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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8N2O7P2.2Na.4H2O
Molecular Weight 388.1144
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOLEDRONATE DISODIUM

SMILES

O.O.O.O.[Na+].[Na+].OC(CN1C=CN=C1)(P(O)([O-])=O)P(O)([O-])=O

InChI

InChIKey=IEJZOPBVBXAOBH-UHFFFAOYSA-L
InChI=1S/C5H10N2O7P2.2Na.4H2O/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);;;4*1H2/q;2*+1;;;;/p-2

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H10N2O7P2
Molecular Weight 272.0896
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Zoledronic acid (Reclast, Aclasta, Zometa) is an intravenous, highly potent amino-bisphosphonate approved worldwide, including in the USA, EU and Japan for use in patients with primary or secondary osteoporosis or low bone mass (approved indications vary between countries). Its high affinity to and long half-life in bone, and long duration of action allow for once-yearly administration, which has the potential to improve adherence to therapy. Zoledronic acid once yearly for up to 3 years improved bone mineral density (BMD) at several skeletal sites, reduced fracture risk and bone turnover, and/or preserved bone structure and mass relative to placebo in clinical studies in patients with primary or secondary osteoporosis. While additional benefits were seen when treatment was continued for up to 6 years, as evidenced by a reduced risk of vertebral fractures and higher BMD relative to 3 years’ therapy, there was the minimal advantage of treatment beyond 6 years. Therefore, in patients with low fracture risk, treatment discontinuation should be considered after approximately 5 years’ therapy. Zoledronic acid administered annually or once in 2 years was also effective in preventing bone loss in patients with low bone mass. Zoledronic acid was generally well tolerated, with the most common adverse events (AEs) being transient, mild-to-moderate post-infusion symptoms, which decreased with subsequent infusions.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
The use of zoledronic acid, a novel, highly potent bisphosphonate, for the treatment of hypercalcemia of malignancy.
2002
The new bisphosphonate, Zometa (zoledronic acid), decreases skeletal complications in both osteolytic and osteoblastic lesions: a comparison to pamidronate.
2002
Advances in the biology and treatment of myeloma bone disease.
2002 Dec
The anti-tumour activity of bisphosphonates.
2002 Dec
Disease modifying and anti-nociceptive effects of the bisphosphonate, zoledronic acid in a model of bone cancer pain.
2002 Dec
Monosodium [1-hydroxy-2-(1H-imidazol-3-ium-4-yl)ethane-1,1-diyl]bis(phosphonate) tetrahydrate (monosodium isozoledronate).
2002 Dec
Pharmacological treatments for prostate cancer.
2002 Dec
The role of osteoclastic activity in prostate cancer skeletal metastases.
2002 Feb
The effects of local administration of Zoledronate solution on the tooth movement and periodontal ligament.
2002 Jul
Pharmacokinetics and pharmacodynamics of zoledronic acid in cancer patients with bone metastases.
2002 Nov
Severe increase in creatinine with hypocalcaemia in thalidomide-treated myeloma patients receiving zoledronic acid infusions.
2002 Nov
Pamidronate causes apoptosis of plasma cells in vivo in patients with multiple myeloma.
2002 Nov
Bisphosphonates inhibit angiogenesis in vitro and testosterone-stimulated vascular regrowth in the ventral prostate in castrated rats.
2002 Nov 15
Development and validation of a highly sensitive RIA for zoledronic acid, a new potent heterocyclic bisphosphonate, in human serum, plasma and urine.
2002 Nov 7
The use of bisphosphonates in patients with breast cancer.
2002 Nov-Dec
Bisphosphonate therapy in multiple myeloma: past, present, future.
2002 Nov-Dec
Zoledronic acid improves the mechanical properties of normal and healing bone.
2002 Nov-Dec
Zoledronic acid.
2002 Nov-Dec
Gateways to clinical trials.
2002 Oct
[Bisphosphonates in bone metastases. Fewer fractures, less pain].
2002 Sep 26
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The maximum recommended dose of Zometa in hypercalcemia of malignancy is 4 mg. The 4 mg dose must be given as a single-dose intravenous infusion over no less than 15 minutes.
Route of Administration: Intravenous
In Vitro Use Guide
For the transfection of the T24 human bladder cancer cells, pCMV6 empty vector (OriGene, Rockville, MD, USA) and pCMV6 TAp73 vector were transfected into cells using Lipofectamine™ 2000 (Invitrogen Life Technologies). After 6 h, the medium was refreshed and cultured for 48 h. Then the cells were treated with ZA (200 μM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:08:07 UTC 2019
Edited
by admin
on Tue Oct 22 00:08:07 UTC 2019
Record UNII
7D7GS1SA24
Record Status Validated (UNII)
Record Version
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Name Type Language
ZOLEDRONATE DISODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
ZOLEDRONATE DISODIUM [USAN]
Common Name English
ZOLEDRONATE DISODIUM TETRAHYDRATE
Common Name English
ZOLEDRONIC ACID DISODIUM SALT TETRAHYDRATE [MI]
Common Name English
ZOLEDRONATE DISODIUM [MART.]
Common Name English
CGP 42446A
Code English
ZOLEDRONATE DISODIUM [WHO-DD]
Common Name English
ZOLEDRONIC ACID DISODIUM SALT TETRAHYDRATE
MI  
Common Name English
DISODIUM DIHYDROGEN (1-HYDROXY-2-IMIDAZOL-1-YLETHYLIDENE)DIPHOSPHONATE, TETRAHYDRATE
Systematic Name English
ZOLEDRONATE DISODIUM HYDRATE
Common Name English
PHOSPHONIC ACID, (1-HYDROXY-2-(1H-IMIDAZOL-1-YL)ETHYLIDENE)BIS-, DISODIUM SALT TETRAHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67439
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
NCI_THESAURUS C443
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
Code System Code Type Description
EVMPD
SUB25233
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY
MERCK INDEX
M11658
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY Merck Index
CAS
165800-07-7
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY
EVMPD
SUB21669
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY
ChEMBL
CHEMBL924
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY
NCI_THESAURUS
C66703
Created by admin on Tue Oct 22 00:08:07 UTC 2019 , Edited by admin on Tue Oct 22 00:08:07 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY