WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H592570
CAS#: 54340-62-4 (free base)
Description: Bufuralol, also known as Ro-34787, is a β-adrenoceptor antagonist with partial agonist activity and is potentially useful for the treatment of hypertension. It is metabolized by CYP2D6. Most beta blockers are aryloxypropanolamine-based. In this rare exception, the benzofuran oxygen is part of a ring instead of derived from the epichlorohydrin precursor.
Hodoodo Cat#: H592570
Name: Bufuralol
CAS#: 54340-62-4 (free base)
Chemical Formula: C16H23NO2
Exact Mass: 261.17
Molecular Weight: 261.370
Elemental Analysis: C, 73.53; H, 8.87; N, 5.36; O, 12.24
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 54340-62-4 (free base) 59652-29-8 (HCl) 60398-91-6 (racemic HCl)
Synonym: Bufuralol; Ro 3-4787; Ro-3-4787; Ro3-4787
IUPAC/Chemical Name: 1-(7-Ethylbenzofuran-2-yl)-2-tert-butylamino-1-hydroxyethane
InChi Key: SSEBTPPFLLCUMN-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H23NO2/c1-5-11-7-6-8-12-9-14(19-15(11)12)13(18)10-17-16(2,3)4/h6-9,13,17-18H,5,10H2,1-4H3
SMILES Code: OC(C1=CC2=CC=CC(CC)=C2O1)CNC(C)(C)C
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:
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The following data is based on the product molecular weight 261.37 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Uehara S, Uno Y, Hagihira Y, Murayama N, Shimizu M, Inoue T, Sasaki E, Yamazaki H. Marmoset cytochrome P450 2D8 in livers and small intestines metabolizes typical human P450 2D6 substrates, metoprolol, bufuralol and dextromethorphan. Xenobiotica. 2015;45(9):766-72. doi: 10.3109/00498254.2015.1019595. Epub 2015 Jul 27. PubMed PMID: 25801057.
2: Cai J, Dai DP, Geng PW, Wang SH, Wang H, Zhan YY, Huang XX, Hu GX, Cai JP. Effects of 22 Novel CYP2D6 Variants Found in the Chinese Population on the Bufuralol and Dextromethorphan Metabolisms In Vitro. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):190-9. doi: 10.1111/bcpt.12478. Epub 2015 Sep 26. PubMed PMID: 26310775.
3: Pringle TH, Francis RJ, East PB, Shanks RG. Pharmacodynamic and pharmacokinetic studies on bufuralol in man. Br J Clin Pharmacol. 1986 Nov;22(5):527-34. PubMed PMID: 2878678; PubMed Central PMCID: PMC1401192.
4: Johnston GD, Finch MB, Shanks RG. Peripheral vascular effects of bufuralol in hypertensive and normal subjects: a comparison with propranolol and pindolol. Eur J Clin Pharmacol. 1986;30(6):649-52. PubMed PMID: 3533562.
5: Mankowski DC. The role of CYP2C19 in the metabolism of (+/-) bufuralol, the prototypic substrate of CYP2D6. Drug Metab Dispos. 1999 Sep;27(9):1024-8. PubMed PMID: 10460802.
6: Balant L, Francis RJ, Tozer TN, Marmy A, Tschopp JM, Fabre J. Influence of renal failure on the hepatic clearance of bufuralol in man. J Pharmacokinet Biopharm. 1980 Oct;8(5):421-38. PubMed PMID: 6114166.
7: Yamazaki H, Guo Z, Persmark M, Mimura M, Inoue K, Guengerich FP, Shimada T. Bufuralol hydroxylation by cytochrome P450 2D6 and 1A2 enzymes in human liver microsomes. Mol Pharmacol. 1994 Sep;46(3):568-77. PubMed PMID: 7935340.
8: Foti RS, Fisher MB. Impact of incubation conditions on bufuralol human clearance predictions: enzyme lability and nonspecific binding. Drug Metab Dispos. 2004 Mar;32(3):295-304. PubMed PMID: 14977863.
9: Shimada T, Tsumura F, Yamazaki H, Guengerich FP, Inoue K. Characterization of (+/-)-bufuralol hydroxylation activities in liver microsomes of Japanese and Caucasian subjects genotyped for CYP2D6. Pharmacogenetics. 2001 Mar;11(2):143-56. PubMed PMID: 11266079.
10: Meyer UA, Gut J, Kronbach T, Skoda C, Meier UT, Catin T, Dayer P. The molecular mechanisms of two common polymorphisms of drug oxidation--evidence for functional changes in cytochrome P-450 isozymes catalysing bufuralol and mephenytoin oxidation. Xenobiotica. 1986 May;16(5):449-64. PubMed PMID: 2874666.
11: Prueksaritanont T, Dwyer LM, Cribb AE. (+)-bufuralol 1'-hydroxylation activity in human and rhesus monkey intestine and liver. Biochem Pharmacol. 1995 Oct 26;50(9):1521-5. PubMed PMID: 7503805.
12: Coleman T, Spellman EF, Rostami-Hodjegan A, Lennard MS, Tucker GT. The 1'-hydroxylation of Rac-bufuralol by rat brain microsomes. Drug Metab Dispos. 2000 Sep;28(9):1094-9. PubMed PMID: 10950855.
13: Matsuo Y, Iwahashi K, Ichikawa Y. Debrisoquine 4-monooxygenase and bufuralol 1'-monooxygenase activities in bovine and rabbit tissues. Biochem Pharmacol. 1992 May 8;43(9):1911-9. PubMed PMID: 1596280.
14: Francis RJ, East PB, Larman J. Kinetics and metabolism of (+)-, (-)- and (+/-)-bufuralol. Eur J Clin Pharmacol. 1982;23(6):529-33. PubMed PMID: 6130953.
15: Mautz DS, Nelson WL, Shen DD. Regioselective and stereoselective oxidation of metoprolol and bufuralol catalyzed by microsomes containing cDNA-expressed human P4502D6. Drug Metab Dispos. 1995 Apr;23(4):513-7. PubMed PMID: 7600921.
16: Dayer P, Leemann T, Küpfer A, Kronbach T, Meyer UA. Stereo- and regioselectivity of hepatic oxidation in man--effect of the debrisoquine/sparteine phenotype on bufuralol hydroxylation. Eur J Clin Pharmacol. 1986;31(3):313-8. PubMed PMID: 2878813.
17: Dayer P, Balant L, Courvoisier F, Kupfer A, Kubli A, Gorgia A, Fabre J. The genetic control of bufuralol metabolism in man. Eur J Drug Metab Pharmacokinet. 1982 Jan-Mar;7(1):73-7. PubMed PMID: 6121708.
18: Kronbach T, Mathys D, Gut J, Catin T, Meyer UA. High-performance liquid chromatographic assays for bufuralol 1'-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Anal Biochem. 1987 Apr;162(1):24-32. PubMed PMID: 3605590.
19: McManus ME, Boobis AR, Minchin RF, Schwartz DM, Murray S, Davies DS, Thorgeirsson SS. Relationship between oxidative metabolism of 2-acetylaminofluorene, debrisoquine, bufuralol, and aldrin in human liver microsomes. Cancer Res. 1984 Dec;44(12 Pt 1):5692-7. PubMed PMID: 6498831.
20: Blaber LC, Burden DT, Eigenmann R, Gerold M. The effects of bufuralol, a beta-adrenoceptor antagonist with predominant beta 2-adrenoceptor agonistic activity, in the cat and the dog. J Cardiovasc Pharmacol. 1984 Jan-Feb;6(1):165-75. PubMed PMID: 6199600.
