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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
Structure of ELOCALCITOL

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

HIDE SMILES / InChI

Molecular Formula C29H43FO2
Molecular Weight 442.6489
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 3
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11473
Gene ID: 7421.0
Gene Symbol: VDR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Human bladder as a novel target for vitamin D receptor ligands.
2005 Feb
Pre-clinical evidence and clinical translation of benign prostatic hyperplasia treatment by the vitamin D receptor agonist BXL-628 (Elocalcitol).
2006 Jul-Aug
Patents

Patents

Sample Use Guides

75 μg/d or 150 μg/d for 4 weeks
Route of Administration: Oral
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:25:42 GMT 2023
Edited
by admin
on Fri Dec 15 18:25:42 GMT 2023
Record UNII
2WDS5F2V6Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELOCALCITOL
INN   MART.  
INN  
Official Name English
ELOCALCITOL [MART.]
Common Name English
1S,3R,5Z,7E,23E)-1-FLUORO-26,27-DIHOMO-9,10-SECOCHOLESTA-5,7,10(19),16,23-PENTAENE-3,25-DIOL
Common Name English
RO-26-9228
Code English
elocalcitol [INN]
Common Name English
Code System Code Type Description
INN
8710
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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FDA UNII
2WDS5F2V6Q
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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PUBCHEM
11396600
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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EPA CompTox
DTXSID10173774
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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SMS_ID
300000034239
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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ChEMBL
CHEMBL3545094
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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CAS
199798-84-0
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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DRUG BANK
DB06194
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
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NCI_THESAURUS
C166600
Created by admin on Fri Dec 15 18:25:42 GMT 2023 , Edited by admin on Fri Dec 15 18:25:42 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
PARENT -> DERIVATIVE
Related Record Type Details
ACTIVE MOIETY