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

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
Determination of the casein content in bovine milk by 31P-NMR.	2002 Aug	12369412
Cytotoxicity and cellular differentiation activity of methylenebis(phosphonate) analogs of tiazofurin and mycophenolic acid adenine dinucleotide in human cancer cell lines.	2002 Jul 8	12430176
Synthesis of stable analogues of thiamine di- and triphosphate as tools for probing a new phosphorylation pathway.	2002 Oct 18	12561105
Effect of technetium-99 conjugated with methylene diphosphonate on IgM-RF, IgG-RF and IgA-RF.	2003	14526429
Escherichia coli response to exogenous pyrophosphate and analogs.	2003	12673060
Biological reactions to a poly(L-lactide)-hydroxyapatite composite: a study in canine mandible.	2003 Apr	12797419
Collagen crosslink excretion and staging of oral cancer.	2003 Apr 7	12671712
Complexation of beryllium(II) ion by phosphinate ligands in aqueous solution. Synthesis and XRPD structure determination of Be[(PhPO2)2CH2](H2O)2.	2003 Apr 7	12665369
Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism.	2003 Apr 7	12657258
Infecton: a 99mTc-ciprofloxacin radiopharmaceutical for the detection of bone infection.	2003 Feb	12588329
Bisphosphonates and osteoprotegerin as inhibitors of myeloma bone disease.	2003 Feb 1	12548581
Effectory site in Escherichia coli inorganic pyrophosphatase is revealed upon mutation at the intertrimeric interface.	2003 Jan	12716061
Solid state coordination chemistry: one-, two-, and three-dimensional materials constructed from molybdophosphonate subunits linked through binuclear copper tetra-2-pyridylpyrazine groups.	2003 Oct 20	14552625
99mTc depreotide scan compared with 99mTc-MDP bone scintigraphy for the detection of bone metastases and prediction of response to hormonal treatment in patients with breast cancer.	2004 Aug	15266172
Efficient synthesis of protected cyclopropyl beta-aspartylphosphates.	2004 Feb 21	14770233
Radionuclide imaging of infection.	2004 Jun	15175400
Elucidating the role of conserved glutamates in H+-pyrophosphatase of Rhodospirillum rubrum.	2004 Jun 25	15107429
Bone scintigraphy in the investigation of occult lameness in the dog.	2004 May	15163049
Calix[4]arene methylenebisphosphonic acids as calf intestine alkaline phosphatase inhibitors.	2004 Nov 7	15505723
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 Dec	16213588
Metal-free PPi activates hydrolysis of MgPPi by an Escherichia coli inorganic pyrophosphatase.	2005 Jan	15701051
Effects of radiosynovectomy with p-32 colloid therapy in hemophilia and rheumatoid arthritis.	2005 Jun	15989482
Technetium-99m diphosphonate imaging of psammocarcinoma of probable ovarian origin: case report and literature review.	2005 Jun	15891291
[A cationic cluster of amino acid residues of inorganic pyrophosphatase from Escherichia coli as a possible site of effector binding].	2005 May-Jun	16004383
Solitary bone metastasis beneath the shoulder shield: coincidence or cause?	2006 Aug	17576452
Synthesis of trans-1,2-cyclohexyldinitrilo tetramethylene phosphonic acid and its radiolabelling with 99mTc for the detection of skeletal metastases.	2006 Aug	16829762
Development of a novel 99mTc-chelate-conjugated bisphosphonate with high affinity for bone as a bone scintigraphic agent.	2006 Dec	17138748
[Effect of calixarene-phosphonic acid on Na+, K+-ATPase activity in plasma membranes of the smooth-muscle cells].	2006 Jan-Feb	17147269
Synthesis and characterization of octa- and hexanuclear polyoxomolybdate wheels: role of the inorganic template and of the counterion.	2006 Jul 24	16841995
Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity.	2006 Jul 3	16618481
[Methylenebisphosphonic acid alters the pattern of pericellular glycosaminoglycans and binding properties of CD44 in human endothelial cells].	2006 Jul-Aug	17236626
Acid resistance of erbium-doped yttrium aluminum garnet laser-treated and phosphoric acid-etched enamels.	2006 Nov	17090176
Novel chikungunya virus variant in travelers returning from Indian Ocean islands.	2006 Oct	17176562
Cytotoxic and genotoxic effects induced by stannous chloride associated to nuclear medicine kits.	2006 Oct	17045172
Is there a role of whole body bone scan in early stages of non small cell lung cancer patients.	2006 Oct-Dec	17309183
Three-level bilateral pediculolysis following osteoporotic lumbar compression fracture.	2006 Sep-Oct	16934724
Safety considerations with bisphosphonates for the treatment of osteoporosis.	2007	17722968
Photo-induced lipid peroxidation of erythrocyte membranes by a bis-methanophosphonate fullerene.	2007 Dec	17686607
Rapid characterization of alkylpolyphosphonates by CZE with indirect photometric and mass spectrometric detection.	2007 Feb	17191280
ATP as effector of inorganic pyrophosphatase of Escherichia coli. The role of residue Lys112 in binding effectors.	2007 Jan	17309443
Binding of substrate at the effector site of pyrophosphatase increases the rate of its hydrolysis at the active site.	2007 Jan	17309439
Metabolic fingerprints of altered brain growth, osmoregulation and neurotransmission in a Rett syndrome model.	2007 Jan 17	17237885
Effect of age and gender on the number and distribution of sites in Paget's disease of bone.	2007 Jul	17646188
PET-CT in pediatric Langerhans cell histiocytosis.	2007 Jul	17564738
Abnormalities in bone mineral density distribution and bone scintigraphy in patients with childhood onset hypopituitarism.	2007 Jul-Sep	17470407
Bisphosphonate rescue in distraction osteogenesis: a case series.	2007 Jun	17513972
Exposure of veterinary personnel to ionising radiation during bone scanning of horses by nuclear scintigraphy with 99mtechnetium methylene diphosphonate.	2007 Jun 16	17575246
Ewing's sarcoma of the third metatarsal: a case report and review of the literature.	2007 Mar-Apr	17557573
Characterization of focal bone lesions in the axial skeleton: performance of planar bone scintigraphy compared with SPECT and SPECT fused with CT.	2007 May	17449746
Alpha-substituted phosphonate analogues of lysophosphatidic acid (LPA) selectively inhibit production and action of LPA.	2007 May	17443831

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

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