Alendronic acid

Identification

Summary

Alendronic acid is a bisphosphonate drug that prevents osteoclastic bone resorption which is used for the prevention and treatment of osteoporosis.

Brand Names
Adrovance, Binosto, Fosamax, Fosamax Plus D, Fosavance
Generic Name
Alendronic acid
DrugBank Accession Number
DB00630
Background

Alendronic acid is a second generation bisphosphonate that is used for the treatment of some forms of osteoperosis and Paget's diseaseLabel1,5. It functions by preventing resorption of boneLabel1.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 249.096
Monoisotopic: 249.016724799
Chemical Formula
C4H13NO7P2
Synonyms
  • (4-amino-1-hydroxybutane-1,1-diyl)bis(phosphonic acid)
  • (4-amino-1-hydroxybutylidene)bisphosphonic acid
  • 4-amino-1-hydroxybutane-1,1-diphosphonic acid
  • ABDP
  • Acide Alendronique
  • Acido Alendronico
  • Acidum Alendronicum
  • Alendronate
  • Alendronic acid
External IDs
  • G 704650
  • GTH 4
  • L 670
  • L 670452
  • MK 217

Pharmacology

Indication

Alendronic acid is indicated for the treatment and prevention of osteoporosis in men and postmenopausal women, treatment of glucocorticoid-induced osteoporosis, and Paget's disease of boneLabel1,2. However, alendronic acid is not indicated for use in pediatric populations or patients with a creatinine clearance <35mL/minLabel.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofOsteogenesis imperfecta••• •••••
Used in combination to treatOsteoporosisCombination Product in combination with: Calcitriol (DB00136)••••••••••••••••••• ••••••• •••••••
Prevention ofOsteoporosis•••••••••••••••••••••••••••
Treatment ofOsteoporosis•••••••••••••••••••••••••••
Used in combination to manageOsteoporosisCombination Product in combination with: Cholecalciferol (DB00169)••••••••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Alendronic acid tablets have a very low oral bioavialabilityLabel2. After administration it distributes into soft tissue and bone or is excreted in the urineLabel. Alendronic acid does not undergo metabolismLabel.

Mechanism of action

Alendronic acid binds to bone hydroxyapatiteLabel. Bone resorption causes local acidification, releasing alendronic acid which is that taken into osteoclasts by fluid-phase endocytosis1. Endocytic vesicles are acidified, releasing alendronic acid to the cytosol of osteoclasts where they induce apoptosis1. Inhibition of osteoclasts results in decreased bone resorption which is shown through decreased urinary calcium, deoxypyridinoline and cross-linked N-telopeptidases of type I collagenLabel.

TargetActionsOrganism
AFarnesyl pyrophosphate synthase
inhibitor
Humans
AHydroxylapatite
antagonist
Humans
UTyrosine-protein phosphatase non-receptor type 4
inhibitor
Humans
UReceptor-type tyrosine-protein phosphatase S
inhibitor
Humans
UReceptor-type tyrosine-protein phosphatase epsilon
inhibitor
Humans
UV-type proton ATPase catalytic subunit A
inhibitor
Humans
Absorption

Mean oral bioavailability of alendronic acid in women is 0.64% and in men is 0.59%Label2. Bioavailability of alendronic acid decreases by up to 40% if it is taken within an hour of a mealLabel.

Volume of distribution

28LLabel.

Protein binding

78%Label. Studies in rats show that plasma protein binding increases with decreasing alendronic acid plasma concentration3 and increasing pH4.

Metabolism

Urinary excretion is the sole method of elimination of alendronic acid and no metabolites are detected upon urine collection2.

Route of elimination

Administration of radiolabeled alendronic acid results in 50% recovery in urine within 72 hoursLabel4. No alendronic acid is recovered in the fecesLabel2,3. Men excrete less alendronic acid than women, though race and advanced age do not affect eliminationLabel.

Half-life

Due to alendronic acid being incorporated into the skeleton, the terminal half life is estimated to be over 10 yearsLabel.

Clearance

71mL/minLabel.

Adverse Effects
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Toxicity

In clinical studies, ≥3% of patients experience abdominal pain, acid regurgitation, constipation, diarrhea, dyspepsia, musculoskeletal pain, and nauseaLabel.

No information for treatment of overdose is available, however patients should be given milk or antacids to bind alendronic acid and vomiting should not be inducedLabel. Patients may experience hypocalcemia, hypophosphatemia, and upper gastrointestinal events.Label.

There are currently no studies for safety and efficacy in pregnancy, though studies in pregnant rats show fetal and maternal complications at 4 times the clinical dose and pregnant rabbits do not show complications at as high as 10 times the clincal doseLabel.

Excretion in breast milk, and therefore safety in lactation, is unknownLabel.

Alendronic acid has been studied for use in pediatric patientsLabel. The oral bioavailability is similar to that in adult patients, but an increase in the portion of patients experiencing vomitingLabel.

There is no significant difference in efficacy or safety of alendronic acid in geriatric populations, though there is potential for even greater sensitivity in patients at a further advanced age than those in the studyLabel.

Alendronic acid is not recommended for patients with creatinine clearance <35mL/min, but no dosage adjustment is necessary in hepatic impairmentLabel.

Pathways
PathwayCategory
Alendronate 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 adverse effects can be increased when Aceclofenac is combined with Alendronic acid.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Alendronic acid.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Alendronic acid.
AcipimoxThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Acipimox.
AcyclovirThe risk or severity of nephrotoxicity and hypocalcemia can be increased when Acyclovir is combined with Alendronic acid.
Food Interactions
  • Administer vitamin supplements. Patients may require supplemental vitamin D.
  • Avoid multivalent ions. Calcium, antacids, and divalent ions may interfere with the absorption of this medication.
  • Take before a meal. Take 30-60 minutes before breakfast.
  • Take with a full glass of water.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Alendronate calcium3JTA994BVH137504-90-6VFAZUESUCBECNE-UHFFFAOYSA-L
Alendronate disodiumI2U0WCC042134606-40-9LMWOPQOPFYJQLI-UHFFFAOYSA-L
Alendronate sodium2UY4M2U3RA121268-17-5DCSBSVSZJRSITC-UHFFFAOYSA-M
Alendronate sodium anhydrous4988K7X26P129318-43-0CAKRAHQRJGUPIG-UHFFFAOYSA-M
Product Images
International/Other Brands
Alenotop (Pliva) / Alned (Laboratorios Belmac) / Arendal (Ivax) / Beenos (Gedeon Richter) / Berlex (Duncan) / Denfos (Biofarma) / Densidron (Mepha) / Dronat (Farmavita) / Durost (Perumed) / Fixopan (Grupo Farma) / Forosa (Kemofarmacija) / Fosagen (Aspen Pharmacare) / Fosalen (Teriak) / Fosmin (Hospimedikka) / Fostolin (Actavis) / Fosval (Saval) / Huesobone (Farmaceutica Latina) / Lendrate (Actavis) / Oseolen (Intipharma) / Ostemax (Polpharma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act AlendronateTablet70 mgOralActavis Pharma Company2005-06-142018-06-12Canada flag
Act AlendronateTablet40 mgOralActavis Pharma Company2005-06-142019-07-08Canada flag
AlendronateTablet70 mgOralSivem Pharmaceuticals Ulc2008-03-13Not applicableCanada flag
AlendronateTablet70 mgOralSanis Health Inc2010-07-30Not applicableCanada flag
AlendronateTablet10 mgOralSanis Health IncNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Accel-alendronateTablet5 mgOralAccel Pharma IncNot applicableNot applicableCanada flag
Accel-alendronateTablet70 mgOralAccel Pharma Inc2015-03-262017-09-13Canada flag
Accel-alendronateTablet10 mgOralAccel Pharma Inc2015-03-262017-09-13Canada flag
Ach-alendronateTablet70 mgOralAccord Healthcare, S.L.U.2012-03-20Not applicableCanada flag
Ach-alendronateTablet5 mgOralAccord Healthcare, S.L.U.2012-03-20Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACIDO ALENDRONICO E COLECALCIFEROLO AUROBINDOAlendronic acid (70 MG) + Cholecalciferol (5600 IU)TabletOralAurobindo Pharma (Italia) S.R.L.2018-03-01Not applicableItaly flag
ACIDO ALENDRONICO E COLECALCIFEROLO AUROBINDOAlendronic acid (70 MG) + Cholecalciferol (2800 IU)TabletOralAurobindo Pharma (Italia) S.R.L.2018-03-01Not applicableItaly flag
ACIDO ALENDRONICO E COLECALCIFEROLO EGAlendronic acid (70 MG) + Cholecalciferol (5600 IU)TabletOralEg S.P.A.2018-03-15Not applicableItaly flag
ACIDO ALENDRONICO E COLECALCIFEROLO EGAlendronic acid (70 MG) + Cholecalciferol (2800 IU)TabletOralEg S.P.A.2018-03-15Not applicableItaly flag
ACIDO ALENDRONICO E COLECALCIFEROLO EGAlendronic acid (70 MG) + Cholecalciferol (5600 IU)TabletOralEg S.P.A.2018-03-15Not applicableItaly flag

