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138844-81-2

138844-81-2 | Phosphonic acid, P,P'-[1-hydroxy-3-(methylpentylamino)propylidene]bis-, sodium salt (1:1)

CAS No: 138844-81-2 Catalog No: AG0019OO MDL No:MFCD07197214

Product Description

Catalog Number:
AG0019OO
Chemical Name:
Phosphonic acid, P,P'-[1-hydroxy-3-(methylpentylamino)propylidene]bis-, sodium salt (1:1)
CAS Number:
138844-81-2
Molecular Formula:
C9H22NNaO7P2
Molecular Weight:
341.2108
MDL Number:
MFCD07197214
IUPAC Name:
sodium;hydroxy-[1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl]phosphinate
InChI:
InChI=1S/C9H23NO7P2.Na/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17;/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17);/q;+1/p-1
InChI Key:
LXLBEOAZMZAZND-UHFFFAOYSA-M
SMILES:
CCCCCN(CCC(P(=O)(O)O)(P(=O)(O)[O-])O)C.[Na+]
UNII:
23Y0B94E49

Properties

Complexity:
377  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
341.077g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
341.212g/mol
Monoisotopic Mass:
341.077g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
141A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0

Literature

Title Journal
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Incidence of maxillary sinusitis and oro-antral fistulae in bisphosphonate-related osteonecrosis of the jaw. Journal of cranio-maxillo-facial surgery : official publication of the European Association for Cranio-Maxillo-Facial Surgery 20121001
Six months of parathyroid Hormone (1-84) administered concurrently versus sequentially with monthly ibandronate over two years: the PTH and ibandronate combination study (PICS) randomized trial. The Journal of clinical endocrinology and metabolism 20121001
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Efficacy of intravenously administered ibandronate in postmenopausal Korean women with insufficient response to orally administered bisphosphonates. Journal of bone and mineral metabolism 20120901
Bisphosphonate-related osteonecrosis of the jaw in patients with oral bisphosphonate exposure: clinical course and outcomes. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons 20120801
Once-monthly oral ibandronate provides significant improvement in bone mineral density in postmenopausal women treated with glucocorticoids for inflammatory rheumatic diseases: a 12-month, randomized, double-blind, placebo-controlled trial. Scandinavian journal of rheumatology 20120801
Monitoring of bone turnover markers does not improve persistence with ibandronate treatment. Joint, bone, spine : revue du rhumatisme 20120701
Bisphosphonate-related osteonecrosis of the mandible secondary to postural pressure. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons 20120701
Adherence with intravenous zoledronate and intravenous ibandronate in the United States Medicare population. Arthritis care & research 20120701
Once-monthly oral ibandronate treatment in an adolescent with recurrent fractures and inadequately low bone mass. Journal of paediatrics and child health 20120701
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Gastrointestinal bleeding following intravenous ibandronate administration. Journal of pharmacy practice 20120601
Monthly ibandronate for the prevention of bone loss in patients after liver transplantation. Transplantation proceedings 20120601
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[Simultaneous determination of alendronate, pamidronate, ibandronate and risedronate using ion chromatography with integrated pulsed amperometric detection]. Se pu = Chinese journal of chromatography 20120401
Effect of dosing interval duration of intermittent ibandronate treatment on the healing process of femoral osteotomy in a rat fracture model. Calcified tissue international 20120301
Phase I clinical study to select a novel oral formulation for ibandronate containing the excipient sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC). Die Pharmazie 20120301
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Ibandronate and calcitriol reduces fracture risk, reverses bone loss, and normalizes bone turnover after LTX. Transplantation 20120215
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Counting touching cell nuclei using fast ellipse detection to assess in vitro cell characteristics: a feasibility study. Clinical oral investigations 20120201
The influence of bisphosphonates on viability, migration, and apoptosis of human oral keratinocytes--in vitro study. Clinical oral investigations 20120201
Bisphosphonate-related osteonecrosis of jaws in 3 osteoporotic patients with history of oral bisphosphonate use treated with single yearly zoledronic acid infusion. Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons 20120201
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Effect of monthly ibandronate on hip structural geometry in men with low bone density. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20120101
Impact of oral ibandronate 150 mg once monthly on bone structure and density in post-menopausal osteoporosis or osteopenia derived from in vivo μCT. Bone 20120101
