司他夫定
描述
司他夫定是一种核苷类似物逆转录酶抑制剂 (NRTI)，主要用于治疗人类免疫缺陷病毒 (HIV) 感染。 它首次在 1966 年被描述，并于 1994 年在美国获准使用 。 司他夫定通过抑制 HIV-1 逆转录酶的活性起作用，该酶对于病毒的复制至关重要 .
作用机制
司他夫定通过与天然底物脱氧鸟苷三磷酸 (dGTP) 竞争并掺入病毒 DNA 中来抑制 HIV-1 逆转录酶的活性。 这种掺入会导致 DNA 合成的终止，从而阻止病毒复制 。 司他夫定被磷酸化为活性代谢产物，这些代谢产物竞争性地掺入病毒 DNA 中，从而抑制酶的活性 .
科学研究应用
Clinical Efficacy
Stavudine Monotherapy vs. Zidovudine
A randomized controlled trial involving 822 HIV-infected adults compared stavudine monotherapy with zidovudine. Results indicated that patients receiving stavudine had a lower rate of clinical progression (26 per 100 person-years) compared to those on zidovudine (32 per 100 person-years), demonstrating a relative risk reduction of 25% for clinical endpoints in the stavudine group (P = 0.03) . The study highlighted the drug's effectiveness across different CD4+ cell strata and clinical stages of HIV disease.
Combination Therapy
In combination therapies, stavudine has been evaluated alongside other antiretroviral agents. A notable trial compared the efficacy of stavudine combined with lamivudine and efavirenz against tenofovir DF with similar combinations. The findings suggested that both regimens effectively reduced HIV RNA levels to below 400 copies/mL, although tenofovir showed a more favorable safety profile .
Pharmacokinetics and Dosage Adjustments
Dose Reduction Studies
Research has indicated that reducing the dose of stavudine can mitigate some adverse effects while maintaining viral suppression. A study demonstrated that switching from a standard 40 mg dose to a reduced 30 mg dose improved mitochondrial function indicators and decreased serum lactate levels without compromising HIV control . This finding is crucial for managing metabolic toxicities often associated with NRTIs.
Adverse Effects and Management
Neuropathy and Metabolic Toxicity
One of the significant concerns with stavudine use is its association with peripheral neuropathy, which occurred in 12% of patients compared to only 4% in those receiving zidovudine . Additionally, metabolic side effects such as lactic acidosis and lipodystrophy have been reported. Strategies to mitigate these effects include careful monitoring and dose adjustments.
Comparative Effectiveness
Phasing Out Stavudine
Recent trends indicate a shift away from stavudine towards newer agents like tenofovir due to concerns regarding toxicity. A study showed that patients on tenofovir had significantly lower rates of drug substitution due to adverse effects compared to those on stavudine . This highlights the ongoing evolution in HIV treatment protocols as newer therapies become available.
Case Studies
- ALBI Trial : This trial assessed the combination of stavudine and didanosine against zidovudine and lamivudine over 24 weeks. The results indicated superior reductions in HIV-1 RNA levels in the stavudine group, reinforcing its efficacy as part of combination therapy .
- Longitudinal Observational Studies : Observations from various cohorts indicated that while stavudine was effective initially, long-term use led to increased rates of side effects, prompting clinicians to consider alternatives like tenofovir or zidovudine .
生化分析
Biochemical Properties
Stavudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) . It is phosphorylated to active metabolites that compete for incorporation into viral DNA . These metabolites inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis .
Cellular Effects
Stavudine influences cell function by inhibiting the activity of HIV-1 reverse transcriptase (RT), an enzyme crucial for the replication of HIV . By competing with the natural substrate dGTP and by its incorporation into viral DNA, Stavudine prevents the formation of the 5’ to 3’ phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated .
Molecular Mechanism
Stavudine exerts its effects at the molecular level by inhibiting the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA . 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 .
Metabolic Pathways
Stavudine is involved in the metabolic pathway of HIV replication. It interacts with the enzyme HIV-1 reverse transcriptase (RT) to inhibit the replication of the virus .
准备方法
合成路线和反应条件： 司他夫定可以通过多种方法合成。一种常见的方法涉及通过一系列化学反应将胸腺嘧啶转化为司他夫定。 该过程通常包括使用三光气和吡啶等试剂，然后进行脱保护步骤以得到最终产物 .
工业生产方法： 在工业环境中，司他夫定是使用大规模化学合成技术生产的。 该过程涉及多个步骤，包括保护官能团、选择性反应以引入所需的修饰以及纯化步骤以获得高纯度的司他夫定 .
化学反应分析
反应类型： 司他夫定会发生各种化学反应，包括：
氧化： 司他夫定可以被氧化形成不同的代谢产物。
还原： 还原反应可以改变司他夫定中的官能团。
取代： 取代反应可以将新的官能团引入司他夫定分子.
常用试剂和条件：
氧化： 常用的氧化剂包括高锰酸钾和过氧化氢。
还原： 使用硼氢化钠等还原剂。
取代： 使用卤代烷和亲核试剂等试剂.
