MEDRONIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	CH6O6P2
Molecular Weight	176.0023
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(=O)CP(O)(O)=O

InChI

InChIKey=MBKDYNNUVRNNRF-UHFFFAOYSA-N

InChI=1S/CH6O6P2/c2-8(3,4)1-9(5,6)7/h1H2,(H2,2,3,4)(H2,5,6,7)

HIDE SMILES / InChI

Molecular Formula	CH6O6P2
Molecular Weight	176.0023
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018124s013lbl.pdf
Curator's Comment: Description was created based on several sources, including: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=9635

Medronic acid (conjugate base, medronate) is a diagnostic agent that is used in complex with technetium Tc-99m for imaging delineate areas of altered osteogenesis. Upon administration the complex binds to hydroxyapatite crystals in bone.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hydroxyapatite crystals in bone 5 Target ID: Hydroxyapatite crystals in bone Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=9635	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Altered osteogenesis 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018124s013lbl.pdf	Diagnostic		Approved 8583	CIS-MDP Approved Use Technetium Tc 99m Medronate Injection may be used as a bone imaging agent to delineate areas of altered osteogenesis. Launch Date 1979

Doses

Dose	Population	Adverse events
10000 uCi single, intravenous Recommended Dose: 10000 uCi Route: intravenous Route: single Dose: 10000 uCi Sources: https://pubmed.ncbi.nlm.nih.gov/2984362/	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2984362/	Disc. AE: Allergic rash... AEs leading to discontinuation/dose reduction: Allergic rash Sources: https://pubmed.ncbi.nlm.nih.gov/2984362/
16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	Other AEs: Leukocytopenia, Anemia... Other AEs: Leukocytopenia (1.7%) Anemia (5.1%) Nausea (1.7%) Elevated liver enzymes (3.4%) Oral ulceration (1.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/

AEs

AE	Significance	Dose	Population
Allergic rash	Disc. AE	10000 uCi single, intravenous Recommended Dose: 10000 uCi Route: intravenous Route: single Dose: 10000 uCi Sources: https://pubmed.ncbi.nlm.nih.gov/2984362/	unhealthy Health Status: unhealthy Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2984362/
Leukocytopenia	1.7%	16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/
Nausea	1.7%	16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/
Oral ulceration	1.7%	16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/
Elevated liver enzymes	3.4%	16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/
Anemia	5.1%	16.5 mg 1 times / day multiple, intravenous Dose: 16.5 mg, 1 times / day Route: intravenous Route: multiple Dose: 16.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/34039871/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inhibitor 2438		inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 P-gp 1741 UMAT 30 CYP19A1 429 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=3714055	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144204525	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/778#sid=3714055	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/777#sid=3714055	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346984#sid=144204525	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/799#sid=3714055	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=3714055	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588550#sid=3714055	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144204525	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=144204525

