ChemFOnt: Showing chemical card for Etidronic acid (CFc000009501)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:39 UTC

Chemfont ID

CFc000009501

Molecule Identification

Common Name

Etidronic acid

Definition

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.

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 Weight

206.027

Monoisotopic Molecular Weight

205.974526594

IUPAC Name

(1-hydroxy-1-phosphonoethyl)phosphonic acid

Traditional Name

etidronic acid

CAS Registry Number

7414-83-7

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 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 )

Functional Ontology

Physiological effect

Health effect

Observation

Vomiting (HMDB: HMDB0015210)

Circulatory system disorder

Blood and lymphatic system disorder

Hypocalcemia (HMDB: HMDB0015210)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015210)
Cell membrane (HMDB: HMDB0015210)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015210)

Source

Exogenous

Exogenous (HMDB: HMDB0015210)

Process

Not Available

Role

Industrial application

Bone density conservation agent (HMDB: HMDB0015210)
Antineoplastic agent (HMDB: HMDB0015210)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0015210)

Food and nutrition

Food and nutrition (HMDB: HMDB0015210)

Indirect biological role

Chelator (HMDB: HMDB0015210)

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon