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Details

Stereochemistry ACHIRAL
Molecular Formula C6H17NO7P2
Molecular Weight 277.1492
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NERIDRONIC ACID

SMILES

NCCCCCC(O)(P(O)(O)=O)P(O)(O)=O

InChI

InChIKey=PUUSSSIBPPTKTP-UHFFFAOYSA-N
InChI=1S/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)

HIDE SMILES / InChI

Molecular Formula C6H17NO7P2
Molecular Weight 277.1492
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02972359 | https://clinicaltrials.gov/ct2/show/NCT02402530 | https://www.drugs.com/international/nerixia.html | https://www.ncbi.nlm.nih.gov/pubmed/19748562 | https://www.ncbi.nlm.nih.gov/pubmed/17574655

Neridronic acid (6-amino-1-idroxyesilidene-1,1-bisphosphonate) is a nitrogen-containing bisphosphonate licensed in Italy for the treatment of osteogenesis imperfecta and Paget’s disease of bone. The pharmacodynamic profile is similar to that of other nitrogen-containing bisphosphonates and is characterized by its high affinity for bone tissue particularly at sites undergoing a process of remodeling. In growing children affected by osteogenesis imperfect, neridronic acid rapidly increases bone mineral density as measured by dual X-ray absorptiometry and this is associated with a significant decrease in fracture cumulative number. Similar results have been obtained also in newborns (<12-month-old) and in adult patients. In Paget’s disease of bone, 200 mg intravenous neridronic acid is associated with a 65% rate of full remission and a biochemical response (decrease of > 75% of bone turnover markers) in 95% of the patients. Neridronic acid treatment has been reported to be effective also in other skeletal diseases such as osteoporosis, algodystrophy, hypercalcemia of malignancy and bone metastasis. Neridronic acid has been developed only for parenteral use, and it is the only one used as the intramuscular injection. This avoids all the limitations of oral bisphosphonates and may be offered for a home treatment with simple nursing assistants

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nerixia

Approved Use

Unknown
Primary
Nerixia

Approved Use

Unknown
Primary
Nerixia

Approved Use

Unknown
Primary
Nerixia

Approved Use

Unknown
Primary
Nerixia

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Intravenous bisphosphonate therapy increases radial width in adults with osteogenesis imperfecta.
2005 Aug
[Modifications of markers of bone resorption in patients affected by glucocorticoid induced osteoporosis (GIOP) treated with neridronate].
2006 Jan
Study of pepsin phosphorylation using immobilized metal affinity chromatography.
2008 Jun
Intramuscular neridronate in postmenopausal women with low bone mineral density.
2008 Nov
Patents

Sample Use Guides

Neridronic acid is licensed in Italy for the treatment of Paget’s disease at the dose of 100 mg dissolved in 250 ml of saline solution given i.v. for 2 consecutive days. Neridronic acid 25 mg i.m. monthly is also effective in fully preventing the changes in bone turnover markers and BMD associated with androgen deprivation therapy for prostatic cancer
Route of Administration: Other
MDA-MB-231, U87-MG and Caco2 cells were used for activity evaluation. Cells were seeded at a density of 10^4 cells per well in 96-well flat-bottom plates (Falcon, Strasbourg, France) and incubated in completed culture medium for 24 h. Then, medium was removed and replaced by 10% FCS-medium containing increasing concentrations of neridronate from 16 nkM to 1 mM and varying concentration of liposomal suspension containing neridronate from 0.27 mkM to 17.56 mkM. After 72 h incubation (free neridronate) or 24 h, 48 h and 72 h incubation (liposomal neridronate), cells were washed with phosphate buffered saline (PBS, Life Technologies) and incubated with 0.1 ml of MTT (2 mg/ml, Sigma–Aldrich) for additional 4 h at 37 C. The insoluble product was then dissolved by addition of 100 mkl of DMSO (Sigma–Aldrich). The absorbance corresponding to the solubilized formazan pellet (which reflects the relative viable cell number) was measured at 570 nm using a Labsystems Multiskan MS microplate reader. Dose–response curves were obtained for free and liposomal neridronate concentrations, allowing the determination of EC50 values, which refer to the concentration inducing a response halfway between the baseline and the maximum plateau reached.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:39:05 GMT 2023
Edited
by admin
on Fri Dec 15 16:39:05 GMT 2023
Record UNII
8U27U3RIN4
Record Status Validated (UNII)
Record Version
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Name Type Language
NERIDRONIC ACID
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NERIDRONIC ACID [MI]
Common Name English
NERIDRONATE
Common Name English
Neridronic acid [WHO-DD]
Common Name English
AHHEXBP
Common Name English
(6-AMINO-1-HYDROXYHEXYLIDENE)DIPHOSPHONIC ACID
Systematic Name English
NERIDRONIC ACID [MART.]
Common Name English
neridronic acid [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 372412
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
NCI_THESAURUS C67439
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
NCI_THESAURUS C443
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID40868545
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
INN
6463
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL55214
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
NCI_THESAURUS
C66230
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
MERCK INDEX
m7828
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB11620
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
FDA UNII
8U27U3RIN4
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
DRUG CENTRAL
3377
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
SMS_ID
100000084177
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
PUBCHEM
71237
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
CAS
79778-41-9
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
WIKIPEDIA
Neridronic acid
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
EVMPD
SUB09205MIG
Created by admin on Fri Dec 15 16:39:05 GMT 2023 , Edited by admin on Fri Dec 15 16:39:05 GMT 2023
PRIMARY
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