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SML2395

Sigma-Aldrich

Elocalcitol

≥98% (HPLC)

Synonym(e):

(1R,3Z,5S)-3-[(2E)-2-[(3aS,7aS)-1-[(1S,3E)-5-ethyl-5-hydroxy-1-methyl-3-hepten-1-yl]-3,3a,5,6,7,7a-hexahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-5-fluoro-4-methylenecyclohexanol, BXL 628, BXL-628, Ro 26-9228

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About This Item

Empirische Formel (Hill-System):
C29H43FO2
CAS-Nummer:
199798-84-0
Molekulargewicht:
442.65
MDL-Nummer:
MFCD09954119
UNSPSC-Code:
12352200

Assay

≥98% (HPLC)

Form

powder

Optische Aktivität

[α]/D +97 to +107°, c = c=1 in methanol

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

−20°C

SMILES String

F[C@H]1C[C@@H](C\C(=C\C=C2\[C@H]3[C@](CCC\2)(C(=CC3)[C@H](C\C=C\C(O)(CC)CC)C)C)\C1=C)O

InChI

1S/C29H43FO2/c1-6-29(32,7-2)17-8-10-20(3)25-14-15-26-22(11-9-16-28(25,26)5)12-13-23-18-24(31)19-27(30)21(23)4/h8,12-14,17,20,24,26-27,31-32H,4,6-7,9-11,15-16,18-19H2,1-3,5H3/b17-8+,22-12+,23-13-/t20-,24+,26-,27-,28+/m0/s1

InChIKey

LRLWXBHFPGSUOX-GJQYOBCGSA-N

Biochem./physiol. Wirkung

Elocalcitol (BX-L628) is an analog of Vitamin D3 that acts as an agonist at vitamin D VDR receptors. It has been shown to inhibit prostate cell growth and RhoA/Rho-kinase signaling. Elocalcitol (BXL-628) downregulated the expression of active RhoA and ROCK activity induced by high glucose and was shown to have renal protective effects.
Elocalcitol is a Vitamin D receptor (VDR) agonist and is an analog of calcitriol. Elocalcitol possesses anti-inflammatory and anti- proliferative properties. It regulates cell apoptosis and cell proliferation by binding to Vitamin D receptors (VDR). It shows a therapeutic effect on people suffering from Benign prostatic hyperplasia (BPH) and lower urinary tract symptoms (LUTS).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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Wei Zhang et al.
Experimental and therapeutic medicine, 13(5), 1969-1976 (2017-06-02)
It has previously been reported that 1,25-(OH)2D3 inhibits high glucose-induced epithelial-to-mesenchymal transition (EMT) in HK-2 cells. However, the mechanism of this renoprotective action remains unclear. Elocalcitol (BXL-628), a vitamin D analog, has been suggested to be effective on the RhoA/Rho
Cristina Antinozzi et al.
The Journal of steroid biochemistry and molecular biology, 167, 169-181 (2017-01-04)
Vitamin D plays a pivotal role to maintain skeletal muscle integrity and health. Vitamin D deficiency characterizes inflammatory myopathy (IM) and diabetes, often overlapping diseases involving skeletal muscle damage. Vitamin D receptor (VDR) agonists likely exert beneficial effects in both
Elocalcitol, a vitamin D3 analog for the potential treatment of benign prostatic hyperplasia, overactive bladder and male infertility.
Tiwari A.
IDrugs : The Investigational Drugs Journal, 12(6), 381-393 (2012)
Elocalcitol (BXL-628): a novel, investigational therapy for the therapeutic management of benign prostatic hyperplasia
Tiwari A.
Expert Opinion on Investigational Drugs, 17(5), 819-824 (2008)
Giuseppe Penna et al.
The Prostate, 69(5), 480-493 (2008-12-25)
Benign prostatic hyperplasia (BPH) is characterized by an important inflammatory component. Stimulation of human prostate stromal cells from BPH tissues with proinflammatory cytokines leads to secretion of IL-8, a chemokine involved in BPH pathogenesis. The vitamin D receptor (VDR) agonist
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