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SML0223

Sigma-Aldrich

Zoledronic acid monohydrate

≥98% (HPLC)

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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
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

Quality Level

100

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

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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Anti-cancer effects of nitrogen-containing bisphosphonates on human cancer cells
Jiang P, et al.
Testing, 7(36), 57932-57932 (2016)
David John Garnett
Journal of cancer research and clinical oncology, 142(3), 611-618 (2015-11-18)
Mevalonate pathway inhibitors are potentially useful chemotherapeutic agents showing growth inhibition and pro-apoptotic effects in cancer cells. The effects of statins and bisphosphonates on cancer growth are attributed to a reduction in protein isoprenylation. Post-translational modification and activation of GTPase
Farnesyl diphosphate synthase is important for the maintenance of glioblastoma stemness
Kim HY, et al.
Experimental & Molecular Medicine, 50(10), 137-137 (2018)
Wei Lei et al.
Scientific reports, 10(1), 7004-7004 (2020-04-26)
The most challenging issue for breast cancer (BC) patients is metastasis to other organs because current therapies do not prevent or eliminate metastatic BC. Here, we show that SM-164, a small molecule inhibitor, which degrades inhibitor of apoptosis proteins (IAPs)
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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