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Showing drug card for Etidronic acid (DB01077)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:05:07
Primary Accession Number DB01077
Secondary Accession Number
  • APRD00964
Name Etidronic acid
Drug Type
  • Approved
  • Small Molecule
Description A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover. [PubChem]
Synonyms
  1. Acetodiphosphonic acid
  2. Acide etidronique [INN-French]
  3. Acido etidronico [INN-Spanish]
  4. Acidum etidronicum [INN-Latin]
  5. EHDP
  6. Etidronate
  7. Etidronate Disodium
  8. Etidronsaeure
  9. HEDP
  10. Hydroxyethanediphosphonic acid
  11. Oxyethylidenediphosphonic acid
Brand Names
  1. Cintichem Technetium 99m Hedspa
  2. Dequest 2010
  3. Dequest 2015
  4. Dequest Z 010
  5. Didronel
  6. Didronel IV
  7. Ferrofos 510
  8. MPI Stannous Diphosphonate
  9. Osteoscan
  10. Turpinal SL
Brand Mixtures
  1. Didrocal (Calcium Carbonate + Etidronate Disodium)
Chemical IUPAC Name (1-hydroxy-1-phosphonoethyl)phosphonic acid
Chemical Formula C2H8O7P2
Chemical Structure Structure
CAS Registry Number 7414-83-7
InChI Identifier InChI=1/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)/f/h4-5,7-8H
InChI Key DBVJJBKOTRCVKF-QHPLZEHWCS
KEGG Drug D00314 Link Image
KEGG Compound C07736 Link Image
PubChem Compound 3305 Link Image
PubChem Substance 626344 Link Image
ChEBI ID Not Available
PharmGKB ID PA449548 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02248686 Link Image
RxList Link http://www.rxlist.com/cgi/generic/didronel.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Etidronic_acid Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 206.0282
Monoisotopic Molecular Weight 205.9745
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.15e+01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -3.8 Source: PhysProp
Predicted LogP -0.77 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.25 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC(O)(P(O)(O)=O)P(O)(O)=O
Canonical SMILES CC(O)(P(O)(O)=O)P(O)(O)=O
Drug Category
  • Antihypocalcemic Agents
  • Antineoplastic Agents
  • Bisphosphonates
  • Bone Density Conservation Agents
  • Osteoporosis Prophylactic
ATC Codes
AHFS Codes
  • 92:00.00
Indication For the treatment of symptomatic Paget's disease of bone and in the prevention and treatment of heterotopic ossification following total hip replacement or due to spinal cord injury.
Pharmacology Etidronic acid is a first generation (non-nitrogenous) bisphosphonate in the same family as clodronate and tiludronate. Etidronic acid affects calcium metabolism and inhibits bone resorption and soft tissue calcification. Of the etidronic acid that is resorbed (from oral preparation) or infused (for intravenous drugs), about 50% is excreted unchanged by the kidney. The remainder has a very high affinity for bone tissue, and is rapidly absorbed onto the bone surface. Etidronic acid has been shown to prevent or delay skeletal-related events and decrease bone pain as well as normalize calcium levels in the presence of hypercalcemia.
Mechanism of Action 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.
Absorption The amount of drug absorbed after an oral dose is approximately 3%.
Toxicity Clinical experience with acute etidronic acid overdosage is extremely limited. Decreases in serum calcium following substantial overdosage may be expected in some patients. Signs and symptoms of hypocalcemia also may occur in some of these patients. Some patients may develop vomiting. In one event, an 18-year-old female who ingested an estimated single dose of 4800 to 6000 mg (67 to 100 mg/kg) of etidronate was reported to be mildly hypocalcemic (7 .5 2 mg/ dl) and experienced paresthesia of the fingers.
Protein Binding Not Available
Biotransformation Not metabolized.
Half Life In normal subjects, plasma half-life of etidronic acid, based on non-compartmental pharmacokinetics is 1 to 6 hours.
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Aluminium Formation of non-absorbable complexes
Bismuth Formation of non-absorbable complexes
Calcium Formation of non-absorbable complexes
Iron Formation of non-absorbable complexes
Magnesium Formation of non-absorbable complexes
Magnesium oxide Formation of non-absorbable complexes
Sucralfate Formation of non-absorbable complexes
Food Interactions
  • Avoid aluminium, calcium, iron and magnesium.
  • Take on an empty stomach.
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Hydroxyapatite
Drug Target 1 [top]
Target 1 ID 930
Target 1 Name Hydroxyapatite
Target 1 Synonyms Not Available
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 502.311
Target 1 Theoretical pI Not Available
Target 1 GO Classification Not Available
Target 1 General Function Hydroxylapatite is the main mineral component of bone. Carbonated-calcium deficient hydroxyapatite is the main mineral of which dental enamel and dentin are comprised.
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function Not Available
Target 1 Signals Not Available
Target 1 Transmembrane Regions Not Available
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence Not Available
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References Not Available
Target 1 Drug References
  1. Ono K, Wada S: [Regulation of calcification by bisphosphonates] Clin Calcium. 2004 Jun;14(6):60-3. [PubMed Link Image]
  2. Takaishi Y: [Treatment of periodontal disease, prevention and bisphosphonate] Clin Calcium. 2003 Feb;13(2):173-6. [PubMed Link Image]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  4. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  5. Grases F, Sanchis P, Perello J, Isern B, Prieto RM, Fernandez-Palomeque C, Torres JJ: Effect of crystallization inhibitors on vascular calcifications induced by vitamin D: a pilot study in Sprague-Dawley rats. Circ J. 2007 Jul;71(7):1152-6. [PubMed Link Image]

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