Pentamidin
Übersicht
Beschreibung
Pentamidine is an antimicrobial medication primarily used to treat African trypanosomiasis, leishmaniasis, Balamuthia infections, babesiosis, and to prevent and treat pneumocystis pneumonia in individuals with compromised immune systems . It belongs to the aromatic diamidine family of medications and has been in medical use since 1937 . Pentamidine is available as a generic medication and is included in the World Health Organization’s List of Essential Medicines .
Wirkmechanismus
Target of Action
Pentamidine is an antiprotozoal and antifungal agent . It is primarily used to treat diseases such as African trypanosomiasis, leishmaniasis, Balamuthia infections, babesiosis, and to prevent and treat pneumocystis pneumonia (PCP) in people with poor immune function . It has also been suggested that pentamidine preferentially targets the outer membrane of Gram-negative bacteria .
Mode of Action
It is thought that the drug interferes with nuclear metabolism, leading to the inhibition of the synthesis of DNA, RNA, phospholipids, and proteins . This interference with the cell’s normal functioning can lead to cell death, thus eliminating the infection .
Biochemical Pathways
Pentamidine is believed to interfere with several biochemical pathways. It has been suggested that it binds nucleic acids, with the positively charged amidinium ions directing it towards the negatively charged phosphate backbone . Additionally, it has been shown to inhibit the PI3K/AKT signaling pathway, which plays a crucial role in cell proliferation, migration, and invasion .
Pharmacokinetics
Pentamidine is completely absorbed when given intravenously or intramuscularly . When inhaled through a nebulizer, pentamidine accumulates in the bronchoalveolar fluid of the lungs at a higher concentration compared to injections . The elimination half-life of pentamidine is between 6.4 and 9.4 hours , and it can remain in the system for as long as 8 months after the first injection .
Result of Action
The result of pentamidine’s action is the inhibition of cell proliferation, migration, and invasion, particularly in the case of endometrial cancer cells . It also reduces the expression of MMP-2 and MMP-9, which are involved in the breakdown of extracellular matrix in normal physiological processes such as embryogenesis and tissue remodeling .
Action Environment
The action of pentamidine can be influenced by various environmental factors. For instance, the efficacy of pentamidine can be affected by the patient’s immune status, as it is often used to treat and prevent infections in people with compromised immune systems . Additionally, the method of administration (intravenous, intramuscular, or inhalation) can influence the drug’s distribution and concentration in the body .
Wissenschaftliche Forschungsanwendungen
Pentamidin hat eine breite Palette an Anwendungen in der wissenschaftlichen Forschung:
Medizin: this compound wird häufig zur Behandlung von Infektionskrankheiten wie afrikanischer Trypanosomiasis, Leishmaniose und Pneumocystis-Pneumonie eingesetzt.
5. Wirkmechanismus
Der genaue Wirkmechanismus von this compound ist nicht vollständig geklärt. Es wird vermutet, dass es den Kernstoffwechsel durch Hemmung der Synthese von DNA, RNA, Phospholipiden und Proteinen beeinflusst . This compound bindet über seine positiv geladenen Amidinium-Ionen an Nukleinsäuren, was es zum negativ geladenen Phosphatrückgrat von DNA und RNA lenkt . Diese Wechselwirkung stört die normale Funktion der Nukleinsäuren, was zu den antimikrobiellen Wirkungen des Arzneimittels führt .
Ähnliche Verbindungen:
Dapsone: Wird zur Behandlung von Dermatitis herpetiformis, Lepra und anderen Hauterkrankungen eingesetzt.
Sulfamethoxazol/Trimethoprim: Eine Antibiotika-Kombination zur Behandlung verschiedener bakterieller Infektionen.
Vergleich: this compound ist einzigartig in seiner Fähigkeit, eine breite Palette von Protozoeninfektionen zu behandeln, darunter afrikanische Trypanosomiasis und Leishmaniose, die typischerweise nicht mit Dapsone oder Sulfamethoxazol/Trimethoprim behandelt werden . Darüber hinaus unterscheidet sich der Wirkmechanismus von this compound, der die Hemmung der Nukleinsäuresynthese umfasst, von anderen antimikrobiellen Wirkstoffen .
