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124351-85-5

124351-85-5 | Phosphonic acid, P,P'-[(cycloheptylamino)methylene]bis-

CAS No: 124351-85-5 Catalog No: AG000LXG MDL No:

Product Description

Catalog Number:
AG000LXG
Chemical Name:
Phosphonic acid, P,P'-[(cycloheptylamino)methylene]bis-
CAS Number:
124351-85-5
Molecular Formula:
C8H19NO6P2
Molecular Weight:
287.1871
IUPAC Name:
[(cycloheptylamino)-phosphonomethyl]phosphonic acid
InChI:
InChI=1S/C8H19NO6P2/c10-16(11,12)8(17(13,14)15)9-7-5-3-1-2-4-6-7/h7-9H,1-6H2,(H2,10,11,12)(H2,13,14,15)
InChI Key:
LWRDQHOZTAOILO-UHFFFAOYSA-N
SMILES:
OP(=O)(C(P(=O)(O)O)NC1CCCCCC1)O
UNII:
G5C4M8847E
NSC Number:
723271

Properties

Complexity:
307  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
287.069g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
287.189g/mol
Monoisotopic Mass:
287.069g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
127A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.5  

Literature

Title Journal
The bisphosphonate incadronate inhibits intraperitoneal dissemination in an in vivo pancreatic cancer model. Oncology reports 20120701
[Long-term and high-dose bisphosphonate administration causes no bone over-mineralization]. Zhonghua yi xue za zhi 20091117
Ibadronate may prevent colorectal carcinogenesis in mice with ulcerative colitis. Anticancer research 20091101
Collagen maturity, glycation induced-pentosidine, and mineralization are increased following 3-year treatment with incadronate in dogs. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20080901
Lung and bone metastases from renal cell carcinoma responsive to bisphosphonates: a case report. International journal of urology : official journal of the Japanese Urological Association 20080601
Sugar synthesis from a gas-phase formose reaction. Astrobiology 20070601
Clinical evaluation of incadronate in korean patients with malignancy-associated hypercalcemia: An open-label, multicenter study. Current therapeutic research, clinical and experimental 20070501
Bisphosphonate incadronate inhibits growth of human T-cell leukaemia virus type I-infected T-cell lines and primary adult T-cell leukaemia cells by interfering with the mevalonate pathway. British journal of haematology 20070201
Inhibition of bone resorption in cultures of mouse calvariae by apicularen A. Planta medica 20070201
Incadronate induces cell detachment and apoptosis in prostatic PC-3 cells. Anticancer research 20070101
Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin. Journal of medicinal chemistry 20061214
Hyperbaric oxygen in addition to antibiotic therapy is effective for bisphosphonate-induced osteonecrosis of the jaw in a patient with multiple myeloma. International journal of hematology 20061101
Incadronate inhibits aminopeptidase N expression in prostatic PC-3 cells. Cancer letters 20060618
Inhibition of caveolin-1 expression by incadronate in PC-3 prostate cells. Anticancer research 20060101
Effect of incadronate on proliferation of mesenchymal tumor cells with or without activated Ras mutation. Journal of experimental & clinical cancer research : CR 20051201
Nitrogen-containing bisphosphonate incadronate augments the inhibitory effect of farnesyl transferase inhibitor tipifarnib on the growth of fresh and cloned myeloma cells in vitro. Leukemia & lymphoma 20051101
Combination therapy with thalidomide, incadronate, and dexamethasone for relapsed or refractory multiple myeloma. International journal of hematology 20051001
Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations. Journal of medicinal chemistry 20050505
Incadronate disodium inhibits joint destruction and periarticular bone loss only in the early phase of rat adjuvant-induced arthritis. Journal of bone and mineral metabolism 20050101
Effect of incadronate on corticosteroid-induced osteopenia in rats. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20040901
Alendronate inhibits urinary calcium microlith formation in a three-dimensional culture model. Urological research 20040601
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates. Journal of medicinal chemistry 20040115
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo. Journal of medicinal chemistry 20040101
3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates. Journal of medicinal chemistry 20031120
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
Nitrogen containing bisphosphonates induce apoptosis and inhibit the mevalonate pathway, impairing Ras membrane localization in prostate cancer cells. The Journal of urology 20030701
Antiinflammatory and chondroprotective effects of the aminobisphosphonate incadronate (YM175) in adjuvant induced arthritis. The Journal of rheumatology 20030601
[Changes of urinary deoxypyridinoline crosslink/creatinine in rats after ovariectomy and anti-osteoporotic intervention]. Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20030601
Incadronate amplifies prostaglandin F2 alpha-induced vascular endothelial growth factor synthesis in osteoblasts. Enhancement of MAPK activity. The Journal of biological chemistry 20030523
Hydronium (cycloheptylammonio)methylene-1,1-bisphosphonate (hydronium incadronate). Acta crystallographica. Section C, Crystal structure communications 20030201
Bisphosphonate therapy for hormone refractory prostate cancer with bone metastasis. The Journal of urology 20030101
Effects of bisphosphonate on bone reaction after placement of titanium implants in tibiae of ovariectomized rats. The International journal of oral & maxillofacial implants 20030101
Incadronate disodium inhibits advanced glycation end products-induced angiogenesis in vitro. Biochemical and biophysical research communications 20020920
Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa). Journal of medicinal chemistry 20020815
Comparison of incadronate and alfacalcidol on increased bone turnover caused by ovariectomy in rats. European journal of pharmacology 20020802
An investigation of bone resorption and Dictyostelium discoideum growth inhibition by bisphosphonate drugs. Journal of medicinal chemistry 20020704
Incadronate and etidronate accelerate phosphate-primed mineralization of MC4 cells via ERK1/2-Cbfa1 signaling pathway in a Ras-independent manner: further involvement of mevalonate-pathway blockade for incadronate. Japanese journal of pharmacology 20010501
Long-term effect of incadronate disodium (YM-175) on fracture healing of femoral shaft in growing rats. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010301
A newly developed bisphosphonate, YM529, is a potent apoptosis inducer of human myeloma cells. Leukemia research 20010101
[A case of effective bisphosphonate therapy of sequential pamidronate and incadronate for bone metastases from breast cancer]. Gan to kagaku ryoho. Cancer & chemotherapy 20000801
[Breast cancer with osteoblastic bone metastasis treated successfully with bisphosphonate: a case report]. Gan to kagaku ryoho. Cancer & chemotherapy 19991001
The bisphosphonate incadronate (YM175) causes apoptosis of human myeloma cells in vitro by inhibiting the mevalonate pathway. Cancer research 19981201
Pharmacokinetics of incadronate, a new bisphosphonate, in healthy volunteers and patients with malignancy-associated hypercalcemia. International journal of clinical pharmacology and therapeutics 19970601

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