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    Chemistry

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    Also known as: 3056-17-5, Sanilvudine, Zerit, 2',3'-didehydro-3'-deoxythymidine, Stavudinum, Zerit xr
    Molecular Formula
    C10H12N2O4
    Molecular Weight
    224.21  g/mol
    InChI Key
    XNKLLVCARDGLGL-JGVFFNPUSA-N
    FDA UNII
    BO9LE4QFZF
    Stavudine
    A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.
    Stavudine is a Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of stavudine is as a Nucleoside Reverse Transcriptase Inhibitor.
    1 2D Structure

    Stavudine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
    2.1.2 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
    2.1.3 InChI Key
    XNKLLVCARDGLGL-JGVFFNPUSA-N
    2.1.4 Canonical SMILES
    CC1=CN(C(=O)NC1=O)C2C=CC(O2)CO
    2.1.5 Isomeric SMILES
    CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
    2.2 Other Identifiers
    2.2.1 UNII
    BO9LE4QFZF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2',3' Didehydro 3' Deoxythymidine

    2. 2',3'-didehydro-2',3'-dideoxythmidine

    3. 2',3'-didehydro-3'-deoxythymidine

    4. Bmy 27857

    5. Bmy-27857

    6. Bmy27857

    7. D4t

    8. Stavudine, Monosodium Salt

    9. Zerit

    2.3.2 Depositor-Supplied Synonyms

    1. 3056-17-5

    2. Sanilvudine

    3. Zerit

    4. 2',3'-didehydro-3'-deoxythymidine

    5. Stavudinum

    6. Zerit Xr

    7. D4t

    8. Bmy-27857

    9. Estavudina

    10. Stavudinum [inn-latin]

    11. Estavudina [inn-spanish]

    12. Thymidine, 2',3'-didehydro-3'-deoxy-

    13. 3'-deoxy-2'-thymidinene

    14. Ddethd

    15. 2',3'-didehydro-3'-deoxythimidine

    16. 3'-deoxy-2',3'-didehydrothymidine

    17. Bmy 27857

    18. 1-((2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

    19. Dideoxydidehydrothymidine

    20. 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)thymine

    21. Nsc 163661

    22. Sanilvudine (jan)

    23. Bo9le4qfzf

    24. Stavudine (d4t)

    25. 1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1h,3h)-dione

    26. Stv

    27. Chembl991

    28. Nsc-759897

    29. Zerut Xr

    30. Mls000028546

    31. D-4t

    32. Chebi:63581

    33. 1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione

    34. Nsc-163661

    35. Ncgc00023212-07

    36. Smr000058350

    37. D 4t (nucleoside)

    38. Sanilvudine [jan]

    39. Dsstox_cid_3819

    40. Dsstox_rid_77198

    41. Dsstox_gsid_23819

    42. 1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

    43. Stavudine [usan:ban:inn]

    44. 1-(2,3-dideoxy-.beta.-d-glycero-pent-2-enofuranosyl)thymine

    45. D 4t

    46. Ddetyd

    47. 1-(cis-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)-5-methylpyrimidine-2,4(1h,3h)-dione

