOBNAWQSF-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H24N2O4/c1-10(2)17-8-14(21)9-22-16-6-5-13(18-12(4)20)7-15(16)11(3)19/h5-7,10,14,17,21H,8-9H2,1-4H3,(H,18,20)
SMILES Code
CC(NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1)=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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.38 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: Coombs TJ, Coulson CJ, Smith VJ. Blood plasma binding of acebutolol and diacetolol in man. Br J Clin Pharmacol. 1980 Apr;9(4):395-7. PubMed PMID: 7378256; PubMed Central PMCID: PMC1429991. 2: Muta K, Fukami T, Nakajima M. A proposed mechanism for the adverse effects of acebutolol: CES2 and CYP2C19-mediated metabolism and antinuclear antibody production. Biochem Pharmacol. 2015 Dec 15;98(4):659-70. doi: 10.1016/j.bcp.2015.09.016. Epub 2015 Sep 25. PubMed PMID: 26408002. 3: Sankey MG, Gulaid A, Kaye CM. Preliminary study of the disposition in man of acebutolol and its metabolite, diacetolol, using a new stereoselective hplc method. J Pharm Pharmacol. 1984 Apr;36(4):276-7. PubMed PMID: 6144783. 4: Ohashi K, Warrington SJ, Kaye CM, Houghton GW, Dennis M, Templeton R, Turner P. Observations on the clinical pharmacology and plasma concentrations of diacetolol, the major human metabolite of acebutolol. Br J Clin Pharmacol. 1981 Oct;12(4):561-5. PubMed PMID: 7295489; PubMed Central PMCID: PMC1401897. 5: Basil B, Jordan R. Pharmacological properties of diacetolol (M & B 16,942), a major metabolite of acebutolol. Eur J Pharmacol. 1982 May 7;80(1):47-56. PubMed PMID: 6124437. 6: Thomas MS, Tattersfield AE. Comparison of beta-adrenoceptor selectivity of acebutolol and its metabolite diacetolol with metoprolol and propranolol in normal man. Eur J Clin Pharmacol. 1986;29(6):679-83. PubMed PMID: 2872056. 7: Choi JS, Burm JP. Pharmacokinetics of acebutolol and its main metabolite, diacetolol after oral administration of acebutolol in rabbits with carbon tetrachloride-induced hepatic failure. Arch Pharm Res. 2002 Aug;25(4):541-5. PubMed PMID: 12214869. 8: Borchard U, Hafner D, Hirth C. In vitro studies on the pharmacological properties of diacetolol, the major metabolite of acebutolol in man. Arch Int Pharmacodyn Ther. 1985 Jan;273(1):4-17. PubMed PMID: 2860878. 9: Mostafavi SA, Foster RT. Influence of cimetidine co-administration on the pharmacokinetics of acebutolol enantiomers and its metabolite diacetolol in a rat model: the effect of gastric pH on double-peak phenomena. Int J Pharm. 2003 Apr 14;255(1-2):81-6. PubMed PMID: 12672604. 10: Flouvat B, Roux A, Chau NP, Viallet M, Andre-Fouet X, Woehrle R, Gregoire J. Pharmacokinetics and bioavailability of diacetolol, the main metabolite of acebutolol. Eur J Clin Pharmacol. 1981 Mar;19(4):287-92. PubMed PMID: 7286031. 11: Mantz J, Blanchot G, Marty J, Farinotti R, Trouvin JH, Hazebroucq J, Desmonts JM. Acebutolol and diacetolol plasma levels in patients undergoing myocardial revascularization with hypothermic cardiopulmonary bypass. J Cardiothorac Anesth. 1990 Oct;4(5):577-81. PubMed PMID: 2132136. 12: Zaman R, Jack DB, Kendall MJ. The penetration of acebutolol and its major metabolite, diacetolol, into human cerebrospinal fluid and saliva. Br J Clin Pharmacol. 1981 Sep;12(3):427-9. PubMed PMID: 7295474; PubMed Central PMCID: PMC1401814. 13: Kukes VG, Gneushev ET, Mamedov TSh, Gneusheva IA. [Acebutolol and diacetolol: their binding to plasma proteins and erythrocytes and secretion with the saliva]. Farmakol Toksikol. 1991 Jan-Feb;54(1):53-5. Russian. PubMed PMID: 1860501. 14: Zaman R, Wilkins MR, Kendall MJ, Jack DB. The effect of food and alcohol on the pharmacokinetics of acebutolol and its metabolite, diacetolol. Biopharm Drug Dispos. 1984 Jan-Mar;5(1):91-5. PubMed PMID: 6704510. 15: Bruchatá K, Némethy A, Čižmáriková R, Račanská E, Habala L. Synthesis and In Vitro Pharmacological Evaluation of 5-(Alkoxymethyl)-2-(3-alkylamino-2-hydroxypropoxy)phenylethanones Related to Acebutolol and Celiprolol. Arch Pharm (Weinheim). 2016 Sep;349(9):733-40. doi: 10.1002/ardp.201600136. Epub 2016 Jul 15. PubMed PMID: 27417385. 16: Jiang H, Randlett C, Junga H, Jiang X, Ji QC. Using supported liquid extraction together with cellobiohydrolase chiral stationary phases-based liquid chromatography with tandem mass spectrometry for enantioselective determination of acebutolol and its active metabolite diacetolol in spiked human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):173-80. doi: 10.1016/j.jchromb.2008.12.006. Epub 2008 Dec 9. PubMed PMID: 19109073. 17: Lilja JJ, Raaska K, Neuvonen PJ. Effects of grapefruit juice on the pharmacokinetics of acebutolol. Br J Clin Pharmacol. 2005 Dec;60(6):659-63. PubMed PMID: 16305592; PubMed Central PMCID: PMC1884877. 18: Boutroy MJ, Bianchetti G, Dubruc C, Vert P, Morselli PL. To nurse when receiving acebutolol: is it dangerous for the neonate? Eur J Clin Pharmacol. 1986;30(6):737-9. PubMed PMID: 3770068. 19: Szymura-Oleksiak J, Walczak M, Bojarski J, Aboul-Enein HY. Enantioselective high performance liquid chromatographic assay of acebutolol and its active metabolite diacetolol in human serum. Chirality. 1999;11(4):267-71. PubMed PMID: 10224653. 20: Zaman R, Jack DB, Wilkins MR, Kendall MJ. Lack of effect of liver disease on the pharmacokinetics of acebutolol and diacetolol: a single dose study. Biopharm Drug Dispos. 1985 Apr-Jun;6(2):131-7. PubMed PMID: 4005393.