Payload Information

General Information of This Payload
Payload ID
PAY0SVMRF
Name
Zoledronic acid
Synonyms
Zoledronic acid; 118072-93-8; Zoledronate; Zometa; Reclast; Aclasta; (1-Hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)diphosphonic acid; CGP 42446; (1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid; Zoledronic Acid Anhydrous; Orazol; C5H10N2O7P2; Anhydrous Zoledronic Acid; (1-hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic acid; Bisphosphonate 3; Phosphonic acid, [1-hydroxy-2-(1H-imidazol-1-yl)ethylidene]bis-; ZOL; CGP-42446; Zometa (Novartis); Reclast (TN); Zoledronic acid [USAN:INN]; Zoledronic-d3 Acid; Zometa (TN); Zoledronic Acid Teva; Zoledronic Acid Medac; ZOL 446; Zoledronic acid (INN); CHEMBL924; Zoledronic Acid, Anhydrous; NSC-721517; [1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl]bis(phosphonic acid); UNII-70HZ18PH24; 2-(imidazol-1-yl)-1-hydroxyethane-1,1-diphosphonic acid; BPH 91; DTXSID0042668; CHEBI:46557; [1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acid; 70HZ18PH24; Zoledronic acid [USAN:INN:BAN]; NCGC00159521-02; (1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acid; CGP 42446A; CGP-42446A; Zoledronate hydrate; Phosphonic acid, (1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bis-; Zoladrona acid mylan; ZOLEDRONIC; Zoledronic acid accord; Zoledronic Acid Actavis; ZOLEDRONIC ACID [INN]; Zoledronic Acid Teva Pharma; Zomera; 1-hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyldiphosphonic acid; (1-hydroxy-2-imidazol-1-yl-phosphonoethyl)phosphonic acid monohydrate; Aclasta and Reclast; KS-1132; [1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene]bisphosphonic acid; zoledronic-acid; Aclasta (TN); Zomera (TN); BPH 91 Orazol; CGP 42'446; CGP-42'446; Zoledronic Acid Mylan; [1-HYDROXY-2-(1H-IMIDAZOL-1-YL)-ETHYLIDENE]BISPHOSPHONIC ACID; D0VM2L; Zoledronic acid, Zoledronate; BIDD:PXR0134; SCHEMBL19054; ZOLEDRONIC ACID [MI]; BIDD:GT0292; Zoledronic Acid (Zoledronate); GTPL3177; JMC515594 Compound 55; DTXCID8022668; BDBM12578; CGP42446A; Novartis brand of zoledronic acid; ZOLEDRONIC ACID [WHO-DD]; XRASPMIURGNCCH-UHFFFAOYSA-N; 2-(imidazol-1-yl)-1-hydroxyethylidene-1,1-bisphosphonic acid; HMS2089O09; BCP22750; CGP-4244; Tox21_111739; C5-H10-N2-O7-P2; HB0674; MFCD00867791; NSC721517; s1314; STL452893; AKOS005145739; AB07564; AC-1092; CS-1829; DB00399; HS-0091; NSC 721517; NCGC00159521-03; NCGC00159521-04; NCGC00159521-05; NCGC00159521-09; NCGC00159521-18; HY-13777; LS-181815; CAS-118072-93-8; FT-0601384; Z0031; D08689; EN300-117269; H11422; S00092; AB01273947-01; AB01273947-02; AB01273947-03; AB01273947_04; A803876; Q218507; SR-05000001436; Q-201946; SR-05000001436-1; Zometa, Zomera, Aclasta and Reclast, Zoledronic Acid; 1-Hydroxy-2-(1-imidazolyl)ethane-1,1-diphosphonic Acid; Z1501485360; (1-Hydroxy-2-(1H-imidazol-1-yl)ethane-1,1-diyl)diphosphonicacid
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Target(s) Geranylgeranyl pyrophosphate synthase (GGPS1)
 Target Info 
Structure
Formula
C5H10N2O7P2
Isosmiles
C1=CN(C=N1)CC(O)(P(=O)(O)O)P(=O)(O)O
PubChem CID
68740
InChI
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)
InChIKey
XRASPMIURGNCCH-UHFFFAOYSA-N
IUPAC Name
(1-hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic acid
Pharmaceutical Properties
Molecule Weight
272.09
Polar area
153
Complexity
327
xlogp Value
-4.3
Heavy Count
16
Rot Bonds
4
Hbond acc
8
Hbond Donor
5
The activity data of This Payload
Standard Type Value Units Cell line Disease Model Cell line ID Reference