Categories

ATC Codes
M05BB03 — Alendronic acid and colecalciferolM05BA04 — Alendronic acidM05BB06 — Alendronic acid and alfacalcidol, sequentialM05BB05 — Alendronic acid, calcium and colecalciferol, sequential
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
Organic phosphonic acids / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Amine / Bisphosphonate / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organophosphonic acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
primary amino compound, 1,1-bis(phosphonic acid) (CHEBI:2567)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
X1J18R4W8P
CAS number
66376-36-1
InChI Key
OGSPWJRAVKPPFI-UHFFFAOYSA-N
InChI
InChI=1S/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)
IUPAC Name
(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid
SMILES
NCCCC(O)(P(O)(O)=O)P(O)(O)=O

References

Synthesis Reference

Masahiko Dohi, Yuji Makino, Takao Hujii, "Sodium alendronate preparation for local administration." U.S. Patent US5958908, issued September, 1997.

US5958908
General References
  1. 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]
  2. Porras AG, Holland SD, Gertz BJ: Pharmacokinetics of alendronate. Clin Pharmacokinet. 1999 May;36(5):315-28. doi: 10.2165/00003088-199936050-00002. [Article]
  3. Lin JH, Chen IW, Deluna FA, Hichens M: Renal handling of alendronate in rats. An uncharacterized renal transport system. Drug Metab Dispos. 1992 Jul-Aug;20(4):608-13. [Article]
  4. Lin JH, Chen IW, deLuna FA, Hichens M: Role of calcium in plasma protein binding and renal handling of alendronate in hypo- and hypercalcemic rats. J Pharmacol Exp Ther. 1993 Nov;267(2):670-5. [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. FDA Approved Drugs: Alendronate [Link]
Human Metabolome Database
HMDB0001915
KEGG Compound
C07752
PubChem Compound
2088
PubChem Substance
46507199
ChemSpider
2004
BindingDB
25313
RxNav
236083
ChEBI
2567
ChEMBL
CHEMBL870
ZINC
ZINC000003801919
Therapeutic Targets Database
DAP000182
PharmGKB
PA448082
PDBe Ligand
212
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Alendronic_acid
PDB Entries
5dz2 / 8b4m
FDA label
Download (383 KB)
MSDS
Download (24.7 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingNot AvailablePostmenopausal Osteoporosis1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingNot AvailablePostmenopausal Osteoporosis / Quality of Life (QOL) / Vertebral Fractures1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAdenocarcinomas / Esophageal Cancer / Squamous Cell Carcinoma (SCC)1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAnkylosing Spondylitis (AS) / Osteoporosis1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAtypical Femoral Fractures / Bisphosphonate Therapy / Osteoporosis1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
  • Merck and co inc
  • Apotex inc
  • Aurobindo pharma ltd
  • Austarpharma llc
  • Barr laboratories inc
  • Cadista pharmaceuticals inc
  • Dr reddys laboratories ltd
  • Genpharm ulc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Sun pharma global inc
  • Teva pharmaceuticals usa
  • Watson laboratories
  • Watson laboratories inc
Packagers
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Arrow Pharm Malta Ltd.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Barr Pharmaceuticals
  • Cipla Ltd.
  • Cobalt Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Lake Erie Medical and Surgical Supply
