Page last updated: 2024-12-07

cimadronate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

cimadronate: increases serum 1,25-dihydroxyvitamin D in rats via stimulating renal 1-hydroxylase activity; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID405386
SCHEMBL ID8370913
MeSH IDM0194266

Synonyms (21)

Synonym
gtpl3174
icandronate
[(cyclohexylamino)(phosphono)methyl]phosphonic acid
nsc722615
nsc-722615
32545-64-5
cimadronate
[(cyclohexylamino)-phosphonomethyl]phosphonic acid
GBBBPWVJGMFZGX-UHFFFAOYSA-N
n-cyclohexyl-1-aminomethane-1,1-diphosphonic acid
SCHEMBL8370913
Q20817244
DTXSID90954285
[(cyclohexylamino)methylene]bis(phosphonic acid)
phosphonic acid, p,p'-[(cyclohexylamino)methylene]bis-
p,p'-[(cyclohexylamino)methylene]bis[phosphonic acid]
unii-66atw42t2c
((cyclohexylamino)-phosphonomethyl)phosphonic acid
p,p'-((cyclohexylamino)methylene)bis(phosphonic acid)
phosphonic acid, p,p'-((cyclohexylamino)methylene)bis-
66atw42t2c ,

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Major toxic symptoms were decreased motility and piloerection and LD50 values were 23 mg/kg for males and 21 mg/kg for females."( Intravenous single and repeated dose toxicity studies of cimadronate (YM175), a novel bisphosphonate, in rats.
East, PW; Matsuzawa, T; Okazaki, A; Perkin, CJ; Sakai, H, 1995
)
0.29
" At 10 mg/kg, both the male and female dog showed toxic signs such as vomiting, decreased locomotor activities and hypothermia and were killed in extremis within a week after dosing."( Intravenous single and repeated dose toxicity studies of cimadronate (YM175), a novel bisphosphonate, in beagle dogs.
Barker, MH; Matsuzawa, T; Okazaki, A; Perkin, CJ, 1995
)
0.29
" In conclusion, rapid infusion of incadronate was a safe treatment and the incadronate therapy was effective against bone metastasis of breast cancer."( [Study on the safety of rapid infusion and the efficacy of incadronate against bone metastasis of breast cancer].
Kokawa, Y; Naito, Y; Oura, S; Sakurai, T; Tamaki, T; Umemura, T; Yoshimura, G, 1999
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" In this study, the pharmacokinetic and pharmacodynamic (PK/PD) analysis model for ascertaining the antihypercalcemic effects of incadronate disodium was developed in rats."( Pharmacokinetic and pharmacodynamic analysis of the antihypercalcemic effect of incadronate disodium in rats.
Iga, T; Ohno, Y; Ohtani, H; Sato, H; Sawada, Y; Takahashi, K; Tsuchiya, F; Usu, T; Yamada, Y, 2001
)
0.31

