ChemFOnt: Showing chemical card for Zoledronate (CFc000008910)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:53 UTC

Chemfont ID

CFc000008910

Molecule Identification

Common Name

Zoledronate

Definition

Zoledronate (zoledronic acid, marketed by Novartis under the trade names Zometa and Reclast) is a bisphosphonate. Zometa is used to prevent skeletal fractures in patients with cancers such as multiple myeloma and prostate cancer. It can also be used to treat hypercalcemia of malignancy and can be helpful for treating pain from bone metastases. An annual dose of Zoledronate may also prevent recurring fractures in patients with a previous hip fracture. Zoledronate is a single 5 mg infusion for the treatment of Paget's disease of bone. In 2007, the FDA also approved Reclast for the treatment of postmenopausal osteoporosis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acid	ChEBI
(1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid	ChEBI
Reclast	ChEBI
ZOL	ChEBI
Zometa	Kegg
(1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonate	Generator
(1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonate	Generator
Zoledronic acid	Generator
2-(Imidazol-1-yl)-1-hydroxyethylidene-1,1-bisphosphonic acid	HMDB
Novartis brand OF zoledronic acid	HMDB
Zoledronic acid anhydrous	HMDB

Chemical Formula

C₅H₁₀N₂O₇P₂

Average Molecular Weight

272.0896

Monoisotopic Molecular Weight

271.996323708

IUPAC Name

[1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acid

Traditional Name

zoledronate

CAS Registry Number

118072-93-8

SMILES

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

InChI Identifier

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)

InChI Key

XRASPMIURGNCCH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Bisphosphonates

Direct Parent

Bisphosphonates

Alternative Parents

Substituents

Bisphosphonate
N-substituted imidazole
Heteroaromatic compound
Organophosphonic acid
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:46557 )
1,1-bis(phosphonic acid) (CHEBI:46557 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014543)
Membrane (HMDB: HMDB0014543)

Source

Exogenous

Exogenous (HMDB: HMDB0014543)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Zoledronate Pathway (HMDB: HMDB0014543)
Zoledronate Action Pathway (PathBank: SMP0000107)

Role

Industrial application

Bone density conservation agent (HMDB: HMDB0014543)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.27 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-3.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	6.67	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.16 m³·mol⁻¹	ChemAxon
Polarizability	20.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon