Zoledronic acid

Identification

Summary

Zoledronic acid is a bisphosphonate used to treat malignancy associated hypercalcemia, multiple myeloma, and bone metastasis from solid tumors.

Brand Names
Aclasta, Reclast, Zometa
Generic Name
Zoledronic acid
DrugBank Accession Number
DB00399
Background

Zoledronic acid, or CGP 42'446,8 is a third generation, nitrogen containing bisphosphonate similar to ibandronic acid, minodronic acid, and risedronic acid.5 Zoledronic acid is used to treat and prevent multiple forms of osteoporosis, hypercalcemia of malignancy, multiple myeloma, bone metastases from solid tumors, and Paget’s disease of bone.14,15,16 Zoledronic acid was first described in the literature in 1994.8

Zoledronic acid was granted FDA approval on 20 August 2001.14

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 272.0896
Monoisotopic: 271.996323708
Chemical Formula
C5H10N2O7P2
Synonyms
  • (1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acid
  • (1-hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid
  • ácido zoledrónico
  • Anhydrous Zoledronic Acid
  • Nanoparticles containing Zoledronic acid
  • Zol
  • Zoledronate
  • Zoledronic acid
  • Zoledronic Acid Anhydrous
  • Zoledronic Acid, Anhydrous
External IDs
  • CGP 42446
  • CGP-42446

Pharmacology

Indication

Zoledronic acid is indicated to treat hypercalcemia of malignancy, multiple myeloma, bone metastases from solid tumors, osteoporosis in men and postmenopausal women, glucocorticoid induced osteoporosis, and Paget's disease of bone in men and women.14,15,16 Zoledronic acid is also indicated for the prevention of osteoporosis in post menopausal women and glucocorticoid induced osteoporosis.14,15,16

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used as adjunct in combination to treatBone metastases•••••••••••••••••••••
Treatment ofHypercalcemia of malignancy•••••••••••••••••••••
Used as adjunct in combination to treatMultiple myeloma (mm)•••••••••••••••••••••
Treatment ofOsteoporosis•••••••••••••••••••••••••• ••••••••••••••• ••••••••• ••••••••
Prevention ofOsteoporosis•••••••••••••••••••••••••••••••• ••••••••• ••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Zoledronic acid is a third generation, nitrogen containing bisphosphonate that inhibits osteoclast function and prevents bone resorption.5 The therapeutic window is wide as patients are unlikely to suffer severe effects from overdoses and the duration of action is long.14,15,16 Patients should be counselled regarding the risk of electrolyte deficiencies, renal impairment, osteonecrosis of the jaw, atypical femoral fractures, bronchoconstriction, hepatic impairment, hypocalcemia, and embryo-fetal toxicity.14,15,16

Mechanism of action

Bisphosphonates are taken into the bone where they bind to hydroxyapatite. Bone resorption by osteoclasts causes local acidification, releasing the bisphosphonate, which is taken into the osteoclast by fluid-phase endocytosis.6 Endocytic vesicles become acidified, releasing bisphosphonates into the cytosol of osteoclasts where they act.6

Osteoclasts mediate resorption of bone.7 When osteoclasts bind to bone they form podosomes, ring structures of F-actin.7 Etidronic acid also inhibits V-ATPases in the osteoclast, though the exact subunits are unknown, preventing F-actin from forming podosomes.12,13,11 Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption.7

Nitrogen containing bisphosphonates such as zoledronate are known to induce apoptosis of hematopoietic tumor cells by inhibiting the components of the mevalonate pathway farnesyl diphosphate synthase, farnesyl diphosphate, and geranylgeranyl diphosphate.10,9 These components are essential for post-translational prenylation of GTP-binding proteins like Rap1.10,9 The lack of prenylation of these proteins interferes with their function, and in the case of Rap1, leads to apoptosis.10,9 zoledronate also activated caspases which further contribute to apoptosis.10,9

TargetActionsOrganism
AGeranylgeranyl pyrophosphate synthase
inhibitor
Humans
AHydroxylapatite
antagonist
binder
Humans
AFarnesyl pyrophosphate synthase
inhibitor
Humans
Absorption

A 4mg intravenous dose reaches a Cmax of 370±78.5ng/mL, with a Tmax of 0.317±0.014h, and an AUC of 788±181ng*h/mL.4 A 5mg intravenous dose reaches a Cmax of 471±76.1ng/mL, with a Tmax of 0.368±0.005h, and an AUC of 917±226ng*h/mL.4

Volume of distribution

Not Available

Protein binding

Zoledronic acid is 23-53% protein bound in plasma.14,15,16

Metabolism

Zoledronic acid is not metabolized in vivio.14,15,16

Route of elimination

Zoledronic acid is 39 ± 16% eliminated in the urine as the unmetabolized parent drug.14,15,16

Half-life

Zoledronic acid has a terminal elimination half life of 146 hours.14,15,16

Clearance

Zoledronic acid has a renal clearance of 3.7 ± 2.0 L/h.14,15,16

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with renal impairment, hypocalcemia, hypophosphatemia, and hypomagnesemia.14,15,16 Overdose should be managed through intravenous administration of the insufficient ions.14,15,16

Pathways
PathwayCategory
Zoledronate Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Aceclofenac is combined with Zoledronic acid.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Acemetacin is combined with Zoledronic acid.
Acetylsalicylic acidThe risk or severity of gastrointestinal bleeding can be increased when Acetylsalicylic acid is combined with Zoledronic acid.
AcyclovirThe risk or severity of nephrotoxicity and hypocalcemia can be increased when Acyclovir is combined with Zoledronic acid.
Adefovir dipivoxilThe risk or severity of nephrotoxicity and hypocalcemia can be increased when Adefovir dipivoxil is combined with Zoledronic acid.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Zoledronate D,L-Lysine MonohydrateNot AvailableNot AvailableNot applicable
Zoledronate disodium7D7GS1SA24165800-07-7IEJZOPBVBXAOBH-UHFFFAOYSA-L
Zoledronate trisodiumARL915IH66165800-08-8HYMYRPXSMHJPGD-UHFFFAOYSA-A
Zoledronic acid hemipentahydrate1K9U67HDIDNot AvailableAZZILOGHCMYHQY-UHFFFAOYSA-N
Zoledronic acid monohydrate6XC1PAD3KF165800-06-6FUXFIVRTGHOMSO-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AclastaInjection, solution5 mg/100mlIntravenousSandoz Pharmaceuticals D.D.2016-09-07Not applicableEU flag
AclastaInjection, solution5 mg/100mlIntravenousSandoz Pharmaceuticals D.D.2016-09-07Not applicableEU flag
AclastaSolution5 mg / 100 mLIntravenousSandoz Canada Incorporated2005-08-22Not applicableCanada flag
Act Zoledronic AcidSolution5 mg / 100 mLIntravenousActavis Pharma CompanyNot applicableNot applicableCanada flag
Act Zoledronic Acid ConcentrateSolution4 mg / 5 mLIntravenousActavis Pharma CompanyNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Jamp-zoledronic AcidSolution4 mg / 5 mLIntravenousJamp Pharma Corporation2020-01-20Not applicableCanada flag
PMS-zoledronic AcidSolution4 mg / 5 mLIntravenousPharmascience Inc2014-11-25Not applicableCanada flag
Taro-zoledronic AcidSolution5 mg / 100 mLIntravenousTaro Pharmaceuticals, Inc.2014-04-02Not applicableCanada flag
Taro-zoledronic Acid ConcentrateSolution4 mg / 5 mLIntravenousTaro Pharmaceuticals, Inc.2014-02-26Not applicableCanada flag
Val-zoledronic AcidSolution4 mg / 5 mLIntravenousBausch Health, Canada Inc.Not applicableNot applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ZOLDRIA 4 MG/5 ML IV INFUZYON ICIN KONSANTRE COZELTI ICEREN FLAKON, 1 ADETZoledronic acid monohydrate (4 mg/5ml)Injection, solution, concentrateIntravenousPHARMADA İLAÇ SAN. VE TİC. A.Ş.2018-07-312024-01-23Turkey flag