  • Merck & Co.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral35 mg
Tablet, effervescentOral
TabletOral70 mg
Tablet, film coatedOral
SolutionOral70 MG
Tablet, film coatedOral70 mg
TabletOral10 mg/1
TabletOral40 mg/1
TabletOral70 mg/1
TabletOral91.35 mg
Tablet, film coatedOral
TabletOral70 MG/2800IE
TabletOral70 MG/5600IE
TabletOral5 MG
Tablet, effervescentOral70 mg/1
Tablet, effervescentOral91.37 mg/1
Tablet, effervescentOral70 MG
SolutionOral
Tablet, effervescentOral
Tablet, effervescentOral70.00 mg
TabletOral
SolutionOral70 mg/75mL
SolutionOral70 mg / 75 mL
TabletOral35 mg/1
TabletOral40 mg
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
TabletOral
TabletOral70 mg
Capsule, liquid filledOral70 mg
TabletOral10.0 mg
TabletOral5.0 mg
TabletOral70.0 mg
Tablet, film coatedOral7000000 mg
CapsuleOral10 mg
SolutionIntravenous5.000 mg
TabletOral70.000 mg
TabletOral10 mg
Tablet
Tablet, effervescentOral91.37 mg
Tablet, delayed releaseOral
Prices
Unit descriptionCostUnit
Fosamax Plus D 4 70-2800 mg-Unit tablet Disp Pack107.66USD disp
Fosamax Plus D 4 70-5600 mg-Unit tablet Disp Pack107.66USD disp
Fosamax 1 Package = 4 tablet (70 mg) Package101.96USD package
Fosamax 1 Package = 4 tablet (35 mg) Package97.2USD package
Alendronate Sodium 4 35 mg tablet Package85.23USD package
Alendronate Sodium 4 70 mg tablet Package85.23USD package
Fosamax 70 mg/75ml Solution 75ml Bottle34.75USD bottle
Fosamax plus d 70 mg-5600 iu25.88USD each
Fosamax 70 mg tablet24.51USD tablet
Fosamax 35 mg tablet23.36USD tablet
Fosamax plus d 70 mg-2800 iu21.85USD each
Alendronate sodium 35 mg tablet20.49USD tablet
Alendronate sodium 70 mg tablet20.49USD tablet
Fosamax 40 mg tablet7.52USD tablet
Alendronate sodium 40 mg tablet6.73USD tablet
Fosamax 5 mg tablet3.4USD tablet
Fosamax 10 mg tablet3.4USD tablet
Alendronate sodium 10 mg tablet2.99USD tablet
Alendronate sodium 5 mg tablet2.99USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5358941No1994-10-252012-12-02US flag
CA2190148No2006-02-142015-05-12Canada flag
CA2294595No2001-08-212018-07-17Canada flag
US5994329Yes1999-11-302019-01-17US flag
US6015801Yes2000-01-182019-01-17US flag
US6225294Yes2001-05-012019-01-17US flag
US7964212No2011-06-212023-03-06US flag
US7488496No2009-02-102023-08-11US flag
US9592195No2017-03-142031-12-05US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)235https://www.tcichemicals.com/eshop/en/us/commodity/A2120/
pKa2.72 (at 25 °C)MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility16.9 mg/mLALOGPS
logP-1.3ALOGPS
logP-4.2Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.69Chemaxon
pKa (Strongest Basic)9.91Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area161.31 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity47.37 m3·mol-1Chemaxon
Polarizability19.4 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9554
Blood Brain Barrier+0.7065
Caco-2 permeable-0.7079
P-glycoprotein substrateNon-substrate0.6606
P-glycoprotein inhibitor INon-inhibitor0.947
P-glycoprotein inhibitor IINon-inhibitor0.9894
Renal organic cation transporterNon-inhibitor0.9205
CYP450 2C9 substrateNon-substrate0.8536
CYP450 2D6 substrateNon-substrate0.7997
CYP450 3A4 substrateNon-substrate0.6792
CYP450 1A2 substrateNon-inhibitor0.7567
CYP450 2C9 inhibitorNon-inhibitor0.9089
CYP450 2D6 inhibitorNon-inhibitor0.9344
CYP450 2C19 inhibitorNon-inhibitor0.9091
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9914
Ames testNon AMES toxic0.7079
CarcinogenicityNon-carcinogens0.7783
