Dolutegravir
Übersicht
Beschreibung
Dolutegravir ist ein antiretrovirales Medikament, das zur Behandlung von HIV/AIDS eingesetzt wird. Es wird als HIV-Integrase-Strangtransfer-Inhibitor klassifiziert, der die Funktion des HIV-Integrase-Enzyms blockiert, das für die Virusreplikation notwendig ist. This compound wurde 2013 in den Vereinigten Staaten für den medizinischen Gebrauch zugelassen und ist in der Liste der unentbehrlichen Arzneimittel der Weltgesundheitsorganisation enthalten .
2. Herstellungsmethoden
Synthetische Routen und Reaktionsbedingungen: Die Synthese von this compound umfasst mehrere Schritte, beginnend mit der Konstruktion eines Pyridonrings. Diesem folgt eine Cyclisierung unter Verwendung von 3-®-Amino-1-butanol und mehreren sequenziellen chemischen Transformationen. Der Prozess kann durch den Einsatz von Durchflusschemie optimiert werden, was die Reaktionszeit erheblich verkürzt und die Ausbeute verbessert .
Industrielle Produktionsmethoden: Die industrielle Produktion von this compound setzt häufig Hochgeschwindigkeits-Homogenisierungs- und Sonifizierungsverfahren ein, um Nanosuspensionen zu erzeugen. Diese Verfahren verbessern die Löslichkeit und Bioverfügbarkeit des Medikaments, wodurch es bei der Behandlung HIV-positiver Personen effektiver wird .
Wirkmechanismus
Dolutegravir is an HIV-1 antiviral agent. It inhibits HIV integrase by binding to the active site and blocking the strand transfer step of retroviral DNA integration in the host cell. The strand transfer step is essential in the HIV replication cycle and results in the inhibition of viral activity. This compound has a mean EC50 value of 0.5 nM (0.21 ng/mL) to 2.1 nM (0.85 ng/mL) in peripheral blood mononuclear cells (PBMCs) and MT-4 cells.
This compound inhibits HIV integrase by binding to the integrase active site and blocking the strand transfer step of retroviral deoxyribonucleic acid (DNA) integration which is essential for the HIV replication cycle. Strand transfer biochemical assays using purified HIV-1 integrase and pre-processed substrate DNA resulted in IC50 values of 2.7 nM and 12.6 nM.
Biochemische Analyse
Biochemical Properties
Dolutegravir interacts with the HIV-1 integrase, an enzyme that facilitates the integration of the viral genome into the host cell . By blocking the strand transfer step of this integration, this compound prevents the replication of the virus . The effect of this compound has no homology in human host cells, which contributes to its excellent tolerability and minimal toxicity .
Cellular Effects
This compound exerts its effects on various types of cells infected with HIV. It influences cell function by inhibiting the integration of the viral genome into the host cell’s DNA, thereby preventing the replication of the virus and the subsequent production of new virus particles . This disruption in the viral life cycle can impact cell signaling pathways, gene expression, and cellular metabolism .
Molecular Mechanism
This compound acts at the molecular level by binding to the active site of the HIV-1 integrase enzyme . This binding interaction inhibits the enzyme’s ability to integrate the viral genome into the host cell’s DNA, a crucial step in the viral replication process . As a result, this compound effectively prevents the proliferation of the virus within the host.
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound have been observed over time. This compound has shown to maintain its stability and effectiveness over extended periods . Long-term effects on cellular function observed in in vitro or in vivo studies include sustained inhibition of viral replication .
Dosage Effects in Animal Models
The effects of this compound have been studied in animal models, with varying dosages showing different effects . At therapeutic doses, this compound has been shown to effectively inhibit viral replication. At higher doses, potential toxic or adverse effects may occur .
Metabolic Pathways
This compound is metabolized primarily through the uridine diphosphate glucuronosyltransferase 1A1 (UGT1A1) pathway and to a lesser extent, by the cytochrome P450 (CYP) 3A4 pathway . These metabolic pathways allow for the breakdown and elimination of this compound from the body.
Transport and Distribution
This compound is distributed within cells and tissues primarily through passive diffusion The distribution of this compound is not limited to specific tissues or cells, allowing it to exert its antiviral effects broadly within the body .
Subcellular Localization
The subcellular localization of this compound is not well defined as it does not target specific compartments or organelles within the cell. Given its mechanism of action, it is likely that this compound localizes to the nucleus where it can interact with the HIV-1 integrase enzyme and inhibit the integration of the viral genome into the host cell’s DNA .
Vorbereitungsmethoden
Synthetic Routes and Reaction Conditions: The synthesis of Dolutegravir involves multiple steps, starting with the construction of a pyridone ring. This is followed by cyclization using 3-®-amino-1-butanol and several sequential chemical transformations. The process can be optimized using continuous flow chemistry, which significantly reduces reaction time and improves yield .
Industrial Production Methods: Industrial production of this compound often employs high-speed homogenization and probe sonication techniques to create nanosuspensions. These methods enhance the solubility and bioavailability of the drug, making it more effective in treating HIV-positive individuals .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Dolutegravir unterliegt verschiedenen chemischen Reaktionen, darunter:
Oxidation: Umfasst die Addition von Sauerstoff oder die Entfernung von Wasserstoff.
