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.

Structure
Thumb
Synonyms
  • (1-hydroxy-ethylidene)diphosphonic acid
  • (1-Hydroxyethylene)diphosphonic acid
  • (1-Hydroxyethylidene)bis(phosphonic acid)
  • (1-Hydroxyethylidene)bisphosphonic acid
  • (1-Hydroxyethylidene)diphosphonic acid
  • (Hydroxyethylidene)diphosphonic acid
  • 1-Hydroxy-1,1-diphosphonoethane
  • 1-hydroxyethane 1,1-diphosphonic acid
  • 1-Hydroxyethane-1,1-bisphosphonic acid
  • 1-Hydroxyethane-1,1-diphosphonate
  • 1-Hydroxyethane-1,1-diphosphonic acid
  • 1-Hydroxyethanediphosphonic acid
  • 1-Hydroxyethylidene-1,1-bisphosphonate
  • 1-Hydroxyethylidene-1,1-diphosphonic acid
  • 1,1,1-Ethanetriol diphosphonate
  • Acetodiphosphonic acid
  • acide étidronique
  • ácido etidrónico
  • acidum etidronicum
  • EHDP
  • Ethane-1-hydroxy-1,1-bisphosphonic acid
  • Ethane-1-hydroxy-1,1-diphosphonate
  • Ethane-1-hydroxy-1,1-diphosphonic acid
  • Etidronate
  • Etidronsäure
  • HEDP
  • Hydroxyethanediphosphonic acid
  • Oxyethylidenediphosphonic acid
External IDs
M05BA01 / NSC-227995
Product Ingredients
IngredientUNIICASInChI Key
Etidronate disodiumM16PXG993G7414-83-7GWBBVOVXJZATQQ-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act EtidronateTablet200 mgOralActavis Pharma Company2004-11-10Not applicableCanada
Act EtidronateTablet400 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Didronel Inj 50mg/mlSolution50 mgIntravenousMgi Pharma Inc.1991-12-312004-09-30Canada
Didronel Tab 200mgTablet200 mgOralProcter And Gamble1993-12-312010-07-07Canada
EtidronateTablet400 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
EtidronateTablet200 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
Mylan-etidronateTablet200 mgOralMylan Pharmaceuticals2003-06-042017-01-09Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-etidronateTablet200 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-etidronateTablet400 mgOralApotex CorporationNot applicableNot applicableCanada
Etidronate DisodiumTablet200 mg/1OralMylan Pharmaceuticals2008-01-022019-11-30Us
Etidronate DisodiumTablet400 mg/1OralMylan Pharmaceuticals2008-01-02Not applicableUs
Etidronate DisodiumTablet200 mg/1OralCarilion Materials Management2008-01-02Not applicableUs
International/Other Brands
Didronel (Procter & Gamble) / Etidron (Gentili)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act EtidrocalEtidronate disodium (400 mg) + Calcium (500 mg)TabletOralActavis Pharma Company2008-04-10Not applicableCanada
DidrocalEtidronate disodium (400 mg) + Calcium (500 mg)Kit; TabletOralWarner Chilcott1995-12-312015-11-19Canada
EtidrocalEtidronate disodium (400 mg) + Calcium (500 mg)TabletOralSanis Health Inc2010-07-26Not applicableCanada
EtidrocalEtidronate disodium (400 mg) + Calcium (500 mg)TabletOralCobalt LaboratoriesNot applicableNot applicableCanada
Mylan-eti-cal CarepacEtidronate disodium (400 mg) + Calcium (500 mg)Kit; TabletOralMylan Pharmaceuticals2008-04-102017-01-09Canada
Novo-etidronatecalEtidronate disodium (400 mg) + Calcium (500 mg)Kit; TabletOralTeva2009-06-15Not applicableCanada
Ntp-etidronate CalciumEtidronate disodium (400 mg) + Calcium (500 mg)Kit; TabletOralTevaNot applicableNot applicableCanada
Categories
UNII
M2F465ROXU
CAS number
2809-21-4
Weight
Average: 206.0282
Monoisotopic: 205.974525634
Chemical Formula
C2H8O7P2
InChI Key
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)
IUPAC Name
(1-hydroxy-1-phosphonoethyl)phosphonic acid
SMILES
CC(O)(P(O)(O)=O)P(O)(O)=O

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.

Structured Indications
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.

TargetActionsOrganism
AAdenosine triphosphate (ATP)
inhibitor
Human
AHydroxylapatite
antagonist
Human
UReceptor-type tyrosine-protein phosphatase S
inhibitor
Human
UV-type proton ATPase catalytic subunit A
inhibitor
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Etidronic acid.Approved
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Etidronic acid.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Etidronic acid.Approved, Vet Approved
AclarubicinAclarubicin may increase the hypocalcemic activities of Etidronic acid.Investigational
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Etidronic acid.Approved
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Etidronic acid.Approved, Withdrawn
AlgeldrateThe serum concentration of Etidronic acid can be decreased when it is combined with Algeldrate.Experimental
AlmagateThe serum concentration of Etidronic acid can be decreased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Etidronic acid can be decreased when it is combined with Almasilate.Experimental
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with Etidronic acid.Experimental
AloglutamolThe serum concentration of Etidronic acid can be decreased when it is combined with Aloglutamol.Experimental
AluminiumThe serum concentration of Etidronic acid can be decreased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Etidronic acid can be decreased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Etidronic acid can be decreased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Etidronic acid can be decreased when it is combined with Aluminum hydroxide.Approved
AmikacinAmikacin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
AmrubicinAmrubicin may increase the hypocalcemic activities of Etidronic acid.Approved, Investigational
AndrographolideThe risk or severity of adverse effects can be increased when Andrographolide is combined with Etidronic acid.Investigational
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Etidronic acid.Investigational
annamycinannamycin may increase the hypocalcemic activities of Etidronic acid.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with Etidronic acid.Approved
ApocyninThe risk or severity of adverse effects can be increased when Apocynin is combined with Etidronic acid.Investigational
ApramycinApramycin may increase the hypocalcemic activities of Etidronic acid.Experimental, Vet Approved
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with Etidronic acid.Approved, Investigational
ArbekacinArbekacin may increase the hypocalcemic activities of Etidronic acid.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Azapropazone is combined with Etidronic acid.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Etidronic acid.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Etidronic acid.Approved, Investigational
BekanamycinBekanamycin may increase the hypocalcemic activities of Etidronic acid.Experimental
BendazacThe risk or severity of adverse effects can be increased when Bendazac is combined with Etidronic acid.Experimental
BenorilateThe risk or severity of adverse effects can be increased when Benorilate is combined with Etidronic acid.Experimental
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Etidronic acid.Withdrawn
BevoniumThe risk or severity of adverse effects can be increased when Bevonium is combined with Etidronic acid.Experimental
Bismuth SubcitrateThe serum concentration of Etidronic acid can be decreased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Etidronic acid can be decreased when it is combined with Bismuth subnitrate.Experimental
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Etidronic acid.Approved
BucillamineThe risk or severity of adverse effects can be increased when Bucillamine is combined with Etidronic acid.Investigational
BufexamacThe risk or severity of adverse effects can be increased when Bufexamac is combined with Etidronic acid.Experimental
BumadizoneThe risk or severity of adverse effects can be increased when Bumadizone is combined with Etidronic acid.Experimental
CalciumThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium.Nutraceutical
Calcium AcetateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium Acetate.Approved
Calcium CarbonateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium Carbonate.Approved
Calcium CitrateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium Citrate.Approved
Calcium glubionateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium glubionate.Approved
Calcium GluceptateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium Gluceptate.Approved
Calcium gluconateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium lactate.Approved, Experimental, Vet Approved
Calcium lactate gluconateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium lactate gluconate.Experimental
Calcium laevulateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium laevulate.Experimental
Calcium pangamateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium pangamate.Experimental
Calcium PhosphateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium Phosphate.Approved
Calcium silicateThe serum concentration of Etidronic acid can be decreased when it is combined with Calcium silicate.Experimental
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Carbaspirin calcium is combined with Etidronic acid.Experimental
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with Etidronic acid.Approved, Vet Approved, Withdrawn
CaseinThe serum concentration of Etidronic acid can be decreased when it is combined with Casein.Approved
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with Etidronic acid.Experimental
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Etidronic acid.Approved, Investigational
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Etidronic acid.Approved, Vet Approved
Choline magnesium trisalicylateThe risk or severity of adverse effects can be increased when Choline magnesium trisalicylate is combined with Etidronic acid.Approved
ClonixinThe risk or severity of adverse effects can be increased when Clonixin is combined with Etidronic acid.Approved
CurcuminThe risk or severity of adverse effects can be increased when Curcumin is combined with Etidronic acid.Investigational
D-LimoneneThe risk or severity of adverse effects can be increased when D-Limonene is combined with Etidronic acid.Investigational
DaunorubicinDaunorubicin may increase the hypocalcemic activities of Etidronic acid.Approved
DeferasiroxThe risk or severity of adverse effects can be increased when Etidronic acid is combined with Deferasirox.Approved, Investigational
DexlansoprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Dexlansoprazole.Approved
DexrabeprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Dexrabeprazole.Experimental
DibekacinDibekacin may increase the hypocalcemic activities of Etidronic acid.Experimental
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Etidronic acid.Approved, Vet Approved
DifenpiramideThe risk or severity of adverse effects can be increased when Difenpiramide is combined with Etidronic acid.Experimental
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Etidronic acid.Approved
DihydrostreptomycinDihydrostreptomycin may increase the hypocalcemic activities of Etidronic acid.Vet Approved
DoxorubicinDoxorubicin may increase the hypocalcemic activities of Etidronic acid.Approved, Investigational
DroxicamThe risk or severity of adverse effects can be increased when Droxicam is combined with Etidronic acid.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Duvelisib is combined with Etidronic acid.Investigational
E-6201The risk or severity of adverse effects can be increased when E-6201 is combined with Etidronic acid.Investigational
EpirizoleThe risk or severity of adverse effects can be increased when Epirizole is combined with Etidronic acid.Approved
EpirubicinEpirubicin may increase the hypocalcemic activities of Etidronic acid.Approved
EsomeprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Esomeprazole.Approved, Investigational
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Etidronic acid.Approved, Investigational
EthenzamideThe risk or severity of adverse effects can be increased when Ethenzamide is combined with Etidronic acid.Experimental
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Etidronic acid.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Etofenamate is combined with Etidronic acid.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with Etidronic acid.Approved, Investigational
Evening primrose oilThe risk or severity of adverse effects can be increased when Evening primrose oil is combined with Etidronic acid.Approved
exisulindThe risk or severity of adverse effects can be increased when exisulind is combined with Etidronic acid.Investigational
FelbinacThe risk or severity of adverse effects can be increased when Felbinac is combined with Etidronic acid.Experimental
FenbufenThe risk or severity of adverse effects can be increased when Fenbufen is combined with Etidronic acid.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Etidronic acid.Approved
FentiazacThe risk or severity of adverse effects can be increased when Fentiazac is combined with Etidronic acid.Experimental
FeprazoneThe risk or severity of adverse effects can be increased when Feprazone is combined with Etidronic acid.Experimental
Ferric CitrateThe serum concentration of Etidronic acid can be decreased when it is combined with Ferric Citrate.Approved
Ferulic acidThe risk or severity of adverse effects can be increased when Ferulic acid is combined with Etidronic acid.Experimental
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Etidronic acid.Approved, Withdrawn
FlunixinThe risk or severity of adverse effects can be increased when Flunixin is combined with Etidronic acid.Vet Approved
FlunoxaprofenThe risk or severity of adverse effects can be increased when Flunoxaprofen is combined with Etidronic acid.Experimental
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Etidronic acid.Approved, Investigational
FramycetinFramycetin may increase the hypocalcemic activities of Etidronic acid.Approved
GeneticinGeneticin may increase the hypocalcemic activities of Etidronic acid.Experimental
GentamicinGentamicin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
GENTAMICIN C1AGENTAMICIN C1A may increase the hypocalcemic activities of Etidronic acid.Experimental
GPX-150GPX-150 may increase the hypocalcemic activities of Etidronic acid.Investigational
GuacetisalThe risk or severity of adverse effects can be increased when Guacetisal is combined with Etidronic acid.Experimental
HigenamineThe risk or severity of adverse effects can be increased when Higenamine is combined with Etidronic acid.Investigational
HydrotalciteThe serum concentration of Etidronic acid can be decreased when it is combined with Hydrotalcite.Experimental
Hygromycin BHygromycin B may increase the hypocalcemic activities of Etidronic acid.Vet Approved
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Etidronic acid.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Ibuproxam is combined with Etidronic acid.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Icatibant is combined with Etidronic acid.Approved
IdarubicinIdarubicin may increase the hypocalcemic activities of Etidronic acid.Approved
Imidazole salicylateThe risk or severity of adverse effects can be increased when Imidazole salicylate is combined with Etidronic acid.Experimental
IndobufenThe risk or severity of adverse effects can be increased when Indobufen is combined with Etidronic acid.Investigational
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Etidronic acid.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Indoprofen is combined with Etidronic acid.Withdrawn
INNO-206INNO-206 may increase the hypocalcemic activities of Etidronic acid.Investigational
Iron saccharateThe serum concentration of Etidronic acid can be decreased when it is combined with Iron saccharate.Approved
IsepamicinIsepamicin may increase the hypocalcemic activities of Etidronic acid.Experimental
IsoxicamThe risk or severity of adverse effects can be increased when Isoxicam is combined with Etidronic acid.Withdrawn
KanamycinKanamycin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
KebuzoneThe risk or severity of adverse effects can be increased when Kebuzone is combined with Etidronic acid.Experimental
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Etidronic acid.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Etidronic acid.Approved
LansoprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Lansoprazole.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with Etidronic acid.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Lisofylline is combined with Etidronic acid.Investigational
LonazolacThe risk or severity of adverse effects can be increased when Lonazolac is combined with Etidronic acid.Experimental
LornoxicamThe risk or severity of adverse effects can be increased when Lornoxicam is combined with Etidronic acid.Approved
LoxoprofenThe risk or severity of adverse effects can be increased when Loxoprofen is combined with Etidronic acid.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Lumiracoxib is combined with Etidronic acid.Approved, Investigational
Magnesium HydroxideThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium peroxide.Experimental
Magnesium salicylateThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium salicylate.Approved
Magnesium silicateThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium silicate.Experimental
Magnesium SulfateThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium Sulfate.Approved, Vet Approved
Magnesium TrisilicateThe serum concentration of Etidronic acid can be decreased when it is combined with Magnesium Trisilicate.Approved
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Etidronic acid.Approved
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Etidronic acid.Approved, Vet Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Etidronic acid.Approved
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Etidronic acid.Approved, Vet Approved
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Etidronic acid.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Etidronic acid.Withdrawn
MetrizamideMetrizamide may increase the hypocalcemic activities of Etidronic acid.Approved
MicronomicinMicronomicin may increase the hypocalcemic activities of Etidronic acid.Experimental
MizoribineThe risk or severity of adverse effects can be increased when Mizoribine is combined with Etidronic acid.Investigational
MofebutazoneThe risk or severity of adverse effects can be increased when Mofebutazone is combined with Etidronic acid.Experimental
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Etidronic acid.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Etidronic acid.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Etidronic acid.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with Etidronic acid.Approved, Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Etidronic acid.Approved
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Etidronic acid.Approved, Vet Approved
NeamineNeamine may increase the hypocalcemic activities of Etidronic acid.Experimental
NeomycinNeomycin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with Etidronic acid.Approved
NetilmicinNetilmicin may increase the hypocalcemic activities of Etidronic acid.Approved
NifenazoneThe risk or severity of adverse effects can be increased when Nifenazone is combined with Etidronic acid.Experimental
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with Etidronic acid.Approved
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Etidronic acid.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Etidronic acid.Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Etidronic acid.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Etidronic acid.Approved
OmeprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Omeprazole.Approved, Investigational, Vet Approved
OrgoteinThe risk or severity of adverse effects can be increased when Orgotein is combined with Etidronic acid.Vet Approved
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Etidronic acid.Approved
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Etidronic acid.Withdrawn
PantoprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Pantoprazole.Approved
ParecoxibThe risk or severity of adverse effects can be increased when Parecoxib is combined with Etidronic acid.Approved
ParomomycinParomomycin may increase the hypocalcemic activities of Etidronic acid.Approved, Investigational
ParthenolideThe risk or severity of adverse effects can be increased when Parthenolide is combined with Etidronic acid.Investigational
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etidronic acid.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Etidronic acid.Approved, Investigational
PirarubicinPirarubicin may increase the hypocalcemic activities of Etidronic acid.Investigational
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with Etidronic acid.Investigational
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Etidronic acid.Approved, Investigational
PirprofenThe risk or severity of adverse effects can be increased when Pirprofen is combined with Etidronic acid.Experimental
PlazomicinPlazomicin may increase the hypocalcemic activities of Etidronic acid.Investigational
PlicamycinPlicamycin may increase the hypocalcemic activities of Etidronic acid.Approved, Withdrawn
PranoprofenThe risk or severity of adverse effects can be increased when Pranoprofen is combined with Etidronic acid.Experimental
ProglumetacinThe risk or severity of adverse effects can be increased when Proglumetacin is combined with Etidronic acid.Experimental
PropacetamolThe risk or severity of adverse effects can be increased when Propacetamol is combined with Etidronic acid.Approved
PropyphenazoneThe risk or severity of adverse effects can be increased when Propyphenazone is combined with Etidronic acid.Experimental
ProquazoneThe risk or severity of adverse effects can be increased when Proquazone is combined with Etidronic acid.Experimental
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with Etidronic acid.Investigational
PuromycinPuromycin may increase the hypocalcemic activities of Etidronic acid.Experimental
RabeprazoleThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Rabeprazole.Approved, Investigational
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Etidronic acid.Experimental, Investigational
RibostamycinRibostamycin may increase the hypocalcemic activities of Etidronic acid.Approved
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Etidronic acid.Investigational, Withdrawn
SabarubicinSabarubicin may increase the hypocalcemic activities of Etidronic acid.Investigational
SalicylamideThe risk or severity of adverse effects can be increased when Salicylamide is combined with Etidronic acid.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Etidronic acid.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Etidronic acid.Approved
SemapimodThe risk or severity of adverse effects can be increased when Semapimod is combined with Etidronic acid.Investigational
SeratrodastThe risk or severity of adverse effects can be increased when Seratrodast is combined with Etidronic acid.Approved
SerrapeptaseThe risk or severity of adverse effects can be increased when Serrapeptase is combined with Etidronic acid.Investigational
SisomicinSisomicin may increase the hypocalcemic activities of Etidronic acid.Investigational
SP1049CSP1049C may increase the hypocalcemic activities of Etidronic acid.Investigational
SpectinomycinSpectinomycin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Etidronic acid.Investigational
StreptomycinStreptomycin may increase the hypocalcemic activities of Etidronic acid.Approved, Vet Approved
StreptozocinStreptozocin may increase the hypocalcemic activities of Etidronic acid.Approved
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Etidronic acid.Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Etidronic acid.Approved
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with Etidronic acid.Approved, Withdrawn
SuxibuzoneThe risk or severity of adverse effects can be increased when Suxibuzone is combined with Etidronic acid.Experimental
TarenflurbilThe risk or severity of adverse effects can be increased when Tarenflurbil is combined with Etidronic acid.Investigational
TenidapThe risk or severity of adverse effects can be increased when Tenidap is combined with Etidronic acid.Experimental
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Etidronic acid.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Tepoxalin is combined with Etidronic acid.Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Teriflunomide is combined with Etidronic acid.Approved
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Etidronic acid.Approved
TinoridineThe risk or severity of adverse effects can be increased when Tinoridine is combined with Etidronic acid.Investigational
TobramycinTobramycin may increase the hypocalcemic activities of Etidronic acid.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Tolfenamic Acid is combined with Etidronic acid.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Etidronic acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with Etidronic acid.Approved, Investigational
TribenosideThe risk or severity of adverse effects can be increased when Tribenoside is combined with Etidronic acid.Experimental
TriptolideThe risk or severity of adverse effects can be increased when Triptolide is combined with Etidronic acid.Investigational
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Etidronic acid.Investigational, Withdrawn
ValrubicinValrubicin may increase the hypocalcemic activities of Etidronic acid.Approved
ZaltoprofenThe risk or severity of adverse effects can be increased when Zaltoprofen is combined with Etidronic acid.Approved
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Etidronic acid.Approved, Investigational, Withdrawn
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with Etidronic acid.Withdrawn
Zoptarelin doxorubicinZoptarelin doxorubicin may increase the hypocalcemic activities of Etidronic acid.Investigational
ZorubicinZorubicin may increase the hypocalcemic activities of Etidronic acid.Experimental
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.

References

Synthesis Reference

Rogovin, L.,Brawn, D.P. and Kalberg, AN.; US. Patent 3,400,147; September 3,1968; assigned to The Procter & Gamble Co.

General References
Not Available
External Links
Human Metabolome Database
HMDB15210
KEGG Drug
D02373
KEGG Compound
C07736
ChemSpider
3189
BindingDB
50115102
ChEBI
4907
ChEMBL
CHEMBL871
Therapeutic Targets Database
DNC000629
PharmGKB
PA449548
HET
911
RxList
RxList Drug Page
Wikipedia
Etidronic_acid
ATC Codes
M05BB01 — Etidronic acid and calcium, sequentialM05BA01 — Etidronic acid
AHFS Codes
  • 92:00.00
PDB Entries
Not Available
FDA label
Download (42 KB)
MSDS
Download (44.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingTreatmentArterial Calcification Due to CD73-Deficiency (ACDC)1
4CompletedTreatmentBone destruction1
Not AvailableCompletedNot AvailableAdenocarcinomas / Esophageal Cancers / Squamous Cell Carcinoma (SCC)1
Not AvailableEnrolling by InvitationNot AvailableAtypical Femoral Fractures / Bisphosphonate Therapy / Bone destruction1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
TabletOral200 mg
TabletOral400 mg
SolutionIntravenous50 mg
TabletOral200 mg/1
TabletOral400 mg/1
Kit; tabletOral
Prices
Unit descriptionCostUnit
Didronel 400 mg tablet8.31USD tablet
Didronel 200 mg tablet4.16USD tablet
Co Etidronate 200 mg Tablet0.86USD tablet
Mylan-Etidronate 200 mg Tablet0.86USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 mg/mLALOGPS
logP-0.77ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.7ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.51 m3·mol-1ChemAxon
Polarizability13.97 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8918
Blood Brain Barrier+0.8901
Caco-2 permeable-0.8581
P-glycoprotein substrateNon-substrate0.7483
P-glycoprotein inhibitor INon-inhibitor0.9639
P-glycoprotein inhibitor IINon-inhibitor0.9951
Renal organic cation transporterNon-inhibitor0.9726
CYP450 2C9 substrateNon-substrate0.7545
CYP450 2D6 substrateNon-substrate0.8473
CYP450 3A4 substrateNon-substrate0.6987
CYP450 1A2 substrateNon-inhibitor0.9061
CYP450 2C9 inhibitorNon-inhibitor0.9047
CYP450 2D6 inhibitorNon-inhibitor0.9222
CYP450 2C19 inhibitorNon-inhibitor0.9186
CYP450 3A4 inhibitorNon-inhibitor0.9595
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9873
Ames testNon AMES toxic0.8875
CarcinogenicityCarcinogens 0.5282
BiodegradationNot ready biodegradable0.7701
Rat acute toxicity1.9653 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9519
hERG inhibition (predictor II)Non-inhibitor0.9495
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0090000000-a9f75f8364e22febc69e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0190000000-7e7c121eec680994473e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-0390000000-f6ab7574deae5f44d8b4
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-08j0-9620000000-0618a9cfbf1724258f3b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-9100000000-cfaba7073e26e33fa329

Taxonomy

Description
This compound 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
Organic phosphonic acids / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
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)

Targets

Kind
Small molecule
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
References
  1. Rogers MJ, Crockett JC, Coxon FP, Monkkonen J: Biochemical and molecular mechanisms of action of bisphosphonates. Bone. 2011 Jul;49(1):34-41. doi: 10.1016/j.bone.2010.11.008. Epub 2010 Nov 26. [PubMed:21111853]
Kind
Small molecule
Organism
Human
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:17587727]
  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:16046206]
  3. Ono K, Wada S: [Regulation of calcification by bisphosphonates]. Clin Calcium. 2004 Jun;14(6):60-3. [PubMed:15577056]
  4. Takaishi Y: [Treatment of periodontal disease, prevention and bisphosphonate]. Clin Calcium. 2003 Feb;13(2):173-6. [PubMed:15775080]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transmembrane receptor protein tyrosine phosphatase activity
Specific Function
Interacts with LAR-interacting protein LIP.1.
Gene Name
PTPRS
Uniprot ID
Q13332
Uniprot Name
Receptor-type tyrosine-protein phosphatase S
Molecular Weight
217039.825 Da
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:8610169]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-transporting atpase activity, rotational mechanism
Specific Function
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.
Gene Name
ATP6V1A
Uniprot ID
P38606
Uniprot Name
V-type proton ATPase catalytic subunit A
Molecular Weight
68303.5 Da
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:8889850]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:52