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Pathogenesis and bisphosphonate treatment of skeletal events and bone pain in metastatic cancer: focus on ibandronate. Onkologie 20120101
Phase II study of loading-dose ibandronate treatment in patients with breast cancer and bone metastases suffering from moderate to severe pain. Onkologie 20120101
Impact of long-term cinacalcet, ibandronate or teriparatide therapy on bone mineral density of hemodialysis patients: a pilot study. American journal of nephrology 20120101
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Daily or monthly ibandronate prevents or restores deteriorations of bone mass, architecture, biomechanical properties and markers of bone turnover in androgen-deficient aged rats. The aging male : the official journal of the International Society for the Study of the Aging Male 20111201
Zoledronate, ibandronate and clodronate enhance osteoblast differentiation in a dose dependent manner--a quantitative in vitro gene expression analysis of Dlx5, Runx2, OCN, MSX1 and MSX2. Journal of cranio-maxillo-facial surgery : official publication of the European Association for Cranio-Maxillo-Facial Surgery 20111201
Renal safety of ibandronate 6 mg infused over 15 min versus 60 min in breast cancer patients with bone metastases: a randomized open-label equivalence trial. Breast (Edinburgh, Scotland) 20111201
Effects of intravenous ibandronate injection on renal function in women with postmenopausal osteoporosis at high risk for renal disease--the DIVINE study. Bone 20111201
Monthly or weekly bisphosphonate? Evaluation of satisfaction in patients with postmenopausal osteoporosis using OPSAT-Q questionnaire during the BOOSTER study in Croatia. Clinical rheumatology 20111201
Integrated model for denosumab and ibandronate pharmacodynamics in postmenopausal women. Biopharmaceutics & drug disposition 20111101
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Effect of ibandronate on disseminated tumor cells in the bone marrow of patients with primary breast cancer: a pilot study. Anticancer research 20111001
Benefit of infusions with ibandronate treatment in children with osteogenesis imperfecta. Chinese medical journal 20111001
Parenteral bisphosphonates for osteoporosis in patients with primary biliary cirrhosis. American journal of therapeutics 20110901
A comparative study of intravenous ibandronate and pamindronate in patients with bone metastases from breast or lung cancer: effect on metastatic bone pain. American journal of therapeutics 20110901
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Administration of sodium ibandronate in the treatment of complicated giant cell tumor of the spine. Spine 20110801
Non-surgical management of stage 3 biphosphonate-related oroantral fistula. The British journal of oral & maxillofacial surgery 20110701
Effect of bisphosphonates on anodized and heat-treated titanium surfaces: an animal experimental study. Journal of periodontology 20110701
[Assessment of volumetric bone mineral density and geometry for hip with clinical CT device]. Clinical calcium 20110701
Effects of intravenous zoledronic acid and oral ibandronate on early changes in markers of bone turnover in patients with bone metastases from non-small cell lung cancer. International journal of clinical oncology 20110601
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The treatment of symptomatic osteoporotic spinal compression fractures. The Journal of the American Academy of Orthopaedic Surgeons 20110301
Stability indicating ion chromatography method for the simultaneous determination of ibandronate sodium drug substance and its impurities. Journal of pharmaceutical and biomedical analysis 20110220
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Bisphosphonates inhibit phosphorylation of signal transducer and activator of transcription 3 and expression of suppressor of cytokine signaling 3: implications for their effects on innate immune function and osteoclastogenesis. Oral surgery, oral medicine, oral pathology, oral radiology, and endodontics 20110201
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Ibandronate promotes osteogenic differentiation of periodontal ligament stem cells by regulating the expression of microRNAs. Biochemical and biophysical research communications 20110107
Differential effects of ibandronate, docetaxel and farnesol treatment alone and in combination on the growth of prostate cancer cell lines. Acta oncologica (Stockholm, Sweden) 20110101
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Increases in hip and spine bone mineral density are predictive for vertebral antifracture efficacy with ibandronate. Calcified tissue international 20101001
The increased expression of receptor activator of nuclear-kappaB ligand (RANKL) of multiple myeloma bone marrow stromal cells is inhibited by the bisphosphonate ibandronate. Journal of cellular biochemistry 20100901
Successful treatment of SAPHO syndrome with ibandronate. Journal of clinical rheumatology : practical reports on rheumatic & musculoskeletal diseases 20100801
