Compound Detail

CHEMBL4303669

ZOLEDRONIC ACID

💊 Approved Drug

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💊 Approved Drug

O.O=P(O)(O)C(O)(Cn1ccnc1)P(=O)(O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4303669
Name	ZOLEDRONIC ACID
Phase	Approved
Structure Type	MOL
InChI Key	FUXFIVRTGHOMSO-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL924
Active Moiety	CHEMBL924

Known Names

Acide zoledronique Acido zoledronico Aclasta AK-156 CGP 42446 CGP-42446 CGP-42446A NSC-721517 Reclast Zerlinda Zoladrona acid mylan Zoledronate hydrate +13 more

Targets

104

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

272.1

MW (Da)

-1.12

ALogP

HBA

HBD

153.1

PSA (Å²)

0.43

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2001
Availability	Prescription
Chirality	Achiral

Routes of Administration

Parenteral

USAN Year

1996

Extended Properties

Molecular Formula	C5H12N2O8P2
MW	290.11
Aromatic Rings	1
Heavy Atoms	16
NP-Likeness	-0.56

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Farnesyl diphosphate synthase inhibitor	INHIBITOR	Farnesyl pyrophosphate synthase	✓	✓

Indications

Bone Diseases Fractures, Bone Hypercalcemia Multiple Myeloma Neoplasm Metastasis Neoplasm Metastasis Osteitis Deformans Osteitis Deformans Osteoporosis Osteoporosis, Postmenopausal Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Arthritis, Rheumatoid Bone Diseases, Metabolic Bone Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Hepatocellular

ATC Classification

M05BA08

zoledronic acid

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: DRUGS FOR TREATMENT OF BONE DISEASES

Activity Summary

IC50 85 meas. best 9.62

EC50 13 meas. best 6.31

Ki 6 meas. best 10.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Farnesyl pyrophosphate synthase CHEMBL1782	Ki	10.15	8.61	0.1	2
Farnesyl pyrophosphate synthase CHEMBL1782	IC50	9.62	7.5617	0.2	23
Mus musculus CHEMBL375	IC50	8.7	6.8967	2.0	3
Farnesyl pyrophosphate synthase CHEMBL2150832	Ki	8.0	8.0	10.0	1
Farnesyl pyrophosphate synthase CHEMBL3693	Ki	7.96	7.96	11.0	1
Unchecked CHEMBL612545	IC50	7.42	6.7867	38.0	6
Carbonic anhydrase 2 CHEMBL205	IC50	7.21	7.21	62.0	2
Carbonic anhydrase 14 CHEMBL3510	IC50	7.04	7.04	92.0	2
Farnesyl pyrophosphate synthase CHEMBL3693	IC50	6.96	6.96	110.0	1
Geranylgeranyl pyrophosphate synthase BTS1 CHEMBL1075251	Ki	6.58	6.58	260.0	1
Carbonic anhydrase 12 CHEMBL3242	IC50	6.5	6.5	316.0	2
Butyrophilin subfamily 3 member A1 CHEMBL4105758	EC50	6.31	5.14	486.6	4
Geranylgeranyl pyrophosphate synthase BTS1 CHEMBL1075251	IC50	6.18	6.18	660.0	1
HFF CHEMBL614071	IC50	6.1	5.35	790.0	4
Toxoplasma gondii CHEMBL612888	EC50	6.08	6.08	840.0	1
Farnesyl diphosphate synthase CHEMBL1075078	IC50	5.96	5.96	1100.0	1
Geranylgeranyl pyrophosphate synthase CHEMBL4769	Ki	5.57	5.57	2700.0	1
Dictyostelium discoideum CHEMBL612373	IC50	5.54	5.54	2900.0	1
Unchecked CHEMBL612545	EC50	5.27	5.27	5400.0	1
Carbonic anhydrase 9 CHEMBL3594	IC50	5.27	5.27	5323.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	5.19	5.0667	6400.0	3
Toxoplasma gondii CHEMBL612888	IC50	5.17	5.17	6700.0	1
72 kDa type IV collagenase CHEMBL333	IC50	5.16	5.16	7000.0	2
J774 CHEMBL614123	IC50	5.11	5.11	7800.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.07	5.07	8600.0	1
CFPAC-1 CHEMBL613506	IC50	5.0	5.0	10000.0	1
PANC-1 CHEMBL614139	IC50	5.0	5.0	10000.0	1
BXPC-3 CHEMBL614530	IC50	5.0	5.0	10000.0	1
HeLa CHEMBL399	IC50	5.0	5.0	10000.0	1
SiHa CHEMBL612542	IC50	5.0	5.0	10000.0	1
Ca-Ski CHEMBL1075403	IC50	5.0	5.0	10000.0	1
RPMI-8226 CHEMBL614882	EC50	4.96	4.96	11000.0	2
NCI-H460 CHEMBL396	IC50	4.93	4.93	11700.0	1
Entamoeba histolytica CHEMBL612853	IC50	4.92	4.92	12000.0	2
Matrix metalloproteinase-14 CHEMBL3869	IC50	4.9	4.9	12600.0	1
MIA PaCa-2 CHEMBL614725	EC50	4.87	4.87	13400.0	1
SF-268 CHEMBL613977	IC50	4.84	4.84	14300.0	1
PANC-1 CHEMBL614139	EC50	4.79	4.79	16100.0	1
Neutrophil collagenase CHEMBL4588	IC50	4.75	4.75	17600.0	1
MCF7 CHEMBL387	IC50	4.64	4.6	23000.0	2
Trypanosoma cruzi CHEMBL368	IC50	4.46	4.46	35000.0	1
LoVo CHEMBL614721	IC50	4.46	4.46	34914.0	1
Matrix metalloproteinase-9 CHEMBL321	IC50	4.28	4.28	52000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.22	4.125	60000.0	2
HCT-116 CHEMBL394	IC50	4.21	4.21	61582.0	1
Geranylgeranyl pyrophosphate synthase CHEMBL4769	IC50	4.01	4.0025	97000.0	4