Half Maximal Cell Growth Inhibitory Concentration (GI50) 10 nM
T-47D cells
Invasive breast carcinoma
CVCL_0553 
[1]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
PANC-1 cells
Pancreatic ductal adenocarcinoma
CVCL_0480 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
HeLa cells
Endocervical adenocarcinoma
CVCL_0030 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
BxPC-3 CDX model cells
Pancreatic ductal adenocarcinoma
CVCL_0186 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
CFPAC-1 cells
Pancreatic ductal adenocarcinoma
CVCL_1119 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
SiHa cells
Cervical squamous cell carcinoma
CVCL_0032 
[2]
Half Maximal Inhibitory Concentration (IC50) 10000 nM
Ca-Ski cells
Cervical squamous cell carcinoma
CVCL_1100 
[2]
Half Maximal Effective Concentration (EC50) >100000 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[3]
Half Maximal Inhibitory Concentration (IC50) >100000 nM
MDA-MB-231 cells (5T4 overexpression)
Breast adenocarcinoma
CVCL_0062 
[4]
Half Maximal Effective Concentration (EC50) 10500 nM
RPMI-8226 cells
Plasma cell myeloma
CVCL_0014 
[5]
Half Maximal Effective Concentration (EC50) 11000 nM
RPMI-8226 cells
Plasma cell myeloma
CVCL_0014 
[6]
Half Maximal Effective Concentration (EC50) 11000 nM
RPMI-8226 cells
Plasma cell myeloma
CVCL_0014 
[7]
Half Maximal Inhibitory Concentration (IC50) 11700 nM
NCI-H460 cells
Lung large cell carcinoma
CVCL_0459 
[8]
Half Maximal Effective Concentration (EC50) 13400 nM
MIA PaCa-2 cells (MSLN expression)
Pancreatic ductal adenocarcinoma
CVCL_0428 
[9]
Half Maximal Inhibitory Concentration (IC50) 14300 nM
SF268 cells
Astrocytoma
CVCL_1689 
[8]
Half Maximal Effective Concentration (EC50) 16100 nM
PANC-1 cells
Pancreatic ductal adenocarcinoma
CVCL_0480 
[9]
Half Maximal Inhibitory Concentration (IC50) >200000 nM
Erythrocyte cells
Normal
Undisclosed [10]
Half Maximal Effective Concentration (EC50) 23000 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[3]
Half Maximal Inhibitory Concentration (IC50) 23000 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[11]
Half Maximal Inhibitory Concentration (IC50) 27700 nM
MCF7-F (fulvestrant resistant) cells
Invasive breast carcinoma
CVCL_0031 
[8]
Half Maximal Inhibitory Concentration (IC50) 34914 nM
LoVo cells
Colon adenocarcinoma
CVCL_0399 
[4]
Half Maximal Effective Concentration (EC50) 5400 nM
T-cells
Normal
Undisclosed [12]
Half Maximal Inhibitory Concentration (IC50) 595800 nM
HL-60 cells
Adult acute myeloid leukemia
CVCL_0002 
[11]
Half Maximal Inhibitory Concentration (IC50) 60000 nM
Huh-7 cells
Adult hepatocellular carcinoma
CVCL_0336 
[13]
Half Maximal Inhibitory Concentration (IC50) 61582 nM
HCT 116 cells
Colon carcinoma
CVCL_0291 
[4]
Half Maximal Inhibitory Concentration (IC50) 7800 nM
J774 cells
Mouse reticulum cell sarcoma
CVCL_4692 
[14]
Half Maximal Inhibitory Concentration (IC50) 790 nM
Human foreskin fibroblasts cells
Normal
Undisclosed [15]
Half Maximal Effective Concentration (EC50) 79000 nM
K-562 cells
Chronic myelogenous leukemia
CVCL_0004 
[3]
Half Maximal Effective Concentration (EC50) 9400 nM
JJN-3 cells
Plasma cell myeloma
CVCL_2078 
[5]
Half Maximal Effective Concentration (EC50) 63.7 uM
KB cells
Human papillomavirus-related endocervical adenocarcinoma
CVCL_0372 
[16]
Each Antibody-drug Conjugate Related to This Payload
References
Ref 1 Dual-functional abeo-taxane derivatives destabilizing microtubule equilibrium and inhibiting NF-B activation. J Med Chem. 2013 Jun 13;56(11):4749-57. doi: 10.1021/jm400479p. Epub 2013 May 31.
