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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H48O4
Molecular Weight 460.689
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of LEXACALCITOL

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@@H](C)OCCCC(O)(CC)CC

InChI

InChIKey=KLZOTDOJMRMLDX-YBBVPDDNSA-N
InChI=1S/C29H48O4/c1-6-29(32,7-2)16-9-17-33-21(4)25-13-14-26-22(10-8-15-28(25,26)5)11-12-23-18-24(30)19-27(31)20(23)3/h11-12,21,24-27,30-32H,3,6-10,13-19H2,1-2,4-5H3/b22-11+,23-12-/t21-,24-,25-,26+,27+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H48O4
Molecular Weight 460.689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12536077

Lexacalcitol (KH1060) is over 100 times more active than 1alpha,25-dihydroxyvitamin D3 and is of potential interest in the treatment of psoriasis and other diseases characterized by accelerated cell growth and T lymphocyte activation, which was studied in the clinical trial. KH1060 also prevents type I diabetes in the preclinical investigation without significant effects on calcium or bone metabolism. In addition also was shown that neuroblastoma (NB) cell lines were more susceptible to growth inhibition by KH1060, suggesting its possible use in NB to potentiate the action of retinoids, which are in clinical use for this disease. The underlying biochemical reasons for the increased biological activity of KH1060 are unknown, but it can include 1) metabolic considerations in addition to explanations based upon 2) enhanced stability of KH1060-liganded transcriptional complexes.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic effects of 1 alpha,25-dihydroxyvitamin D3 and synthetic vitamin D3 analogues on a glioma cell line.
1996 Feb 27
Targacept active conformation search: a new method for predicting the conformation of a ligand bound to its protein target.
2004 Dec 30
Patents

Patents

Sample Use Guides

psoriasis: ointment 0.2 microgram/g
Route of Administration: Topical
It was investigated the possible synergistic effect exerted by Cyclosporin A (CsA) in combination with KH 1060 (Lexacalcitol), on the proliferative response of T lymphocytes obtained from active ulcerative colitis patients. The T lymphocyte-enriched population was treated with phytohemagglutinin and CsA (doses from 1 ng to 1000 ng/ml) alone or in association with KH 1060 (0.1, 1, 10 nM final concentration). Cell proliferation was determined by [3H]thymidine incorporation and analyzed on day 5 of culture. There was obtained the lowest CsA dose and the lowest KH 1060 concentration, in addition, there was suggested an alternative therapeutic approach in these patients, reducing the dose, and consequently the toxicity, of CsA.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:15:14 GMT 2023
Edited
by admin
on Fri Dec 15 16:15:14 GMT 2023
Record UNII
9G3DCA3958
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEXACALCITOL
INN  
INN  
Official Name English
KH-106
Code English
KH106
Code English
KH-1060
Code English
KH1060
Code English
(5Z,7E,20R)-20-((4-ETHYL-4-HYDROXYHEXYL)OXY)-9,10-SECOPREGNA-5,7,10(19)-TRIENE-1.ALPHA.,3.BETA.-DIOL
Common Name English
lexacalcitol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C39713
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
Code System Code Type Description
PUBCHEM
5288670
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
EVMPD
SUB08497MIG
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
CAS
131875-08-6
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
SMS_ID
100000082286
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
INN
7255
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
DRUG BANK
DB03451
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
FDA UNII
9G3DCA3958
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID10869807
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL432600
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
NCI_THESAURUS
C80885
Created by admin on Fri Dec 15 16:15:14 GMT 2023 , Edited by admin on Fri Dec 15 16:15:14 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
Related Record Type Details
ACTIVE MOIETY