Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H12N2O7P2.H2O |
| Molecular Weight | 340.1636 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC(CC1=CN=C2C=CC=CN12)(P(O)(O)=O)P(O)(O)=O
InChI
InChIKey=GPAPAOGRNKUFGH-UHFFFAOYSA-N
InChI=1S/C9H12N2O7P2.H2O/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);1H2
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 |
0.67 µM [IC50] | ||
Target ID: CHEMBL1782 |
0.003 µM [IC50] | ||
Target ID: CHEMBL3137277 |
62.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | BONOTEO Approved UseThe drug was developed for the treatment of osteoporosis. Launch Date2009 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. | 2001 Feb |
|
| Effects of YM529, a novel minodronic acid, on adjuvant arthritis in rats. | 2004 Jan-Feb |
|
| Minodronic acid influences receptor activator of nuclear factor kappaB ligand expression and suppresses bone resorption by osteoclasts in rats with collagen-induced arthritis. | 2007 |
|
| Combined effects of a third-generation bisphosphonate, zoledronic acid with other anticancer agents against murine osteosarcoma. | 2007 Jan 29 |
|
| Minodronic acid, a third-generation bisphosphonate, antagonizes purinergic P2X(2/3) receptor function and exerts an analgesic effect in pain models. | 2008 Jul 28 |
|
| 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 |
|
| [New development in bisphosphonate treatment. Review of the preventive effect of minodronic acid on fracture in Japanese patients with osteoporosis]. | 2009 Jan |
|
| Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic acid. | 2010 May 13 |
|
| Reduction of metastasis, cell invasion, and adhesion in mouse osteosarcoma by YM529/ONO-5920-induced blockade of the Ras/MEK/ERK and Ras/PI3K/Akt pathway. | 2012 Mar 15 |
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
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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100000125990
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m7554
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PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD
