Identification
- Summary
Stavudine is a dideoxynucleoside used in the treatment of HIV infection.
- Brand Names
- Zerit
- Generic Name
- Stavudine
- DrugBank Accession Number
- DB00649
- Background
A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Stavudine (DB00649)
- Weight
- Average: 224.2133
Monoisotopic: 224.079706882 - Chemical Formula
- C10H12N2O4
- Synonyms
- 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine
- 2',3'-Didehydro-3'-deoxythimidine
- 3'-Deoxy-2'-thymidinene
- Estavudina
- Sanilvudine
- Stavudin
- Stavudine
- Stavudinum
- STV
- External IDs
- BMY 27857
- BMY-27857
- d4T
- NSC-163661
Pharmacology
- Indication
For the treatment of human immunovirus (HIV) infections.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Hiv infection •••••••••••• - Contraindications & Blackbox Warnings
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Stavudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Stavudine 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. 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.
- Mechanism of action
Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.
Target Actions Organism AReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 1 - Absorption
Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).
- Volume of distribution
- 46 ± 21 L
- Protein binding
Negligible
- Metabolism
Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase.
- Route of elimination
Not Available
- Half-life
0.8-1.5 hours (in adults)
- Clearance
- Renal cl=272 mL/min [Healthy subjects receiving 80 mg PO]
- 594 +/- 164 mL/min [HIV-infected adult and pediatric patients following 1-hour IV infusion]
- 9.75 +/- 3.76 mL/min/kg [HIV- Exposed or -Infected Pediatric Patients(Age 5 weeks – 15 years) following 1-hour IV infusion]
- Adverse Effects
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Side effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.
- Pathways
Pathway Category Stavudine Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAcetazolamide The excretion of Stavudine can be decreased when combined with Acetazolamide. Acetophenazine Stavudine may increase the neurotoxic activities of Acetophenazine. Acetylsalicylic acid The excretion of Stavudine can be decreased when combined with Acetylsalicylic acid. Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Stavudine is combined with Acipimox. Acyclovir The excretion of Stavudine can be decreased when combined with Acyclovir. - Food Interactions
- Avoid alcohol. Ingesting alcohol while taking stavudine may increase the risk of liver damage and pancreatitis.
- Take with or without food.
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
- International/Other Brands
- Actastav (Actavis) / Ai Fu Ding (Wujing Medicine) / Avostav (Ranbaxy Laboratories) / Estavudox (Biotoscana) / Exvihr (Biogen) / Flamistav (Flamingo Pharmacueticals) / Landstav (Landsteiner) / Lion (Filaxis) / Mai Si Ting (Meijisi Pharmaceutical) / S.T.V. (Ivax) / Sazi (NEGPF) / Stadine (Stadine) / Stag (Hetero) / Stamar (LKM) / Stavex (Aurobindo) / Stavir (Cipla) / Stavubergen (Paylos) / Zerit XR (Bristol-Myers Squibb)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Zerit Powder, for solution 200 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 2020-10-13 EU 
Zerit Capsule, gelatin coated 30 mg/1 Oral Physicians Total Care, Inc. 1994-06-24 2010-06-30 US 