Categories

ATC Codes
M05BB08 — Zoledronic acid, calcium and colecalciferol, sequentialM05BA08 — Zoledronic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
N-substituted imidazoles / Organic phosphonic acids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteromonocyclic compound / Azacycle / Azole / Bisphosphonate / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / N-substituted imidazole / Organic nitrogen compound / Organic oxide
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, 1,1-bis(phosphonic acid) (CHEBI:46557)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
70HZ18PH24
CAS number
118072-93-8
InChI Key
XRASPMIURGNCCH-UHFFFAOYSA-N
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)
IUPAC Name
[1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acid
SMILES
OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O

References

Synthesis Reference

Judith Aronhime, Revital Lifshitz-Liron, "Zoledronic acid crystal forms, zoledronate sodium salt crystal forms, amorphous zoledronate sodium salt, and processes for their preparation." U.S. Patent US20050054616, issued March 10, 2005.

US20050054616
General References
  1. Lyles KW, Colon-Emeric CS, Magaziner JS, Adachi JD, Pieper CF, Mautalen C, Hyldstrup L, Recknor C, Nordsletten L, Moore KA, Lavecchia C, Zhang J, Mesenbrink P, Hodgson PK, Abrams K, Orloff JJ, Horowitz Z, Eriksen EF, Boonen S: Zoledronic acid and clinical fractures and mortality after hip fracture. N Engl J Med. 2007 Nov 1;357(18):1799-809. Epub 2007 Sep 17. [Article]
  2. Reid IR, Brown JP, Burckhardt P, Horowitz Z, Richardson P, Trechsel U, Widmer A, Devogelaer JP, Kaufman JM, Jaeger P, Body JJ, Brandi ML, Broell J, Di Micco R, Genazzani AR, Felsenberg D, Happ J, Hooper MJ, Ittner J, Leb G, Mallmin H, Murray T, Ortolani S, Rubinacci A, Saaf M, Samsioe G, Verbruggen L, Meunier PJ: Intravenous zoledronic acid in postmenopausal women with low bone mineral density. N Engl J Med. 2002 Feb 28;346(9):653-61. [Article]
  3. Durie BG, Katz M, Crowley J: Osteonecrosis of the jaw and bisphosphonates. N Engl J Med. 2005 Jul 7;353(1):99-102; discussion 99-102. [Article]
  4. Shiraki M, Tanaka S, Suzuki H, Ueda S, Nakamura T: Safety, pharmacokinetics, and changes in bone metabolism associated with zoledronic acid treatment in Japanese patients with primary osteoporosis. J Bone Miner Metab. 2017 Nov;35(6):675-684. doi: 10.1007/s00774-016-0806-3. Epub 2016 Dec 20. [Article]
  5. Cremers S, Drake MT, Ebetino FH, Bilezikian JP, Russell RGG: Pharmacology of bisphosphonates. Br J Clin Pharmacol. 2019 Jun;85(6):1052-1062. doi: 10.1111/bcp.13867. Epub 2019 Feb 28. [Article]
  6. Russell RG, Watts NB, Ebetino FH, Rogers MJ: Mechanisms of action of bisphosphonates: similarities and differences and their potential influence on clinical efficacy. Osteoporos Int. 2008 Jun;19(6):733-59. doi: 10.1007/s00198-007-0540-8. [Article]
  7. Murakami H, Takahashi N, Tanaka S, Nakamura I, Udagawa N, Nakajo S, Nakaya K, Abe M, Yuda Y, Konno F, Barbier A, Suda T: Tiludronate inhibits protein tyrosine phosphatase activity in osteoclasts. Bone. 1997 May;20(5):399-404. [Article]
  8. Green JR, Muller K, Jaeggi KA: Preclinical pharmacology of CGP 42'446, a new, potent, heterocyclic bisphosphonate compound. J Bone Miner Res. 1994 May;9(5):745-51. doi: 10.1002/jbmr.5650090521. [Article]
  9. Ullen A, Schwarz S, Lennartsson L, Kalkner KM, Sandstrom P, Costa F, Lennernas B, Linder S, Nilsson S: Zoledronic acid induces caspase-dependent apoptosis in renal cancer cell lines. Scand J Urol Nephrol. 2009;43(2):98-103. doi: 10.1080/00365590802475904. [Article]
  10. Miwa A, Takezako N, Hayakawa H, Hayakawa M, Tominaga S, Yanagisawa K: YM-175 induces apoptosis of human native monocyte-lineage cells via inhibition of prenylation. Am J Hematol. 2012 Dec;87(12):1084-8. doi: 10.1002/ajh.23328. Epub 2012 Oct 9. [Article]
  11. Russell RG: Bisphosphonates: the first 40 years. Bone. 2011 Jul;49(1):2-19. doi: 10.1016/j.bone.2011.04.022. Epub 2011 May 1. [Article]
  12. Qin A, Cheng TS, Pavlos NJ, Lin Z, Dai KR, Zheng MH: V-ATPases in osteoclasts: structure, function and potential inhibitors of bone resorption. Int J Biochem Cell Biol. 2012 Sep;44(9):1422-35. doi: 10.1016/j.biocel.2012.05.014. Epub 2012 May 29. [Article]
  13. Duan X, Yang S, Zhang L, Yang T: V-ATPases and osteoclasts: ambiguous future of V-ATPases inhibitors in osteoporosis. Theranostics. 2018 Oct 26;8(19):5379-5399. doi: 10.7150/thno.28391. eCollection 2018. [Article]
  14. FDA Approved Drug Products: Zometa Zoledronic Acid Intravenous Injection [Link]
  15. FDA Approved Drug Products: Reclast Zoledronic Acid Intravenous Injection [Link]
  16. FDA Approved Drug Products: Reclast Zoledronic Acid Injection [Link]
Human Metabolome Database
HMDB0014543
KEGG Drug
D01968
PubChem Compound
68740
PubChem Substance
46507310
ChemSpider
61986
BindingDB
12578
RxNav
1546014
ChEBI
46557
ChEMBL
CHEMBL924
ZINC
ZINC000003803652
Therapeutic Targets Database
DAP001539
PharmGKB
PA10235
PDBe Ligand
ZOL
RxList
RxList Drug Page
Wikipedia
Zoledronic_acid
PDB Entries
1zw5 / 2e91 / 2f8c / 2f8z / 2f9k / 2q58 / 3ez3 / 3iba / 3ldw / 3n45
show 10 more
MSDS
Download (57.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionBariatric Surgery Candidates / Bone Loss1
4Active Not RecruitingTreatmentOsteoporosis / Sarcopenia1
4Active Not RecruitingTreatmentStage I Breast Cancer1
4CompletedPreventionBariatric Surgery Candidates1
4CompletedPreventionBone Fractures / Liver Transplantation / Osteoporosis1

