ContaminantDB: Etidronic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:58:40 UTC

Update Date

2016-11-09 01:08:52 UTC

Accession Number

CHEM002506

Identification

Common Name

Etidronic acid

Class

Small Molecule

Description

Etidronic 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.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Antihypocalcemic Agent
Antineoplastic Agent
Bisphosphonate
Bone Density Conservation Agent
Drug
Food Toxin
Household Toxin
Metabolite
Organic Compound
Osteoporosis Prophylactic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1-Hydroxyethylene)diphosphonic acid	ChEBI
(1-Hydroxyethylidene)bis(phosphonic acid)	ChEBI
(1-Hydroxyethylidene)bisphosphonic acid	ChEBI
(1-Hydroxyethylidene)diphosphonic acid	ChEBI
(Hydroxyethylidene)diphosphonic acid	ChEBI
1,1,1-Ethanetriol diphosphonate	ChEBI
1-Hydroxy-1,1-diphosphonoethane	ChEBI
1-Hydroxyethane-1,1-bisphosphonic acid	ChEBI
1-Hydroxyethane-1,1-diphosphonate	ChEBI
1-Hydroxyethane-1,1-diphosphonic acid	ChEBI
1-Hydroxyethanediphosphonic acid	ChEBI
1-Hydroxyethylidene-1,1-bisphosphonate	ChEBI
1-Hydroxyethylidene-1,1-diphosphonic acid	ChEBI
Acetodiphosphonic acid	ChEBI
Acide etidronique	ChEBI
Acido etidronico	ChEBI
Acidum etidronicum	ChEBI
EHDP	ChEBI
Ethane-1-hydroxy-1,1-bisphosphonic acid	ChEBI
Ethane-1-hydroxy-1,1-diphosphonate	ChEBI
Ethane-1-hydroxy-1,1-diphosphonic acid	ChEBI
Etidronate	ChEBI
Etidronsaeure	ChEBI
HEDP	ChEBI
Hydroxyethanediphosphonic acid	ChEBI
Oxyethylidenediphosphonic acid	ChEBI
Ethane-1-hydroxy-1,1-bisphosphonate	Kegg
(1-Hydroxyethylene)diphosphonate	Generator
(1-Hydroxyethylidene)bis(phosphonate)	Generator
(1-Hydroxyethylidene)bisphosphonate	Generator
(1-Hydroxyethylidene)diphosphonate	Generator
(Hydroxyethylidene)diphosphonate	Generator
1,1,1-Ethanetriol diphosphonic acid	Generator
1-Hydroxyethane-1,1-bisphosphonate	Generator
1-Hydroxyethanediphosphonate	Generator
1-Hydroxyethylidene-1,1-bisphosphonic acid	Generator
1-Hydroxyethylidene-1,1-diphosphonate	Generator
Acetodiphosphonate	Generator
Hydroxyethanediphosphonate	Generator
Oxyethylidenediphosphonate	Generator
Etidronate disodium	HMDB
1 Hydroxyethane 1,1 diphosphonate	HMDB
1,1 Hydroxyethylenediphosphonate	HMDB
Dicalcium ehdp	HMDB
Dicalcium etidronate	HMDB
Diphosphonic acid, hydroxyethylidene	HMDB
Etidronate, sodium	HMDB
Hydroxyethylidene diphosphonic acid	HMDB
Sodium etidronate	HMDB
Xidiphon	HMDB
(1-Hydroxyethylene)diphosphonic acid, tetrapotassium salt	HMDB
Didronel	HMDB
Disodium 1-hydroxyethylene diphosphonate	HMDB
Ethanehydroxydiphosphonate	HMDB
Ethanehydroxyphosphate	HMDB
Salt etidronate, tetrapotassium	HMDB
1 Hydroxyethylidene 1,1 bisphosphonate	HMDB
1,1-Hydroxyethylenediphosphonate	HMDB
Diphosphonate, disodium 1-hydroxyethylene	HMDB
Disodium 1 hydroxyethylene diphosphonate	HMDB
EHDP, dicalcium	HMDB
Etidronate, disodium	HMDB
Etidronate, tetrapotassium salt	HMDB
Phosphonic acid, (1-hydroxyethylidene)bis-, disodium salt	HMDB
Tetrapotassium salt etidronate	HMDB
Xidifon	HMDB
Xydiphone	HMDB
1-Hydroxyethylene diphosphonate, disodium	HMDB
Disodium etidronate	HMDB
Etidronate, dicalcium	HMDB
HEDSPA	HMDB

Chemical Formula

C₂H₈O₇P₂

Average Molecular Mass

206.027 g/mol

Monoisotopic Mass

205.975 g/mol

CAS Registry Number

7414-83-7

IUPAC Name

(1-hydroxy-1-phosphonoethyl)phosphonic acid

Traditional Name

etidronic acid

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 Key

DBVJJBKOTRCVKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Bisphosphonates

Direct Parent

Bisphosphonates

Alternative Parents

Substituents

Bisphosphonate
Organophosphonic acid
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1,1-bis(phosphonic acid) (CHEBI:4907 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

chelator

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.15e+01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	11.5 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	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.51 m³·mol⁻¹	ChemAxon
Polarizability	13.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9310000000-2caef035e19867df64bf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9540000000-38ec250196bc1c488215	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0090000000-a9f75f8364e22febc69e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0190000000-7e7c121eec680994473e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0390000000-f6ab7574deae5f44d8b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08j0-9620000000-0618a9cfbf1724258f3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-9100000000-cfaba7073e26e33fa329	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0960000000-dc95e917c594d7c69a00	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0560-6900000000-42d2a2563e015073e66b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9300000000-995ddbe23b852a05ae3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-2980000000-d59d8cb7d24ab907283d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fni-4920000000-15809f5e174b6322f374	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9100000000-9b55901243a14d80a6f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1910000000-38d2c6a97af6630a8fa3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9470000000-42c471e70e6c11b7b6d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-92dadebcb6c35ccc4a68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-72d943e9ef38c579f95a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9200000000-57c7611567781ad9597a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-fcbb693760d15d6e4929	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

The amount of drug absorbed after an oral dose is approximately 3%.

Mechanism of Toxicity

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.

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.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

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.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01077

HMDB ID

HMDB0015210

FooDB ID

FDB001018

Phenol Explorer ID