Stavudine
Übersicht
Beschreibung
Stavudine is a nucleoside analog reverse-transcriptase inhibitor (NRTI) used primarily in the treatment of Human Immunodeficiency Virus (HIV) infection. It was first described in 1966 and approved for use in the United States in 1994 . This compound works by inhibiting the activity of HIV-1 reverse transcriptase, an enzyme crucial for the replication of the virus .
Wirkmechanismus
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 this compound to d4T-triphosphate appears to be complex, involving several steps and enzymes. This compound 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.
This compound is phosphorylated by cellular kinases to the active metabolite this compound triphosphate. This compound 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 this compound lacks the essential 3'-OH group. This compound 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 this compound and other nucleosides in humans.
Wissenschaftliche Forschungsanwendungen
Stavudin hat verschiedene Anwendungen in der wissenschaftlichen Forschung, darunter:
Chemie: Wird als Modellverbindung verwendet, um Nukleosid-Analoga und ihre chemischen Eigenschaften zu untersuchen.
Biologie: Wird in der Forschung zur Virusreplikation und Entwicklung von antiviralen Medikamenten eingesetzt.
Medizin: Wird in klinischen Studien eingesetzt, um seine Wirksamkeit und Sicherheit bei der Behandlung von HIV-Infektionen zu beurteilen.
5. Wirkmechanismus
Stavudin hemmt die Aktivität der HIV-1-Reverse-Transkriptase, indem es mit dem natürlichen Substrat Desoxyguanosintriphosphat (dGTP) konkurriert und in die virale DNA eingebaut wird. Dieser Einbau führt zur Beendigung der DNA-Synthese und verhindert die Replikation des Virus . Stavudin wird zu aktiven Metaboliten phosphoryliert, die um den Einbau in die virale DNA konkurrieren und das Enzym kompetitiv hemmen .
Biochemische Analyse
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
This compound 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, this compound 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
This compound 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
This compound 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 .
Vorbereitungsmethoden
Synthetische Wege und Reaktionsbedingungen: Stavudin kann auf verschiedene Weise synthetisiert werden. Eine gängige Methode beinhaltet die Umwandlung von Thymidin in Stavudin über eine Reihe von chemischen Reaktionen. Der Prozess beinhaltet typischerweise die Verwendung von Reagenzien wie Triphosgen und Pyridin, gefolgt von Entschützungsstufen, um das Endprodukt zu erhalten .
Industrielle Produktionsmethoden: In industriellen Umgebungen wird Stavudin unter Verwendung chemischer Synthesetechniken im großen Maßstab hergestellt. Der Prozess umfasst mehrere Schritte, darunter den Schutz von funktionellen Gruppen, selektive Reaktionen zur Einführung der gewünschten Modifikationen und Reinigungsschritte, um hochreines Stavudin zu erhalten .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Stavudin durchläuft verschiedene chemische Reaktionen, darunter:
Oxidation: Stavudin kann oxidiert werden, um verschiedene Metaboliten zu bilden.
Reduktion: Reduktionsreaktionen können die funktionellen Gruppen in Stavudin modifizieren.
Substitution: Substitutionsreaktionen können neue funktionelle Gruppen in das Stavudin-Molekül einführen.
Häufige Reagenzien und Bedingungen:
Oxidation: Häufige Oxidationsmittel sind Kaliumpermanganat und Wasserstoffperoxid.
Reduktion: Reduktionsmittel wie Natriumborhydrid werden verwendet.
Substitution: Reagenzien wie Alkylhalogenide und Nukleophile werden eingesetzt.
Hauptsächlich gebildete Produkte: Die wichtigsten Produkte, die aus diesen Reaktionen entstehen, sind verschiedene Metaboliten und modifizierte Stavudinderivate, die unterschiedliche pharmakologische Eigenschaften haben können .
Vergleich Mit ähnlichen Verbindungen
Stavudin ähnelt anderen Nukleosid-Analogon-Reverse-Transkriptase-Inhibitoren wie Didanosin und Zalcitabin. Es hat jedoch einzigartige Eigenschaften, die es von diesen Verbindungen unterscheiden:
Didanosin: Ebenfalls ein NRTI, unterscheidet sich aber in seiner chemischen Struktur und Pharmakokinetik.
Zalcitabin: Ein weiterer NRTI mit einem anderen Wirkmechanismus und Nebenwirkungsprofil.
Liste ähnlicher Verbindungen:
- Didanosin
- Zalcitabin
- Zidovudin
Die einzigartige chemische Struktur und der Wirkmechanismus von Stavudin machen es zu einer wertvollen Verbindung bei der Behandlung von HIV-Infektionen und einem Gegenstand laufender wissenschaftlicher Forschung.
Eigenschaften
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 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID1023819 |
Source
|
| Record name | Stavudine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID1023819 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20175 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| 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. | |
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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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20175 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Stavudine | |
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| URL | https://www.drugbank.ca/drugs/DB00649 | |
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| Record name | STAVUDINE | |
| 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. | |
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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 | |
| 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. | |
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. |
Source
|
| Record name | Stavudine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00649 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | STAVUDINE | |
| 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. | |
Color/Form |
White to off white crystalline solid, Colorless granular solid from ethanol/benzene | |
CAS No. |
3056-17-5 |
Source
|
| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20175 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Stavudine | |
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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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| 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. | |
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Melting Point |
318 to 320 °F (NTP, 1992), 159-160 °C, 165-166 °C, 159 - 160 °C |
Source
|
| Record name | 2',3'-DIDEHYDRO-3'-DEOXYTHYMIDINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20175 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Stavudine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00649 | |
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| Record name | STAVUDINE | |
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| 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. | |
Retrosynthesis Analysis
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| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
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![3-[(4S)-5-Oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinolin-4-YL]benzonitrile](/img/structure/B1682409.png)
![2-ethyl-4-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methoxy]-5,6,7,8-tetrahydroquinoline;hydrochloride](/img/structure/B1682413.png)