Dosage Studied

ExcerptRelevanceReference
" Urinary excretion of YM175 up to 24 h after dosing was as low as 10."( Pharmacokinetics of incadronate, a new bisphosphonate, in healthy volunteers and patients with malignancy-associated hypercalcemia.
Higuchi, S; Ikeda, K; Ogata, E; Oiso, Y; Tomita, A; Uchida, T; Usui, T; Watanabe, T, 1997
)
0.3
" 3) INC induced Cbfa1-nuclear localization within hours; and in an in vivo experiment using ovariectomized mice, its 3 weeks dosing exhibited the same effect in tibial extracts."( 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.
Fujita, T; Fukuyama, R; Izumo, N; Koida, M; Meguro, T; Nakamuta, H; Yasutomi, C, 2001
)
0.31
" The dosing procedure lasted for three years."( [Long-term and high-dose bisphosphonate administration causes no bone over-mineralization].
Cao, YP; Liu, C; Mashiba, T; Mori, S; Yang, X, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Farnesyl pyrophosphate synthaseHomo sapiens (human)IC50 (µMol)0.18630.00020.71099.3600AID318593; AID318594; AID72667; AID72669
Farnesyl pyrophosphate synthaseHomo sapiens (human)Ki0.02950.00010.21651.9000AID318593; AID318594; AID72668
Farnesyl pyrophosphate synthase Leishmania donovaniIC50 (µMol)0.16000.11000.15600.1700AID72651
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processFarnesyl pyrophosphate synthaseHomo sapiens (human)
geranyl diphosphate biosynthetic processFarnesyl pyrophosphate synthaseHomo sapiens (human)
farnesyl diphosphate biosynthetic processFarnesyl pyrophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
RNA bindingFarnesyl pyrophosphate synthaseHomo sapiens (human)
protein bindingFarnesyl pyrophosphate synthaseHomo sapiens (human)
metal ion bindingFarnesyl pyrophosphate synthaseHomo sapiens (human)
dimethylallyltranstransferase activityFarnesyl pyrophosphate synthaseHomo sapiens (human)
geranyltranstransferase activityFarnesyl pyrophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
nucleoplasmFarnesyl pyrophosphate synthaseHomo sapiens (human)
cytosolFarnesyl pyrophosphate synthaseHomo sapiens (human)
cytoplasmFarnesyl pyrophosphate synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID275056Antibacterial activity against Escherichia coli pTMV19 in presence of mevalonate2006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.
AID67525In vitro growth inhibition against Entamoeba histolytica2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.
AID1110776Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase at 1 mM after 30 min by hemibiosynthetic assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID318593Inhibition of human recombinant FPPS expressed in Escherichia coli BL212008Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7
Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.
AID1110786Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase assessed as inhibition of glutamine synthesis from glutamic acid after 15 min by biosynthetic assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID1090682Inhibition of Arabidopsis thaliana P5C reductase catalytic activity assessed as residual concentration of enzyme at 535 nm OD at 0.5 mM by P5C utilization assay2007Journal of agricultural and food chemistry, May-30, Volume: 55, Issue:11
Plant P5C reductase as a new target for aminomethylenebisphosphonates.
AID1110777Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase at 1 mM by transferase assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1110788Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase by transferase assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID72667Inhibitory activity against farnesyl Pyrophosphate Synthase was determined2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates.
AID96034Toxicity evaluated against human nasopharyngeal carcinoma KB cell line2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.
AID71578Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells, using a constrained maximum TNF-alpha release of 2700 pg/mL2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.
AID71580pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using a constrained maximum TNF-alpha release of 2700 pg/mL2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.
AID318595Inhibition of bone resorption in rat assessed as phosphate2008Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7
Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.
AID1588483Antiparasitic activity against Trypanosoma cruzi amastigote infected in African green monkey Vero cells decrease in parasite viability measured at day 3 of post infection by red fluorescent protein based fluorescence method2019Bioorganic & medicinal chemistry, 08-15, Volume: 27, Issue:16
Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii.
AID318594Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10 mins2008Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7
Structure-activity relationships among the nitrogen containing bisphosphonates in clinical use and other analogues: time-dependent inhibition of human farnesyl pyrophosphate synthase.
AID275054Antibacterial activity against Escherichia coli W31102006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.
AID208084In vitro growth inhibition of bloodstream-form Trypanosoma brucei rhodesiense Trypomastigotes2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Activity of bisphosphonates against Trypanosoma brucei rhodesiense.
AID1110787Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase after 30 min by hemibiosynthetic assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID9382850% lethal dose for inhibition of KB cells growth2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Activity of bisphosphonates against Trypanosoma brucei rhodesiense.
AID235247Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Entamoeba histolytica2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.
AID235219Therapeutic index measured as the ratio of LD50 (KB cells) to IC50 (T.b. rhodesiense)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Activity of bisphosphonates against Trypanosoma brucei rhodesiense.
AID72668Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates.
AID496826Antimicrobial activity against Entamoeba histolytica2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1090681Inhibition of Arabidopsis thaliana P5C reductase catalytic activity assessed as inhibition of NADPH oxidation at 340 nm OD at 0.2 mM by NADPH oxidation assay2007Journal of agricultural and food chemistry, May-30, Volume: 55, Issue:11
Plant P5C reductase as a new target for aminomethylenebisphosphonates.
AID71581pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using individual observed maximum TNF-alpha release2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.
AID72669Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M)2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates.
AID1110775Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase assessed as inhibition of glutamine synthesis from glutamic acid at 1 mM after 15 min by biosynthetic assay2004Journal of agricultural and food chemistry, Jun-02, Volume: 52, Issue:11
Herbicidal pyridyl derivatives of aminomethylene-bisphosphonic acid inhibit plant glutamine synthetase.
AID275055Antibacterial activity against Escherichia coli pTMV192006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.
AID72651Inhibitory activity against Leishmania major Farnesyl diphosphate synthase2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.
AID71579Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells, using individual observed maximum TNF-alpha release2004Journal of medicinal chemistry, Jan-15, Volume: 47, Issue:2
Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.
AID158550In vitro growth inhibition against Plasmodium falciparum2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.
AID208217Predicted pIC50 against Trypomastigotes Brucei rhodesiense.2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Activity of bisphosphonates against Trypanosoma brucei rhodesiense.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (100)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's39 (39.00)18.2507
2000's56 (56.00)29.6817
2010's5 (5.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (2.86%)5.53%
Reviews2 (1.90%)6.00%
Case Studies4 (3.81%)4.05%
Observational0 (0.00%)0.25%
Other96 (91.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]