    48. 1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

    49. 220020-60-0

    50. Cas-3056-17-5

    51. Zerit(tm)

    52. Zerit (tn)

    53. Hsdb 7338

    54. Sr-01000075802

    55. Unii-bo9le4qfzf

    56. Stavudine (usan/inn)

    57. Brn 0618327

    58. D4t & Gm-csf

    59. 2'-thymidinene, 3'-deoxy-

    60. Nsc163661

    61. Stavudine [usan:usp:inn:ban]

    62. Stavudine (dt4)

    63. Stavudine- Bio-x

    64. D4tmby-27857-3

    65. Stavudine [inn]

    66. Stavudine [mi]

    67. Stavudine [hsdb]

    68. Stavudine [usan]

    69. Opera_id_1281

    70. 3'-deoxythymidin-2'-ene

    71. Stavudine [mart.]

    72. D 1413

    73. Cid_5155

    74. Stavudine [usp-rs]

    75. Stavudine [who-dd]

    76. Stavudine [who-ip]

    77. 1-((2r,5s)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

    78. 3''-deoxy-2''-thymidine

    79. Lopac0_000336

    80. Schembl38661

    81. Stavudine [ema Epar]

    82. Cid_18283

    83. Mls000759504

    84. Mls001055348

    85. Mls001077292

    86. Mls001424091

    87. Mls006011922

    88. Bidd:gt0082

    89. 2',3'-anhydrothymidine; D4t

    90. Stavudine [ep Impurity]

    91. Stavudine [orange Book]

    92. Dtxsid1023819

    93. Stavudine [ep Monograph]

    94. 1-(2,3-dideoxy-beta-d-glycero-2-pentenofuranosyl)thymine

    95. Stavudine [usp Monograph]

    96. Stavudinum [who-ip Latin]

    97. Hms2051o20

    98. Hms2234c10

    99. Hms3039o05

    100. Hms3259l21

    101. Hms3261c13

    102. Hms3428c07

    103. Hms3714n22

    104. Pharmakon1600-01502339

    105. Stavudine (d4t) [vandf]

    106. Stavudine (dt4) [vandf]

    107. Zinc137884

    108. Bcp02952

    109. Hy-b0116

    110. Tox21_110886

    111. Tox21_201393

    112. Tox21_300583

    113. Tox21_500336

    114. Bbl033763

    115. Bdbm50013111

    116. Nsc759897

    117. Stk801888

    118. Akos005622554

    119. Tox21_110886_1

    120. Ac-5263

    121. Ccg-100902

    122. Cs-1872

    123. Db00649

    124. Ks-1115

    125. Lp00336

    126. Nc00152

    127. Nc00684

    128. Sdccgsbi-0050324.p002

    129. Zidovudine Impurity A [who-ip]

    130. 2'',3''-didehydro-3''-deoxythymidine

    131. 3''-deoxy-2'',3''-didehydrothymidine

    132. Ncgc00023212-03

    133. Ncgc00023212-04

    134. Ncgc00023212-05

    135. Ncgc00023212-08

    136. Ncgc00023212-09

    137. Ncgc00023212-10

    138. Ncgc00023212-11

    139. Ncgc00023212-12

    140. Ncgc00023212-13

    141. Ncgc00023212-14

    142. Ncgc00023212-25

    143. Ncgc00023212-30

    144. Ncgc00254372-01

    145. Ncgc00258944-01

    146. Ncgc00261021-01

    147. Stavudine 100 Microg/ml In Acetonitrile

    148. 1-[5-(hydroxymethyl)-2,5-dihydro-2-furanyl]-5-methyl-2,4(1h,3h)-pyrimidinedione & Colony-stimulating Factor 2

    149. Bd164571

    150. Smr000673569

    151. Thymidine, 2',3'-didehydro-, 3'-deoxy-

    152. Zidovudine Impurity A [ep Impurity]

    153. D3580

    154. Eu-0100336

    155. 2'',3''-dideoxy-2'',3''-didehydrothymidine

    156. C07312

    157. D00445

    158. Ab00383018_18

    159. 056s175

    160. Q423984

    161. J-700246

    162. Q-201742

    163. Sr-01000075802-1

    164. Sr-01000075802-4

    165. 2',3'-didehydro-3'-deoxythymidine, >=98% (tlc)

    166. Z1695906749

    167. Stavudine, European Pharmacopoeia (ep) Reference Standard

    168. Stavudine, United States Pharmacopeia (usp) Reference Standard

    169. Thymine, 1-(2,3-dideoxy-beta-d-glycero-pent-2-enofuranosyl)-

    170. 1-(5-hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione

    171. 1-(5-hydroxymethyl-2,5-dihydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione (ddethd)

    172. 1-[(2r,5s)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-methyl-2,4(1h,3h)-pyrimidinedione

    173. 3'- Azido-3'-deoxythymidine & Granulocyte-macrophage Colony-stimulating Factor

    174. Stavudine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 224.21 g/mol
    Molecular Formula C10H12N2O4
    XLogP3-0.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass224.07970687 g/mol
    Monoisotopic Mass224.07970687 g/mol
    Topological Polar Surface Area78.9 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity388
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameStavudine
    PubMed HealthStavudine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelStavudine (d4T), a synthetic thymidine nucleoside analogue, active against the human immunodeficiency virus (HIV). Stavudine Capsules are supplied for oral administration in strengths of 15, 20, 30, and 40 mg of stavudine. Each capsule also contains...
    Active IngredientStavudine
    Dosage FormCapsule; For solution
    Routeoral; Oral
    Strength1mg/ml; 30mg; 15mg; 40mg; 20mg
    Market StatusTentative Approval; Prescription
    CompanyHetero Labs Ltd Iii; Aurobindo Pharma; Cipla; Matrix Labs; Emcure Pharma; Strides Acrolab; Mylan

    2 of 4  
    Drug NameZerit
    PubMed HealthStavudine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelZERIT is the brand name for stavudine (d4T), a synthetic thymidine nucleoside analogue, active against the human immunodeficiency virus (HIV).ZERIT (stavudine) Capsules are supplied for oral administration in strengths of 15, 20, 30, and 40 mg of s...
    Active IngredientStavudine
    Dosage FormCapsule; For solution
    RouteOral
    Strength1mg/ml; 30mg; 15mg; 40mg; 20mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    3 of 4  
    Drug NameStavudine
    PubMed HealthStavudine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelStavudine (d4T), a synthetic thymidine nucleoside analogue, active against the human immunodeficiency virus (HIV). Stavudine Capsules are supplied for oral administration in strengths of 15, 20, 30, and 40 mg of stavudine. Each capsule also contains...
    Active IngredientStavudine
    Dosage FormCapsule; For solution
    Routeoral; Oral
    Strength1mg/ml; 30mg; 15mg; 40mg; 20mg
    Market StatusTentative Approval; Prescription
    CompanyHetero Labs Ltd Iii; Aurobindo Pharma; Cipla; Matrix Labs; Emcure Pharma; Strides Acrolab; Mylan

    4 of 4  
    Drug NameZerit
    PubMed HealthStavudine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelZERIT is the brand name for stavudine (d4T), a synthetic thymidine nucleoside analogue, active against the human immunodeficiency virus (HIV).ZERIT (stavudine) Capsules are supplied for oral administration in strengths of 15, 20, 30, and 40 mg of s...
    Active IngredientStavudine
    Dosage FormCapsule; For solution
    RouteOral
    Strength1mg/ml; 30mg; 15mg; 40mg; 20mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    4.2 Therapeutic Uses

    Stavudine in combination with other antiretroviral agents is indicated for the treatment of HIV-1 infection. Additionally, stavudine is indicated for the treatment of patients with HIV infection who have received prolonged previous treatment with zidovudine. /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 2676

    4.3 Drug Warning

    Lactic acidosis and severe hepatomegaly with steatosis, including some fatalities, have been reported rarely in patients receiving stavudine and also have been reported in patients receiving other NRTIs. Female gender, obesity, and long-term therapy with NRTIs may be risk factors. Fatal lactic acidosis has been reported in pregnant women who received antiretroviral regimens that included both didanosine and stavudine. Stavudine should be used with caution in patients with known risk factors for liver disease; however, lactic acidosis and severe hepatomegaly with steatosis have been reported in patients with no known risk factors. Generalized fatigue, digestive symptoms (nausea, vomiting, abdominal pain, sudden unexplained weight loss), respiratory symptoms (tachypnea, dyspnea), or neurologic symptoms (including motor weakness) might be indicative of lactic acidosis development, and patients should be advised to contact their clinician immediately if these symptoms occur. Stavudine therapy should be discontinued in any patient with clinical or laboratory findings suggestive of lactic acidosis or pronounced hepatotoxicity (which may include hepatomegaly and steatosis even in the absence of marked increases in serum aminotransferase concentrations). Permanent discontinuance of stavudine therapy should be considered in patients with confirmed lactic acidosis. Because an increased risk of potentially fatal hepatotoxicity may occur in patients receiving stavudine in conjunction with didanosine and hydroxyurea, patients receiving such regimens should be closely monitored for signs of hepatotoxicity.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 721

    Lactic acidosis is a serious complication of antiretroviral therapy. Symptomatic hyperlactatemia is a milder form of this syndrome, but its incidence is unclear. In this prospective ongoing observational study of a large cohort of HIV-infected adults, hyperlactataemia was diagnosed in 64 patients. Incidences were 18.3/1000 person-years with antiretroviral therapy, and 35.8/1000 person-years for stavudine (d4T) regimens. Ten of the 64 patients developed lactic acidosis during the first 13 months of treatment (incidence 2.9/1000 treated person-years). In four of ten patients, symptoms were absent or mild. More patients on d4T first-line therapy developed lactic acidosis than patients previously treated with other drugs (p = 0.008). Despite the occurrence of one death, the subsequent outcome for the remaining patients was favourable after antiretroviral therapy was stopped and supportive treatment with vitamins and antioxidants initiated. The early diagnosis of cases was the result of great vigilance and, combined with routine measurements of the anion gap, might be the most crucial factor explaining the low mortality rate observed here.

