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Details

Stereochemistry ACHIRAL
Molecular Formula C5H10N2O7P2.H2O
Molecular Weight 290.1049
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOLEDRONIC ACID

SMILES

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

InChI

InChIKey=FUXFIVRTGHOMSO-UHFFFAOYSA-N
InChI=1S/C5H10N2O7P2.H2O/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);1H2

HIDE SMILES / InChI

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
U.S. Food and Drug Administration drug approval summaries: imatinib mesylate, mesna tablets, and zoledronic acid.
2002
The role of bisphosphonates in breast cancer management: review article.
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
New drugs 2002, part III.
2002 Jul
Osteoporosis: challenges and new opportunities for therapy.
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
Zoledronic acid: new preparation. Just a me-too: no advance in hypercalcemia of malignancy.
2002 Oct
Intravenous zoledronic acid in postmenopausal women with low bone mineral density.
2002 Oct
The IL-6 receptor super-antagonist Sant7 enhances antiproliferative and apoptotic effects induced by dexamethasone and zoledronic acid on multiple myeloma cells.
2002 Oct
Use of zoledronate to treat osteoblastic versus osteolytic lesions in a severe-combined-immunodeficient mouse model.
2002 Oct 1
A randomized, placebo-controlled trial of zoledronic acid in patients with hormone-refractory metastatic prostate carcinoma.
2002 Oct 2
American Society of Clinical Oncology clinical practice guidelines: the role of bisphosphonates in multiple myeloma.
2002 Sep 1
[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 Mon Oct 21 20:47:05 UTC 2019
Edited
by admin
on Mon Oct 21 20:47:05 UTC 2019
Record UNII
6XC1PAD3KF
Record Status Validated (UNII)
Record Version
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Name Type Language
ZOLEDRONIC ACID
EMA EPAR   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
ZOLEDRONIC ACID MONOHYDRATE [MI]
Common Name English
CGP-42446
Code English
CGP-42446A
Code English
CGP 42446
Code English
ZOLEDRONIC ACID MONOHYDRATE [WHO-DD]
Common Name English
ZOLEDRONIC ACID TEVA
Brand Name English
ZOLEDRONIC ACID ACCORD
Brand Name English
ZOLEDRONIC ACID ACTAVIS
Brand Name English
ZOLADRONA ACID MYLAN
Brand Name English
ZOLEDRONIC ACID [EMA EPAR]
Common Name English
ZOLEDRONIC ACID [ORANGE BOOK]
Common Name English
ZOLEDRONIC [VANDF]
Common Name English
ZOLEDRONIC ACID MEDAC
Brand Name English
ZOLEDRONIC
VANDF  
Common Name English
PHOSPHONIC ACID, (1-HYDROXY-2-(1H-IMIDAZOL-1-YL)ETHYLIDENE)BIS-, MONOHYDRATE
Common Name English
ZOLEDRONIC ACID HYDRATE
JAN  
Common Name English
RECLAST
Brand Name English
ZOLEDRONIC ACID [USAN]
Common Name English
ZOMETA
Brand Name English
AK-156
Code English
ZOLEDRONIC ACID TEVA GENERICS
Brand Name English
ZOLEDRONIC ACID [VANDF]
Common Name English
ACLASTA
Brand Name English
ZOLEDRONIC ACID HYDRATE [JAN]
Common Name English
ZOLEDRONIC ACID TEVA PHARMA
Brand Name English
ZOLEDRONATE HYDRATE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 543616
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
WHO-VATC QM05BA08
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA PHARMA (AUTHORIZED: OSTEOPOROSIS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA PHARMA (AUTHORIZED: OSTEITIS DEFORMANS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
WHO-ATC M05BB08
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOMETA (AUTHORIZED: BONES, FRACTURE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
LIVERTOX 1051
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID ACCORD (AUTHORIZED: FRACTURES, BONE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ACLASTA (AUTHORIZED: OSTEITIS DEFORMANS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA GENERICS (AUTHORIZED: OSTEITIS DEFORMANS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
WHO-ATC M05BA08
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID MEDAC (AUTHORIZED: FRACTURES, BONE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA GENERICS (AUTHORIZED: OSTEOPOROSIS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
NDF-RT N0000175579
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
NCI_THESAURUS C2136
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EU-Orphan Drug Zoledronic acid
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
NCI_THESAURUS C67439
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA (AUTHORIZED: FRACTURES, BONE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ACLASTA (AUTHORIZED: OSTEOPOROSIS, MENOPAUSAL)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
FDA ORPHAN DRUG 374112
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID MYLAN (AUTHORIZED: FRACTURES, BONE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ACLASTA (AUTHORIZED: OSTEOPOROSIS)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
NCI_THESAURUS C443
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
EMA ASSESSMENT REPORTS ZOLEDRONIC ACID TEVA PHARMA (AUTHORIZED: OSTEOPOROSIS, POSTMENOPAUSAL)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
Code System Code Type Description
EMA ASSESSMENT REPORTS
ZOLEDRONIC ACID ACTAVIS (AUTHORIZED: FRACTURES, BONE)
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/002667/human_med_001722.jsp&mid=WC0b01ac058001d124
CAS
165800-06-6
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
EVMPD
SUB21645
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
RXCUI
77655
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY RxNorm
MESH
C088658
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
ChEMBL
CHEMBL924
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
IUPHAR
3177
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
EPA CompTox
165800-06-6
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
WIKIPEDIA
ZOLEDRONIC ACID
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
LactMed
165800-06-6
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
PUBCHEM
121586
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
MERCK INDEX
M11658
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C1699
Created by admin on Mon Oct 21 20:47:05 UTC 2019 , Edited by admin on Mon Oct 21 20:47:05 UTC 2019
PRIMARY
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