Reduktion: Umfasst die Addition von Wasserstoff oder die Entfernung von Sauerstoff.
Substitution: Umfasst den Austausch eines Atoms oder einer Atomgruppe durch ein anderes.
Häufige Reagenzien und Bedingungen: Häufige Reagenzien, die in diesen Reaktionen verwendet werden, umfassen Oxidationsmittel wie Kaliumpermanganat und Reduktionsmittel wie Lithiumaluminiumhydrid. Reaktionsbedingungen beinhalten oft kontrollierte Temperaturen und pH-Werte, um optimale Ergebnisse zu gewährleisten .
Hauptprodukte, die gebildet werden: Die Hauptprodukte, die aus diesen Reaktionen gebildet werden, umfassen verschiedene Zwischenprodukte, die weiterverarbeitet werden, um die endgültige this compound-Verbindung zu erhalten .
Wissenschaftliche Forschungsanwendungen
Dolutegravir hat eine breite Palette an Anwendungen in der wissenschaftlichen Forschung:
Chemie: Wird als Modellverbindung in der Untersuchung von Integrase-Inhibitoren und deren Wirkmechanismen verwendet.
Biologie: Hilft beim Verständnis des Replikationsprozesses von HIV und der Rolle von Integrase-Enzymen.
Medizin: Wird häufig zur Behandlung von HIV/AIDS eingesetzt, sowohl als Einzelwirkstoff als auch in Kombination mit anderen Antiretroviralen.
Industrie: Wird bei der Entwicklung neuer Arzneimittelformulierungen und -verabreichungssysteme eingesetzt, um die Bioverfügbarkeit und Wirksamkeit zu verbessern
5. Wirkmechanismus
This compound hemmt die Replikation von HIV-1, indem es an die aktive Stelle des Integrase-Enzyms bindet. Dies verhindert den Strangtransfer-Schritt der retroviralen DNA-Integration in das Genom der Wirtszelle, der für die Virusreplikation unerlässlich ist. Durch die Blockierung dieses Schrittes hemmt this compound effektiv die Virusaktivität und reduziert die Viruslast im Körper des Patienten .
Ähnliche Verbindungen:
Raltegravir: Der erste Integrase-Inhibitor, der zur Behandlung von HIV zugelassen wurde.
Elvitegravir: Ein weiterer Integrase-Inhibitor, der eine pharmakologische Verstärkung erfordert.
Bictegravir: Ein neuerer Integrase-Inhibitor mit vergleichbarer Wirksamkeit wie this compound.
Cabotegravir: Kürzlich zugelassener Integrase-Inhibitor mit einer langwirksamen Formulierung
Einzigartigkeit von this compound: this compound zeichnet sich durch seine hohe Wirksamkeit, minimale Arzneimittelwechselwirkungen und die Möglichkeit aus, ohne pharmakologische Verstärkung verabreicht zu werden. Es behält auch die Aktivität gegen einige HIV-Stämme bei, die gegen andere Integrase-Inhibitoren resistent sind, was es zu einer wertvollen Option in der HIV-Behandlung macht .
Vergleich Mit ähnlichen Verbindungen
Raltegravir: The first integrase inhibitor approved for HIV treatment.
Elvitegravir: Another integrase inhibitor that requires pharmacologic boosting.
Bictegravir: A newer integrase inhibitor with similar efficacy to Dolutegravir.
Cabotegravir: Recently approved integrase inhibitor with a long-acting formulation
Uniqueness of this compound: this compound stands out due to its high efficacy, minimal drug interactions, and ability to be administered without pharmacologic boosting. It also retains activity against some strains of HIV that are resistant to other integrase inhibitors, making it a valuable option in HIV treatment .
Eigenschaften
IUPAC Name |
(3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-methyl-9,12-dioxo-4-oxa-1,8-diazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-13-carboxamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
RHWKPHLQXYSBKR-BMIGLBTASA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1CCOC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C[C@@H]1CCO[C@@H]2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H19F2N3O5 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID90909356 |
Source
|
| Record name | Dolutegravir | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90909356 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
419.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Solubility |
Slightly soluble |
Source
|
| Record name | Dolutegravir | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08930 | |
| 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) | |
Mechanism of Action |
Dolutegravir is an HIV-1 antiviral agent. It inhibits HIV integrase by binding to the active site and blocking the strand transfer step of retroviral DNA integration in the host cell. The strand transfer step is essential in the HIV replication cycle and results in the inhibition of viral activity. Dolutegravir has a mean EC50 value of 0.5 nM (0.21 ng/mL) to 2.1 nM (0.85 ng/mL) in peripheral blood mononuclear cells (PBMCs) and MT-4 cells., Dolutegravir inhibits HIV integrase by binding to the integrase active site and blocking the strand transfer step of retroviral deoxyribonucleic acid (DNA) integration which is essential for the HIV replication cycle. Strand transfer biochemical assays using purified HIV-1 integrase and pre-processed substrate DNA resulted in IC50 values of 2.7 nM and 12.6 nM. |
Source
|
| Record name | Dolutegravir | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08930 | |
| 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 | Dolutegravir | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8152 | |
| 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. | |
CAS No. |
1051375-16-6 |
Source
|
| Record name | Dolutegravir | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=1051375-16-6 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Dolutegravir [USAN:INN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=1051375166 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Dolutegravir | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08930 | |
| 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 | Dolutegravir | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID90909356 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.237.735 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | DOLUTEGRAVIR | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/DKO1W9H7M1 | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | Dolutegravir | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8152 | |
| 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. | |
Melting Point |
190-193ºC |
Source
|
| Record name | Dolutegravir | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB08930 | |
| 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) | |
Q1: What is the primary target of Dolutegravir?