Zerit Capsule 30 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 2020-10-13 EU Zerit Capsule, gelatin coated 40 mg/1 Oral State of Florida DOH Central Pharmacy 2009-07-01 Not applicable US Zerit Capsule 20 mg Oral Bristol Myers Squibb Pharma Eeig 2016-09-08 2020-10-13 EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Stavudine Capsule 20 mg/1 Oral Rising Pharmaceuticals, Inc. 2008-12-29 Not applicable US Stavudine Capsule 40 mg/1 Oral State of Florida DOH Central Pharmacy 2009-07-01 Not applicable US Stavudine Capsule 30 mg/1 Oral Aurobindo Pharma Limited 2008-12-29 Not applicable US Stavudine Capsule 30 mg/1 Oral Camber Pharmaceuticals 2008-12-29 Not applicable US Stavudine For solution 1 mg/1mL Oral Cipla Ltd. 2009-03-20 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image จีพีโอเวียร์ เอส 30 Stavudine (30 MG) + Lamivudine (150 MG) + Nevirapine (200 MG) องค์การเภสัชกรรม 2003-11-14 Not applicable Thailand 
Categories
- ATC Codes
- J05AF04 — Stavudine
- J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Agents Causing Muscle Toxicity
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antimetabolites
- Antiviral Agents
- Antivirals for Systemic Use
- Antivirals used in combination for the treatment of HIV infections
- Deoxyribonucleosides
- Dideoxynucleosides
- Direct Acting Antivirals
- Enzyme Inhibitors
- 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
- Pyrimidine Nucleosides
- Pyrimidines
- Reverse Transcriptase Inhibitors
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Nucleoside and nucleotide analogues
- Sub Class
- Not Available
- Direct Parent
- Nucleoside and nucleotide analogues
- Alternative Parents
- Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Dihydrofurans / Ureas / Lactams / Oxacyclic compounds / Azacyclic compounds / Primary alcohols show 4 more
- Substituents
- Alcohol / Aromatic heteromonocyclic compound / Azacycle / Dihydrofuran / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organic molecular entity, dihydrofuran, nucleoside analogue (CHEBI:63581)
- Affected organisms
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- BO9LE4QFZF
- CAS number
- 3056-17-5
- InChI Key
- XNKLLVCARDGLGL-JGVFFNPUSA-N
- InChI
- InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1
- IUPAC Name
- 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O
References
- Synthesis Reference
Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla, "Process for the Large Scale Production of Stavudine." U.S. Patent US20080312428, issued December 18, 2008.
US20080312428- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014787
- KEGG Drug
- D00445
- KEGG Compound
- C07312
- PubChem Compound
- 18283
- PubChem Substance
- 46506943
- ChemSpider
- 17270
- BindingDB
- 50013111
- 59763
- ChEBI
- 63581
- ChEMBL
- CHEMBL991
- ZINC
- ZINC000000137884
- Therapeutic Targets Database
- DAP000172
- PharmGKB
- PA451494
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Stavudine
- FDA label
- Download (289 KB)
- MSDS
- Download (36.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Diagnostic AIDS-Related Opportunistic Infections / Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Diagnostic Cardiovascular Disease (CVD) / HIV Lipodystrophy Syndrome 1 4 Completed Diagnostic Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies 1 4 Completed Treatment Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Bristol myers squibb co
- Aurobindo pharma ltd
- Hetero drugs ltd
- Matrix laboratories ltd
- Mylan pharmaceuticals inc
- Bristol myers squibb co pharmaceutical research institute
- Cipla ltd
- Packagers
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Bristol-Myers Squibb Co.
- Camber Pharmaceuticals Inc.
- Cipla Ltd.
- DAVA Pharmaceuticals
- Dept Health Central Pharmacy
- Dispensing Solutions
- E.R. Squibb and Sons LLC
- Greenstone LLC
- Hetero Drugs Ltd.
