131875-08-6

Basic information

• Product Name: Lexacalcitol
• Synonyms: Lexacalcitol;KH 1060;(1S*,3R*,5Z),7aalpha))-(5Z,7E,20R)-20-((4-Ethyl-4-hydroxyhexyl)oxy)-9,10-secopregna-5,7,10(19)-triene-1alpha,3beta-diol;KH 106;(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aS)-1-[(1R)-1-(4-ethyl-4-hydroxyhexoxy)ethyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS NO: 131875-08-6
• Molecular Formula: C₂₉H₄₈O₄
• Molecular Weight: 460.694
• Mol File: 131875-08-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 600.3 °C at 760 mmHg
• Flash Point: 316.8 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 6.49E-17mmHg at 25°C
• Refractive Index: 1.541
• PKA: 14.43±0.40(Predicted)
• CAS DataBase Reference: Lexacalcitol(CAS DataBase Reference)
• NIST Chemistry Reference: Lexacalcitol(131875-08-6)
• EPA Substance Registry System: Lexacalcitol(131875-08-6)

Safety Data

• Hazardous Substances Data: 131875-08-6(Hazardous Substances Data)

Usage

General Description

Lexacalcitol is a synthetic analog of vitamin D that is primarily used for the treatment of hyperparathyroidism and secondary hyperparathyroidism in patients with chronic kidney disease. It works by binding to the vitamin D receptors in the parathyroid glands, leading to a decrease in parathyroid hormone levels and a reduction in the release of calcium and phosphorus from the bones. This helps to maintain normal levels of these minerals in the blood and prevent the development of bone disorders such as osteoporosis. Lexacalcitol is administered orally and has been shown to be effective in lowering parathyroid hormone levels and improving bone health in patients with chronic kidney disease. However, it may also cause side effects such as gastrointestinal disturbances, headaches, and skin rashes, so it should be used with caution and under the guidance of a healthcare professional.

InChI:InChI=1/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

Upstream product

• 305371-61-3 (20R)-De-A,B-8β,25-bis[(tert-butyldimethylsilyl)oxy]-24,26,27-trihomo-22-oxacholestane 
• 305371-62-4 (20R)-De-A,B-8-bromomethylene-24,26,27-trihomo-22-oxacholestan-25-ol 
• 305371-59-9 toluene-4-sulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-hexyl ester 
• 305371-60-2 3-ethyl-6-iodohexan-3-ol tert-butyldimethylsilyl ether 
• 147725-65-3 (20R)-De-A,B-24,26,27-trihomo-25-hydroxy-22-oxacholestane-8-one 
• 171231-49-5 (20R)-De-A,B-24,26,27-trihomo-22-oxacholestane-8β,25-diol 
• 125573-88-8 Toluene-4-sulfonic acid 4-ethyl-4-hydroxy-hexyl ester 
• 1113-00-4 4-ethyl-hexane-1,4-diol 

Relevant articles and documents

Highly potent cell differentiation-inducing analogues of 1α,25-dihydroxyvitamin D3: Synthesis and biological activity of 2-methyl-1,25-dihydroxyvitamin D3 with side-chain modifications

Eight 2-methyl substituted analogues of 20-epi-22R-methyl-1α,25-dihydroxyvitamin D3 (5) and 20-epi-24,26,27-trihomo-22-oxa-1α,25-dihydroxyvitamin D3 (6: KH-1060) were convergently synthesized. Preparation of the CD-ring portions with modified side chains of 5 and 6, followed by palladium-catalyzed cross-coupling with the A-ring enyne synthons (20a-d), (3S,4S,5R)-, (3S,4R,5R)-, (3S,4S,5S)- and (3R,4R,5S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methyloct-1-en-7-yne, afforded two sets of four A-ring stereoisomers of 20-epi-2,22-dimethyl-1,25-dihydroxyvitamin D3 (7a-d) and 20-epi-24,26,27-trihomo-2-methyl-22-oxa-1,25-dihydroxyvitamin D3 (8a-d). The biological profiles of the hybrid analogues were assessed in terms of affinity for vitamin D receptor (VDR) and HL-60 cell differentiation-inducing activity in comparison with the natural hormone. The combined modifications of the A-ring at the 2-position and the side chain yielded analogues with high potency.