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SML0223

Sigma-Aldrich

Zoledronic acid monohydrate

≥98% (HPLC)

Synonym(s):

P,P′-[1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene]bisphosphonic acid monohydrate, Zoledronate monohydrate, [1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl]bis(phosphonic acid) monohydrate

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About This Item

Empirical Formula (Hill Notation):
C5H10N2O7P2·H2O
CAS Number:
165800-06-6
Molecular Weight:
290.10
MDL number:
MFCD08448695
UNSPSC Code:
12352204
PubChem Substance ID:
329825242
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

white to beige

solubility

H2O: ≥2 mg/mL

storage temp.

2-8°C

SMILES string

O.OC(Cn1ccnc1)(P(O)(O)=O)P(O)(O)=O

InChI

1S/C5H10N2O7P2.H2O/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7;/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14);1H2

InChI key

FUXFIVRTGHOMSO-UHFFFAOYSA-N

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Application

Zoledronic acid monohydrate has been used:
  • as an inhibitor for cell proliferation in glioblastoma, breast cancer tumor and prostate cancer cell line LAPC4
  • as a conjugate with D,L-lactide 75: glycolide 25 (PLGA) to analyze its bone formation functionality in distal femur
  • as an inhibitor for farnesyl diphosphate synthase enzyme in glioblastoma cells

Biochem/physiol Actions

Zoledronic acid (zoledronate) is a bisphosphonate bone resorption inhibitor, an inhibitor of farnesyl diphosphate (FPP) synthase which results in downstream inhibition of osteoclast activity and reduced bone resorption and turnover. It has been used to treat postmenopausal osteoporosis, Paget′s disease, hypercalcemia, and along with cancer chemotherapy to treat bone damage caused by cancer that has spread to the bones.

Preparation Note

This product is extremely unstable in solution and should be used shortly after reconstitution. If storage of the solution is necessary it can be held at 2-8ºC for no more than 24 hours.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Low-dose zoledronate for the treatment of bone metastasis secondary to prostate cancer
Akoury E, et al.
Cancer Cell International, 19(1), 28-28 (2019)
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Parasitology international, 66(2), 89-99 (2016-12-07)
Recent evidence suggests that 1α,25-dihydroxyvitamin D3 (calcitriol, VD3), the active form of vitamin D (VD), can inhibit the proliferation of microorganisms. In the present study, we conducted in vitro experiments and utilized in vivo murine models to investigate the antimalarial
Xu Li et al.
ACS applied materials & interfaces, 11(7), 7311-7319 (2019-01-29)
Bisphosphonates are generally used to treat bone diseases, such as bone metastasis from cancer. There is evidence that, through the modification of the pharmacokinetics and biodistribution of bisphosphonates by formulating them into nanoparticles, they may be able to treat extraskeletal
Controlled delivery of zoledronate improved bone formation locally in vivo
Gou W, et al.
PLoS ONE, 9(3), e91317-e91317 (2014)
Claudia B Colon-Echevarria et al.
Cancers, 12(9) (2020-09-24)
Multiple studies suggest that chronic stress accelerates the growth of existing tumors by activating the sympathetic nervous system. Data suggest that sustained adrenergic signaling can induce tumor growth, secretion of pro-inflammatory cytokines, and macrophage infiltration. Our goal was to study
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