- Kaiser Foundation Hospital
- Matrix Laboratories Ltd.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Nucare Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Remedy Repack
- Tya Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral Capsule, coated Oral 40 mg Tablet, film coated Oral Capsule, coated Oral 30 mg Tablet Capsule Oral 15 mg/1 Capsule Oral 20 mg/1 Capsule Oral 30 mg/1 Capsule Oral 40 mg/1 For solution Oral 1 mg/1mL Powder, for solution Oral 1 mg/1mL Solution Oral 1 mg/1mL Capsule, gelatin coated Oral 15 mg/1 Capsule, gelatin coated Oral 20 mg/1 Capsule, gelatin coated Oral 30 mg/1 Capsule, gelatin coated Oral 40 mg/1 Powder, for solution Oral 1 mg / mL Powder, for solution Oral 200 MG Capsule Oral 15 mg Capsule Oral 20 mg Capsule Oral 40 mg Capsule, coated Oral 15 mg Capsule, coated Oral 20 mg Powder, for solution Oral 100 mg Capsule Oral 30 mg - Prices
Unit description Cost Unit Zerit 1 mg/ml Solution 200ml Bottle 88.11USD bottle Zerit 40 mg capsule 7.75USD capsule Zerit 30 mg capsule 7.61USD capsule Zerit 20 mg capsule 7.17USD capsule Stavudine 40 mg capsule 6.99USD capsule Zerit 15 mg capsule 6.89USD capsule Stavudine 30 mg capsule 6.72USD capsule Stavudine 20 mg capsule 6.33USD capsule Stavudine 15 mg capsule 6.08USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7135465 Yes 2006-11-14 2023-08-18 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 159-160 °C Not Available water solubility 5-10 g/100 mL at 21 °C Not Available logP -0.72 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 40.5 mg/mL ALOGPS logP -0.73 ALOGPS logP -0.23 Chemaxon logS -0.74 ALOGPS pKa (Strongest Acidic) 9.95 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 78.87 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 55.32 m3·mol-1 Chemaxon Polarizability 21.33 Å3 Chemaxon Number of Rings 2 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 + 0.9889 Blood Brain Barrier + 0.9381 Caco-2 permeable - 0.8958 P-glycoprotein substrate Non-substrate 0.7949 P-glycoprotein inhibitor I Non-inhibitor 0.9073 P-glycoprotein inhibitor II Non-inhibitor 0.7979 Renal organic cation transporter Non-inhibitor 0.9226 CYP450 2C9 substrate Non-substrate 0.6707 CYP450 2D6 substrate Non-substrate 0.8872 CYP450 3A4 substrate Non-substrate 0.6011 CYP450 1A2 substrate Non-inhibitor 0.9336 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9269 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9445 Ames test Non AMES toxic 0.7275 Carcinogenicity Non-carcinogens 0.8131 Biodegradation Not ready biodegradable 0.6132 Rat acute toxicity 1.7802 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9413 hERG inhibition (predictor II) Non-inhibitor 0.9375
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004i-9710000000-ec1b8accee7609d895af Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0059-6910000000-ee6276bb4983704d536c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0290000000-12b63ee41b4c51c88333 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-053r-9300000000-ac384902323df1ff4053 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-9400000000-c72ca17c2cd4c5d99043 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a5c-9600000000-73308caa87c5d7c1fac1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9600000000-f1ede0bee7340eda0bbd Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.3054758 predictedDarkChem Lite v0.1.0 [M-H]- 158.46 predictedDarkChem Lite v0.1.0 [M-H]- 157.8131758 predictedDarkChem Lite v0.1.0 [M-H]- 150.8308 predictedDeepCCS 1.0 (2019) [M+H]+ 159.9202758 predictedDarkChem Lite v0.1.0 [M+H]+ 161.3 predictedDarkChem Lite v0.1.0 [M+H]+ 158.5818758 predictedDarkChem Lite v0.1.0 [M+H]+ 153.22636 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.2775758 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.94 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.5629758 predictedDarkChem Lite v0.1.0 [M+Na]+ 159.13899 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum 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
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- 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
- Pyrimidine- and adenine-specific:sodium symporter activity
- Specific Function
- Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine)....
- Gene Name
- SLC28A1
- Uniprot ID
- O00337
- Uniprot Name
- Sodium/nucleoside cotransporter 1
- Molecular Weight
- 71583.18 Da
References
- Cano-Soldado P, Lorrayoz IM, Molina-Arcas M, Casado FJ, Martinez-Picado J, Lostao MP, Pastor-Anglada M: Interaction of nucleoside inhibitors of HIV-1 reverse transcriptase with the concentrative nucleoside transporter-1 (SLC28A1). Antivir Ther. 2004 Dec;9(6):993-1002. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54