MedKoo Cat#: 561723 | Name: 16alpha-Hydroxyprednisolone

Description:

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

16alpha-Hydroxyprednisolone is a major CYP3A-dependent metabolite of budesonide.

Chemical Structure

16alpha-Hydroxyprednisolone
16alpha-Hydroxyprednisolone
CAS#13951-70-7

Theoretical Analysis

MedKoo Cat#: 561723

Name: 16alpha-Hydroxyprednisolone

CAS#: 13951-70-7

Chemical Formula: C21H28O6

Exact Mass: 376.1886

Molecular Weight: 376.44

Elemental Analysis: C, 67.00; H, 7.50; O, 25.50

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 #
No Data
Synonym
16alpha-Hydroxyprednisolone; 16alpha Hydroxyprednisolone; OH-PRED; OH PRED;
IUPAC/Chemical Name
(8S,9S,10R,11S,13S,14S,16R,17S)-11,16,17-Trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
InChi Key
SEKYBDYVXDAYPY-ILNISADRSA-N
InChi Code
InChI=1S/C21H28O6/c1-19-6-5-12(23)7-11(19)3-4-13-14-8-16(25)21(27,17(26)10-22)20(14,2)9-15(24)18(13)19/h5-7,13-16,18,22,24-25,27H,3-4,8-10H2,1-2H3/t13-,14-,15-,16+,18+,19-,20-,21-/m0/s1
SMILES Code
O=C1C=C[C@]2(C)[C@@]3([H])[C@@H](O)C[C@]4(C)[C@](C(CO)=O)(O)[C@H](O)C[C@@]4([H])[C@]3([H])CCC2=C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 376.44 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: Barton AK, Heinemann H, Schenk I, Machnik M, Gehlen H. Influence of respiratory tract disease and mode of inhalation on detectability of budesonide in equine urine and plasma. Am J Vet Res. 2017 Feb;78(2):244-250. doi: 10.2460/ajvr.78.2.244. PubMed PMID: 28140635. 2: Gazzotti T, Barbarossa A, Zironi E, Roncada P, Pietra M, Pagliuca G. An LC-MS/MS method for the determination of budesonide and 16α-hydroxyprednisolone in dog plasma. MethodsX. 2016 Feb 24;3:139-43. doi: 10.1016/j.mex.2016.02.004. eCollection 2016. PubMed PMID: 27408833; PubMed Central PMCID: PMC4929248. 3: Dilger K, Halter J, Bertz H, Lopez-Lazaro L, Gratwohl A, Finke J. Pharmacokinetics and pharmacodynamic action of budesonide after buccal administration in healthy subjects and patients with oral chronic graft-versus-host disease. Biol Blood Marrow Transplant. 2009 Mar;15(3):336-43. doi: 10.1016/j.bbmt.2008.12.001. PubMed PMID: 19203724. 4: Fitzgerald M, Evill L, Banz K, Carroll S, Rodger J. Mineralocorticoids restore quiescent morphology and reduce VEGF receptor expression in inflamed choroidal endothelial cells in vitro. Ophthalmic Res. 2009;41(1):44-52. doi: 10.1159/000164799. Epub 2008 Oct 22. PubMed PMID: 18946227. 5: Ferraboschi P, Bertacche V, Maccone I, Pini E, Ragonesi L, Venturini A, Stradi R. Estimation and characterisation of budesonide tablets impurities. J Pharm Biomed Anal. 2008 Jul 15;47(3):636-40. doi: 10.1016/j.jpba.2008.01.050. Epub 2008 Feb 16. PubMed PMID: 18367362. 6: Dilger K, Fux R, Röck D, Mörike K, Gleiter CH. Effect of high-dose metronidazole on pharmacokinetics of oral budesonide and vice versa: a double drug interaction study. J Clin Pharmacol. 2007 Dec;47(12):1532-9. PubMed PMID: 18048573. 7: Deventer K, Mikulcíková P, Van Hoecke H, Van Eenoo P, Delbeke FT. Detection of budesonide in human urine after inhalation by liquid chromatography-mass spectrometry. J Pharm Biomed Anal. 2006 Oct 11;42(4):474-9. Epub 2006 Jul 12. PubMed PMID: 16842962. 8: Dilger K, Denk A, Heeg MH, Beuers U. No relevant effect of ursodeoxycholic acid on cytochrome P450 3A metabolism in primary biliary cirrhosis. Hepatology. 2005 Mar;41(3):595-602. PubMed PMID: 15726657. 9: Wang Y, Tang Y, Moellmann H, Hochhaus G. Simultaneous quantification of budesonide and its two metabolites, 6beta-hydroxybudesonide and 16alpha-hydroxyprednisolone, in human plasma by liquid chromatography negative electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2003 Mar-Apr;17(2-3):158-64. PubMed PMID: 12717805. 10: Faarvang HJ, Lauritsen OS. The relative effects of cortisone and triamcinolone (9alpha-fluoro-16alpha-hydroxyprednisolone) on the urinary excretion of trsin inhibitor in man. Acta Endocrinol (Copenh). 1969 Jul;61(3):477-82. PubMed PMID: 5820058. 11: Fauve RM, Pierce-Chase CH. Comparative effects of corticosteroids on host resistance to infection in relation to chemical structure. J Exp Med. 1967 May 1;125(5):807-21. PubMed PMID: 4960741; PubMed Central PMCID: PMC2138213.