Doxercalciferol

Base Information

• Chemical Name: Doxercalciferol
• CAS No.: 54573-75-0
• Deprecated CAS: 125285-48-5,87649-67-0
• Molecular Formula: C28H44O2
• Molecular Weight: 412.656
• Hs Code.: 2936299055
• European Community (EC) Number: 643-005-9
• UNII: 3DIZ9LF5Y9
• ChEMBL ID: CHEMBL1200810
• DSSTox Substance ID: DTXSID1034214
• Metabolomics Workbench ID: 35512
• NCI Thesaurus Code: C2645
• Pharos Ligand ID: MGGVJDMQN8KC
• RXCUI: 11516
• Wikidata: Q5303688
• Wikipedia: Doxercalciferol
• Mol file: 54573-75-0.mol

Synonyms:1 alpha-hydroxyergocalciferol;1alpha(OH)2D2;1alpha-hydroxyvitamin D2;1alpha-OHD2;doxacalciferol;doxercalciferol;Hectorol

Chemical Property of Doxercalciferol

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 138-140 °C
• Refractive Index: 1.541
• Boiling Point: 538.7 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 224 °C
• PSA: 40.46000
• Density: 1.01 g/cm³
• LogP: 6.61180
• Storage Temp.: Desiccate at -20°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 412.334130642
• Heavy Atom Count: 30
• Complexity: 712

Purity/Quality:

99% ^*data from raw suppliers

Doxercalciferol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C
• Recent ClinicalTrials: Safety and Efficacy of Hectorol in Pediatric Patients With Chronic Kidney Disease Stage 3 and 4 With Secondary Hyperparathyroidism Not Yet on Dialysis
• Recent EU Clinical Trials: A Multicenter, Open-Label Study of Hectorol (doxercalciferol capsules) for the Treatment of Secondary Hyperparathyroidism
• Description: Doxercalciferol is a synthetic vitamin D2 analog introduced in the US as Hectorol for the treatment of secondary hyperparathyroidism (SHPT) in patients with end-stage renal failure. It is actually 1-alpha-hydroxyvitamin D2 (one-alpha- D2) and can be synthesized by direct hydroxylation of vitamin D2 tosylate or in 5 steps from ergosterol. Doxercalciferol itself is inactive until metabolized by the liver into active 1,24-dihydroxyvitamin D2, showing a pharmacokinetic profile similar to calcitriol. During placebo-controlled clinical trials, patients with moderate to severe SHPT were treated with 1-alpha-D2 (10 μg doses) for 16 to 24 weeks; in 9 patients out of 10, blood levels of parathyroid hormone were considerably reduced, so maintaining a good control of the parathyroid hyperplasia. Moreover, only a moderate tendency to raise calcium and phosphate was observed. Doxercalciferol is orally-active and less toxic than other vitamin D analogs like alfacalcidol; it shows differentially controlled effects and has an improved safety profile compared to calcitriol.
• Uses: Synthetic vitamin D prohormone. A new active Vitamin D analog which inhibits growth of human neuroblastoma. Antihyperparathyroid

Technology Process of Doxercalciferol

There total 14 articles about Doxercalciferol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 1α-Hydroxyergocalciferol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Aus Acetat 11 durch UV-Bestrahlung, Produkt (12) erhitzen, anschl. Rk. mit KOH/Methanol;

DOI:10.1016/0039-128X(77)90056-3

Reference yield:

→ 4-Methylene-5-[2-[7a-methyl-1-((E)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexane-1,3-diol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Acetylverb. (6c) durch Hydrolyse;

DOI:10.1073/pnas.75.5.2080

Reference yield:

→ (1R,3S)-4-Methylene-5-[2-[7a-methyl-1-((E)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexane-1,3-diol (54573-75-0,74007-20-8,125136-22-3,127516-23-8,146727-87-9,87649-67-0)

Guidance literature:

Diacetoxy-Produkt (7a), KOH, Me.;

upstream raw materials:

5,6-cis-1α-Hydroxyvitamin D₂ 3-acetate

3,5-Cyclovitamin D₂

1α-Hydroxy-3,5-cyclovitamin D₂

Vitamin D₂ tosylate

Refernces

• 1、 Paaren, Herbert E.,DeLuca, Hector F.,Schnoes, Heinrich K.. "Direct C(1) Hydroxylation of Vitamin D3 and Related Compounds". . p. 3253 - 3258. Retrieved 2007/10/02.