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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:28 UTC
HMDB IDHMDB0015210
Secondary Accession Numbers
  • HMDB15210
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
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 FormulaC2H8O7P2
Average Molecular Weight206.027
Monoisotopic Molecular Weight205.974526594
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 KeyDBVJJBKOTRCVKF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphonic acids and derivatives
Direct ParentBisphosphonates
Alternative Parents
Substituents
  • Bisphosphonate
  • Organophosphonic acid
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Metabolism and nutrition disorders:

    Gastrointestinal disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.5 g/LNot Available
LogP-3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.51 m³·mol⁻¹ChemAxon
Polarizability13.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9310000000-2caef035e19867df64bfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9540000000-38ec250196bc1c488215View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-a9f75f8364e22febc69eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0190000000-7e7c121eec680994473eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0390000000-f6ab7574deae5f44d8b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-08j0-9620000000-0618a9cfbf1724258f3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-9100000000-cfaba7073e26e33fa329View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0960000000-dc95e917c594d7c69a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-6900000000-42d2a2563e015073e66bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9300000000-995ddbe23b852a05ae3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-2980000000-d59d8cb7d24ab907283dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fni-4920000000-15809f5e174b6322f374View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9100000000-9b55901243a14d80a6f7View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01077 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01077 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
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. [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 ]