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

• ChemBase ID: 1243
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: O[C@@H]1C/C(=C/C=C\2/[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(C)C)C)(CCC2)C)/C(=C)[C@@H](O)C1
• 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-AVJTYSNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: alfacalcidol; etα
• Brand Name: One Alpha; Alsiodol
• Synonyms: 1alpha-hydroxycholecalciferol; 1alpha-hydroxyvitamin D3; 1-hydroxycholecalciferol; Alfacalcidol; 5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol; 1-α-Hydroxycholecalciferol; 1-α-Hydroxyvitamin D3; Alpharol; Alpha D3; Etalpha; Oxydevit

Database IDs

• CAS Number: 41294-56-8
• PubChem SID: 160964703; 46505115
• PubChem CID: 5282181

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 6.68
• LOG S: -5.39
• Solubility (Water): 1.63e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 135-137C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB01436

• Drug Groups: approved; nutraceutical
• Description: Alfacalcidol is an active metabolite of Vitamin D, which performs important functions in regulation of the calcium balance and the bone metabolism. Alfacalcidol is Vitamin D-hormone analog which is activated by the enzyme 25-hydroxylase in the liver for systemic and in osteoblasts for local D-hormone actions. It possesses a unique pattern of pleiotropic effects on, e.g. gut, bone, pararthyroids, muscle and brain. Alfacalcidol is superior to plain vitamin D (cholecalciferol) because the final kidney activation of the latter is regulated by a negative feedback mechanism. (PMID:17438884,17668216)
• Indication: Alfacalcidol is an active metabolite of Vitamin D, which performs important functions in regulation of the calcium balance and the bone metabolism.
• Pharmacology: Alfacalcidol is Vitamin D-hormone analog which is activated by the enzyme 25-hydroxylase in the liver for systemic and in osteoblasts for local D-hormone actions.
• Toxicity: Hypercalcemia - Early symptoms of hypercalcemia, include nausea and vomiting, weakness, headache, somnolence, dry mouth, constipation, metallic taste, muscle pain and bone pain. Late symptoms and signs of hypercalcemia, include polyuria, polydipsia, anorexia, weight loss, nocturia, conjunctivitis, pancreatitis, photophobia, rhinorrhea, pruritis, hyperthermia, decreased libido, elevated BUN, albuminuria, hypercholesterolemia, elevated ALT (SGPT) and AST (SGOT), ectopic calcification, nephrocalcinosis, hypertension and cardiac arrhythmias.
• Affected Organisms: Humans and other mammals

Toronto Research Chemicals - A524000

A synthetic analog of Calcitiol (the hormonal form of vitamin D3), which shows identical potency with respect to stimulation of intestinal calcium absorption and bone mineral mobilization. Vitamin D source.

REFERENCES

• Holick, et al.: Science, 180, 190 (1973)
• Morisaki, M., et al.: Chem. Pharm. Bull., 23, 3272 (1973)