MedKoo Cat#: 584517 | Name: Bunitrolol

Description:

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

Bunitrolol is a beta-adrenergic receptor antagonist with weak antiarrhythmic activity and minor ability to decrease the heart rate.

Chemical Structure

Bunitrolol
Bunitrolol
CAS#34915-68-9 (free base)

Theoretical Analysis

MedKoo Cat#: 584517

Name: Bunitrolol

CAS#: 34915-68-9 (free base)

Chemical Formula: C14H20N2O2

Exact Mass: 248.1525

Molecular Weight: 248.33

Elemental Analysis: C, 67.72; H, 8.12; N, 11.28; O, 12.89

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Synonym
Bunitrolol; KO 1366; KO1366; KO-1366
IUPAC/Chemical Name
(RS)-2-(3-(tert-Butylamino)-2-hydroxypropoxy)benzonitril
InChi Key
VCVQSRCYSKKPBA-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3
SMILES Code
N#CC1=CC=CC=C1OCC(O)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

Preparing Stock Solutions

The following data is based on the product molecular weight 248.33 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
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Vet Res Commun. 2006 Jul;30(5):505-12. doi: 10.1007/s11259-006-3213-8. PMID: 16755362. 5: Masuda K, Tamagake K, Katsu T, Torigoe F, Saito K, Hanioka N, Yamano S, Yamamoto S, Narimatsu S. Roles of phenylalanine at position 120 and glutamic acid at position 222 in the oxidation of chiral substrates by cytochrome P450 2D6. Chirality. 2006 Feb;18(3):167-76. doi: 10.1002/chir.20246. PMID: 16432914. 6: Cruciani G, Carosati E, De Boeck B, Ethirajulu K, Mackie C, Howe T, Vianello R. MetaSite: understanding metabolism in human cytochromes from the perspective of the chemist. J Med Chem. 2005 Nov 3;48(22):6970-9. doi: 10.1021/jm050529c. PMID: 16250655. 7: Tsuzuki D, Hichiya H, Okuda Y, Yamamoto S, Tamagake K, Shinoda S, Narimatsu S. Alteration in catalytic properties of human CYP2D6 caused by substitution of glycine-42 with arginine, lysine and glutamic acid. Drug Metab Pharmacokinet. 2003;18(1):79-85. doi: 10.2133/dmpk.18.79. PMID: 15618721. 8: Wachowiak R, Tezyk A. 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Characterization of hepatic cytochrome P450 isozyme composition in the transgenic rat expressing low level human growth hormone. Xenobiotica. 1999 Dec;29(12):1203-12. doi: 10.1080/004982599237886. PMID: 10647907. 12: Matsuzaki J, Yamamoto C, Miyama T, Takanaga H, Matsuo H, Ishizuka H, Kawahara Y, Kuwano M, Naito M, Tsuruo T, Sawada Y. Contribution of P-glycoprotein to bunitrolol efflux across blood-brain barrier. Biopharm Drug Dispos. 1999 Mar;20(2):85-90. doi: 10.1002/(sici)1099-081x(199903)20:2<85::aid- bdd159>3.0.co;2-3. PMID: 10206323. 13: Narimatsu S, Kato R, Horie T, Ono S, Tsutsui M, Yabusaki Y, Ohmori S, Kitada M, Ichioka T, Shimada N, Kato R, Ishikawa T. Enantioselectivity of bunitrolol 4-hydroxylation is reversed by the change of an amino acid residue from valine to methionine at position 374 of cytochrome P450-2D6. Chirality. 1999;11(1):1-9. doi: 10.1002/(SICI)1520-636X(1999)11:1<1::AID-CHIR1>3.0.CO;2-E. PMID: 9914647. 14: Yamamoto Y, Ishizuka M, Takada A, Fujita S. Cloning, tissue distribution, and functional expression of two novel rabbit cytochrome P450 isozymes, CYP2D23 and CYP2D24. J Biochem. 1998 Sep;124(3):503-8. doi: 10.1093/oxfordjournals.jbchem.a022141. PMID: 9722658. 15: Yamamoto Y, Tasaki T, Nakamura A, Iwata H, Kazusaka A, Gonzalez FJ, Fujita S. Molecular basis of the Dark Agouti rat drug oxidation polymorphism: importance of CYP2D1 and CYP2D2. Pharmacogenetics. 1998 Feb;8(1):73-82. doi: 10.1097/00008571-199802000-00010. PMID: 9511184. 16: Tasaki T, Nakamura A, Itoh S, Ohashi K, Yamamoto Y, Masuda M, Iwata H, Kazusaka A, Kamataki T, Fujita S. Expression and characterization of dog CYP2D15 using baculovirus expression system. J Biochem. 1998 Jan;123(1):162-8. doi: 10.1093/oxfordjournals.jbchem.a021905. PMID: 9504424. 17: Umehara K, Kudo S, Odomi M. Involvement of CYP2D1 in the metabolism of carteolol by male rat liver microsomes. Xenobiotica. 1997 Nov;27(11):1121-9. doi: 10.1080/004982597239886. PMID: 9413916. 18: Masubuchi Y, Iwasa T, Hosokawa S, Suzuki T, Horie T, Imaoka S, Funae Y, Narimatsu S. Selective deficiency of debrisoquine 4-hydroxylase activity in mouse liver microsomes. J Pharmacol Exp Ther. 1997 Sep;282(3):1435-41. PMID: 9316857. 19: Narimatsu S, Mizukami T, Huang Y, Masubuchi Y, Suzuki T. In-vitro metabolic interaction of bunitrolol enantiomers in rabbit liver microsomes. J Pharm Pharmacol. 1996 Nov;48(11):1185-9. doi: 10.1111/j.2042-7158.1996.tb03918.x. PMID: 8961170. 20: Narimatsu S, Gotoh M, Masubuchi Y, Horie T, Ohmori S, Kitada M, Kageyama T, Asaoka K, Yamamoto I, Suzuki T. Stereoselectivity in bunitrolol 4-hydroxylation in liver microsomes from marmosets and Japanese monkeys. Biol Pharm Bull. 1996 Nov;19(11):1429-33. doi: 10.1248/bpb.19.1429. PMID: 8951158.