BiodegradationReady biodegradable0.6547
Rat acute toxicity1.6956 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8571
hERG inhibition (predictor II)Non-inhibitor0.8929
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-9010000000-6b540b3cfe12455ee047
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-014i-2930000000-99692afb4ed253251947
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-001i-0900000000-d2c07307d66e1c7d52e8
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0kdl-9500000000-c82a6e6e898154627c7d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0690000000-25cd5b4411b59e10a4be
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-6d902d0751b43d9c4776
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-005a-7090000000-24135a0d63c1dfe6724d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1940000000-31efc7087b6be8aae85d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-d0628e787262be8ff1d8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9100000000-a369b26cd4b37f60e4ee
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]-153.41846
predicted
DarkChem Lite v0.1.0
[M-H]-153.45226
predicted
DarkChem Lite v0.1.0
[M-H]-135.94868
predicted
DeepCCS 1.0 (2019)
[M+H]+153.55836
predicted
DarkChem Lite v0.1.0
[M+H]+153.35606
predicted
DarkChem Lite v0.1.0
[M+H]+139.53654
predicted
DeepCCS 1.0 (2019)
[M+Na]+153.51436
predicted
DarkChem Lite v0.1.0
[M+Na]+153.31266
predicted
DarkChem Lite v0.1.0
[M+Na]+148.16539
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General 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, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate
Specific Function
dimethylallyltranstransferase activity
Gene Name
FDPS
Uniprot ID
P14324
Uniprot Name
Farnesyl pyrophosphate synthase
Molecular Weight
48275.03 Da
References
  1. Bergstrom JD, Bostedor RG, Masarachia PJ, Reszka AA, Rodan G: Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase. Arch Biochem Biophys. 2000 Jan 1;373(1):231-41. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. 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]
  4. 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
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatase that plays a role in immunity, learning, synaptic plasticity or cell homeostasis (PubMed:25825441, PubMed:27246854). Regulates neuronal cell homeostasis by protecting neurons against apoptosis (PubMed:20086240). Negatively regulates TLR4-induced interferon beta production by dephosphorylating adapter TICAM2 and inhibiting subsequent TRAM-TRIF interaction (PubMed:25825441). Dephosphorylates also the immunoreceptor tyrosine-based activation motifs/ITAMs of the TCR zeta subunit and thereby negatively regulates TCR-mediated signaling pathway (By similarity). May act at junctions between the membrane and the cytoskeleton
Specific Function
cytoskeletal protein binding
Gene Name
PTPN4
Uniprot ID
P29074
Uniprot Name
Tyrosine-protein phosphatase non-receptor type 4
Molecular Weight
105910.315 Da
References
