Showing Compound Etidronic acid (FDB001018)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:48 UTC

Update date

2018-05-28 18:38:56 UTC

Primary ID

FDB001018

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Etidronic acid

Description

Food contaminant arising from its use as a boiler water additive for prepn. of steam used in food processing. Component of antimicrobial washes for poultry carcasses and fruit 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.

CAS Number

7414-83-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(1-hydroxy-1-phosphonoethyl)phosphonic acid	biospider
(1-hydroxyethane-1,1-diyl)bis(phosphonic acid)	biospider
(1-Hydroxyethylene)dionate	Generator
(1-Hydroxyethylene)dionic acid	ChEBI
(1-Hydroxyethylidene)bis(onate)	Generator
(1-Hydroxyethylidene)bis(onic acid)	ChEBI
(1-Hydroxyethylidene)bisonate	Generator
(1-Hydroxyethylidene)bisonic acid	ChEBI
(1-Hydroxyethylidene)bisphosphonic acid, 9CI	db_source
(1-Hydroxyethylidene)dionate	Generator
(1-Hydroxyethylidene)dionic acid	ChEBI
(1-Hydroxyethylidene)diphoshonic acid	biospider
(Hydroxyethylidene)dionate	Generator
(Hydroxyethylidene)dionic acid	ChEBI
(hydroxyethylidene)diphosphonic acid	biospider
1-Hydroxy-1,1-dionoethane	ChEBI
1-Hydroxyethane-1, 1-bisphosphonic acid	biospider
1-Hydroxyethane-1,1-bisonate	Generator
1-Hydroxyethane-1,1-bisonic acid	ChEBI
1-Hydroxyethane-1,1-dionate	ChEBI
1-Hydroxyethane-1,1-dionic acid	ChEBI
1-Hydroxyethane-1,1,-diphosphonic acid	biospider
1-Hydroxyethanedionate	Generator
1-Hydroxyethanedionic acid	ChEBI
1-Hydroxyethylidene-1, 1-diphosphonic acid	biospider
1-Hydroxyethylidene-1,1-biphosphonate	biospider
1-Hydroxyethylidene-1,1-bisonate	ChEBI
1-Hydroxyethylidene-1,1-bisonic acid	Generator
1-Hydroxyethylidene-1,1-dionate	Generator
1-Hydroxyethylidene-1,1-dionic acid	ChEBI
1-Hydroxyethylidenediphosphonic acid	biospider
1,1,1-Ethanetriol dionate	ChEBI
1,1,1-Ethanetriol dionic acid	Generator
Acetodionate	Generator
Acetodionic acid	ChEBI
Dequest 2010	db_source
Dequest 2015	db_source
Dequest Z 010	biospider
Diphosphonate (base)	biospider
Ethane-1-hydroxy-1, 1-diphosphonate	biospider
Ethane-1-hydroxy-1,1-bisonate	Generator
Ethane-1-hydroxy-1,1-bisonic acid	ChEBI
Ethane-1-hydroxy-1,1-dionate	ChEBI
Ethane-1-hydroxy-1,1-dionic acid	ChEBI
Etidronic acid	biospider
Etidronic acid (usan/inn)	biospider
Etidronic acid [usan:inn:ban]	biospider
Etidronic acid monohydrate	biospider
Etidronic acid, BAN, INN, USAN	db_source
Etidronic acid(usan)	biospider
Ferrofos 510	biospider
HEBP	db_source
Hydroxyethane-1,1-diphosphonic acid	biospider
Hydroxyethanedionate	Generator
Hydroxyethanedionic acid	ChEBI
Ksidifon	db_source
Oxyethylidenedionate	Generator
Oxyethylidenedionic acid	ChEBI
Phosphonic acid, (1-hydroxyethylidene)bis-	biospider
Phosphonic acid, (1-hydroxyethylidene)di-	biospider
Phosphonic acid, 1-hydroxy-1,1-ethanediyl ester	biospider
Phosphonic acid, P,P'-(1-hydroxyethylidene)bis-	biospider
Turpinal SL	biospider
Xidiphone	db_source

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

Chemical Formula

C2H8O7P2

IUPAC name

(1-hydroxy-1-phosphonoethyl)phosphonic acid

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

Isomeric SMILES

CC(O)(P(O)(O)=O)P(O)(O)=O

Average Molecular Weight

206.027

Monoisotopic Molecular Weight

205.974526594

Classification

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Hypocalcemia

Gastrointestinal disorders:

Vomiting

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Antineoplastic agent:

Antitumor

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 11.66%; H 3.91%; O 54.36%; P 30.07%	DFC
Melting Point	Mp 105°	DFC
Boiling Point	Not Available
Experimental Water Solubility	690 mg/mL at 20 oC	MERCK INDEX (1996)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Etidronic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9310000000-2caef035e19867df64bf	Spectrum
Predicted GC-MS	Etidronic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9540000000-38ec250196bc1c488215	Spectrum
Predicted GC-MS	Etidronic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0090000000-a9f75f8364e22febc69e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0190000000-7e7c121eec680994473e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0390000000-f6ab7574deae5f44d8b4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08j0-9620000000-0618a9cfbf1724258f3b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-03di-9100000000-cfaba7073e26e33fa329	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0960000000-dc95e917c594d7c69a00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0560-6900000000-42d2a2563e015073e66b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9300000000-995ddbe23b852a05ae3b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-2980000000-d59d8cb7d24ab907283d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fni-4920000000-15809f5e174b6322f374	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9100000000-9b55901243a14d80a6f7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1910000000-38d2c6a97af6630a8fa3	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9470000000-42c471e70e6c11b7b6d9	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-92dadebcb6c35ccc4a68	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-72d943e9ef38c579f95a	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9200000000-57c7611567781ad9597a	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9000000000-fcbb693760d15d6e4929	2021-10-11	View Spectrum