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MedKoo Cat#: 530402 | Name: BI-135585
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Description:

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

BI-135585 is a potent and selective 11β-HSD1 inhibitor. BI 135585 was safe and well tolerated over 14 days and can be dosed once daily.

Chemical Structure

BI-135585
BI-135585
CAS#1114561-85-1 (free base)

Theoretical Analysis

MedKoo Cat#: 530402

Name: BI-135585

CAS#: 1114561-85-1 (free base)

Chemical Formula: C28H32N2O4

Exact Mass: 460.2362

Molecular Weight: 460.57

Elemental Analysis: C, 73.02; H, 7.00; N, 6.08; O, 13.89

Price and Availability

Size Price Availability Quantity
2mg USD 190.00 Ready to ship
5mg USD 350.00 Ready to ship
10mg USD 550.00 Ready to ship
25mg USD 950.00 Ready to ship
50mg USD 1,650.00 Ready to ship
100mg USD 2,450.00 Ready to ship
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Related CAS #
1374032-89-9 (hydrate) 1114561-85-1 (free base)
Synonym
BI-135585; BI 135585; BI135585.
IUPAC/Chemical Name
(S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one
InChi Key
TXNPQZGSVXLGGP-MMTVBGGISA-N
InChi Code
InChI=1S/C28H32N2O4/c1-20(21-10-12-22(13-11-21)23-14-16-29(4)25(31)18-23)30-17-15-28(34-26(30)32,19-27(2,3)33)24-8-6-5-7-9-24/h5-14,16,18,20,33H,15,17,19H2,1-4H3/t20-,28-/m0/s1
SMILES Code
O=C1O[C@](C2=CC=CC=C2)(CC(C)(O)C)CCN1[C@H](C3=CC=C(C(C=CN4C)=CC4=O)C=C3)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
>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:
BI-135585 is a potent and selective 11β-HSD1 inhibitor.
In vitro activity:
BI-135585 inhibited 11β HSD1 activity in human adipocytes with an IC50 of 4.3 nM. Reference: Bioorg Med Chem. 2017 Jul 15;25(14):3649-3657. https://www.sciencedirect.com/science/article/abs/pii/S096808961730593X?via%3Dihub
In vivo activity:
HPA axis over-activation leading androgen excess would be undesirable in a therapeutic intervention designed to treat a chronic condition such as the metabolic syndrome. To address whether 11β-HSD1 inhibition would lead to excess androgens, we treated female cynomolgus monkeys with a selective inhibitor, BI 135558, for 4 weeks. Continual action of the compound over the dosing period was confirmed by constant plasma exposure, and a maintained change in urinary glucocorticoid metabolites consistent with 11β-HSD1 inhibition. No significant changes in adrenal function, as evidenced by an adrenocorticotropic hormone (ATCH) challenge, were observed. An examination of androgenic hormones revealed a slight increase in dehydroepiandrosterone sulfate (DHEA-S), while other hormones such as testosterone remained within reference values. Overall, treatment with BI 135558 in monkeys did not result in obvious over-activation of the HPA axis. Reference: Eur J Pharmacol. 2016 Oct 15;789:68-74. https://pubmed.ncbi.nlm.nih.gov/27393460/
Solvent mg/mL mM comments
Solubility
DMSO 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 460.57 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
Formulation protocol:
1. Hamilton BS, Schoelch C, Schuler-Metz A, Krosky P, Lala DS, Claremon DA, McGeehan GM. Influence of sub-chronic selective 11β-hydroxysteroid dehydrogenase 1 inhibition on the hypothalamic-pituitary-adrenal axis in female cynomolgus monkeys. Eur J Pharmacol. 2016 Oct 15;789:68-74. doi: 10.1016/j.ejphar.2016.07.004. Epub 2016 Jul 5. PMID: 27393460. 2. Zhuang L, Tice CM, Xu Z, Zhao W, Cacatian S, Ye YJ, Singh SB, Lindblom P, McKeever BM, Krosky PM, Zhao Y, Lala D, Kruk BA, Meng S, Howard L, Johnson JA, Bukhtiyarov Y, Panemangalore R, Guo J, Guo R, Himmelsbach F, Hamilton B, Schuler-Metz A, Schauerte H, Gregg R, McGeehan GM, Leftheris K, Claremon DA. Discovery of BI 135585, an in vivo efficacious oxazinanonebased 11β hydroxysteroid dehydrogenase type 1 inhibitor. Bioorg Med Chem. 2017 Jul 15;25(14):3649-3657. doi: 10.1016/j.bmc.2017.04.033. Epub 2017 Apr 29. PMID: 28528082.
In vitro protocol:
TBD
In vivo protocol:
1. Hamilton BS, Schoelch C, Schuler-Metz A, Krosky P, Lala DS, Claremon DA, McGeehan GM. Influence of sub-chronic selective 11β-hydroxysteroid dehydrogenase 1 inhibition on the hypothalamic-pituitary-adrenal axis in female cynomolgus monkeys. Eur J Pharmacol. 2016 Oct 15;789:68-74. doi: 10.1016/j.ejphar.2016.07.004. Epub 2016 Jul 5. PMID: 27393460. 2. Zhuang L, Tice CM, Xu Z, Zhao W, Cacatian S, Ye YJ, Singh SB, Lindblom P, McKeever BM, Krosky PM, Zhao Y, Lala D, Kruk BA, Meng S, Howard L, Johnson JA, Bukhtiyarov Y, Panemangalore R, Guo J, Guo R, Himmelsbach F, Hamilton B, Schuler-Metz A, Schauerte H, Gregg R, McGeehan GM, Leftheris K, Claremon DA. Discovery of BI 135585, an in vivo efficacious oxazinanonebased 11β hydroxysteroid dehydrogenase type 1 inhibitor. Bioorg Med Chem. 2017 Jul 15;25(14):3649-3657. doi: 10.1016/j.bmc.2017.04.033. Epub 2017 Apr 29. PMID: 28528082.
1: Freude S, Heise T, Woerle HJ, Jungnik A, Rauch T, Hamilton B, Schölch C, Huang F, Graefe-Mody U. Safety, pharmacokinetics and pharmacodynamics of BI 135585, a selective 11β-hydroxysteroid dehydrogenase-1 (HSD1) inhibitor in humans: liver and adipose tissue 11β-HSD1 inhibition after acute and multiple administrations over 2 weeks. Diabetes Obes Metab. 2016 May;18(5):483-90. doi: 10.1111/dom.12635. PubMed PMID: 26799632. 2: Hamilton BS, Himmelsbach F, Nar H, Schuler-Metz A, Krosky P, Guo J, Guo R, Meng S, Zhao Y, Lala DS, Zhuang L, Claremon DA, McGeehan GM. Pharmacological characterization of the selective 11β-hydroxysteroid dehydrogenase 1 inhibitor, BI 135585, a clinical candidate for the treatment of type 2 diabetes. Eur J Pharmacol. 2015 Jan 5;746:50-5. doi: 10.1016/j.ejphar.2014.10.053. PubMed PMID: 25445047.