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Efficacy and safety of monthly ibandronate in men with low bone density. Bone 20100401
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Long-term renal safety profile of ibandronate 6 mg infused over 15 minutes. Onkologie 20100101
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Ibandronate increases cortical bone density in patients with systemic lupus erythematosus on long-term glucocorticoid. Arthritis research & therapy 20100101
Bisphosphonates in calcific aortic stenosis: association with slower progression in mild disease--a pilot retrospective study. Cardiology 20100101
The efficiency of Bonviva (Ibadronate) in women with pre-post menopause. Medicinski arhiv 20100101
Osteonecrosis of the jaw in patients with multiple myeloma treated with bisphosphanates. Prilozi 20100101
Apoptosis-mediated cytotoxic effects of ibandronic acid on hormone- and drug-refractory prostate cancer cells and human breast cancer cells. The Journal of international medical research 20100101
Metronomic administration of ibandronate and its anti-angiogenic effects in vitro. Microvascular research 20091201
Update on monthly oral bisphosphonate therapy for the treatment of osteoporosis: focus on ibandronate 150 mg and risedronate 150 mg. Current medical research and opinion 20091201
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Longitudinal cohort study of risk factors in cancer patients of bisphosphonate-related osteonecrosis of the jaw. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20091110
Efficacy of ibandronate for the treatment of skeletal events in patients with metastatic breast cancer. European journal of cancer care 20091101
Comparison of monthly ibandronate versus weekly risedronate in preference, convenience, and bone turnover markers in Korean postmenopausal osteoporotic women. Calcified tissue international 20091101
A retrospective clinical and radiographic study on healing of periradicular lesions in patients taking oral bisphosphonates. Journal of endodontics 20091101
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Ibandronate reduces endogenous reactive oxygen species levels in cultured prostate cancer and endothelial cells. Microvascular research 20090901
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Pricey osteoporosis remedy doesn't beat older drugs. Consumer reports 20090801
Ibandronate prevents bone loss and reduces vertebral fracture risk in male cardiac transplant patients: a randomized double-blind, placebo-controlled trial. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20090701
Patient satisfaction in postmenopausal women treated with a weekly bisphosphonate transitioned to once-monthly ibandronate. Journal of women's health (2002) 20090701
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Improved GI tolerability with monthly ibandronate in women previously using weekly bisphosphonates. Southern medical journal 20090501
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Efficacy and safety of monthly oral ibandronate in the prevention of postmenopausal bone loss. Bone 20090301
Preference for weekly and monthly bisphosphonates among patients with postmenopausal osteoporosis: results from the Croatian PROMO Study. Clinical rheumatology 20090301
Ibandronate dose response is associated with increases in bone mineral density and reductions in clinical fractures: results of a meta-analysis. Bone 20090301
The effect of surface immobilized bisphosphonates on the fixation of hydroxyapatite-coated titanium implants in ovariectomized rats. Biomaterials 20090301
Ibandronate for the prevention of nonvertebral fractures: a pooled analysis of individual patient data. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20090201
Plain film and CBCT findings in a case of bisphosphonate-related osteonecrosis of the jaw. Quintessence international (Berlin, Germany : 1985) 20090201
Efficacy of bisphosphonates in reducing fracture risk in postmenopausal osteoporosis. The American journal of medicine 20090201
Higher incidence of Osteonecrosis of the Jaw (ONJ) in patients with metastatic castration resistant prostate cancer treated with anti-angiogenic agents. Cancer investigation 20090201
Once-monthly oral ibandronate improves biomechanical determinants of bone strength in women with postmenopausal osteoporosis. The Journal of clinical endocrinology and metabolism 20090101
Oral ibandronate preserves trabecular microarchitecture: micro-computed tomography findings from the oral iBandronate Osteoporosis vertebral fracture trial in North America and Europe study. Journal of clinical densitometry : the official journal of the International Society for Clinical Densitometry 20090101
[New development in bisphosphonate treatment. Characteristics and effectiveness of intermittent bisphophonates]. Clinical calcium 20090101
Identification of secondary targets of N-containing bisphosphonates in mammalian cells via parallel competition analysis of the barcoded yeast deletion collection. Genome biology 20090101
Gastrointestinal tolerability with ibandronate after previous weekly bisphosphonate treatment. Clinical interventions in aging 20090101
