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MedKoo Cat#: 208242 | Name: (R)-Bambuterol

Description:

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

Bambuterol is a prodrug of β2-agonist commonly used for the treatment of asthma and chronic obstructive pulmonary disease (COPD) with the advantage of once daily dosing and favorable side effect profile. Administration of a single-dose of R-bambuterol resulted in dose-dependent reductions in the levels of plasma LDL-C, high-density lipoprotein cholesterol (HDL-C), total cholesterol (TC), apolipoprotein B (ApoB) and apolipoprotein A1 (ApoA1) at Tmax. R-bambuterol can lower the plasma levels of LDL-C, and marginally raise the ratio of ApoA1/ApoB (indicator of HDL-C/LDL-C) with both a single dose and multiple doses. R-bambuterol was more potent in LDL-C lowering than rac-bambutero

Chemical Structure

(R)-Bambuterol
(R)-Bambuterol
CAS#788821-30-7

Theoretical Analysis

MedKoo Cat#: 208242

Name: (R)-Bambuterol

CAS#: 788821-30-7

Chemical Formula: C18H29N3O5

Exact Mass: 367.2107

Molecular Weight: 367.45

Elemental Analysis: C, 58.84; H, 7.96; N, 11.44; O, 21.77

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 #
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Synonym
(R)Bambuterol, (r)-Bambuterol, (r)Bambuterol
IUPAC/Chemical Name
[3-[(1R)-2-(tert-Butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,N-dimethylcarbamate
InChi Key
ANZXOIAKUNOVQU-HNNXBMFYSA-N
InChi Code
InChI=1S/C18H29N3O5/c1-18(2,3)19-11-15(22)12-8-13(25-16(23)20(4)5)10-14(9-12)26-17(24)21(6)7/h8-10,15,19,22H,11H2,1-7H3/t15-/m0/s1
SMILES Code
O=C(OC1=CC(OC(N(C)C)=O)=CC([C@@H](O)CNC(C)(C)C)=C1)N(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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 367.45 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: Ye Y, Xu H, Quan L, Zhu L, Zeng J, Zhou T, Zou C, Cheng Q, Bu S, Tan W. The Lipid-lowering Effects of R-bambuterol in Healthy Chinese Volunteers: A Randomized Phase I Clinical Study. EBioMedicine. 2015 Feb 13;2(4):356-64. doi: 10.1016/j.ebiom.2015.02.006. PMID: 26137575; PMCID: PMC4485901. 2: Deng L, Wang S, Guo H, Liu X, Zou X, Zhang R, Lin Y, Tan W. (RS)-bambuterol and its enantiomers: Potential improvement of (R)-bambuterol in mice with colitis. Int Immunopharmacol. 2022 Feb;103:108501. doi: 10.1016/j.intimp.2021.108501. Epub 2021 Dec 30. PMID: 34974400. 3: Liu W, Cao Y, Lin Y, Tan KS, Zhao H, Guo H, Tan W. Enhancement of Fear Extinction Memory and Resistance to Age-Related Cognitive Decline in Butyrylcholinesterase Knockout Mice and (R)-Bambuterol Treated Mice. Biology (Basel). 2021 May 5;10(5):404. doi: 10.3390/biology10050404. PMID: 34062954; PMCID: PMC8147965. 4: Zhou T, Zeng D, Zhao T, Yang Y, Liu S, Wu J, Xu L, Tan W. In vivo metabolism study of (R)-bambuterol in humans using ultra high performance liquid chromatography with tandem mass spectrometry. J Sep Sci. 2016 Aug;39(15):2896-906. doi: 10.1002/jssc.201600424. Epub 2016 Jun 27. PMID: 27273913. 5: Pistolozzi M, Du H, Wei H, Tan W. Stereoselective inhibition of human butyrylcholinesterase by the enantiomers of bambuterol and their intermediates. Drug Metab Dispos. 2015 Mar;43(3):344-52. doi: 10.1124/dmd.114.060251. Epub 2014 Dec 11. PMID: 25504505. 6: Zhou T, Zhao T, Cheng Q, Liu S, Xu L, Tan W. A sensitive LC-MS/MS method for simultaneous determination of R-bambuterol and its active metabolite R-terbutaline in human plasma and urine with application to a clinical pharmacokinetic study. Biomed Chromatogr. 2014 Jul;28(7):994-1002. doi: 10.1002/bmc.3107. Epub 2013 Dec 20. PMID: 24357101. 7: Srinivas NR. Enantioselective Pharmacokinetics of Bambuterol in Preclinical Species: Does S-bambuterol Influence the Clearance of the R-antipode? Eur J Drug Metab Pharmacokinet. 2016 Apr;41(2):197-8. doi: 10.1007/s13318-015-0317-y. PMID: 26801943. 8: Guan S, Hu CY, He MY, Yang YY, Tang YX, Chen JD, Huang LJ, Tan W. Comparative pharmacokinetics and bile transformation of R-enantiomer and racemic bambuterol after single-dose intravenous, oral administration in rats and beagle dogs. Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):453-60. doi: 10.1007/s13318-014-0228-3. Epub 2014 Oct 4. PMID: 25281237. 9: Wu J, Liu F, Wang S, Wang H, Liu Q, Song X, Li J, Xu L, Tan W. Resolution of Rac-Bambuterol via Diastereoisomeric Salt Formation with o-Chloromandelic Acid and Differences in the Enantiomers' Pharmacodynamical Effects in Guinea Pigs and Beagles. Chirality. 2016 Apr;28(4):306-12. doi: 10.1002/chir.22573. Epub 2016 Jan 25. PMID: 26969816. 10: Bosak A, Gazić I, Vinković V, Kovarik Z. Stereoselective inhibition of human, mouse, and horse cholinesterases by bambuterol enantiomers. Chem Biol Interact. 2008 Sep 25;175(1-3):192-5. doi: 10.1016/j.cbi.2008.04.050. Epub 2008 May 21. PMID: 18582854.