相似化合物的比较
司他夫定与其他核苷类似物逆转录酶抑制剂（如齐多夫定和扎西他滨）相似。 它具有独特的特性，使其与这些化合物区分开来：
齐多夫定： 也是一种 NRTI，但在化学结构和药代动力学方面有所不同。
扎西他滨： 另一种 NRTI，具有不同的作用机制和副作用特征.
类似化合物的清单：
- 齐多夫定
- 扎西他滨
- 叠氮胸苷
司他夫定的独特化学结构和作用机制使其成为治疗 HIV 感染的宝贵化合物，也是正在进行的科学研究的主题。
生物活性
Stavudine, also known as d4T, is a nucleoside reverse transcriptase inhibitor (NRTI) primarily used in the treatment of HIV-1 infection. Its mechanism of action, pharmacokinetics, and associated toxicities have been extensively studied, revealing significant insights into its biological activity.
Stavudine is phosphorylated within cells to active metabolites that competitively inhibit the HIV-1 reverse transcriptase enzyme. This inhibition occurs through two primary mechanisms:
- Competitive Inhibition : Stavudine competes with the natural substrate deoxyguanosine triphosphate (dGTP) for incorporation into viral DNA.
- Chain Termination : Once incorporated, stavudine lacks a 3'-OH group, preventing the formation of the essential 5' to 3' phosphodiester linkage required for DNA chain elongation. This results in termination of viral DNA synthesis .
Pharmacokinetics
Stavudine exhibits rapid absorption following oral administration, with bioavailability ranging from 68% to 104% . It is primarily eliminated through renal clearance and hepatic metabolism, with approximately 40% excreted unchanged in urine . The pharmacokinetic profile suggests that stavudine can be effectively combined with other antiretroviral agents without significant drug interactions .
Efficacy and Dosage
Research has shown that a reduced dosage of stavudine (30 mg twice daily) can maintain efficacy comparable to the standard dose (40 mg twice daily) while reducing adverse effects such as mitochondrial toxicity and bone mineral density loss . A systematic review indicated that lower doses could preserve virological suppression while improving mitochondrial indices in patients .
Table 1: Comparison of Stavudine Dosages and Outcomes
| Dosage (mg) | Efficacy | Mitochondrial Toxicity | Bone Mineral Density Loss |
|---|---|---|---|
| 40 mg | High | Significant | Significant |
| 30 mg | Equivalent | Reduced | Minimal |
Toxicity Profile
Stavudine is associated with several toxicities, including:
- Peripheral Neuropathy : A common side effect, often dose-dependent.
- Hyperlactatemia : Increased lactate levels can lead to lactic acidosis.
- Mitochondrial Toxicity : Changes in mitochondrial DNA content have been observed, particularly in adipose tissue and muscle .
A longitudinal study found that reducing the stavudine dose led to improvements in mitochondrial function, as evidenced by increased fat mtDNA and decreased lactate levels while maintaining HIV suppression .
Case Studies
- Longitudinal Study on Stavudine Toxicity : This study tracked a cohort over several years, identifying peripheral neuropathy as a predominant toxicity. Patients who switched to lower doses reported fewer side effects without loss of virological control .
- Comparative Study with Abacavir : A retrospective analysis compared treatment outcomes in HIV-infected children receiving either stavudine or abacavir. The results demonstrated comparable efficacy but highlighted differences in toxicity profiles, with stavudine showing higher rates of peripheral neuropathy .
属性
IUPAC Name |
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XNKLLVCARDGLGL-JGVFFNPUSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=CN(C(=O)NC1=O)C2C=CC(O2)CO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H12N2O4 |
Source
|
| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20175 | |
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| URL | https://pubchem.ncbi.nlm.nih.gov | |
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DSSTOX Substance ID |
DTXSID1023819 |
Source
|
| Record name | Stavudine | |
| Source | EPA DSSTox | |
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Molecular Weight |
224.21 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
2',3'-didehydro-3'-deoxythymidine appears as white crystalline solid or powder. Odorless. (NTP, 1992), Solid |
Source
|
| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
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| Record name | Stavudine | |
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Solubility |
50 to 100 mg/mL at 70 °F (NTP, 1992), 5-10 g/100 mL at 21 °C, 30 mg/mL in propylene glycol at 23 °C, In water, 83 mg/mL at 23 °C, 4.05e+01 g/L |
Source
|
| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
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Vapor Pressure |
9.5X10-12 mm Hg at 25 °C /Estimated/ |
Source
|
| Record name | STAVUDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7338 | |
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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., 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., 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. |
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| Record name | Stavudine | |
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| Record name | STAVUDINE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7338 | |
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Color/Form |
White to off white crystalline solid, Colorless granular solid from ethanol/benzene | |
CAS No. |
3056-17-5 |
Source
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| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
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| Record name | 1-((2R, 5S)-5-(hydroxymethyl)-2,5-dihydro-2-furanyl)-5-methyl-2,4(1H, 3H)-pyrimidinedione | |
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Melting Point |
318 to 320 °F (NTP, 1992), 159-160 °C, 165-166 °C, 159 - 160 °C |
Source
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| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
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| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7338 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Stavudine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014787 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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