WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326994
CAS#: 60398-91-6 (racemic HCl),
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#: H326994
Name: Bufuralol HCl
CAS#: 60398-91-6 (racemic HCl),
Chemical Formula: C16H24ClNO2
Exact Mass: 0.00
Molecular Weight: 297.823
Elemental Analysis: C, 64.53; H, 8.12; Cl, 11.90; N, 4.70; O, 10.74
Related CAS #: 54340-62-4 (free base) 59652-29-8 (HCl) 60398-91-6 (racemic HCl)
Synonym: (±)-Bufuralol DL-Bufuralol; Bufuralol; Bufuralol HCl; Bufuralol hudrochloride; Ro-34787; Ro 34787; Ro34787; Ro3-4787; Ro 3-4787; Ro3-4787. Angium
IUPAC/Chemical Name: 1-(7-Ethylbenzofuran-2-yl)-2-tert-butylamino-1-hydroxyethane hydrochloride
InChi Key: KJBONRGCLLBWCJ-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H23NO2.ClH/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;1H
SMILES Code: OC(C1=CC2=CC=CC(CC)=C2O1)CNC(C)(C)C.[H]Cl
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 297.82 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: 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.
2: 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.
3: Johnston EV, Bogár K, Bäckvall JE. Enantioselective synthesis of (R)-bufuralol via dynamic kinetic resolution in the key step. J Org Chem. 2010 Jul 2;75(13):4596-9. doi: 10.1021/jo100936f. PubMed PMID: 20524620.
4: Uno Y, Uehara S, Kohara S, Murayama N, Yamazaki H. Cynomolgus monkey CYP2D44 newly identified in liver, metabolizes bufuralol, and dextromethorphan. Drug Metab Dispos. 2010 Sep;38(9):1486-92. doi: 10.1124/dmd.110.033274. Epub 2010 May 25. PubMed PMID: 20501912.
5: Haddad S, Poulin P, Funk C. Extrapolating in vitro metabolic interactions to isolated perfused liver: predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine. J Pharm Sci. 2010 Oct;99(10):4406-26. doi: 10.1002/jps.22136. PubMed PMID: 20310018.
6: Narimatsu S, Kazamori D, Masuda K, Katsu T, Funae Y, Naito S, Nakura H, Yamano S, Hanioka N. The mechanism causing the difference in kinetic properties between rat CYP2D4 and human CYP2D6 in the oxidation of dextromethorphan and bufuralol. Biochem Pharmacol. 2009 Mar 1;77(5):920-31. doi: 10.1016/j.bcp.2008.11.006. Epub 2008 Nov 17. PubMed PMID: 19059219.
7: Hefnawy MM, Sultan MA, Al-Shehri MM. HPLC separation technique for analysis of bufuralol enantiomers in plasma and pharmaceutical formulations using a vancomycin chiral stationary phase and UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 1;856(1-2):328-36. Epub 2007 Jun 29. PubMed PMID: 17681871.
8: Crespi CL, Chang TK, Waxman DJ. CYP2D6-dependent bufuralol 1'-hydroxylation assayed by reverse-phase ion-pair high-performance liquid chromatography with fluorescence detection. Methods Mol Biol. 2006;320:121-5. PubMed PMID: 16719382.
9: Bonifacio A, Keizers PH, Commandeur JN, Vermeulen NP, Robert B, Gooijer C, van der Zwan G. Binding of bufuralol, dextromethorphan, and 3,4-methylenedioxymethylamphetamine to wild-type and F120A mutant cytochrome P450 2D6 studied by resonance Raman spectroscopy. Biochem Biophys Res Commun. 2006 May 12;343(3):772-9. Epub 2006 Mar 20. PubMed PMID: 16563352.
10: Isobe T, Hichiya H, Hanioka N, Yamamoto S, Shinoda S, Funae Y, Satoh T, Yamano S, Narimatsu S. Different effects of desipramine on bufuralol 1''-hydroxylation by rat and human CYP2D enzymes. Biol Pharm Bull. 2005 Apr;28(4):634-40. PubMed PMID: 15802801.
11: Masuda K, Tamagake K, Okuda Y, Torigoe F, Tsuzuki D, Isobe T, Hichiya H, Hanioka N, Yamamoto S, Narimatsu S. Change in enantioselectivity in bufuralol 1''-hydroxylation by the substitution of phenylalanine-120 by alanine in cytochrome P450 2D6. Chirality. 2005 Jan;17(1):37-43. PubMed PMID: 15526337.
12: 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.
13: Crespi CL, Chang TK, Waxman DJ. CYP2D6-dependent bufuralol 1'-hydroxylation assayed by reversed-phase ion-pair high-performance liquid chromatography with fluorescence detection. Methods Mol Biol. 1998;107:141-5. PubMed PMID: 14577223.
14: Narimatsu S, Takemi C, Kuramoto S, Tsuzuki D, Hichiya H, Tamagake K, Yamamoto S. Stereoselectivity in the oxidation of bufuralol, a chiral substrate, by human cytochrome P450s. Chirality. 2003 May 5;15(4):333-9. Review. PubMed PMID: 12666241.
15: Narimatsu S, Takemi C, Tsuzuki D, Kataoka H, Yamamoto S, Shimada N, Suzuki S, Satoh T, Meyer UA, Gonzalez FJ. Stereoselective metabolism of bufuralol racemate and enantiomers in human liver microsomes. J Pharmacol Exp Ther. 2002 Oct;303(1):172-8. PubMed PMID: 12235248.
16: Marcucci KA, Pearce RE, Crespi C, Steimel DT, Leeder JS, Gaedigk A. Characterization of cytochrome P450 2D6.1 (CYP2D6.1), CYP2D6.2, and CYP2D6.17 activities toward model CYP2D6 substrates dextromethorphan, bufuralol, and debrisoquine. Drug Metab Dispos. 2002 May;30(5):595-601. PubMed PMID: 11950793.
17: Hanna IH, Kim MS, Guengerich FP. Heterologous expression of cytochrome P450 2D6 mutants, electron transfer, and catalysis of bufuralol hydroxylation: the role of aspartate 301 in structural integrity. Arch Biochem Biophys. 2001 Sep 15;393(2):255-61. PubMed PMID: 11556812.
18: Colby HD, Nowak DM, Longhurst PA, Zhang X, Hayes JR, Voigt JM. Bufuralol metabolism by guinea pig adrenal and hepatic microsomes. Pharmacology. 2001 May;62(4):229-33. PubMed PMID: 11360000.
19: 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.
20: 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.
