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Home > Imidazoles > 180064-38-4
180064-38-4 | Phosphonic acid, P,P'-(1-hydroxy-2-imidazo[1,2-a]pyridin-3-ylethylidene)bis-
CAS No: 180064-38-4 Catalog No: AG0021ON MDL No:MFCD00890772
Product Description
Catalog Number:
AG0021ON
Chemical Name:
Phosphonic acid, P,P'-(1-hydroxy-2-imidazo[1,2-a]pyridin-3-ylethylidene)bis-
CAS Number:
180064-38-4
Molecular Formula:
C9H12N2O7P2
Molecular Weight:
322.1483
MDL Number:
MFCD00890772
IUPAC Name:
(1-hydroxy-2-imidazo[1,2-a]pyridin-3-yl-1-phosphonoethyl)phosphonic acid
InChI:
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)
InChI Key:
VMMKGHQPQIEGSQ-UHFFFAOYSA-N
SMILES:
OP(=O)(C(P(=O)(O)O)(Cc1cnc2n1cccc2)O)O
UNII:
40SGR63TGL
NSC Number:
725590
Properties
Complexity:
439
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
322.012g/mol
Formal Charge:
0
Heavy Atom Count:
20
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
5
Isotope Atom Count:
0
Molecular Weight:
322.15g/mol
Monoisotopic Mass:
322.012g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
153A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.2
Literature
| Title | Journal |
|---|---|
| Efficacy and safety of monthly oral minodronate in patients with involutional osteoporosis. | Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20120601 |
| [New approved drugs for osteoporosis in Japan]. | Clinical calcium 20120601 |
| 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. | Toxicology and applied pharmacology 20120315 |
| Synergistic Effect of Geranylgeranyltransferase Inhibitor, GGTI, and Docetaxel on the Growth of Prostate Cancer Cells. | Prostate cancer 20120101 |
| Gastric ulcerogenic and healing impairment effects of risedronate, a nitrogen-containing bisphosphonate in rats. Comparison with alendronate and minodronate. | Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20111201 |
| [Frontiers in vitamin D; Basic research and clinical application. The effects of eldecalcitol on bone mineral density and fracture prevention--Post hoc analysis]. | Clinical calcium 20111101 |
| Synthesis, stereochemistry and SAR of a series of minodronate analogues as RGGT inhibitors. | European journal of medicinal chemistry 20111001 |
| A serendipitous phosphonocarboxylate complex of boron: when vessel becomes reagent. | Chemical communications (Cambridge, England) 20110614 |
| Computational insights into binding of bisphosphates to farnesyl pyrophosphate synthase. | Current medicinal chemistry 20110101 |
| [Minodronic acid- its clinical efficacy and prospects for once-a-month dosing regimen]. | Clinical calcium 20110101 |
| Alendronate (ALN) combined with osteoprotegerin (OPG) significantly improves mechanical properties of long bone than the single use of ALN or OPG in the ovariectomized rats. | Journal of orthopaedic surgery and research 20110101 |
| Nitrogen-containing bisphosphonate, YM529/ONO-5920, inhibits tumor metastasis in mouse melanoma through suppression of the Rho/ROCK pathway. | Clinical & experimental metastasis 20101001 |
| 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. | Journal of medicinal chemistry 20100513 |
| Minodronate for the treatment of osteoporosis. | Drugs of today (Barcelona, Spain : 1998) 20100101 |
| Expression of Msx-1 is suppressed in bisphosphonate associated osteonecrosis related jaw tissue-etiopathology considerations respecting jaw developmental biology-related unique features. | Journal of translational medicine 20100101 |
| Anti-tumour activity of bisphosphonates in preclinical models of breast cancer. | Breast cancer research : BCR 20100101 |
| [Pharmacological profile and clinical efficacy of minodronic acid hydrate as a new therapeutic agent for osteoporosis]. | Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20090901 |
| Effect of daily oral minodronate on vertebral fractures in Japanese postmenopausal women with established osteoporosis: a randomized placebo-controlled double-blind study. | Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20090801 |
| A double-blinded head-to-head trial of minodronate and alendronate in women with postmenopausal osteoporosis. | Bone 20090601 |
| [Drugs under development for osteoporosis ]. | Nihon rinsho. Japanese journal of clinical medicine 20090501 |
| [New development in bisphosphonate treatment. Review of effect on bone metabolism by minodronic acid in primary osteoporosis]. | Clinical calcium 20090101 |
| [New development in bisphosphonate treatment. Review of the preventive effect of minodronic acid on fracture in Japanese patients with osteoporosis]. | Clinical calcium 20090101 |
| New bisphosphonates and trends in drug therapy for osteoporosis: preface. | Clinical calcium 20090101 |
| 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. | Bone 20081101 |
| Minodronic acid (ONO-5920/YM529) prevents decrease in bone mineral density and bone strength, and improves bone microarchitecture in ovariectomized cynomolgus monkeys. | Bone 20081101 |
| Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation. | Journal of medicinal chemistry 20080925 |
| Minodronic acid, a third-generation bisphosphonate, antagonizes purinergic P2X(2/3) receptor function and exerts an analgesic effect in pain models. | European journal of pharmacology 20080728 |
| Efficacy of a nitrogen-containing bisphosphonate, minodronate, in conjunction with a p38 mitogen activated protein kinase inhibitor or doxorubicin against malignant bone tumor cells. | Cancer chemotherapy and pharmacology 20080601 |
| Farnesyl pyrophosphate synthase enantiospecificity with a chiral risedronate analog, [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) (NE-10501): Synthetic, structural, and modeling studies. | Bioorganic & medicinal chemistry letters 20080501 |