    PMID:12942856 Gerard Y et al; Therapie 58 (2): 153-8 (2003)

    Potentially severe peripheral neuropathy, manifested by numbness, tingling, or pain in the hands or feet, has been reported in about 52% of patients receiving stavudine alone and in 8-21% of patients receiving stavudine in conjunction with other antiretroviral agents (indinavir and either lamivudine or didanosine). Stavudine-associated peripheral neuropathy appears to be dose-related, and has been reported most frequently in patients with advanced HIV, patients with a history of peripheral neuropathy, or patients receiving other neurotoxic drugs, including didanosine. Symptoms of peripheral neuropathy generally resolve if stavudine therapy is promptly discontinued; however, symptoms may worsen temporarily in some patients following discontinuance of the drug. If such symptoms resolve completely, patients may tolerate resumption of stavudine therapy using a reduced dosage. If neuropathy recurs after stavudine therapy is reinitiated, consideration should be given to permanently discontinuing the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 720

    Pancreatitis, which has been fatal in some cases, has occurred in patients receiving stavudine in conjunction with didanosine (with or without hydroxyurea) and has been reported in both treatment-naive and previously treated patients, regardless of degree of immunosuppression. In an early clinical study evaluating stavudine, pancreatitis was observed in less than 1% of adult patients receiving stavudine monotherapy. Patients receiving didanosine in conjunction with stavudine (with or without hydroxyurea) may be at increased risk of pancreatitis; there have been at least 2 fatalities related to pancreatitis in patients receiving didanosine concomitantly with stavudine, indinavir, and hydroxyurea. There also has been at least one death related to pancreatitis in a patient receiving didanosine in conjunction with stavudine and nelfinavir. Stavudine, didanosine, hydroxyurea, and any other agent toxic to the pancreas should be discontinued in any patient who develops suspected pancreatitis.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 720

    For more Drug Warnings (Complete) data for STAVUDINE (20 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment of human immunovirus (HIV) infections.

    FDA Label

    * Hard capsules:

    Zerit is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-infected adult patients and paediatric patients (over the age of three months) only when other antiretrovirals can not be used. The duration of therapy with Zerit should be limited to the shortest time possible.

    * Powder for oral solution:

    Zerit is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-infected adult patients and paediatric patients (from birth) only when other antiretrovirals can not be used. The duration of therapy with Zerit should be limited to the shortest time possible.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    Antimetabolites

    Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

    Reverse Transcriptase Inhibitors

    Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    STAVUDINE
    5.3.2 FDA UNII
    BO9LE4QFZF
    5.3.3 Pharmacological Classes
    Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
    5.4 ATC Code

    J05AF04

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

    J05AF04 - Stavudine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).

    Volume of Distribution

    46 21 L

    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]

    Stavudine is rapidly absorbed following oral administration, and peak plasma concentrations of the drug are attained within 1 hour after the dose. Oral bioavailability of stavudine is reported to be about 86% in adults and 77% in pediatric patients 5 weeks to 15 years of age.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    Data from single- and multiple-dose studies indicate that peak plasma concentrations and AUC of stavudine increase in proportion to dose over the dosage range 0.03 -4 mg/kg; there is no evidence that accumulation occurs following multiple doses.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    Binding of stavudine to serum proteins is negligible over the concentration range of 0.01-11.4 ug/mL.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    Distribution of stavudine into body tissues and fluids has not been fully characterized. The apparent volume of distribution of stavudine following a single oral dose averages 66 L in HIV-infected adults. Following a single IV dose in HIV-infected individuals, the volume of distribution is 58 L in adults and 0.73 L/kg in pediatric patients 5 weeks to 15 years of age.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    For more Absorption, Distribution and Excretion (Complete) data for STAVUDINE (12 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase.

