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Identification
NameZoledronic acid
Accession NumberDB00399  (APRD01294, DB06286)
TypeSmall Molecule
GroupsApproved
Description

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
Thumb
Synonyms
(1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acid
(1-hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid
Anhydrous Zoledronic Acid
Zol
Zoledronate
Zoledronic Acid Anhydrous
Zoledronic Acid, Anhydrous
External Identifiers
  • CGP 42446
  • CGP-42446
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aclastasolution5 mgintravenousNovartis Pharmaceuticals Canada Inc2005-08-22Not applicableCanada
Act Zoledronic Acidsolution5 mgintravenousActavis Pharma CompanyNot applicableNot applicableCanada
Act Zoledronic Acid Concentratesolution4 mgintravenousActavis Pharma CompanyNot applicableNot applicableCanada
PMS-zoledronic Acidsolution4 mgintravenousPharmascience Inc2014-11-25Not applicableCanada
Reclastinjection, solution5 mg/100mLintravenousNovartis Pharmaceuticals Corporation2007-04-01Not applicableUs
Taro-zoledronic Acidsolution5 mgintravenousTaro Pharmaceuticals Inc2014-04-02Not applicableCanada
Taro-zoledronic Acid Concentratesolution4 mgintravenousTaro Pharmaceuticals Inc2014-02-26Not applicableCanada
Zoledronic Acidinjection, solution.04 mg/mLintravenousSagent Pharmaceuticals2013-03-02Not applicableUs
Zoledronic Acid - Asolution5 mgintravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Zoledronic Acid - Zsolution4 mgintravenousSandoz Canada Incorporated2014-01-15Not applicableCanada
Zoledronic Acid Concentratesolution4 mgintravenousApotex IncNot applicableNot applicableCanada
Zoledronic Acid Concentrate for Injectionsolution4 mgintravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Zoledronic Acid for Injectionsolution4 mgintravenousFresenius Kabi Canada Ltd2016-02-10Not applicableCanada
Zoledronic Acid for Injectionsolution4 mgintravenousHospira Healthcare Corporation2014-03-19Not applicableCanada
Zoledronic Acid for Injectionsolution4 mgintravenousMda Inc.2016-04-27Not applicableCanada
Zoledronic Acid for Injectionsolution4 mgintravenousTeva Canada Limited2014-02-26Not applicableCanada
Zoledronic Acid for Injection Concentratesolution4 mgintravenousDr Reddys Laboratories Ltd2014-05-28Not applicableCanada
Zoledronic Acid for Injection Concentratesolution4 mgintravenousOmega Laboratories Ltd2014-04-04Not applicableCanada
Zoledronic Acid Injectionsolution5 mgintravenousDr Reddys Laboratories Ltd2014-05-28Not applicableCanada
Zoledronic Acid Injectionsolution4 mgintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Zoledronic Acid Injectionsolution5 mgintravenousTeva Canada Limited2014-02-26Not applicableCanada
Zometainjection, solution, concentrate4 mg/5mLintravenousNovartis Pharmaceuticals Corporation2001-08-20Not applicableUs
Zometainjection, solution, concentrate4 mg/100mLintravenousNovartis Pharmaceuticals Corporation2001-08-20Not applicableUs
Zometa Concentratesolution4 mgintravenousNovartis Pharmaceuticals Canada Inc2004-10-14Not applicableCanada
Zometa Lyophilized Powderpowder for solution4 mgintravenousNovartis Pharmaceuticals Canada Inc2000-09-272008-10-31Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousActavis Pharma, Inc.2015-01-05Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousWest Ward Pharmaceuticals Corp2013-06-03Not applicableUs
Zoledronic AcidkitSun Pharma Global FZE2013-03-04Not applicableUs
Zoledronic Acidinjection, solution, concentrate.8 mg/mLintravenousSagent Pharmaceuticals2014-12-29Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousApotex Corp2013-09-20Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousDr.Reddy's Laboratories Inc2013-08-19Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousHeritage Pharmaceuticals Inc.2012-12-20Not applicableUs
Zoledronic Acidinjection4 mg/5mLintravenousWockhardt Limited2013-03-02Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousDr. Reddy's Laboratories Inc.2013-03-04Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousGland Pharma Limited2013-09-20Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousHeritage Pharmaceuticals Inc.2012-12-20Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousWockhardt Limited2013-03-02Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousMylan Institutional LLC2013-03-05Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousJHP Pharmaceuticals, LLC.2013-05-07Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousHeritage Pharmaceuticals Inc.2012-12-20Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousDr.Reddy's Laboratories Ltd2013-04-03Not applicableUs
Zoledronic Acidinjection4 mg/5mLintravenousWockhardt USA LLC.2013-03-02Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousPar Pharmaceutical Companies, Inc.2013-08-05Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousDr. Reddy's Laboratories Limited2013-03-04Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousAkorn2014-05-22Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousPar Pharmaceutical Companies, Inc.2013-03-04Not applicableUs
Zoledronic Acidinjection, solution5 mg/100mLintravenousWockhardt USA LLC.2013-03-02Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousSun Pharma Global FZE2013-03-04Not applicableUs
Zoledronic Acidsolution5 mg/100mLintravenousAkorn, Inc.2014-08-21Not applicableUs
Zoledronic Acidinjection, solution, concentrate4 mg/5mLintravenousAmneal Agila, Llc2012-04-23Not applicableUs
Zoledronic Acidinjection, solution.05 mg/mLintravenousSagent Pharmaceuticals2013-03-02Not applicableUs
Zoledronic Acidinjection4 mg/5mLintravenousFresenius Kabi USA, LLC2014-09-04Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Zoledronate disodium
ThumbNot applicableDBSALT001757
Zoledronate trisodium
ThumbNot applicableDBSALT001758
Zoledronic acid monohydrate
165800-06-6
ThumbNot applicableDBSALT001759
CategoriesNot Available
UNII70HZ18PH24
CAS number118072-93-8
WeightAverage: 272.0896
Monoisotopic: 271.996323708
Chemical FormulaC5H10N2O7P2
InChI KeyXRASPMIURGNCCH-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
Alternative Parents
Substituents
  • Bisphosphonate
  • N-substituted imidazole
  • Heteroaromatic compound
  • Organophosphonic acid
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of hypercalcemia of malignancy. Also for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. In May of 2007, the drug was approved for treatment of Paget’s Disease.
PharmacodynamicsZoledronate is a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronate is used to prevent osteoporosis and skeletal fractures, particularly in patients with cancers such as multiple myeloma and prostate cancer. It can also be used to treat hypercalcemia, particularly hypercalcemia of malignancy. It can also be helpful for treating pain from bone metastases.
Mechanism of actionThe action of zoledronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Zoledronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates such as zoledronate appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.
Related Articles
AbsorptionPoorly absorbed (oral absorption is about 1% of what intravenous absorption is).
Volume of distributionNot Available
Protein bindingApproximately 22% bound in human plasma, independent of the concentration. However, Canadian product information states binding to human plasma protein is approximately 56%.
Metabolism

