79778-41-9

Basic information

• Product Name: NERIDRONATE SODIUM HYDRATE
• Synonyms: 6-AMINO-1-HYDROXYHEXYLIDENE BISPHOSPHONIC ACID;NERIXIA;NERIDRONATE;NERIDRONATE SODIUM HYDRATE;NERIDRONIC ACID;6-amino-1-hydroxyhexane-1,1-diphosphonate;Neridronic;6-Amino-1-hydroxyhexylidene bisphosphonic acid, Neridronic acid, Nerixia
• CAS NO: 79778-41-9
• Molecular Formula: C₆H₁₇NO₇P₂
• Molecular Weight: 277.15
• EINECS: 200-258-5
• Mol File: 79778-41-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 245°
• Boiling Point: 600.1 °C at 760 mmHg
• Flash Point: 316.7 °C
• Appearance: white/solid
• Density: 1.658 g/cm³
• Vapor Pressure: 6.66E-17mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• Solubility: H2O: 8 mg/mL, soluble
• PKA: 1.93±0.10(Predicted)
• CAS DataBase Reference: NERIDRONATE SODIUM HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: NERIDRONATE SODIUM HYDRATE(79778-41-9)
• EPA Substance Registry System: NERIDRONATE SODIUM HYDRATE(79778-41-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 79778-41-9(Hazardous Substances Data)

Usage

Description

Neridronic acid, also known as NERIDRONATE SODIUM HYDRATE, is an amino bisphosphonate that inhibits bone resorption and increases bone mineral density. It is structurally related to the second generation of bisphosphonates and can be synthesized by treating E-aminocaproic acid with phosphoric acid and phosphorous trichloride. Neridronic acid is used for the treatment of osteogenesis imperfecta, an "orphan disease" characterized by bone fragility, frequent fractures, and bone deformation.

Uses

Used in Pharmaceutical Industry:
NERIDRONATE SODIUM HYDRATE is used as a drug for the treatment of osteogenesis imperfecta, a condition characterized by bone fragility and frequent fractures. It is the first drug launched worldwide for this "orphan disease" and has been shown to increase bone mass in young growing individuals and improve bone mineral density in adults.
Used in Osteoporosis Treatment:
NERIDRONATE SODIUM HYDRATE is used as an anti-resorptive agent for the treatment of osteoporosis, a condition characterized by reduced bone mineral density and increased risk of fractures. It inhibits the activity of osteoclasts and promotes their death, leading to a decrease in bone resorption and an increase in bone mineral density.
Used in Cancer Therapy:
NERIDRONATE SODIUM HYDRATE is used as an inhibitor of farnesyl pyrophosphate (FPP) synthase, an enzyme involved in the mevalonate pathway. It has been shown to decrease the differentiation of RAW 264.7 cells into osteoclasts in a co-culture model of osteoclastogenesis and inhibit FGF2-induced proliferation and tube formation in human umbilical vein endothelial cells (HUVECs), suggesting potential applications in cancer therapy.
Brand Name: Nerixia

Originator

lnstituto Gentili (Italy)

Biochem/physiol Actions

Neridronate is a bone resorption inhibitor. It is used to treat Osteogenesis Imperfecta, an "orphan disease" characterized by a fragility of the bone enough to be named the "illness of bones of crystal".

Synthesis

6- Aminohexanoic acid (152) was reacted with phosphorus trichloride and phosphorous acid at 85°C, and then water was added to generate free diphosphonic acid 16 in 78% overall yield [59].

InChI:InChI=1/C6H17NO7P2/c7-5-3-1-2-4-6(8,15(9,10)11)16(12,13)14/h8H,1-5,7H2,(H2,9,10,11)(H2,12,13,14)

Upstream product

• 60-32-2 6-aminohexanoic acid 
• 948317-80-4 [6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-hydroxy-1-phosphonohexyl]phosphonic acid 
• 4443-26-9 6-phthalimidohexanoic acid 
• 31968-60-2 6-phthalimidohexanoyl chloride 
• 10294-56-1 phosphorous acid 

Relevant articles and documents

Biocompatible organic coatings based on bisphosphonic acid RGD‐derivatives for PEO‐modified titanium implants

Currently, significant attention is attracted to the problem of the development of the specific architecture and composition of the surface layer in order to control the biocompatibility of implants made of titanium and its alloys. The titanium surface properties can be tuned both by creating an inorganic sublayer with the desired morphology and by organic top coating contributing to bioactivity. In this work, we developed a composite biologically active coatings based on hybrid molecules obtained by chemical crosslinking of amino acid bisphosphonates with a linear tripeptide RGD, in combination with inorganic porous sublayer created on titanium by plasma electrolytic oxidation (PEO). After the addition of organic molecules, the PEO coated surface gets nobler, but corrosion currents increase. In vitro studies on proliferation and viability of fibroblasts, mesenchymal stem cells and osteoblastlike cells showed the significant dependence of the molecule bioactivity on the structure of bisphosphonate anchor and the linker. Several RGDmodified bisphosphonates of β–alanine, γ–aminobutyric and ε–aminocaproic acids with BMPS or SMCC linkers can be recommended as promising candidates for further in vivo research.

Microwave-assisted efficient synthesis of bisphosphonate libraries: A useful procedure for the preparation of bisphosphonates containing nitrogen and sulfur

Microwave-assisted rapid and efficient procedure for the synthesis of bisphosphonate and their libraries is described in solvent-free medium. Bisphosphonates having nitrogen and sulfur are synthesized following this new procedure. This procedure is simple and can be useful for the generation of compound libraries of a class of bone-resorptive inhibitors such as N- and N-, S- containing bisphosphonates.

Process for producing biphosphonic acids and forms thereof

Disclosed herein is a process for producing bisphosphonic acids and salts thereof. The process comprising reacting a carboxylic acid of Formula [I] with phosphorous acid and halophosphorus compound in the presence of a solvent selected from aliphatic hydrocarbon or water miscible cyclic ether. Further, the present invention also provides novel forms of bisphosphonic acids and process for preparation thereof.