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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:53 UTC
HMDB IDHMDB15210
Secondary Accession NumbersNone
Metabolite Identification
Common NameEtidronic acid
DescriptionEtidronic 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 fully 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 cellular energy metabolism. The osteoclast initiates apoptosis and dies, leading to an overall decrease in the breakdown of bone.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC2H8O7P2
Average Molecular Weight206.0282
Monoisotopic Molecular Weight205.974525634
IUPAC Name(1-hydroxy-1-phosphonoethyl)phosphonic acid
Traditional Nameetidronic acid
CAS Registry Number7414-83-7
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 KeyInChIKey=DBVJJBKOTRCVKF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
Alternative Parents
Substituents
  • Bisphosphonate
  • Organophosphonic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antihypocalcemic Agents
  • Antineoplastic Agents
  • Bisphosphonates
  • Bone Density Conservation Agents
  • Osteoporosis Prophylactic
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.15e+01 g/LNot Available
LogP-3.8Not Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01077
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01077
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01077
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001018
KNApSAcK IDNot Available
Chemspider ID3189
KEGG Compound IDC07736
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtidronic_acid
NuGOwiki LinkHMDB15210
Metagene LinkHMDB15210
METLIN IDNot Available
PubChem Compound3305
PDB ID911
ChEBI ID4907
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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. [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. [8610169 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]