Didanosine
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Identification
- Summary
Didanosine is a reverse transcriptase inhibitor used to treat HIV.
- Generic Name
- Didanosine
- DrugBank Accession Number
- DB00900
- Background
A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 236.2273
Monoisotopic: 236.09094027 - Chemical Formula
- C10H12N4O3
- Synonyms
- 2,3-Dideoxyinosine
- 9-((2R,5S)-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
- 9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
- 9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol
- 9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
- ddI
- ddIno
- Didanosina
- Didanosine
- Didanosinum
- Dideoxyinosine
- External IDs
- BMY-40900
Pharmacology
- Indication
For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Hiv-1 infection •••••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Didanosine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Didanosine is a hypoxanthine attached to the sugar ring, unlike other nucleoside analogues. Didanosine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. Didanosine is effective against HIV, and usually used in combination with other antiviral therapy. Switching from long term AZT treatment to didanosine has been shown to be beneficial. Didanosine has weak acid stability and therefore, it is often combined with an antacid.
- Mechanism of action
Didanosine (ddI) is metabolized intracellularly by a series of cellular enzymes to its active moiety, dideoxyadenosine triphosphate (ddATP), which inhibits the HIV reverse transcriptase enzyme competitively by competing with natural dATP. It also acts as a chain terminator by its incorporation into viral DNA as the lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.
Target Actions Organism AReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 1 AGag-Pol polyprotein inhibitorUPurine nucleoside phosphorylase substrateHumans - Absorption
Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.
- Volume of distribution
Not Available
- Protein binding
Low (<5%)
- Metabolism
Rapidly metabolized intracellularly to its active moiety, 2,3-dideoxyadenosine-5-triphosphate (ddA-TP). It is then further metabolized hepatically to yield hypoxanthine, xanthine, and uric acid.
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- Route of elimination
Based on data from in vitro and animal studies, it is presumed that the metabolism of didanosine in man occurs by the same pathways responsible for the elimination of endogenous purines. Purines are eliminated by the kidneys.
- Half-life
30 minutes in plasma and more than 12 hours in intracellular environment.
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction
- Pathways
Pathway Category Didanosine Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Didanosine may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Didanosine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Didanosine which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Didanosine which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Didanosine which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Avoid alcohol.
- Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Videx Powder, for solution 10 mg/1mL Oral Bristol-Myers Squibb Company 1991-10-09 2021-02-28 US Videx Powder, for solution 10 mg/1mL Oral Bristol-Myers Squibb Company 1991-10-09 2019-11-30 US Videx Chewable Dispersible Tab 100mg Tablet 100 mg Oral Bristol Myers Squibb 1991-12-31 2008-03-27 Canada Videx Chewable Dispersible Tab 150mg Tablet 150 mg Oral Bristol Myers Squibb 1991-12-31 2007-05-01 Canada Videx Chewable Dispersible Tab 25mg Tablet 25 mg Oral Bristol Myers Squibb 1991-12-31 2007-01-02 Canada - Generic Prescription Products
Categories
- ATC Codes
- J05AF02 — Didanosine
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antimetabolites
- Antiviral Agents
- Antivirals for Systemic Use
- Deoxyribonucleosides
- Dideoxynucleosides
- Direct Acting Antivirals
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
- Neurotoxic agents
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
- Nucleoside Reverse Transcriptase Inhibitors
- Nucleosides
- OAT1/SLC22A6 Substrates
- Purine Nucleosides
- Purines
- Reverse Transcriptase Inhibitors
- Ribonucleosides
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleosides
- Sub Class
- Purine 2',3'-dideoxyribonucleosides
- Direct Parent
- Purine 2',3'-dideoxyribonucleosides
- Alternative Parents
- Hypoxanthines / 6-oxopurines / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Primary alcohols show 4 more
- Substituents
- 6-oxopurine / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Hypoxanthine / Imidazole / Imidazopyrimidine show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- purine 2',3'-dideoxyribonucleoside (CHEBI:490877)
- Affected organisms
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- K3GDH6OH08
- CAS number
- 69655-05-6
- InChI Key
- BXZVVICBKDXVGW-NKWVEPMBSA-N
- InChI
- InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
- IUPAC Name
- 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
- SMILES
- OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O
References
- Synthesis Reference
Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy, Dasari Muralidhara Reddy, Kesireddy Subash Chander Reddy, "Novel Process for the Preparation of Didanosine Using Novel Intermediates." U.S. Patent US20080293938, issued November 27, 2008.
US20080293938- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015037
- KEGG Drug
- D00296
- KEGG Compound
- C06953
- PubChem Compound
- 50599
- PubChem Substance
- 46506255
- ChemSpider
- 45864
- BindingDB
- 50404252
- 3364
- ChEBI
- 490877
- ChEMBL
- CHEMBL1460
- ZINC
- ZINC000013597823
- Therapeutic Targets Database
- DNC000528
- PharmGKB
- PA449301
- PDBe Ligand
- 2DI
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Didanosine
- PDB Entries
- 1v3q
- FDA label
- Download (86.1 KB)
- MSDS
- Download (36.5 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 Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide Not Available Completed Treatment Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections 20 somestatus stop reason just information to hide Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leucoencephalopathy (PML) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Aurobindo pharma ltd
- Barr laboratories inc
- Matrix laboratories ltd
- Bristol myers squibb co
- Bristol myers squibb co pharmaceutical research institute
- Packagers
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Barr Pharmaceuticals
- Bristol-Myers Squibb Co.
- Dept Health Central Pharmacy
- Kaiser Foundation Hospital
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Physicians Total Care Inc.
- Prepak Systems Inc.
- Remedy Repack
- Dosage Forms
Form Route Strength Capsule, extended release Oral 125 mg Tablet, chewable Buccal 25 mg Tablet, chewable Oral 150 mg Capsule, extended release Oral 250 mg Tablet, chewable Oral 100 mg Capsule, coated Oral 400 mg Tablet, chewable Oral 25 mg Capsule, delayed release Oral 125 mg/1 Capsule, delayed release Oral 200 mg/1 Capsule, delayed release pellets Oral 200 mg/1 Capsule, delayed release pellets Oral 250 mg/1 Capsule, delayed release pellets Oral 400 mg/1 Powder, for solution Oral 10 mg/1mL Tablet, for suspension Oral 100 mg/1 Tablet, for suspension Oral 150 mg/1 Tablet, for suspension Oral 200 mg/1 Tablet, delayed release Oral 400 mg Capsule, coated Oral 250 mg Capsule, extended release Oral 400 mg Tablet, chewable Oral 10 mg Tablet, chewable Oral 50 mg Capsule, delayed release Oral Powder Oral Tablet, chewable Oral Tablet Oral 100 mg Tablet Oral 150 mg Tablet Oral 25 mg Tablet Oral 50 mg Capsule, delayed release Oral 125 mg Capsule, delayed release Oral 200 mg Capsule, delayed release Oral 250 mg Capsule, delayed release Oral 250 mg/1 Capsule, delayed release Oral 400 mg Capsule, delayed release Oral 400 mg/1 Powder, for solution Oral 4 g / bottle - Prices
Unit description Cost Unit Videx 4 gm Solution 200ml Bottle 124.51USD bottle Videx 2 gm Solution 100ml Bottle 58.4USD bottle Videx EC 400 mg Delayed Release Capsule 14.75USD capsule Videx ec 400 mg capsule 14.18USD capsule Didanosine 400 mg Delayed Release Capsule 12.78USD capsule Videx EC 250 mg Delayed Release Capsule 9.44USD capsule Videx ec 250 mg capsule 9.08USD capsule Didanosine 250 mg Delayed Release Capsule 8.18USD capsule Videx ec 200 mg capsule 7.12USD capsule Didanosine 200 mg Delayed Release Capsule 6.42USD capsule Videx ec 125 mg capsule 4.45USD capsule Videx 4 gm pediatric solution 0.6USD ml Videx 2 gm pediatric solution 0.55USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5880106 No 1999-03-09 2012-01-22 US CA2332922 No 2008-02-12 2018-08-04 Canada CA2072573 No 1996-05-28 2011-01-03 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 160-163 °C PhysProp water solubility 15.8 mg/mL Not Available logP -1.24 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 6.58 mg/mL ALOGPS logP -0.99 ALOGPS logP -0.35 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 10.94 Chemaxon pKa (Strongest Basic) 2.76 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 88.74 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.59 m3·mol-1 Chemaxon Polarizability 22.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.996 Blood Brain Barrier + 0.823 Caco-2 permeable - 0.9019 P-glycoprotein substrate Non-substrate 0.5948 P-glycoprotein inhibitor I Non-inhibitor 0.945 P-glycoprotein inhibitor II Non-inhibitor 0.6378 Renal organic cation transporter Non-inhibitor 0.8049 CYP450 2C9 substrate Non-substrate 0.8065 CYP450 2D6 substrate Non-substrate 0.7777 CYP450 3A4 substrate Non-substrate 0.5234 CYP450 1A2 substrate Non-inhibitor 0.6934 CYP450 2C9 inhibitor Non-inhibitor 0.9064 CYP450 2D6 inhibitor Non-inhibitor 0.9145 CYP450 2C19 inhibitor Non-inhibitor 0.8646 CYP450 3A4 inhibitor Non-inhibitor 0.9608 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7288 Ames test AMES toxic 0.8682 Carcinogenicity Non-carcinogens 0.9094 Biodegradation Not ready biodegradable 0.8478 Rat acute toxicity 2.0874 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9451 hERG inhibition (predictor II) Non-inhibitor 0.8735
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 154.7287669 predictedDarkChem Lite v0.1.0 [M-H]- 153.6281589 predictedDarkChem Lite v0.1.0 [M-H]- 154.8945669 predictedDarkChem Lite v0.1.0 [M-H]- 146.30229 predictedDeepCCS 1.0 (2019) [M+H]+ 155.4599669 predictedDarkChem Lite v0.1.0 [M+H]+ 151.6100057 predictedDarkChem Lite v0.1.0 [M+H]+ 155.1671669 predictedDarkChem Lite v0.1.0 [M+H]+ 148.69785 predictedDeepCCS 1.0 (2019) [M+Na]+ 154.8669669 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.9169224 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.9248669 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.61037 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- aspartic-type endopeptidase activity
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
- Faulds D, Brogden RN: Didanosine. A review of its antiviral activity, pharmacokinetic properties and therapeutic potential in human immunodeficiency virus infection. Drugs. 1992 Jul;44(1):94-116. [Article]
- De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Gag-Pol polyprotein Mediates, with Gag polyprotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spherical particles, recruiting the viral Env proteins, and packaging the genomic RNA via direct interactions with the RNA packaging sequence (Psi). Gag-Pol polyprotein may regulate its own translation, by the binding genomic RNA in the 5'-UTR. At low concentration, the polyprotein would promote translation, whereas at high concentration, the polyprotein would encapsidate genomic RNA and then shut off translation.