Is there a role for ibandronate in the treatment of prostate cancer patients with bony metastases? Acta oncologica (Stockholm, Sweden) 20090101
Dendritic multishell architectures for drug and dye transport. Journal of controlled release : official journal of the Controlled Release Society 20081218
Oral versus intravenous ibandronic acid: a comparison of treatment options for metastatic bone disease. Journal of cancer research and clinical oncology 20081201
Clinical and radiologic response in patients with bone metastases managed with combined radiotherapy and bisphosphonates. Journal of surgical oncology 20081201
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Ibandronate: is there an effect on nonvertebral fractures? Clinical rheumatology 20081001
An open-label pilot trial of ibandronate for complex regional pain syndrome. The Clinical journal of pain 20081001
Prevention of anastrozole-induced bone loss with monthly oral ibandronate during adjuvant aromatase inhibitor therapy for breast cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 20081001
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Intravenous ibandronate rapidly reduces pain, neurochemical indices of central sensitization, tumor burden, and skeletal destruction in a mouse model of bone cancer. Journal of pain and symptom management 20080901
Acute phase reaction with intravenous ibandronate. The American journal of medicine 20080901
Nonvertebral fracture risk reduction with nitrogen-containing bisphosphonates. Current osteoporosis reports 20080901
Therapies for treatment of osteoporosis in US women: cost-effectiveness and budget impact considerations. The American journal of managed care 20080901
[Update on treatment of postmenopausal osteoporosis]. Revue medicale de Bruxelles 20080901
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Renal safety profiles of ibandronate 6 mg infused over 15 and 60 min: a randomized, open-label study. Annals of oncology : official journal of the European Society for Medical Oncology 20080701
Identification of novel bone-specific molecular targets of binge alcohol and ibandronate by transcriptome analysis. Alcoholism, clinical and experimental research 20080701
Oral osteonecrosis associated with the use of ibandronate: report of a case and clinical implications. Oral surgery, oral medicine, oral pathology, oral radiology, and endodontics 20080701
Ibandronate in profile: drug characteristics and clinical efficacy. Expert opinion on drug metabolism & toxicology 20080701
Preclinical evidence for nitrogen-containing bisphosphonate inhibition of farnesyl diphosphate (FPP) synthase in the kidney: implications for renal safety. Toxicology in vitro : an international journal published in association with BIBRA 20080601
Changes in bone remodelling and antifracture efficacy of intermittent bisphosphonate therapy: implications from clinical studies with ibandronate. Postgraduate medical journal 20080601
Treatment preference for monthly oral ibandronate and weekly oral alendronate in women with postmenopausal osteoporosis: A randomized, crossover study (BALTO II). Joint, bone, spine : revue du rhumatisme 20080501
Ibandronate in benign bone disease. Reviews on recent clinical trials 20080501
Quarterly intravenous ibandronate for postmenopausal osteoporosis. Women's health (London, England) 20080501
Effects of the bisphosphonate ibandronate on hyperalgesia, substance P, and cytokine levels in a rat model of persistent inflammatory pain. European journal of pain (London, England) 20080401
Adherence to and gastrointestinal tolerability of monthly oral or quarterly intravenous ibandronate therapy in women with previous intolerance to oral bisphosphonates: a 12-month, open-label, prospective evaluation. Clinical therapeutics 20080401
A Phase II trial evaluating the palliative benefit of second-line oral ibandronate in breast cancer patients with either a skeletal related event (SRE) or progressive bone metastases (BM) despite standard bisphosphonate (BP) therapy. Breast cancer research and treatment 20080301
Bone turnover and bone collagen maturation in osteoporosis: effects of antiresorptive therapies. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20080301
Cost-effectiveness of a fixed dose combination of alendronate and cholecalciferol in the treatment and prevention of osteoporosis in the United Kingdom and The Netherlands. Current medical research and opinion 20080301
Efficacy and tolerability of intravenous ibandronate injections in postmenopausal osteoporosis: 2-year results from the DIVA study. The Journal of rheumatology 20080301
[Osteonecrosis of the jaw developing during bisphosphonate treatment]. Magyar onkologia 20080301
Reply to the article 'oral ibandronate is as active as intravenous zoledronic acid for reducing bone turnover markers in women with breast cancer and bone metastases' by J.-J. Body et al. (Ann Oncol 2007; 18: 1165-1171). Annals of oncology : official journal of the European Society for Medical Oncology 20080201
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