    The metabolic fate of stavudine has not been elucidated in humans. Intracellularly, in both virus-infected and uninfected cells, stavudine is converted to stavudine monophosphate by cellular thymidine kinase. The monophosphate is subsequently converted to stavudine diphosphate and then to stavudine triphosphate, presumably by the same cellular kinases involved in the metabolism of zidovudine. Intracellular (host cell) conversion of stavudine to the triphosphate derivative is necessary for the antiviral activity of the drug.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    5.7 Biological Half-Life

    0.8-1.5 hours (in adults)

    Intracellular half life of stavudine triphosphate: Approximately 3.5 hours. /Stavudine triphosphate/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 2676

    Normal renal function: Adults: 0.8 to 1.5 hours (intravenous); 1.14 to 1.74 hours (oral). Children (5 weeks to 15 years): 0.83 to 1/39 hours (intravenous); 0.7 to 1.22 hours (oral). Neonates (14 to 28 days) 1.3 to 1.88 (oral). Neonates (day of birth): 3.26 to 7.28 (oral). Renal function impairment (creatinine clearance 26 to 50 mL/min): Approximately 1 to 6 hours. Renal function impairment (creatinine clearance 9 to 25 mL/min): Approximately 3.7 to 5.5 hours. Renal function impairment (creatinine clearance > 50 mL/min): Approximately 1.3 to 2.1 hours. Renal function impairment (hemodialysis patients): Approximately 4.0 to 6.8 hours.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 2676

    Twenty-two patients were studied after the first oral dose of 0.67, 1.33, 2.67, or 4 mg/kg of body weight; 17 of them underwent an additional steady-state pharmacokinetic evaluation after thrice-daily dosing of the above doses. ... The mean values for plasma elimination half-life ranged from 1 to 1.6 hr.

    PMID:1323615 Dudley MN et al; J Infect Dis 166 (3):480-5 (1992)

    5.8 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.

    Enzymatic conversion of stavudine to d4T-triphosphate appears to be complex, involving several steps and enzymes. Stavudine is first converted to dideoxydidehydrothymidine-5'-monophosphate (d4T-monophosphate) by thymidine kinase. Subsequently, d4T-monophosphate is converted to dideoxydidehydrothymidine-5'-diphosphate (d4T-diphosphate), and then to d4T-triphosphate, presumably by the same cellular kinases involved in the metabolism of zidovudine. ... d4T-Triphosphate is a structural analog of thymidine triphosphate, the natural substrate for viral RNA-directed DNA polymerase. ... d4T-triphosphate appears to compete with thymidine triphosphate for viral RNA-directed DNA polymerase and incorporation into viral DNA. Following incorporation of d4T-triphosphate into the viral DNA chain instead of thymidine triphosphate, synthesis is terminated prematurely because the absence of the 3'-hydroxy group on the drug prevents further 5' to 3' phosphodiester linkages.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

    Stavudine is phosphorylated by cellular kinases to the active metabolite stavudine triphosphate. Stavudine triphosphate inhibits the activity of HIV reverse transcriptase both by competing with the natural substrate deoxythymidine triphosphate (Ki =0.0083 to 0.032 uM), and by its incorporation into viral DNA causing a termination of DNA chain elongation because stavudine lacks the essential 3'-OH group. Stavudine triphosphate inhibits cellular DNA polymerase beta and gamma, and markedly reduces the synthesis of mitochondrial DNA.

    Physicians Desk Reference. 59th ed. Thomson PDR. Montvale, NJ 2005., p. 1087

    d4T-Triphosphate can bind to and inhibit some mammalian cellular DNA polymerases, particularly beta- and gamma-polymerases, in vitro, and markedly reduce the synthesis of mitochondrial DNA. ...gamma-polymerase, an enzyme involved in mitochondrial DNA synthesis, is the polymerase most susceptible to inhibition. However, d4T-triphosphate and other dideoxynucleoside triphosphates appear to have much greater affinity for viral RNA-directed DNA polymerase than for mammalian DNA polymerases. ... Inhibition of beta- and gamma-polymerases by these drugs may account, to some extent, for the toxic effects associated with stavudine and other nucleosides in humans.

    McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 723

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