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Details

Stereochemistry ACHIRAL
Molecular Formula C5H10N2O7P2
Molecular Weight 272.0896
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOLEDRONIC ACID ANHYDROUS

SMILES

OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O

InChI

InChIKey=XRASPMIURGNCCH-UHFFFAOYSA-N
InChI=1S/C5H10N2O7P2/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)

HIDE SMILES / InChI

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
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 use of bisphosphonates in patients with breast cancer.
2002 Nov-Dec
Bisphosphonate therapy in multiple myeloma: past, present, future.
2002 Nov-Dec
Gateways to clinical trials.
2002 Oct
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).
Name Type Language
ZOLEDRONIC ACID ANHYDROUS
Common Name English
PHOSPHONIC ACID, (1-HYDROXY-2-(1H-IMIDAZOL-1-YL)ETHYLIDENE)BIS-
Common Name English
ANHYDROUS ZOLEDRONIC ACID
Common Name English
(1-HYDROXY-2-IMIDAZOL-1-YLETHYLIDENE)DIPHOSPHONIC ACID
Systematic Name English
ZOLEDRONIC ACID [INN]
Common Name English
ZOLEDRONIC ACID [WHO-DD]
Common Name English
ZOLEDRONIC ACID [MI]
Common Name English
ZOLEDRONATE
Common Name English
Classification Tree Code System Code
NDF-RT N0000175579
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
WHO-ATC M05BA08
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
NDF-RT N0000007707
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
Code System Code Type Description
RXCUI
1546014
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY RxNorm
EPA CompTox
118072-93-8
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
INN
7254
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
MERCK INDEX
M11658
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY Merck Index
LactMed
118072-93-8
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
EVMPD
SUB00176MIG
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
CAS
118072-93-8
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
NCI_THESAURUS
C80120
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
EVMPD
SUB12624MIG
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
DRUG BANK
DB00399
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY
PUBCHEM
68740
Created by admin on Tue Mar 06 11:20:08 UTC 2018 , Edited by admin on Tue Mar 06 11:20:08 UTC 2018
PRIMARY SWITZERF