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

• ChemBase ID: 154372
• Molecular Formular: C28H44O2
• Molecular Mass: 412.64776
• Monoisotopic Mass: 412.33413065
• SMILES: C[C@H](C=C[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](C[C@@H](C1=C)O)O)C
• Canonical SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C/C=C/2\CCC[C@]3([C@H]2CC[C@@H]3[C@@H](C=C[C@@H](C(C)C)C)C)C)/C1
• InChI: InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/t19-,20+,24+,25+,26-,27-,28+/m0/s1
• InChIKey: HKXBNHCUPKIYDM-CEANPDOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1α,3β-diol; (5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1?,3?-diol; 1α-Hydroxyergocalciferol; 1α-Hydroxyvitamin D2; 1α-OHD2; 1-α-Hydroxyvitamin D2; 1-Hydroxyergocalciferol; TSA 840; Doxercalciferol

Database IDs

• CAS Number: 54573-75-0
• MDL Number: MFCD00871065
• PubChem SID: 162248511
• PubChem CID: 71311851

CALCULATED PROPERTIES

• Rotatable Bonds: 5
• Lipinski's Rule of Five: false
• Acid pKa: 14.392874
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.746953
• LogD (pH = 7.4): 5.746953
• Log P: 5.746953
• Molar Refractivity: 130.3616 cm^3
• Polarizability: 50.44043 Å^3
• Polar Surface Area: 40.46 Å^2

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C28H44O2

DETAILS

Sigma Aldrich - D0196

Biochem/physiol Actions
Doxercalciferol is a Vitamin D2 analogue, a Vitamin D Receptor Activator (VDRA). Doxercalciferol acts as a pro-hormone, needing 25-hydroxylation in the liver for bioactivation into 1α, 25-hydroxyvitamin D2. Pivotal studies in adults on dialysis have demonstrated control of secondary hyperparathyroidism that is superior to placebo therapy, without undue suppression of 1st IMA-PTH < 300 pg/mL, or occurrences of hypercalcemia. Doxercalciferol has been shown to be effective in controlling secondary hyperparathyroidism of adult patients with CKD stages 3-4.
Doxercalciferol is a vitamin D2 analog that acts as a pro-hormone, activated in the liver to 1α,25-dihydroxyvitamin D2. Despite its relatively low affinity for the vitamin D receptor (VDR) (before activation), it is effective at suppressing expression of the parathyroid hormone (PTH) gene, and appears to act through the VDR.