A1: this compound targets HIV-1 integrase, a viral enzyme crucial for integrating viral DNA into the host cell genome. [, , , , , , , , , , , , , , ]
Q2: How does this compound interact with HIV-1 integrase?
A2: this compound binds to the integrase-DNA complex, specifically at the catalytic core domain, preventing the strand transfer reaction. This interaction blocks the integration of viral DNA into the host cell chromosome, effectively inhibiting viral replication. [, , , , , , , , , , , ]
Q3: What are the downstream effects of this compound's inhibition of HIV-1 integrase?
A3: By preventing viral DNA integration, this compound inhibits the production of new viral particles, leading to a decrease in viral load and suppression of HIV-1 replication. [, , , , , , , , , , , , , , ]
Q4: What is the molecular formula and weight of this compound?
A4: While the provided papers discuss the pharmacokinetics and pharmacodynamics of this compound, they do not explicitly mention its molecular formula or weight. More specific chemical databases would be needed for this information.
Q5: Is there information available on the material compatibility and stability of this compound in various conditions?
A5: The provided papers primarily focus on this compound's activity and behavior within biological systems, with limited information on its material compatibility and stability under various environmental conditions.
Q6: Does this compound exhibit any catalytic properties itself?
A6: this compound acts as an inhibitor of the enzyme HIV-1 integrase and does not possess intrinsic catalytic properties. [, , , , , , , , , , , , , , ]
Q7: Have computational methods been used to study this compound?
A7: Yes, computational modeling has been used to investigate the binding interactions between this compound and HIV-1 integrase. These studies help to understand the structural basis of drug resistance and guide the development of next-generation inhibitors. [, ]
Q8: How do structural modifications of this compound impact its activity?
A8: While the provided papers do not extensively detail SAR studies, they highlight that mutations in the HIV-1 integrase enzyme can lead to this compound resistance. These mutations alter the drug's binding affinity and impact its ability to inhibit viral replication. [, , ]
Q9: What are the formulation strategies employed to enhance this compound's stability and bioavailability?
A9: Research indicates that the co-formulation of this compound with other antiretroviral agents, such as abacavir and lamivudine, offers advantages in terms of patient adherence and simplified treatment regimens. [, , , ]
Q10: Do the provided research papers discuss SHE regulations regarding this compound?
A10: The provided research papers primarily focus on the scientific aspects of this compound, including its mechanism of action, efficacy, and resistance. These papers do not explicitly address SHE (Safety, Health, and Environment) regulations, which would typically be covered in regulatory documents and guidelines.
Q11: How is this compound metabolized and excreted?
A11: this compound is primarily metabolized in the liver, mainly by UDP-glucuronosyltransferase 1A1 (UGT1A1), forming an inactive ether glucuronide as the main metabolite. Other minor metabolic pathways involve CYP3A4-mediated oxidation. Excretion occurs through both fecal (major route) and urinary routes. []
Q12: Are there any clinically significant drug-drug interactions with this compound?
A12: Yes, this compound shows clinically relevant drug-drug interactions. Co-administration with certain anticonvulsants, rifampicin (a tuberculosis drug), and atazanavir (another HIV drug) can alter this compound's plasma concentrations, requiring dose adjustments or therapeutic drug monitoring. [, , , ]
Q13: What evidence supports the clinical efficacy of this compound in HIV-infected individuals?
A13: Clinical trials have demonstrated the efficacy and safety of this compound-based regimens for treating HIV-infected individuals, including both treatment-naïve and treatment-experienced populations. These trials show high rates of viral suppression and immunological recovery with this compound. [, , , , , , , , ]
Q14: What are the known mechanisms of resistance to this compound?
A14: Resistance to this compound primarily arises from mutations in the HIV-1 integrase gene. Common mutations include N155H, Q148H/K/R, and G140S/C, which reduce this compound's binding affinity and decrease its inhibitory activity. [, , , ]
Q15: Does this compound exhibit cross-resistance with other antiretroviral drugs?
A15: While this compound demonstrates activity against viruses resistant to first-generation integrase inhibitors (raltegravir and elvitegravir), the emergence of this compound resistance mutations can lead to cross-resistance within the integrase inhibitor class. [, , , ]
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