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
Packagers
  • Novartis AG
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous4 mg
Powder, for solutionParenteral4 MG
Injection, solution, concentrateIntravenous; Parenteral4 MG/5ML
Injection, solution
Solution5 mg/100ml
Injection, solutionIntravenous; Parenteral5 MG/100ML
Injection, solutionParenteral5 MG
SolutionIntravenous5 mg / 100 mL
SolutionParenteral5 MG
SolutionParenteral5 MG/100ML
SolutionIntravenous5 mg
SolutionIntravenous0.8 mg/ml
SolutionParenteral4 MG/100ML
SolutionParenteral4 MG/5ML
SolutionParenteral4 MG
InjectionIntravenous
Solution0.8000 mg
SolutionIntravenous4.000 mg
Solution, concentrateIntravenous4 mg
SolutionIntravenous4.625 mg
Injection, solution, concentrateIntravenous5 mg/100ml
SolutionIntravenous4.265 mg
SolutionIntravenous4.264 mg
SolutionIntravenous5.33 mg
SolutionParenteral4.000 mg
SolutionIntravenous0.8528 mg
SolutionIntravenous
SolutionIntravenous0.800 mg
Solution
SolutionIntravenous5.000 mg
SolutionIntravenous4 mg / 5 mL
SolutionIntravenous4.26 mg
SolutionIntravenous0.04 mg
SolutionIntravenous4 mg
Injection, solution, concentrateIntravenous4.00 mg/5ml
SolutionIntravenous4.00 mg
Injection, solution, concentrateIntravenous4 mg
Injection, powder, lyophilized, for solutionIntravenous; Parenteral4 mg
InjectionIntravenous4 mg/5mL
InjectionIntravenous4 mg/100mL
InjectionIntravenous5 mg/100mL
Injection, solutionIntravenous0.04 mg/1mL
Injection, solutionIntravenous0.05 mg/1mL
Injection, solutionIntravenous4 mg/100mL
Injection, solutionIntravenous5 mg/100mL
Injection, solution, concentrateIntravenous0.8 mg/1mL
Injection, solution, concentrateIntravenous4 mg/5mL
KitIntravenous4 mg/5mL
SolutionIntravenous4 mg/100mL
SolutionIntravenous5 mg/100mL
InjectionIntravenous4 mg
Injection, solutionIntravenous5 mg
SolutionParenteral
Injection, solution, concentrateIntravenous
SolutionIntravenous4 mg/5ml
Injection, powder, for solutionIntravenous4 mg
Injection, solution, concentrateIntravenous4 mg/100mL
Powder, for solutionIntravenous4 MG
SolutionParenteral
Solution4 mg/100ml
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous4.0 mg/5ml
Powder, for solutionIntravenous4 mg / vial
Injection, solution4 mg/100ml
Injection, solution5 mg/100ml
Injection, solutionIntravenous4 mg/5ml
Solution4 mg/5ml
Prices
Unit descriptionCostUnit
Zometa 4 mg/5ml Concentrate 5ml Vial1095.69USD vial
Reclast 5 mg/100ml Solution13.39USD ml
Reclast 5 mg/100 ml solution12.88USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US4939130No1990-07-032013-03-02US flag
CA1338937No1997-02-252014-02-25Canada flag
CA1338895No1997-02-042014-02-04Canada flag
US8324189Yes2012-12-042025-11-29US flag
US7932241Yes2011-04-262028-08-05US flag
US8052987No2011-11-082023-10-27US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySparingly solubleFDA Label
Predicted Properties
PropertyValueSource
Water Solubility3.27 mg/mLALOGPS
logP-0.93ALOGPS
logP-3.9Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.66Chemaxon
pKa (Strongest Basic)6.67Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area153.11 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity52.16 m3·mol-1Chemaxon
Polarizability20.1 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9723
Blood Brain Barrier+0.825
Caco-2 permeable-0.6418
P-glycoprotein substrateNon-substrate0.5602
P-glycoprotein inhibitor INon-inhibitor0.943
P-glycoprotein inhibitor IINon-inhibitor0.9961
Renal organic cation transporterNon-inhibitor0.9366
CYP450 2C9 substrateNon-substrate0.8319
CYP450 2D6 substrateNon-substrate0.8201
CYP450 3A4 substrateNon-substrate0.7551
CYP450 1A2 substrateNon-inhibitor0.8531
CYP450 2C9 inhibitorNon-inhibitor0.8576
CYP450 2D6 inhibitorNon-inhibitor0.8935
CYP450 2C19 inhibitorNon-inhibitor0.8319
CYP450 3A4 inhibitorNon-inhibitor0.9334