- Specific Function
- aspartic-type endopeptidase activity
- Gene Name
- gag-pol
- Uniprot ID
- P03366
- Uniprot Name
- Gag-Pol polyprotein
- Molecular Weight
- 163287.51 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate (PubMed:23438750, PubMed:9305964). Preferentially acts on 6-oxopurine nucleosides including inosine and guanosine (PubMed:9305964)
- Specific Function
- guanosine phosphorylase activity
- Gene Name
- PNP
- Uniprot ID
- P00491
- Uniprot Name
- Purine nucleoside phosphorylase
- Molecular Weight
- 32117.69 Da
References
- Birmingham WR, Starbird CA, Panosian TD, Nannemann DP, Iverson TM, Bachmann BO: Bioretrosynthetic construction of a didanosine biosynthetic pathway. Nat Chem Biol. 2014 May;10(5):392-9. doi: 10.1038/nchembio.1494. Epub 2014 Mar 23. [Article]
- Ray AS, Olson L, Fridland A: Role of purine nucleoside phosphorylase in interactions between 2',3'-dideoxyinosine and allopurinol, ganciclovir, or tenofovir. Antimicrob Agents Chemother. 2004 Apr;48(4):1089-95. doi: 10.1128/aac.48.4.1089-1095.2004. [Article]
- Weibel M, Balzarini J, Bernhardt A, Mamont P: Potentiating effect of (2-[2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methyl]-phenyl]ethenyl) -phosphonic acid (MDL 74,428), a potent inhibitor of purine nucleoside phosphorylase, on the antiretroviral activities of 2',3'-dideoxyinosine combined with ribavirin in mice. Biochem Pharmacol. 1994 Jul 19;48(2):245-52. doi: 10.1016/0006-2952(94)90094-9. [Article]
- Singhal D, Ho NF, Anderson BD: Absorption and intestinal metabolism of purine dideoxynucleosides and an adenosine deaminase-activated prodrug of 2',3'-dideoxyinosine in the mesenteric vein cannulated rat ileum. J Pharm Sci. 1998 May;87(5):569-77. doi: 10.1021/js9703582. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [Article]
- Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Uniporter involved in the facilitative transport of nucleosides and nucleobases, and contributes to maintaining their cellular homeostasis (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:21795683, PubMed:26406980, PubMed:27995448, PubMed:35790189, PubMed:8986748). Functions as a Na(+)-independent transporter (PubMed:8986748). Involved in the transport of nucleosides such as adenosine, guanosine, inosine, uridine, thymidine and cytidine (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:26406980, PubMed:8986748). Also transports purine nucleobases (hypoxanthine, adenine, guanine) and pyrimidine nucleobases (thymine, uracil) (PubMed:21795683, PubMed:27995448). Mediates basolateral nucleoside uptake into Sertoli cells, thereby regulating the transport of nucleosides in testis across the blood-testis barrier (By similarity). Regulates inosine levels in brown adipocytes tissues (BAT) and extracellular inosine levels, which controls BAT-dependent energy expenditure (PubMed:35790189)
- Specific Function
- adenine transmembrane transporter activity
- Gene Name
- SLC29A1
- Uniprot ID
- Q99808
- Uniprot Name
- Equilibrative nucleoside transporter 1
- Molecular Weight
- 50218.805 Da
References
- Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD: Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Bidirectional uniporter involved in the facilitative transport of nucleosides and nucleobases, and contributes to maintaining their cellular homeostasis (PubMed:10722669, PubMed:12527552, PubMed:12590919, PubMed:16214850, PubMed:21795683, PubMed:9396714, PubMed:9478986). Functions as a Na(+)-independent, passive transporter (PubMed:9478986). Involved in the transport of nucleosides such as inosine, adenosine, uridine, thymidine, cytidine and guanosine (PubMed:10722669, PubMed:12527552, PubMed:12590919, PubMed:16214850, PubMed:21795683, PubMed:9396714, PubMed:9478986). Also able to transport purine nucleobases (hypoxanthine, adenine, guanine) and pyrimidine nucleobases (thymine, uracil) (PubMed:16214850, PubMed:21795683). Involved in nucleoside transport at basolateral membrane of kidney cells, allowing liver absorption of nucleoside metabolites (PubMed:12527552). Mediates apical nucleoside uptake into Sertoli cells, thereby regulating the transport of nucleosides in testis across the blood-testis-barrier (PubMed:23639800). Mediates both the influx and efflux of hypoxanthine in skeletal muscle microvascular endothelial cells to control the amount of intracellular hypoxanthine available for xanthine oxidase-mediated ROS production (By similarity)
- Specific Function
- adenine transmembrane transporter activity
- Gene Name
- SLC29A2
- Uniprot ID
- Q14542
- Uniprot Name
- Equilibrative nucleoside transporter 2
- Molecular Weight
- 50112.335 Da
References
- Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD: Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 08:50