Ref 2 Synthesis and biological evaluation of indolylglyoxylamide bisphosphonates, antimitotic microtubule-targeting derivatives of indibulin with improved aqueous solubility. Bioorg Med Chem Lett. 2020 Dec 1;30(23):127635. doi: 10.1016/j.bmcl.2020.127635. Epub 2020 Oct 22.
Ref 3 Synthesis and Bioactivity of the Alanyl Phosphonamidate Stereoisomers Derived from a Butyrophilin Ligand. ACS Med Chem Lett. 2019 Aug 6;10(9):1284-1289. doi: 10.1021/acsmedchemlett.9b00153. eCollection 2019 Sep 12.
Ref 4 Structure-based virtual screening and biological evaluation of novel non-bisphosphonate farnesyl pyrophosphate synthase inhibitors. Eur J Med Chem. 2020 Jan 15;186:111905. doi: 10.1016/j.ejmech.2019.111905. Epub 2019 Nov 22.
Ref 5 Design and synthesis of active site inhibitors of the human farnesyl pyrophosphate synthase: apoptosis and inhibition of ERK phosphorylation in multiple myeloma cells. J Med Chem. 2012 Apr 12;55(7):3201-15. doi: 10.1021/jm201657x. Epub 2012 Mar 19.
Ref 6 Thienopyrimidine bisphosphonate (ThPBP) inhibitors of the human farnesyl pyrophosphate synthase: optimization and characterization of the mode of inhibition. J Med Chem. 2013 Oct 24;56(20):7939-50. doi: 10.1021/jm400946f. Epub 2013 Oct 3.
Ref 7 Unraveling the Prenylation-Cancer Paradox in Multiple Myeloma with Novel Geranylgeranyl Pyrophosphate Synthase (GGPPS) Inhibitors. J Med Chem. 2018 Aug 9;61(15):6904-6917. doi: 10.1021/acs.jmedchem.8b00886. Epub 2018 Jul 25.
Ref 8 Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines. J Med Chem. 2006 Sep 21;49(19):5804-14. doi: 10.1021/jm060280e.
Ref 9 Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells. J Med Chem. 2019 Dec 12;62(23):10867-10896. doi: 10.1021/acs.jmedchem.9b01405. Epub 2019 Dec 2.
Ref 10 Bisphosphonates, Old Friends of Bones and New Trends in Clinics. J Med Chem. 2021 Feb 11;64(3):1260-1282. doi: 10.1021/acs.jmedchem.0c01292. Epub 2021 Feb 1.
Ref 11 Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3475-9. doi: 10.1016/j.bmcl.2014.05.071. Epub 2014 Jun 2.
Ref 12 Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. J Med Chem. 2005 Apr 21;48(8):2957-63. doi: 10.1021/jm040209d.
Ref 13 Bisphosphonate prodrugs: synthesis and biological evaluation in HuH7 hepatocarcinoma cells. Eur J Med Chem. 2014 Apr 22;77:56-64. doi: 10.1016/j.ejmech.2014.02.054. Epub 2014 Feb 23.
Ref 14 Dual carbonic anhydrase/matrix metalloproteinase inhibitors incorporating bisphosphonic acid moieties targeting bone tumors. Bioorg Med Chem Lett. 2014 Jun 15;24(12):2617-20. doi: 10.1016/j.bmcl.2014.04.077. Epub 2014 Apr 30.
Ref 15 Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations. J Med Chem. 2005 May 5;48(9):3130-40. doi: 10.1021/jm040132t.
Ref 16 Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase. J Med Chem. 2005 Sep 22;48(19):6128-39. doi: 10.1021/jm058220g.

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