PubMed

Title	Date	PubMed
Photo-induced lipid peroxidation of erythrocyte membranes by a bis-methanophosphonate fullerene.	2007-12	17686607
Effect of age and gender on the number and distribution of sites in Paget's disease of bone.	2007-07	17646188
PET-CT in pediatric Langerhans cell histiocytosis.	2007-07	17564738
Exposure of veterinary personnel to ionising radiation during bone scanning of horses by nuclear scintigraphy with 99mtechnetium methylene diphosphonate.	2007-06-16	17575246
Ewing's sarcoma of the third metatarsal: a case report and review of the literature.	2007-06-15	17557573
Bisphosphonate rescue in distraction osteogenesis: a case series.	2007-06	17513972
Characterization of focal bone lesions in the axial skeleton: performance of planar bone scintigraphy compared with SPECT and SPECT fused with CT.	2007-05	17449746
Alpha-substituted phosphonate analogues of lysophosphatidic acid (LPA) selectively inhibit production and action of LPA.	2007-05	17443831
Is there a role of whole body bone scan in early stages of non small cell lung cancer patients.	2007-02-20	17309183
Rapid characterization of alkylpolyphosphonates by CZE with indirect photometric and mass spectrometric detection.	2007-02	17191280
[Methylenebisphosphonic acid alters the pattern of pericellular glycosaminoglycans and binding properties of CD44 in human endothelial cells].	2007-01-24	17236626
Metabolic fingerprints of altered brain growth, osmoregulation and neurotransmission in a Rett syndrome model.	2007-01-17	17237885
Abnormalities in bone mineral density distribution and bone scintigraphy in patients with childhood onset hypopituitarism.	2007-01-15	17470407
ATP as effector of inorganic pyrophosphatase of Escherichia coli. The role of residue Lys112 in binding effectors.	2007-01	17309443
Binding of substrate at the effector site of pyrophosphatase increases the rate of its hydrolysis at the active site.	2007-01	17309439
Safety considerations with bisphosphonates for the treatment of osteoporosis.	2007	17722968
[Effect of calixarene-phosphonic acid on Na+, K+-ATPase activity in plasma membranes of the smooth-muscle cells].	2006-12-07	17147269
Development of a novel 99mTc-chelate-conjugated bisphosphonate with high affinity for bone as a bone scintigraphic agent.	2006-12	17138748
Influence of phosphonation and phosphation on surface acid-base and morphological properties of CaO as investigated by in situ FTIR spectroscopy and electron microscopy.	2006-11-01	16934283
Acid resistance of erbium-doped yttrium aluminum garnet laser-treated and phosphoric acid-etched enamels.	2006-11	17090176
Synthesis of bisphosphonate derivatives of ATP by T4 RNA ligase.	2006-10-16	17010342
Novel chikungunya virus variant in travelers returning from Indian Ocean islands.	2006-10	17176562
Cytotoxic and genotoxic effects induced by stannous chloride associated to nuclear medicine kits.	2006-10	17045172
Growth modification of the mandible with ultrasound in baboons: a preliminary report.	2006-10	17045140
Metastatic pulmonary calcification in a dialysis patient: case report and a review.	2006-10	17022753
Nuclear medicine methods for evaluation of skeletal infection among other diagnostic modalities.	2006-09	16868532
Solitary bone metastasis beneath the shoulder shield: coincidence or cause?	2006-08	17576452
Usefulness of 18F-FDG PET-directed skeletal biopsy for metastatic neoplasm.	2006-08	16843854
Synthesis of trans-1,2-cyclohexyldinitrilo tetramethylene phosphonic acid and its radiolabelling with 99mTc for the detection of skeletal metastases.	2006-08	16829762
Synthesis and characterization of octa- and hexanuclear polyoxomolybdate wheels: role of the inorganic template and of the counterion.	2006-07-24	16841995
Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity.	2006-07-03	16618481
The role of SPECT/CT with 99mTc-MDP image fusion to diagnose temporomandibular dysfunction.	2006-02	16448926
The internal thoracic artery skeletonization study: a paired, within-patient comparison [NCT00265499].	2006-01-05	16542027
Use of scintigraphy for diagnosis of equine paranasal sinus disorders.	2006-01	16409416
Characterization of industrial alkylpolyphosphonates by infusion electrospray ionization-ion trap mass spectrometry with identification of the impurities by tandem capillary zone electrophoresis.	2006-01	16287032
Synthesis and antiviral evaluation of alkoxyalkyl esters of phosphonopropoxymethyl-guanine and phosphonopropoxymethyl-diaminopurine.	2006	17042330
Voltammetry as a virtual potentiometric sensor in modelling of a metal-ligand system and refinement of stability constants. Part 4. An electrochemical study of NiII complexes with methylene diphosphonic acid.	2005-12	16213588
Biochemical and imaging alterations of renal bone disease in newly detected predialysis and on maintenance dialysis patients.	2005-10	16223439
Three-level bilateral pediculolysis following osteoporotic lumbar compression fracture.	2005-09-08	16934724
[A cationic cluster of amino acid residues of inorganic pyrophosphatase from Escherichia coli as a possible site of effector binding].	2005-07-12	16004383
Cyclic ADP-ribose analogues containing the methylenebisphosphonate linkage: effect of pyrophosphate modifications on Ca2+ release activity.	2005-06-16	15943490
Effects of radiosynovectomy with p-32 colloid therapy in hemophilia and rheumatoid arthritis.	2005-06	15989482
Technetium-99m diphosphonate imaging of psammocarcinoma of probable ovarian origin: case report and literature review.	2005-06	15891291
Solid-state molecular organization and solution behavior of methane-1,1-diphosphonic acid derivatives of heterocyclic amines: the role of the topochemical ring modification and the intramolecular hydrogen bonds in monosubstituted piperid-1-ylmethane-1,1-diphosphonic acids.	2005-04-08	15669076
Metal-free PPi activates hydrolysis of MgPPi by an Escherichia coli inorganic pyrophosphatase.	2005-01	15701051
31P MRS analysis of the phospholipid composition of normal human peripheral blood mononuclear cells (PBMC).	2005	16217549
Calix[4]arene methylenebisphosphonic acids as calf intestine alkaline phosphatase inhibitors.	2004-11-07	15505723
Solid-state coordination chemistry of the oxomolybdate-organodiphosphonate/nickel-organoimine system: structural influences of the secondary metal coordination cation and diphosphonate tether lengths.	2004-11-01	15500339
[Menopause in 2004: "hormone replacement therapy" is not what it used to be anymore].	2004-11	15501350
Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate.	2004-10-04	15341963

Patents

Sample Use Guides

In Vivo Use Guide

The suggested dose range of Technetium Tc 99m Medronate Injection in the average adult patient (70 kg) is 370-740 megabecquerels: (10-20 millicuries) given intravenously.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:56 GMT 2025`
Record UNII	73OS0QIN3O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYLENE DIPHOSPHONIC ACID

Preferred Name

English

MEDRONIC ACID

Official Name

English

MEDRONATE

Common Name

English

Methylenediphosphonic acid

Systematic Name

English

MEDRONIC ACID [MART.]

Common Name

English

METHANEBISPHOSPHONIC ACID

Systematic Name

English

MEDRONIC ACID [II]

Common Name

English

PHOSPHONIC ACID, METHYLENEDI-

Common Name

English

MEDRONIC ACID [USAN]

Common Name

English

MEDRONIC ACID [MI]

Common Name

English

Medronic acid [WHO-DD]

Common Name

English

medronic acid [INN]

Common Name

English

METHYLENE DIPHOSPHONIC ACID [VANDF]

Common Name

English

METHANEDIPHOSPHONIC ACID

Systematic Name

English

PHOSPHONIC ACID, METHYLENEBIS-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C443