Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H43FO2 |
Molecular Weight | 442.6489 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC=C([C@@H](C)C\C=C\C(O)(CC)CC)[C@@]1(C)CCC\C2=C/C=C3/C[C@@H](O)C[C@H](F)C3=C
InChI
InChIKey=LRLWXBHFPGSUOX-GJQYOBCGSA-N
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
Elocalcitol (also known as BXL-628), a vitamin D3 analog. This compound regulates cell proliferation and apoptosis via its binding to the vitamin D receptor (VDR) having anti-proliferative and anti-inflammatory properties in benign prostatic hyperplasia (BPH) treatment. In a phase, IIb trial in patients with BPH, treatment with elocalcitol resulted in a significantly reduced prostate volume compared with placebo; irritative urinary symptoms (frequency, urgency, and nocturia) and urodynamic parameters were comparable to the alpha1-adrenoceptor antagonist tamsulosin. In a phase IIa trial in patients with prostatitis, elocalcitol significantly reduced levels of IL-8 in semen, suggesting improved quality and forward motility of sperm. However, phase IIb trial data from patients with overactive bladder (OAB) were less promising: elocalcitol failed to meet the primary endpoint despite demonstrating good efficacy in a phase IIa trial. Based largely on these disappointing data, BioXell decided to terminate all further clinical development of elocalcitol, including an uncompleted phase IIa trial in patients with male infertility. Recently was shown, that VDR agonists as elocalcitol could be therapeutic tools for skeletal muscle integrity/function maintenance, an indispensable condition for health homeostasis.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11473 Gene ID: 7421.0 Gene Symbol: VDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15572423 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22626580
75 μg/d or 150 μg/d for 4 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28565795
The effects of 1,25-(OH)2D3 and its analog BXL-628 on HK-2 cells treated with high glucose for 2 h were was investigated. Active RhoA protein expression in the HG group was significantly upregulated compared with the NC group (P<0.05), and treatment with 1,25-(OH)2D3 or BXL-628 significantly decreased the expression of active RhoA protein (both P<0.05). Additionally, ROCK activity was evaluated by measuring the phospho-MBS level. It was revealed that ROCK activity was significantly lower in the VD3 and BXL groups compared with the high glucose group. In addition, both 1,25-(OH)2D3 and BXL-628 significantly decreased the expression of collagen I and fibronectin compared with the HG group (P<0.01 for collagen protein, collagen mRNA and fibronectin mRNA; P<0.05 for fibronectin protein.
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2WDS5F2V6Q
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11396600
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DTXSID10173774
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300000034239
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CHEMBL3545094
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199798-84-0
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DB06194
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C166600
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ACTIVE MOIETY