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Neridronate

Neridronate structure

CAS No:
79778-41-9
Formula:
C6H17NO7P2
Chemical Name:
Neridronate
Synonyms:
Phosphonic acid,P,P′-(6-amino-1-hydroxyhexylidene)bis-;Phosphonic acid,(6-amino-1-hydroxyhexylidene)bis-;P,P′-(6-Amino-1-hydroxyhexylidene)bis[phosphonic acid];6-Amino-1-hydroxyhexane-1,1-diphosphonic acid;6-Amino-1-hydroxyhexylidenediphosphonic acid;Neridronic acid;6-Amino-1-hydroxyhexylidene-1,1-bis(phosphonic acid);Nerixia;Neridronate;(6-Amino-1-hydroxyhexane-1,1-diyl)diphosphonic acid;437763-00-3
Categories:
Organic Chemistry > Phosphines

Description

Neridronate is an aminobisphosphonate, licensed in Italy for the treatment of osteogenesis imperfecta (OI) and Paget’s disease of bone (PDB). Neridronate is effective also in other skeletal diseases such as osteoporosis, algodystrophy, hypercalcemia of malignancy, and bone metastases[1][2].

Neridronic acid is a 1,1-bis(phosphonic acid).|Neridronic Acid is a third-generation, aminohexane bisphosphonate with anti-resorptive and anti-hypercalcemic activities. Although the exact mechanism of action has yet to be fully elucidated, neridronic acid binds to and adsorbs onto hydroxyapatite crystals in bone matrix, thereby preventing osteoclast resorption. This agent also binds to and inhibits farnesyl pyrophosphate synthase, an enzyme that plays an important role in the mevalonate pathway. This inhibits the formation of isoprenoids that are substrates for protein prenylation. This prevents farnesylation and geranylgeranylation of proteins essential for osteoclast function, thereby leading to the induction of apoptosis of osteoclasts. By preventing osteoclast-mediated bone resorption, neridronic acid decreases bone turnover rate, stabilizes the bone matrix and reduces hypercalcemia.

Neridronate Basic Attributes

Molecular Weight：

277.15

Exact Mass：

277.15

UNII：

8U27U3RIN4

NCI Thesaurus Code：

C66230

Characteristics

PSA：

161

XLogP3：

-3.36

Appearance：

white solid

Density：

1.7±0.1 g/cm3

Melting Point：

247-249 °C

Boiling Point：

600.1±65.0 °C at 760 mmHg

Flash Point：

316.7±34.3 °C

Refractive Index：

1.569

Water Solubility：

H2O: 8 mg/mL, soluble

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

Marks：

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.

Drug Information

MeSH Entry Terms：

6-AHHDP

Computed Properties

Molecular Weight:277.15
XLogP3:-5.8
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:7
Exact Mass:277.04802588
Monoisotopic Mass:277.04802588
Topological Polar Surface Area:161
Heavy Atom Count:16
Complexity:286
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes