Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H12N2O7P2 |
Molecular Weight | 322.1483 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CC1=CN=C2C=CC=CN12)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=VMMKGHQPQIEGSQ-UHFFFAOYSA-N
InChI=1S/C9H12N2O7P2/c12-9(19(13,14)15,20(16,17)18)5-7-6-10-8-3-1-2-4-11(7)8/h1-4,6,12H,5H2,(H2,13,14,15)(H2,16,17,18)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.astellas.com/en/corporate/news/pdf/110915_en_2.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21110804
Curator's Comment: description was created based on several sources, including
https://www.astellas.com/en/corporate/news/pdf/110915_en_2.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21110804
Minodronic acid (RECALBON®, Bonoteo®), a third-generation bisphosphonate, was approved in Japan for the oral treatment of osteoporosis. This drug increases the bone mineral density and the strength by inhibiting osteoclastic bone resorption. Nitrogen-containing bisphosphonates, such as minodronic acid (RECALBON®, Bonoteo®) induce osteoclast apoptosis by inhibiting farnesyl pyrophosphate synthase (FPPS), a key enzyme in the mevalonate pathway. Inhibition of FPPS in osteoclasts prevents the biosynthesis of isoprenoid lipids that are required for the prenylation of small GTPase signaling proteins necessary for osteoclast function. Similarly, nitrogen-containing bisphosphonates have been shown to inhibit farnesyl pyrophosphate/geranyl pyrophosphate synthase activity.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4769 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21110804 |
0.67 µM [IC50] | ||
Target ID: CHEMBL1782 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21110804 |
0.003 µM [IC50] | ||
Target ID: CHEMBL3137277 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28243795 |
62.7 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BONOTEO Approved UseThe drug was developed for the treatment of osteoporosis. Launch Date1.23240959E12 |
PubMed
Title | Date | PubMed |
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Effects of YM529, a novel minodronic acid, on adjuvant arthritis in rats. | 2004 Jan-Feb |
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Efficacy of a nitrogen-containing bisphosphonate, minodronate, in conjunction with a p38 mitogen activated protein kinase inhibitor or doxorubicin against malignant bone tumor cells. | 2008 Jun |
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Minodronic acid (ONO-5920/YM529) prevents decrease in bone mineral density and bone strength, and improves bone microarchitecture in ovariectomized cynomolgus monkeys. | 2008 Nov |
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Long-term minodronic acid (ONO-5920/YM529) treatment suppresses increased bone turnover, plus prevents reduction in bone mass and bone strength in ovariectomized rats with established osteopenia. | 2008 Nov |
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Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation. | 2008 Sep 25 |
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[New development in bisphosphonate treatment. Review of the preventive effect of minodronic acid on fracture in Japanese patients with osteoporosis]. | 2009 Jan |
Patents
Sample Use Guides
Normally in adults, 1 mg of minodronic acid (RECALBON®, Bonoteo®) is taken orally together with enough amount of water (180 ml) (or lukewarm water) once a day at the time of awakening. The drug must be taken without lying down at least for 30 minutes before the first food, beverage (other than plain water), and other oral medication.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28243795
The bone-binding characteristics of minodronic acid and morphological changes in rabbit osteoclasts were analyzed in vitro. In an osteoclast culture with 1 uM minodronic acid, 65% of minodronic acid was bound to bone, and C-terminal cross-linking telopeptide release was inhibited by 96%. Cultured osteoclasts without minodronic acid treatment formed ruffled borders and bone resorption lacunae and had rich cytoplasm, whereas those treated with 1 uM minodronic acid were not multinucleated, stained densely with toluidine blue, and were detached from the bone surface.
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NCI_THESAURUS |
C67439
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CHEMBL319144
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DTXSID4048779
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725590
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DB06548
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180064-38-4
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C81673
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7651
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SUB08981MIG
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4074
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40SGR63TGL
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100000080641
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C087958
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130956
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m7554
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MINODRONIC ACID
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)