(1R,3S)-5-{2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

• ChemBase ID: 72695
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: C1[C@H](C[C@@H](C(=C)/C/1=C/C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CCCC(C)C)C)C)O)O
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C/C=C/1\C[C@@H](O)C[C@@H](C1=C)O)C)C
• InChI: InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11-,22-12+/t19-,23-,24-,25+,26+,27-/m1/s1
• InChIKey: OFHCOWSQAMBJIW-GITLSTMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-5-{2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol; (1R,3S,5E)-5-{2-[(1R,3aS,4Z,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S)-5-{2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol; 1α-hydroxypregnacalciferol
• Synonyms: Alphacalcidol; 1-Hydroxycholecalciferol; Alpha D3; Etalpha; Alfacalcidol

Database IDs

• CAS Number: 41294-56-8
• PubChem SID: 162037616
• PubChem CID: 5282181; 5284515
• ATC CODE: A11CC03
• CHEMBL: 32540
• Chemspider ID: 4445376
• DrugBank ID: DB01436
• KEGG ID: D01518
• Unique Ingredient Identifier: URQ2517572
• Wikipedia Title: Alfacalcidol

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.8218555
• LogD (pH = 7.4): 5.8218555
• Log P: 5.8218555
• Molar Refractivity: 124.6964 cm^3
• Polarizability: 48.829468 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: VDR

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1468

Research Area: cancer
Biological Activity:
Alfacalcidol is a non-selective VDR activator medication. It is used in both adults and children to treat Vitamin D deficiency that leads to serious bone defects like osteomalacia and rickets. [1]In a recently published study, 378 community-dwelling women (n=191) and men (n=187) averaging 75 years old and with normal vitamin D serum levels were randomized to receive double-blindedly 1 µg of either alfacalcidol or placebo daily for 9 months. Compared to placebo, the treatment with alfacalcidol was associated with a significant reduction in the number of fallers (odds ratio 0.45, 95% confidence interval 0.21–0.97, P=0,04) and number of falls (odds ratio 0.46, 95% confidence interval 0.22–0.99, P=0.045) in participants with total calcium intake of more than 500 mg daily.[2]In an animal study on ovarectomized rats treated with alfacalcidol 0.1 and 0.2 µg/kg four months bone biopsies were again analyzed with a µCT-Scanner. Results show that bone loss in these ovarectomized animals could be stopped with alfacalcido. [3]References on Alfacalcidol[] Cancer Res, 2004, 64:4931-4941

REFERENCES

• www.medicallook.com/reviews/Alfacalcidol.com