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Identification
Name Etidronic acid
Accession Number DB01077 (APRD00964)
Type small molecule
Groups approved
Description

A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Acetodiphosphonic acid
Acide etidronique [INN-French]
Acido etidronico [INN-Spanish]
Acidum etidronicum [INN-Latin]
EHDP
Etidronate
Etidronate Disodium
Etidronsaeure
HEDP
Hydroxyethanediphosphonic acid
Oxyethylidenediphosphonic acid
First Prev Next Last
Salts Not Available
Brand names
Name Company
Cintichem Technetium 99m Hedspa
Dequest 2010
Dequest 2015
Dequest Z 010
Didronel Procter & Gamble
Didronel IV
Ferrofos 510
MPI Stannous Diphosphonate
Osteoscan
Turpinal SL
Brand mixtures
Brand Name Ingredients
Didrocal Etidronate Disodium + Calcium Carbonate
Categories
  • Antineoplastic Agents
  • Antihypocalcemic Agents
  • Bisphosphonates
  • Osteoporosis Prophylactic
  • Bone Density Conservation Agents
CAS number 7414-83-7
Weight Average: 206.0282
Monoisotopic: 205.974525634
Chemical Formula C2H8O7P2
InChI Key InChIKey=DBVJJBKOTRCVKF-UHFFFAOYSA-N
InChI
InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)
Plain Text
IUPAC Name
(1-hydroxy-1-phosphonoethyl)phosphonic acid
SMILES
CC(O)(P(O)(O)=O)P(O)(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Bisphosphonates
Substructures
  • Hydroxy Compounds
  • Carboxylic Acids and Derivatives
  • Phosphonic Acids and Derivatives
  • Phosphinic Acids and Derivatives
  • Bisphosphonates
Pharmacology
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.
Pharmacodynamics 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%.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not metabolized.
Route of elimination Etidronate disodium is not metabolized. Within 24 hours, approximately half the absorbed dose is excreted in urine; the remainder is distributed to bone compartments from which it is slowly eliminated. Unabsorbed drug is excreted intact in the feces.
Half life In normal subjects, plasma half-life of etidronic acid, based on non-compartmental pharmacokinetics is 1 to 6 hours.
Clearance Not Available
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.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Mgi pharma inc
  • Procter and gamble pharmaceuticals inc sub procter and gamble co
  • Mylan pharmaceuticals inc
  • Ge healthcare
  • Mallinckrodt inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral 200 mg
Tablet Oral 400 mg
Prices
Unit description Cost Unit
Didronel 400 mg tablet 8.31 USD tablet
Didronel 200 mg tablet 4.16 USD tablet
Co Etidronate 200 mg Tablet 0.86 USD tablet
Mylan-Etidronate 200 mg Tablet 0.86 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP -3.8 Not Available
Predicted Properties
Property Value Source
water solubility 1.15e+01 g/l ALOGPS
logP -0.77 ALOGPS
logP -2.3 ChemAxon
logS -1.2 ALOGPS
pKa (strongest acidic) 0.7 ChemAxon
pKa (strongest basic) -5.1 ChemAxon
physiological charge -2 ChemAxon
hydrogen acceptor count 7 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 135.29 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 34.51 ChemAxon
polarizability 13.97 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00314 Link_out
KEGG Compound C07736 Link_out
PubChem Compound 3305 Link_out
PubChem Substance 46507694 Link_out
ChemSpider 3189 Link_out
BindingDB 50115102 Link_out
ChEBI 4907 Link_out
ChEMBL 4907 Link_out
Therapeutic Targets Database DNC000629 Link_out
PharmGKB PA449548 Link_out
Drug Product Database 2248686 Link_out
RxList http://www.rxlist.com/cgi/generic/didronel.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Etidronic_acid Link_out
ATC Codes
  • M05BA01
  • M05BB01
AHFS Codes
  • 92:00.00
PDB Entries Not Available
FDA label show (42 KB)
MSDS show (44.4 KB)
Interactions
Drug Interactions
Drug Interaction
Aluminium Formation of non-absorbable complexes
Calcium Formation of non-absorbable complexes
Calcium Acetate Calcium Salts may decrease the serum concentration of Bisphosphonate Derivatives such as etidronic acid (etidronate). Avoid administration of oral calcium supplements within 2 hours before or after tiludronate/clodronate/etidronate.
Calcium Chloride Calcium salts may decrease the serum concentration of bisphosphonate derivatives. Avoid administration of oral calcium supplements within 2 hours before or after tiludronate/clodronate/etidronate.
Iron Formation of non-absorbable complexes
Iron Dextran 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 within 2 hours of taking medication.
  • Take on an empty stomach with a full glass of water.
Targets

1. Hydroxyapatite

Pharmacological action: yes
Actions: antagonist

References:
  1. 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
  2. Nancollas GH, Tang R, Phipps RJ, Henneman Z, Gulde S, Wu W, Mangood A, Russell RG, Ebetino FH: Novel insights into actions of bisphosphonates on bone: differences in interactions with hydroxyapatite. Bone. 2006 May;38(5):617-27. Epub 2005 Jul 20. Pubmed
  3. Ono K, Wada S: [Regulation of calcification by bisphosphonates] Clin Calcium. 2004 Jun;14(6):60-3. Pubmed
  4. Takaishi Y: [Treatment of periodontal disease, prevention and bisphosphonate] Clin Calcium. 2003 Feb;13(2):173-6. Pubmed

2. Receptor-type tyrosine-protein phosphatase S

Pharmacological action: unknown
Actions: inhibitor

Interacts with LAR-interacting protein LIP.1

Organism class: human
UniProt ID: Q13332 Link_out
Gene: PTPRS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. V-type proton ATPase catalytic subunit A

Pharmacological action: unknown
Actions: inhibitor

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

Organism class: human
UniProt ID: P38606 Link_out
Gene: ATP6V1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19