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9904
Ames testNon AMES toxic0.5596
CarcinogenicityNon-carcinogens0.8194
BiodegradationNot ready biodegradable0.5431
Rat acute toxicity2.3342 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8515
hERG inhibition (predictor II)Non-inhibitor0.8616
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-9120000000-239c3921d9c0513b29bf
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSsplash10-000i-0910000000-6c7cee1b60ea3968e2f7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0590000000-85effe1f71ec78e3a35a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0090000000-dacd042b8005d501192f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ik9-9040000000-5ce349a866c3aab5f030
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0390000000-4e5df6b1956046fc3bd7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-9110000000-babdbc8ddf70f2f270ea
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-9000000000-a7132f68d8c2aaa59953
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.2670571
predicted
DarkChem Lite v0.1.0
[M-H]-155.5622571
predicted
DarkChem Lite v0.1.0
[M-H]-138.84532
predicted
DeepCCS 1.0 (2019)
[M+H]+156.1771571
predicted
DarkChem Lite v0.1.0
[M+H]+155.1736571
predicted
DarkChem Lite v0.1.0
[M+H]+141.24092
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.9639571
predicted
DarkChem Lite v0.1.0
[M+Na]+154.4681571
predicted
DarkChem Lite v0.1.0
[M+Na]+147.15344
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name
GGPS1
Uniprot ID
O95749
Uniprot Name
Geranylgeranyl pyrophosphate synthase
Molecular Weight
34870.625 Da
References
  1. Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH: Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. Proc Natl Acad Sci U S A. 2007 Jun 12;104(24):10022-7. Epub 2007 May 29. [Article]
Kind
Small molecule
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Binder
References
  1. Jahnke W, Henry C: An in vitro assay to measure targeted drug delivery to bone mineral. ChemMedChem. 2010 May 3;5(5):770-6. doi: 10.1002/cmdc.201000016. [Article]
  2. Nancollas GH, Tang R, Phipps RJ, Henneman Z, Gulde S, Wu W, Mangood A, Russell RG, Ebetino FH: Novel insights into actions of bisphosphonates on bone: differences in interactions with hydroxyapatite. Bone. 2006 May;38(5):617-27. Epub 2005 Jul 20. [Article]
  3. Cremers S, Drake MT, Ebetino FH, Bilezikian JP, Russell RGG: Pharmacology of bisphosphonates. Br J Clin Pharmacol. 2019 Jun;85(6):1052-1062. doi: 10.1111/bcp.13867. Epub 2019 Feb 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Poly(a) rna binding
Specific Function
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids...
Gene Name
FDPS
Uniprot ID
P14324
Uniprot Name
Farnesyl pyrophosphate synthase
Molecular Weight
48275.03 Da
References
  1. Dunford JE, Thompson K, Coxon FP, Luckman SP, Hahn FM, Poulter CD, Ebetino FH, Rogers MJ: Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J Pharmacol Exp Ther. 2001 Feb;296(2):235-42. [Article]
  2. Glickman JF, Schmid A: Farnesyl pyrophosphate synthase: real-time kinetics and inhibition by nitrogen-containing bisphosphonates in a scintillation assay. Assay Drug Dev Technol. 2007 Apr;5(2):205-14. [Article]
  3. Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH: Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. Proc Natl Acad Sci U S A. 2007 Jun 12;104(24):10022-7. Epub 2007 May 29. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Yildiz M, Celik-Ozenci C, Akan S, Akan I, Sati L, Demir R, Savas B, Ozben T, Samur M, Ozdogan M, Artac M, Bozcuk H: Zoledronic acid is synergic with vinblastine to induce apoptosis in a multidrug resistance protein-1 dependent way: an in vitro study. Cell Biol Int. 2006 Mar;30(3):278-82. Epub 2006 Feb 2. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06