Zoledronate does not inhibit human P450 enzymes in vitro and does not undergo biotransformation in vivo.

Route of eliminationIn 64 patients with cancer and bone metastases, on average (± s.d.) 39 ± 16% of the administered zoledronic acid dose was recovered in the urine within 24 hours, with only trace amounts of drug found in urine post-Day 2.
Half life146 hours
Clearance
  • Renal cl=3.7 +/- 2.0 L/h
ToxicityThere is no experience of acute overdose. Two patients received zoledronate (32 mg) over 5 minutes in clinical trials. Neither patient experienced any clinical or laboratory toxicity. Overdosage may cause clinically significant hypocalcemia, hypophosphatemia, and hypomagnesemia.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Zoledronate Action PathwayDrug actionSMP00107
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
Solutionintravenous5 mg
Injection, solutionintravenous5 mg/100mL
Injectionintravenous4 mg/5mL
Injection, solutionintravenous.04 mg/mL
Injection, solutionintravenous.05 mg/mL
Injection, solution, concentrateintravenous.8 mg/mL
Kit
Solutionintravenous5 mg/100mL
Injection, solution, concentrateintravenous4 mg/5mL
Injection, solution, concentrateintravenous4 mg/100mL
Solutionintravenous4 mg
Powder for solutionintravenous4 mg
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)
CA1338895 No1997-02-042014-02-04Canada
CA1338937 No1997-02-252014-02-25Canada
US4939130 No1993-03-022013-03-02Us
US7932241 Yes2008-08-052028-08-05Us
US8052987 No2003-10-272023-10-27Us
US8324189 Yes2005-11-292025-11-29Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySparingly solubleNot Available
logP-4.2Not Available
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-2ChemAxon
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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. [PubMed:17878149 ]
  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. [PubMed:11870242 ]
  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. [PubMed:16000365 ]
External Links
ATC CodesM05BB08M05BA08
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (57.9 KB)
Interactions
Drug Interactions
Drug
AmikacinAmikacin may increase the activities of Zoledronate.
ArbekacinArbekacin may increase the activities of Zoledronate.
BevacizumabThe risk or severity of adverse effects can be increased when Bevacizumab is combined with Zoledronate.
DeferasiroxThe risk or severity of adverse effects can be increased when Zoledronate is combined with Deferasirox.
EsomeprazoleThe therapeutic efficacy of Zoledronate can be decreased when used in combination with Esomeprazole.
FramycetinFramycetin may increase the activities of Zoledronate.
GentamicinGentamicin may increase the activities of Zoledronate.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Zoledronate.
KanamycinKanamycin may increase the activities of Zoledronate.
LansoprazoleThe therapeutic efficacy of Zoledronate can be decreased when used in combination with Lansoprazole.
NeomycinNeomycin may increase the activities of Zoledronate.
NetilmicinNetilmicin may increase the activities of Zoledronate.
OmeprazoleThe therapeutic efficacy of Zoledronate can be decreased when used in combination with Omeprazole.
PantoprazoleThe therapeutic efficacy of Zoledronate can be decreased when used in combination with Pantoprazole.
RibostamycinRibostamycin may increase the activities of Zoledronate.
Salmon CalcitoninSalmon Calcitonin may increase the activities of Zoledronate.
SpectinomycinSpectinomycin may increase the activities of Zoledronate.
StreptomycinStreptomycin may increase the activities of Zoledronate.
ThalidomideThe risk or severity of adverse effects can be increased when Thalidomide is combined with Zoledronate.
TobramycinTobramycin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, d...
Gene Name:
FDPS
Uniprot ID:
P14324
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. [PubMed:11160603 ]
  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. [PubMed:17477829 ]
  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. [PubMed:17535895 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
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
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. [PubMed:17535895 ]
Kind
Small molecule
Organism
Human
Pharmacological action
yes
Actions
antagonist
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. [PubMed:20209564 ]
  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. [PubMed:16046206 ]

Transporters

Kind
Protein
Organism
Human
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, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
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. [PubMed:16458542 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 03:05