| 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 |
|
| Name |
Etidronic acid |
| Drug Type |
|
| Description |
A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover. [PubChem] |
| 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
|
| Brand Names |
- Cintichem Technetium 99m Hedspa
- Dequest 2010
- Dequest 2015
- Dequest Z 010
- Didronel
- Didronel IV
- Ferrofos 510
- MPI Stannous Diphosphonate
- Osteoscan
- Turpinal SL
|
| Brand Mixtures |
- Didrocal (Calcium Carbonate + Etidronate Disodium)
|
| Chemical IUPAC Name |
(1-hydroxy-1-phosphonoethyl)phosphonic acid |
| Chemical Formula |
C2H8O7P2 |
| Chemical 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  |
| KEGG Compound |
C07736 |
| PubChem Compound |
3305 |
| PubChem Substance |
626344 |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA449548 |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02248686 |
| RxList Link |
http://www.rxlist.com/cgi/generic/didronel.htm |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Etidronic_acid |
| 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 | Download |
| SDF File |
Show | Download |
| PDB File |
Show | Download |
| 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 |
|
| 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 |
|
| Patient Information |
Not Available |
| Contraindications |
Show |
| Interactions |
Show |
| 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 |
- Wikipedia
- RxList
|
| Organisms Affected |
|
| Targets |
- 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 |
- Ono K, Wada S: [Regulation of calcification by bisphosphonates] Clin Calcium. 2004 Jun;14(6):60-3. [PubMed ]
- Takaishi Y: [Treatment of periodontal disease, prevention and bisphosphonate] Clin Calcium. 2003 Feb;13(2):173-6. [PubMed ]
- 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 ]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed ]
- 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 ]
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