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

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

Uses

Used in Pharmaceutical Industry:
Maxacalcitol is used as a treatment for secondary hyperparathyroidism (SHPT) associated with chronic renal failure. It is effective in suppressing parathyroid hormone synthesis and secretion, making it a valuable option for managing this condition.
Used in Renal Care:
Maxacalcitol is used as a therapeutic agent for patients with chronic renal failure who suffer from SHPT. Its ability to inhibit parathyroid hormone synthesis and secretion without causing hypercalcemia and hyperphosphatemia makes it a safer choice for these patients.
Brand Names:
Maxacalcitol is marketed under the brand names Prezios (Chugai Pharmaceutical Co., Ltd., Japan) and Oxarol.

Originator

Chugai (Japan)

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

• 20998-18-9 1α,3β-dihydroxy-androst-5-en-17-one 
• 103909-78-0 4-{(S)-1-[(1S,3R,9S,10R,13S,14R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-2-methyl-butan-2-ol 
• 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 

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

Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3

Synthesis of two tritiated 1α,25-dihydloxy-22-oxavitamin D3 (OCT), [26-3H3]OCT (3) and [2β-3H]OCT (4), is described. [26-3H3]OCT (3) was prepared by tritiation at the side chain with tritia

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.

A MARTHA calciferol preparation method (by machine translation)

The invention belongs to the field of pharmaceutical chemistry, and in particular relates to a preparation method of MARTHA calciferol. The method as the compound 1 as the starting material, through the tosylates selective protection secondary hydroxy, under the action of alkali, in methanol occurs in the intramolecular cyclization reaction to produce the compound 3, 3 through the alkene third oxidation, selective protection secondary hydroxy to obtain compound 5, compound 5 in opened under the effect of triatomic acid to obtain compound 6, compound 6 deprotected base to obtain the target compound. The invention raw materials are easy, simple operation, the step is short, only 6 step reaction. (by machine translation)

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.

Industrial synthesis of maxacalcitol, the antihyperparathyroidism and antipsoriatic vitamin D3 analogue exhibiting low calcemic activity

Maxacalcitol, the 22-oxa-derivative of 1α,25-dihydroxyvitamin D 3 and used currently as an antihyperparathyroidism and antipsoriatic drug, has been synthesized in seven chemical steps from 1α- hydroxydehydroepiandrosterone on the basis of our previously developed route. The present synthesis allows the production of the protected form of the penultimate intermediate in 26% overall yield in a kilogram scale reaction employing neither difficult reaction conditions nor chromatographic purification, having overcome all the difficulties involved in the previous route.

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.

Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1α-25-dihydroxy-22-oxavitamin D3 analogues

Six analogues of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 26,27-dimethyl OCT (5), 26,27-diethyl OCT (6), 24-norOCT (7), 24-homoOCT (8), 24-dihomoOCT (9), and 24-trihomoOCT (10) were synthesized from the 20(S)-alcohol (11) as the common start