  1. Opas EE, Rutledge SJ, Golub E, Stern A, Zimolo Z, Rodan GA, Schmidt A: Alendronate inhibition of protein-tyrosine-phosphatase-meg1. Biochem Pharmacol. 1997 Sep 15;54(6):721-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Cell surface receptor that binds to glycosaminoglycans, including chondroitin sulfate proteoglycans and heparan sulfate proteoglycan (PubMed:21454754). Binding to chondroitin sulfate and heparan sulfate proteoglycans has opposite effects on PTPRS oligomerization and regulation of neurite outgrowth. Contributes to the inhibition of neurite and axonal outgrowth by chondroitin sulfate proteoglycans, also after nerve transection. Plays a role in stimulating neurite outgrowth in response to the heparan sulfate proteoglycan GPC2. Required for normal brain development, especially for normal development of the pituitary gland and the olfactory bulb. Functions as a tyrosine phosphatase (PubMed:8524829). Mediates dephosphorylation of NTRK1, NTRK2 and NTRK3 (By similarity). Plays a role in down-regulation of signaling cascades that lead to the activation of Akt and MAP kinases (By similarity). Down-regulates TLR9-mediated activation of NF-kappa-B, as well as production of TNF, interferon alpha and interferon beta (PubMed:26231120)
Specific Function
chondroitin sulfate binding
Gene Name
PTPRS
Uniprot ID
Q13332
Uniprot Name
Receptor-type tyrosine-protein phosphatase S
Molecular Weight
217039.825 Da
References
  1. Opas EE, Rutledge SJ, Golub E, Stern A, Zimolo Z, Rodan GA, Schmidt A: Alendronate inhibition of protein-tyrosine-phosphatase-meg1. Biochem Pharmacol. 1997 Sep 15;54(6):721-7. [Article]
  2. Schmidt A, Rutledge SJ, Endo N, Opas EE, Tanaka H, Wesolowski G, Leu CT, Huang Z, Ramachandaran C, Rodan SB, Rodan GA: Protein-tyrosine phosphatase activity regulates osteoclast formation and function: inhibition by alendronate. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):3068-73. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Isoform 1 plays a critical role in signaling transduction pathways and phosphoprotein network topology in red blood cells. May play a role in osteoclast formation and function (By similarity)
Specific Function
protein tyrosine phosphatase activity
Gene Name
PTPRE
Uniprot ID
P23469
Uniprot Name
Receptor-type tyrosine-protein phosphatase epsilon
Molecular Weight
80641.165 Da
References
  1. Schmidt A, Rutledge SJ, Endo N, Opas EE, Tanaka H, Wesolowski G, Leu CT, Huang Z, Ramachandaran C, Rodan SB, Rodan GA: Protein-tyrosine phosphatase activity regulates osteoclast formation and function: inhibition by alendronate. Proc Natl Acad Sci U S A. 1996 Apr 2;93(7):3068-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Catalytic subunit of the V1 complex of vacuolar(H+)-ATPase (V-ATPase), a multisubunit enzyme composed of a peripheral complex (V1) that hydrolyzes ATP and a membrane integral complex (V0) that translocates protons (PubMed:8463241). V-ATPase is responsible for acidifying and maintaining the pH of intracellular compartments and in some cell types, is targeted to the plasma membrane, where it is responsible for acidifying the extracellular environment (PubMed:32001091). In aerobic conditions, involved in intracellular iron homeostasis, thus triggering the activity of Fe(2+) prolyl hydroxylase (PHD) enzymes, and leading to HIF1A hydroxylation and subsequent proteasomal degradation (PubMed:28296633). May play a role in neurite development and synaptic connectivity (PubMed:29668857)
Specific Function
ATP binding
Gene Name
ATP6V1A
Uniprot ID
P38606
Uniprot Name
V-type proton ATPase catalytic subunit A
Molecular Weight
68303.5 Da
References
  1. David P, Nguyen H, Barbier A, Baron R: The bisphosphonate tiludronate is a potent inhibitor of the osteoclast vacuolar H(+)-ATPase. J Bone Miner Res. 1996 Oct;11(10):1498-507. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 13, 2024 03:36