LEXACALCITOL

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9389535
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.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Psoriasis 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7817684	Primary	Phase I 428	Unknown Approved Use Unknown
Type 1 diabetes mellitus 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7867594	Preventing	Preclinical	Unknown Approved Use Unknown
Neuroblastoma 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12536077	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	3780AH	https://aksci.com/item_detail.php?cat=3780AH
AbovChem LLC	HY-32340	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-32340
BLD Pharm	BD136256	http://www.bldpharm.com/search/Search.html?keyword=BD136256
BOC Sciences	131875-08-6	http://www.bocsci.com/description.asp?cas=131875-08-6
Hangzhou APIChem Technology	AC-8889
MolPort	MolPort-028-744-634	https://www.molport.com/shop/molecule-link/MolPort-028-744-634
eMolecules	56967871	https://orderbb.emolecules.com/search/#?query=56967871
mcule	MCULE-4692389171	https://mcule.com/MCULE-4692389171/

PubMed

Title	Date	PubMed
Studies on two new vitamin D analogs, EB 1089 and KH 1060: effects on bone resorption and osteoclast recruitment in vitro.	1995 Oct	8573413
Inhibition of MG-63 cell cycle progression by synthetic vitamin D3 analogs mediated by p27, Cdk2, cyclin E, and the retinoblastoma protein.	2003 Aug 1	12907249
Human cathelicidin antimicrobial peptide (CAMP) gene is a direct target of the vitamin D receptor and is strongly up-regulated in myeloid cells by 1,25-dihydroxyvitamin D3.	2005 Jul	15985530

Patents

Sample Use Guides

In Vivo Use Guide

psoriasis: ointment 0.2 microgram/g

Route of Administration: Topical

In Vitro Use Guide

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.

Name

Type

Language

LEXACALCITOL

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