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Etidronic acid

July 24, 2017
Common Name

Etidronic acid Description

Etidronic acid is only found in individuals that have used or taken this drug. It is a diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover. [PubChem]Bisphosphonates, when attached to bone tissue, are absorbed by osteoclasts, the bone cells that breaks down bone tissue. Although the mechanism of action of non-nitrogenous bisphosphonates has not been flily elucidated, available data suggest that they bind strongly to hydroxyapatite crystals in the bone matrix, preferentially at the sites of increased bone turnover and inhibit the formation and dissolution of the crystals. Other actions may include direct inhibition of mature osteoclast function, promotion of osteoclast apoptosis, and interference with osteoblast-mediated osteoclast activation. Etidronic acid does not interfere with bone mineralization. In malignancy-related hypercalcemia, etidronic acid decreases serum calcium by inhibiting tumour-induced bone resorption and reducing calcium flow from the resorbing bone into the blood. Etidronic acid also reduces morbidity of osteolytic bone metastases by inhibiting tumour-induced bone resorption. Etidronic acid may promote osteoclast apoptosis by competing with adenosine triphosphate (ATP) in the cellliar energy metabolism. The osteoclast initiates apoptosis and dies, leading to an overall decrease in the breakdown of bone. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (1-Hydroxyethylene)diphosphonic acidChEBI (1-Hydroxyethylidene)bis(phosphonic acid)ChEBI (1-Hydroxyethylidene)bisphosphonic acidChEBI (1-Hydroxyethylidene)diphosphonic acidChEBI (Hydroxyethylidene)diphosphonic acidChEBI 1,1,1-Ethanetriol diphosphonateChEBI 1-Hydroxy-1,1-diphosphonoethaneChEBI 1-Hydroxyethane-1,1-bisphosphonic acidChEBI 1-Hydroxyethane-1,1-diphosphonateChEBI 1-Hydroxyethane-1,1-diphosphonic acidChEBI 1-Hydroxyethanediphosphonic acidChEBI 1-Hydroxyethylidene-1,1-bisphosphonateChEBI 1-Hydroxyethylidene-1,1-diphosphonic acidChEBI Acetodiphosphonic acidChEBI Acide etidroniqueChEBI acido EtidronicoChEBI Acidum etidronicumChEBI EHDPChEBI Ethane-1-hydroxy-1,1-bisphosphonic acidChEBI Ethane-1-hydroxy-1,1-diphosphonateChEBI Ethane-1-hydroxy-1,1-diphosphonic acidChEBI EtidronateChEBI EtidronsaeureChEBI HEDPChEBI Hydroxyethanediphosphonic acidChEBI Oxyethylidenediphosphonic acidChEBI (1-Hydroxyethylene)diphosphonateGenerator (1-Hydroxyethylidene)bis(phosphonate)Generator (1-Hydroxyethylidene)bisphosphonateGenerator (1-Hydroxyethylidene)diphosphonateGenerator (Hydroxyethylidene)diphosphonateGenerator 1,1,1-Ethanetriol diphosphonic acidGenerator 1-Hydroxyethane-1,1-bisphosphonateGenerator 1-HydroxyethanediphosphonateGenerator 1-Hydroxyethylidene-1,1-bisphosphonic acidGenerator 1-Hydroxyethylidene-1,1-diphosphonateGenerator AcetodiphosphonateGenerator Ethane-1-hydroxy-1,1-bisphosphonateGenerator HydroxyethanediphosphonateGenerator OxyethylidenediphosphonateGenerator Etidronate disodiumHMDB 1 Hydroxyethane 1,1 diphosphonateMeSH 1,1 HydroxyethylenediphosphonateMeSH Dicalcium ehdpMeSH Dicalcium etidronateMeSH Diphosphonic acid, hydroxyethylideneMeSH Etidronate, sodiumMeSH Hydroxyethylidene diphosphonic acidMeSH Sodium etidronateMeSH XidiphonMeSH (1-Hydroxyethylene)diphosphonic acid, tetrapotassium saltMeSH DidronelMeSH Disodium 1-hydroxyethylene diphosphonateMeSH EthanehydroxydiphosphonateMeSH EthanehydroxyphosphateMeSH Salt etidronate, tetrapotassiumMeSH 1 Hydroxyethylidene 1,1 bisphosphonateMeSH 1,1-HydroxyethylenediphosphonateMeSH Diphosphonate, disodium 1-hydroxyethyleneMeSH Disodium 1 hydroxyethylene diphosphonateMeSH EHDP, dicalciumMeSH Etidronate, disodiumMeSH Etidronate, tetrapotassium saltMeSH Phosphonic acid, (1-hydroxyethylidene)bis-, disodium saltMeSH Tetrapotassium salt etidronateMeSH XidifonMeSH XydiphoneMeSH 1-Hydroxyethylene diphosphonate, disodiumMeSH Disodium etidronateMeSH Etidronate, dicalciumMeSH HEDSPAMeSH

