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Alfacalcidol

July 24, 2017
Common Name

Alfacalcidol Description

Alfacalcidol is an active metabolite of Vitamin D, which performs important functions in regliation 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 regliated by a negative feedback mechanism. (PMID:17438884 ,17668216 ). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (5Z,7E)-9,10-seco-5,7,10(19)-Cholestatrien-1alpha,3beta-diolChEBI 1alpha-Hydroxy-vitamin D3ChEBI 1alpha-HydroxycholecalciferolChEBI 1alpha-Hydroxyvitamin D3ChEBI 9,10-Secocholesta-5,7,10(19)-triene-1alpha,3beta-diolChEBI AlfacalcidolumChEBI AlsiodolChEBI (5Z,7E)-9,10-seco-5,7,10(19)-Cholestatrien-1a,3b-diolGenerator (5Z,7E)-9,10-seco-5,7,10(19)-Cholestatrien-1α,3β-diolGenerator 1a-Hydroxy-vitamin D3Generator 1α-hydroxy-vitamin D3Generator 1a-HydroxycholecalciferolGenerator 1α-hydroxycholecalciferolGenerator 1a-Hydroxyvitamin D3Generator 1α-hydroxyvitamin D3Generator 9,10-Secocholesta-5,7,10(19)-triene-1a,3b-diolGenerator 9,10-Secocholesta-5,7,10(19)-triene-1α,3β-diolGenerator 1-HydroxycholecalciferolHMDB 1 alpha-HydroxycholecalciferolMeSH 1-alpha-OxycholecalciferolMeSH 1-Hydroxycholecalciferol, (1alpha,3alpha-(5Z,7E))-isomerMeSH 1-Hydroxycholecalciferol, (1beta)-(5Z)-isomerMeSH 1alpha-OHD3MeSH AlfaDMeSH OksidevitMeSH Un-alfaMeSH 1 alpha-Hydroxyvitamin D3MeSH 1-Hydroxycholecalciferol, (1beta,3beta-(5E,7E))-isomerMeSH BondiolMeSH Doss brand OF alfacalcidolMeSH AlphacalcidolMeSH 1-Hydroxycholecalciferol, aluminum saltMeSH EinsAlphaMeSH EtalphaMeSH EenalfadrieMeSH One-AlphaMeSH

Chemical Formlia

C27H44O2 Average Molecliar Weight

400.6371 Monoisotopic Molecliar Weight

400.334130652 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 Traditional Name

etα CAS Registry Number

41294-56-8 SMILES

CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(CCC[C@]12C)=CC=C1C[C@@H](O)C[C@H](O)C1=C

InChI Identifier

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

InChI Key

OFHCOWSQAMBJIW-AVJTYSNKSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Vitamin D and derivatives Direct Parent

Vitamin D and derivatives Alternative Parents

  • Triterpenoids
  • Secondary alcohols
  • Cyclic alcohols and derivatives
  • Hydrocarbon derivatives

    • Substituents

  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • diol (CHEBI:31186 )
  • seco-cholestane (CHEBI:31186 )
  • D3 vitamins (CHEBI:31186 )
  • hydroxycalciol (CHEBI:31186 )
  • Vitamin D3 and derivatives (LMST03020231 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Bone Density Conservation Agents
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point136 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.63e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0016 mg/mLALOGPS logP6.68ALOGPS logP5.82ChemAxon logS-5.4ALOGPS pKa (Strongest Acidic)14.39ChemAxon pKa (Strongest Basic)-2.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area40.46 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity124.7 m3·mol-1ChemAxon Polarizability50.55 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01436

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01436

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01436 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4445376 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15504 Metagene Link

    HMDB15504 METLIN ID

    Not Available PubChem Compound

    5282181 PDB ID

    Not Available ChEBI ID

    1125553

    Product: (R)-Lansoprazole

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Galesanu C, Ciubotariu C, Melnic G, Galesanu MR: [Postmenopausal osteoporosis. Digital Rx radiogrammetry in the diagnosis and follow-up of treatment with alfacalcidol]. Rev Med Chir Soc Med Nat Iasi. 2006 Oct-Dec;110(4):833-41. [PubMed:17438884 ]
    2. Ringe JD, Schacht E: Improving the outcome of established therapies for osteoporosis by adding the active D-hormone analog alfacalcidol. Rheumatol Int. 2007 Dec;28(2):103-11. Epub 2007 Aug 1. [PubMed:17668216 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
    Gene Name:
    CYP27B1
    Uniprot ID:
    O15528
    Molecular weight:
    56503.475
    References
    1. Uchida E, Kagawa N, Sakaki T, Urushino N, Sawada N, Kamakura M, Ohta M, Kato S, Inouye K: Purification and characterization of mouse CYP27B1 overproduced by an Escherichia coli system coexpressing molecular chaperonins GroEL/ES. Biochem Biophys Res Commun. 2004 Oct 15;323(2):505-11. [PubMed:15369780 ]
    General function:
    Involved in sequence-specific DNA binding transcription factor activity
    Specific function:
    Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Regulates transcription of hormone sensitive genes via its association with the WINAC complex, a chromatin-remodeling complex. Recruited to promoters via its interaction with the WINAC complex subunit BAZ1B/WSTF, which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis
    Gene Name:
    VDR
    Uniprot ID:
    P11473
    Molecular weight:
    48288.6
    References
    1. Reinhart GA: Vitamin D analogs: novel therapeutic agents for cardiovascular disease? Curr Opin Investig Drugs. 2004 Sep;5(9):947-51. [PubMed:15503649 ]
    2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    3. Fujishima T, Tsuji G, Tanaka C, Harayama H: Novel vitamin D receptor ligands having a carboxyl group as an anchor to arginine 274 in the ligand-binding domain. J Steroid Biochem Mol Biol. 2010 Jul;121(1-2):60-2. doi: 10.1016/j.jsbmb.2010.04.020. Epub 2010 May 6. [PubMed:20435140 ]

    PMID: 21947006

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