| Nitrogen-containing bisphosphonate, YM529/ONO-5920, inhibits macrophage inflammatory protein 1 alpha expression and secretion in mouse myeloma cells. | Cancer science 20080101 |
| [New bone density conservation agents for osteoporosis under research and development: Minodronic acid]. | Nihon rinsho. Japanese journal of clinical medicine 20071128 |
| Induction of mitochondria-dependent apoptosis through the inhibition of mevalonate pathway in human breast cancer cells by YM529, a new third generation bisphosphonate. | Cancer letters 20070808 |
| Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. | Proceedings of the National Academy of Sciences of the United States of America 20070612 |
| Combined effects of a third-generation bisphosphonate, zoledronic acid with other anticancer agents against murine osteosarcoma. | British journal of cancer 20070129 |
| [Therapeutic agents for disorders of bone and calcium metabolism: Minodronic acid hydrate]. | Clinical calcium 20070101 |
| Anti-tumor effect of bisphosphonate (YM529) on non-small cell lung cancer cell lines. | BMC cancer 20070101 |
| Minodronic acid influences receptor activator of nuclear factor kappaB ligand expression and suppresses bone resorption by osteoclasts in rats with collagen-induced arthritis. | Modern rheumatology 20070101 |
| Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin. | Journal of medicinal chemistry 20061214 |
| A third-generation bisphosphonate, minodronic acid (YM529), successfully prevented the growth of bladder cancer in vitro and in vivo. | British journal of cancer 20061120 |
| Minodronate suppresses prostaglandin F2alpha-induced vascular endothelial growth factor synthesis in osteoblasts. | Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20060301 |
| Minodronate, a nitrogen-containing bisphosphonate, is a promising remedy for treating patients with diabetic retinopathy. | Medical hypotheses 20060101 |
| The effect of bisphosphonates on gene expression: GAPDH as a housekeeping or a new target gene? | BMC cancer 20060101 |
| Effect of combination therapy with a novel bisphosphonate, minodronate (YM529), and docetaxel on a model of bone metastasis by human transitional cell carcinoma. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050915 |
| Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations. | Journal of medicinal chemistry 20050505 |
| Nitrogen-containing bisphosphonate, YM529/ONO-5920 (a novel minodronic acid), inhibits RANKL expression in a cultured bone marrow stromal cell line ST2. | Biochemical and biophysical research communications 20050304 |
| A third-generation bisphosphonate, minodronic acid (YM529), augments the interferon alpha/beta-mediated inhibition of renal cell cancer cell growth both in vitro and in vivo. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050115 |
| [Minodronic acid hydrate as a new therapeutic agent for osteoporosis]. | Clinical calcium 20050101 |
| Minodronate, a nitrogen-containing bisphosphonate, inhibits advanced glycation end product-induced vascular cell adhesion molecule-1 expression in endothelial cells by suppressing reactive oxygen species generation. | International journal of tissue reactions 20050101 |
| Minodronate, a newly developed nitrogen-containing bisphosphonate, suppresses melanoma growth and improves survival in nude mice by blocking vascular endothelial growth factor signaling. | The American journal of pathology 20041201 |
| Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates. | Journal of medicinal chemistry 20040115 |
| Effects of YM529, a novel minodronic acid, on adjuvant arthritis in rats. | Clinical and experimental rheumatology 20040101 |
| Combined therapy with a new bisphosphonate, minodronate (YM529), and chemotherapy for multiple organ metastases of small cell lung cancer cells in severe combined immunodeficient mice. | Clinical cancer research : an official journal of the American Association for Cancer Research 20031101 |
| A new bisphosphonate, YM529 induces apoptosis in HL60 cells by decreasing phosphorylation of single survival signal ERK. | Life sciences 20031010 |
| Nitrogen-containing bisphosphonates induce S-phase cell cycle arrest and apoptosis of myeloma cells by activating MAPK pathway and inhibiting mevalonate pathway. | Cellular signalling 20030701 |
| Effect of minodronic acid (ONO-5920) on bone mineral density and arthritis in adult rats with collagen-induced arthritis. | Arthritis and rheumatism 20030601 |
| A new stressed test to predict the foreign matter formation of minodronic acid in solution. | International journal of pharmaceutics 20030130 |
| Failure of stability prediction for minodronic acid injectable by accelerated stability testing. | International journal of pharmaceutics 20020708 |
| An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs. | Journal of medicinal chemistry 20020704 |
| Synergistic growth inhibition of YM529 with biologic response modifiers (BRMs) in myeloma cells. | International journal of hematology 20020601 |
| Conflicting actions of parathyroid hormone-related protein and serum calcium as regulators of 25-hydroxyvitamin D(3)-1 alpha-hydroxylase expression in a nude rat model of humoral hypercalcemia of malignancy. | The Journal of endocrinology 20011101 |
| Stabilization of minodronic acid in aqueous solution for parenteral formulation. | International journal of pharmaceutics 20010703 |
| Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. | The Journal of pharmacology and experimental therapeutics 20010201 |
| A newly developed bisphosphonate, YM529, is a potent apoptosis inducer of human myeloma cells. | Leukemia research 20010101 |
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