Chemical Formlia

C2H8O7P2 Average Molecliar Weight

206.027 Monoisotopic Molecliar Weight

205.974526594 IUPAC Name

(1-hydroxy-1-phosphonoethyl)phosphonic acid Traditional Name

etidronic acid CAS Registry Number

7414-83-7 SMILES

CC(O)(P(O)(O)=O)P(O)(O)=O

InChI Identifier

InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)

InChI Key

DBVJJBKOTRCVKF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Organic phosphonic acids and derivatives Direct Parent

Bisphosphonates Alternative Parents

  • Organic phosphonic acids
  • Organopnictogen compounds
  • Organophosphorus compounds
  • Organooxygen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Bisphosphonate
  • Organophosphonic acid
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • 1,1-bis(phosphonic acid) (CHEBI:4907 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antihypocalcemic Agents
  • Antineoplastic Agents
  • Bisphosphonates
  • Bone Density Conservation Agents
  • Osteoporosis Prophylactic

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.15e+01 g/LNot Available LogP-3.8Not Available

    Predicted Properties

    Property Value Source Water Solubility11.5 mg/mLALOGPS logP-0.77ALOGPS logP-2.3ChemAxon logS-1.2ALOGPS pKa (Strongest Acidic)0.7ChemAxon pKa (Strongest Basic)-5.1ChemAxon Physiological Charge-3ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count5ChemAxon Polar Surface Area135.29 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity34.51 m3·mol-1ChemAxon Polarizability13.97 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0a4i-0090000000-a9f75f8364e22febc69eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0a4i-0190000000-7e7c121eec680994473eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-0a4i-0390000000-f6ab7574deae5f44d8b4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-08j0-9620000000-0618a9cfbf1724258f3bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-03di-9100000000-cfaba7073e26e33fa329View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • 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 DB01077

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01077

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01077 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB001018 KNApSAcK ID

    Not Available Chemspider ID

    3189 KEGG Compound ID

    C07736 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Etidronic_acid NuGOwiki Link

    HMDB15210 Metagene Link

    HMDB15210 METLIN ID

    Not Available PubChem Compound

    3305 PDB ID

    911 ChEBI ID

    4907

    Product: IWR-2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in ATP binding
    Specific function:
    Catalytic subunit of the peripheral V1 complex of vacuolar ATPase. V-ATPase vacuolar ATPase is responsible for acidifying a variety of intracellular compartments in eukaryotic cells.
    Gene Name:
    ATP6V1A
    Uniprot ID:
    P38606
    Molecular weight:
    68303.5
    References
    1. David P, Nguyen H, Barbier A, Baron R: The bisphosphonate tiludronate is a potent inhibitor of the osteoclast vacuolar H(+)-ATPase. J Bone Miner Res. 1996 Oct;11(10):1498-507. [PubMed:8889850 ]
    General function:
    Involved in phosphatase activity
    Specific function:
    Interacts with LAR-interacting protein LIP.1.
    Gene Name:
    PTPRS
    Uniprot ID:
    Q13332
    Molecular weight:
    217039.825
    References
    1. Schmidt A, Rutledge SJ, Endo N, Opas EE, Tanaka H, Wesolowski G, Leu CT, Huang Z, Ramachandaran C, Rodan SB, Rodan GA: Protein-tyrosine phosphatase activity regulates osteoclast formation and function: inhibition by alendronate. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):3068-73. [PubMed:8610169 ]
    2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 18416830

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