103909-75-7

Basic information

• Product Name: Maxacalcitol
• Synonyms: MAXACALCITOL;(5Z,7E)-9,10-Seco-22-oxacholesta-5,7,10(19)-triene-1α,3β,25-triol;22-Oxa-1α,25-dihydroxycholecalciferol;Oxacalcitriol;(+)-(5Z,7E)-(1S,3R,20S)-20-(3-Hydroxy-3-methylbutyloxy)-9,10-secopregna-5,7,10(19)-triene-1,3-diol;1,3-Cyclohexanediol, 4-methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)-;(1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1S,3aS,7aS)-octahydro-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol;4-methylene-5Z-[2E-[(3aS)-octahydro-1S-[1S-(3-hydroxy-3-methylbutoxy)ethyl]-7aS-methyl-4H-inden-4-ylidene]ethylidene]-1R,3S-cyclohexanediol
• CAS NO: 103909-75-7
• Molecular Formula: C₂₆H₄₂O₄
• Molecular Weight: 418.61
• Mol File: 103909-75-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 122°
• Boiling Point: 581.4 °C at 760mmHg
• Flash Point: 305.4 °C
• Appearance: /
• Density: 1.09 g/cm³
• Vapor Pressure: 6.11E-16mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Store at -20°C
• Solubility: Soluble in DMSO
• PKA: 14.43±0.40(Predicted)
• CAS DataBase Reference: Maxacalcitol(CAS DataBase Reference)
• NIST Chemistry Reference: Maxacalcitol(103909-75-7)
• EPA Substance Registry System: Maxacalcitol(103909-75-7)

Safety Data

• Hazardous Substances Data: 103909-75-7(Hazardous Substances Data)

Usage

Description

Maxacalcitol is the third synthetic vitamin D analog, after paricalcitol and doxercalciferol, to be marketed for the treatment of secondary hyperparathyroidism (SHPT) associated with chronic renal failure. It is a new vitamin D3 derivative with an oxygen atom in 22-position as main structural feature (22-oxacalcitriol, OCT). This vitamin D receptor agonist has a strong inhibitory effect on synthesis and secretion of parathyroid hormone in the setting of severe parathyroid hyperplasia. Maxacalcitol induced only minor effects on calcium and phosphate metabolism unlike an agent such as 1, 25(OH)2D3 that produced hypercalcemia and hyperphosphatemia. Maxacalcitol is.

Originator

Chugai (Japan)

Uses

22-Oxacalcitriol is the noncalcemic analogue of vitamine D and was found to suppress parathyroid hormone synthesis and secretion.

Brand name

Prezios (Chugai Pharmaceutical Co., Ltd., Japan);Prezios, Oxarol.

InChI:InChI=1/C26H42O4/c1-17-20(15-21(27)16-24(17)28)9-8-19-7-6-12-26(5)22(10-11-23(19)26)18(2)30-14-13-25(3,4)29/h8-9,18,21-24,27-29H,1,6-7,10-16H2,2-5H3/b19-8+,20-9-/t18-,21+,22+,23-,24-,26+/m0/s1

Upstream product

• 81522-68-1 [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide 
• 152397-54-1 (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-hydroxy-3-methylbuthyloxy)pregn-5-ene 
• 1120-79-2 1-bromomethyl-2,2-dimethyloxirane 
• 143101-51-3 (17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5, 17-dien 
• 111594-61-7 1α,3β-bis<(tert-butyldimethylsilyl)oxy>androst-5-en-17-one 
• 115-18-4 2-methyl-3-buten-2-ol 
• 870-63-3 prenyl bromide 
• 20998-18-9 1α,3β-dihydroxy-androst-5-en-17-one 

Downstream Products

• 338956-92-6 (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene 
• 338956-90-4 (5Z,7E,1S,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene 
• 221696-52-2 (1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-trimethylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-[(S)-1-(3-methyl-3-trimethylsilanyloxy-butoxy)-ethyl]-octahydro-indene 

Relevant articles and documents

Improved and efficient synthesis of Maxacalcitol

Maxacalcitol, the 22-oxa-derivative of 1α, 25-dihydroxyvitamin D 3, has been used as an antihyperparathyroidism and antipsoriatic drug. In this paper, an alternative synthetic route has been developed using commercially available vitamin D

Stereoselective synthesis of 22-oxacalcitriol (OCT) and analogues modified at C25

The stereoselective synthesis of 22-oxacalcitriol (OCT) has been achieved. The triene system was introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach to couple ketoester 7 with A ring phosphine oxide 8. The value of the resulting ester 6 for synthesis of C25-modified OCT analogues is exemplified by the synthesis of 5.

SYNTHETIC INTERMEDIATE OF MAXACALCITOL, PREPARATION METHOD THEREFOR AND USE THEREOF

The present invention provides a new method for synthesizing maxacalcitol and an intermediate thereof. According to the method, the maxacalcitol is creatively synthesized through the steps of: taking vitamin D2 as an initial raw material, obtaining a compound represented by formula II, oxidizing, chirally reducing, grafting with a side chain, introducing a hydroxyl group on the C-1 position, and photochemically overturning.

Ultraviolet irradiation apparatus for photochemical reaction and preparation process of vitamin D derivative making use of the same

Disclosed herein are an ultraviolet irradiation apparatus for photochemical reactions which can irradiate the photo-reactive solution with ultraviolet rays having a specific wavelength suitable for the intended photochemical reaction at a high efficiency, and a process by which a provitamin D derivative can be converted into a provitamin D derivative at a high efficiency by means of a photochemical reaction by one-step process of light irradiation, thereby preparing a vitamin D derivative at a high efficiency. The ultraviolet irradiation apparatus irradiates the photo-reactive solution with the ultraviolet rays having the specific wavelength through a quartz rod. Specifically, the apparatus is constructed by an electric discharge lamp, a condensing and reflecting mirror and a plane mirror both having wavelength selective property, an optical filter which transmits the ultraviolet rays having the specific wavelength, and a quartz rod on which the ultraviolet rays having the specific wavelength are struck. The photo-reactive solution is irradiated with the ultraviolet rays from the quartz rod. The quartz rod is immersed in the photo-reactive solution, or a reaction vessel is irradiated with the ultraviolet rays from the quartz rod. In the preparation process of the vitamin D derivative, an ultraviolet irradiation apparatus for photochemical reactions having an ultraviolet radiation-emitting lamp, an optical system having wavelength selective property and a quartz rod on which the ultraviolet rays having the specific wavelength from the optical system are struck is used, and a solution of a provitamin D derivative is irradiated with the ultraviolet rays having the specific wavelength emitted from the quartz rod to cause a photochemical reaction of the provitamin D derivative solution, thereby forming a previtamin D derivative. The previtamin D derivative is further subjected to a thermal isomerization reaction to prepare the vitamin D derivative.