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	2.2	mL.min-1.kg-1	Homo sapiens
CL	2.2	mL.min-1.kg-1	Homo sapiens
Fu	0.78	-	Homo sapiens
MRT	4.5	hr	Homo sapiens
T1/2	11.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Farnesyl pyrophosphate synthase	Ki	=	0.07	nM	10.15	Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10...	18327899
Farnesyl pyrophosphate synthase	IC50	=	0.2399	nM	9.62	Negative logarithm of inhibitory concentration against bone resorption	12825934
Farnesyl pyrophosphate synthase	IC50	=	2.0	nM	8.7	Inhibition of N-terminal His-tagged human FPPS (1 to 353 residues) expressed in ...	31577901
Mus musculus	IC50	=	2.0	nM	8.7	Inhibition of bone resorption in the calvaria assay of mouse	12166945
Farnesyl pyrophosphate synthase	IC50	=	3.0	nM	8.52	Inhibition of FDPS (unknown origin)	31699606
Farnesyl pyrophosphate synthase	IC50	=	3.0	nM	8.52	Allosteric inhibition of human recombinant FPPS using GPP and [3H]IPP as substra...	24911527
Farnesyl pyrophosphate synthase	IC50	=	3.0	nM	8.52	Inhibition of recombinant human FPPS expressed in Escherichia coli by scintillat...	21780776
Farnesyl pyrophosphate synthase	IC50	=	4.1	nM	8.39	Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10...	18327899
Farnesyl pyrophosphate synthase	IC50	=	4.1	nM	8.39	Inhibition of human FPPS expressed in Escherichia coli BL21 (DE3) preincubated f...	34236862
Farnesyl pyrophosphate synthase	IC50	=	4.1	nM	8.39	Inhibition of human recombinant N-terminal-His6 tagged FPPS expressed in Escheri...	22390415
Farnesyl pyrophosphate synthase	IC50	=	4.1	nM	8.39	Inhibition of human FPP synthase expressed in Escherichia coli BL21 (DE3)	18937434
Farnesyl pyrophosphate synthase	IC50	=	4.1	nM	8.39	Inhibition of human FPPS	25630225
Farnesyl pyrophosphate synthase	Ki	=	10.0	nM	8.0	Inhibition of recombinant Leishmania major FPPS expressed in Escherichia coli BL...	32979487
Farnesyl pyrophosphate synthase	Ki	=	11.0	nM	7.96	Binding affinity towards Farnesyl diphosphate synthase from leishmania major	15828834
Mus musculus	IC50	=	34.0	nM	7.47	In vitro inhibitory concentration against bone resorption in 17 day old fetal mo...	15828834
Unchecked	IC50	=	38.0	nM	7.42	Inhibition of Escherichia coli OPPS	17535895
Farnesyl pyrophosphate synthase	IC50	=	60.0	nM	7.22	Inhibition of recombinant human C-terminal His6-tagged FPPS expressed in Escheri...	30216851
Carbonic anhydrase 2	IC50	=	62.0	nM	7.21	Inhibition of human recombinant carbonic anhydrase 2 pretreated for 15 mins by s...	24813742
Carbonic anhydrase 2	IC50	=	62.0	nM	7.21	Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins by...	24650641
Unchecked	IC50	=	70.0	nM	7.16	Inhibition of Toxoplasma gondii FPPS incubated for 30 mins by scintillation coun...	34894691

Literature References

PubMed	DOI	Target Context	# Activities
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
33522236	10.1021/acs.jmedchem.0c01292	ADMET	12
33175535	10.1021/acs.jmedchem.0c01201	Mus musculus	10
31725297	10.1021/acs.jmedchem.9b01405	Farnesyl pyrophosphate synthase	8
12166945	10.1021/jm020819i	Rattus norvegicus	8
33175535	10.1021/acs.jmedchem.0c01201	ADMET	7
31725297	10.1021/acs.jmedchem.9b01405	PANC-1	6
30216851	10.1016/j.ejmech.2018.08.044	Bone marrow cell	6
30016091	10.1021/acs.jmedchem.8b00886	RPMI-8226	5
18937434	10.1021/jm801003y	BT-549	5
18327899	10.1021/jm7015733	Farnesyl pyrophosphate synthase	4
18426954	10.1124/dmd.108.020479	ADMET	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
24607589	10.1016/j.ejmech.2014.02.054	NON-PROTEIN TARGET	4
15857119	10.1021/jm040132t	HFF	4
30216851	10.1016/j.ejmech.2018.08.044	RAW264.7	4
29457898	10.1021/acs.jmedchem.7b01824	Butyrophilin subfamily 3 member A1	3
22390415	10.1021/jm201657x	Farnesyl pyrophosphate synthase	3
22390415	10.1021/jm201657x	NON-PROTEIN TARGET	3
31531198	10.1021/acsmedchemlett.9b00153	Butyrophilin subfamily 3 member A1	3

Data from ChEMBL 36 via Core Engine