Biochemische Analyse
Biochemical Properties
Pentamidine interacts with various biomolecules within the cell. It is thought to interfere with nuclear metabolism, inhibiting the synthesis of DNA, RNA, phospholipids, and proteins . This disruption of essential biochemical reactions is believed to contribute to its antifungal and antiprotozoal effects .
Cellular Effects
Pentamidine has significant effects on various types of cells and cellular processes. It is known to cause diabetes mellitus, central nervous system damage, and other toxic effects . In addition, it has been found to reduce mitochondrial protein abundance and trigger progressive loss of kinetoplast DNA and disruption of mitochondrial membrane potential .
Molecular Mechanism
It is believed to exert its effects at the molecular level through binding interactions with biomolecules, enzyme inhibition or activation, and changes in gene expression . For instance, it has been found to inhibit mitosis and cytokinesis .
Temporal Effects in Laboratory Settings
Over time, Pentamidine has been observed to have various effects in laboratory settings. For instance, it has been found to cause hypoglycemia and nephrotoxicity in up to 27% and 25% of treatment courses, respectively .
Dosage Effects in Animal Models
The effects of Pentamidine vary with different dosages in animal models. For instance, it has been found to effectively decrease the burden of Chlamydia trachomatis upon local or systemic application in mice .
Metabolic Pathways
Pentamidine is involved in various metabolic pathways. It is thought to change the metabolism of host cells, impairing chlamydia growth .
Transport and Distribution
Pentamidine is transported and distributed within cells and tissues via various mechanisms. It has been found to be involved in pentamidine transport at the human and mouse blood-brain barrier (BBB) via the organic cation transporter 1 (OCT1) .
Subcellular Localization
Pentamidine localizes in various subcellular compartments. It has been found to localize in parasite nuclei and kDNA, with greater intensity in the latter structure . Furthermore, it also concentrates in non-DNA-containing cytoplasmic organelles, possibly acidocalcisomes .
Vorbereitungsmethoden
Synthesewege und Reaktionsbedingungen: Pentamidin kann durch einen mehrstufigen Prozess synthetisiert werden, bei dem 4,4’-Dihydroxybenzophenon mit Pentamethylenbromid zu 4,4’-Bis(pentamethylendioxy)benzophenon umgesetzt wird. Dieser Zwischenstoff wird dann durch Reaktion mit Ammoniumchlorid und Natriumcyanid zu 4,4’-Bis(pentamethylendioxy)dibenzamidin umgesetzt .
Industrielle Produktionsmethoden: In industriellen Umgebungen wird this compound typischerweise durch Rekonstitution des Arzneimittels mit Wasser für Injektionen hergestellt. Die rekonstituierte Lösung wird dann vor der Verabreichung weiter verdünnt. Bei intravenöser Infusion wird das Arzneimittel über einen Zeitraum von 60 bis 120 Minuten mit einer elektronisch gesteuerten Infusionsvorrichtung verabreicht .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Pentamidin durchläuft verschiedene chemische Reaktionen, darunter Reduktions- und Substitutionsreaktionen. Eine bemerkenswerte Reaktion ist seine elektrochemische Reduktion, die mittels zyklischer Voltammetrie untersucht wurde .
Häufige Reagenzien und Bedingungen:
Reduktion: In einem Phosphatpuffer vom pH-Wert 8,5 erzeugt this compound eine empfindliche Reduktionswelle bei einem Potential von -1,56 V (gegenüber
Substitution: this compound kann Substitutionsreaktionen mit Nukleophilen eingehen, was zur Bildung verschiedener Derivate führt.
Hauptprodukte: Die Hauptprodukte, die aus diesen Reaktionen gebildet werden, umfassen reduzierte Formen von this compound und seine verschiedenen substituierten Derivate .
Vergleich Mit ähnlichen Verbindungen
Dapsone: Used for the treatment of dermatitis herpetiformis, leprosy, and other skin conditions.
Sulfamethoxazole/Trimethoprim: An antibiotic combination used to treat various bacterial infections.
Comparison: Pentamidine is unique in its ability to treat a wide range of protozoal infections, including African trypanosomiasis and leishmaniasis, which are not typically treated with dapsone or sulfamethoxazole/trimethoprim . Additionally, pentamidine’s mechanism of action, involving the inhibition of nucleic acid synthesis, sets it apart from other antimicrobial agents .
Eigenschaften
IUPAC Name |
4-[5-(4-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XDRYMKDFEDOLFX-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=CC=C1C(=N)N)OCCCCCOC2=CC=C(C=C2)C(=N)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H24N4O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID7023431 |
Source
|
| Record name | Pentamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7023431 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
340.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Pentamidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014876 | |
| 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. | |
Solubility |
Complete, Mol wt: 592.69. Hygroscopic, very bitter crystals, mp approx 180 °C. Slight butyric odor. Sol in water (approx 1 in 10 at 25 °C, approx 1 in 4 at 100 °C); sol in glycerol, more readily on warming; slightly sol in alcohol. Insol in ether, acetone, chloroform, liq petr. pH of a 5% w/v soln in water: 4.5 to 6.5. /Isethioante/, 2.36e-02 g/L |
Source
|
| Record name | Pentamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00738 | |
| 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 | PENTAMIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7474 | |
| 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 | Pentamidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014876 | |
| 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. | |
Mechanism of Action |
The mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins., ... Up to now, it has been thought that therapeutic compounds causing QT prolongation are associated with direct block of the cardiac potassium channel human ether a-go-go-related gene (hERG), which encodes the alpha subunit of cardiac I(Kr) currents. /The authors/ show that pentamidine has no acute effects on currents produced by hERG, KvLQT1/mink, Kv4.3, or SCNA5. Cardiac calcium currents and the guinea pig cardiac action potential were also not affected. After overnight exposure, however, pentamidine reduced hERG currents and inhibited trafficking and maturation of hERG with IC(50) values of 5 to 8 uM similar to therapeutic concentrations. Surface expression determined in a chemiluminescence assay was reduced on exposure to 10, 30, and 100 uM pentamidine by about 30, 40, and 70%, respectively. These effects were specific for hERG since expression of hKv1.5, KvLQT1/minK, and Kv4.3 was not altered. In isolated guinea pig ventricular myocytes, 10 uM pentamidine prolonged action potential duration APD(90) from 374.3 or + or - 57.1 to 893.9 + or - 86.2 ms on overnight incubation. I(Kr) tail current density was reduced from 0.61 + or - 0.09 to 0.39 + or - 0.04 pA/pF. /The authors/ conclude that pentamidine prolongs the cardiac action potential by block of hERG trafficking and reduction of the number of functional hERG channels at the cell surface. /The authors/ propose that pentamidine, like arsenic trioxide, produces QT prolongation and torsades de pointes in patients by inhibition of hERG trafficking., ... Inhibition in vitro of trypanosomal mitochondrial topoisomerase II and plasma Ca+2, Mg+2-ATPase also has been reported ... Pentamidine promotes linearization of trypanosome kinetoplast DNA, consistent with its being a type II topoisomerase inhibitor ... The drug also inhibits ATP-dependent topoisomerases in extracts of Pneumocystis carinii ..., Not clearly defined; pentamidine may interfere with incorporation of nucleotides into RNA and DNA and inhibit oxidative phosphorylation and biosynthesis of DNA, RNA, protein, and phospholipid; may also interfere with folate transformation., ... The cytotoxic properties of pentamidine isethionate (2) towards the promastigotes of the protozoan parasite Leishmania infantum /was determined/. The leishmanicidal activity of 2 was 60 times higher after 72 hr of incubation than that of cisplatin. The pentamidine salt 2 induced a higher amount of programmed cell death (PCD) than cisplatin, which is associated with inhibition of DNA synthesis and cell-cycle arrest in the G2/M phase. Circular dichroism (CD) data indicate that binding of 2 to calf-thymus DNA (CT-DNA) induces conformational changes in the DNA double helix, consistent with a B-->A transition. Moreover, the interaction of 2 with ubiquitin led to a 6% increase in the beta-sheet content of the protein as observed by CD spectroscopy. Fluorescence-spectroscopy studies agreed with the CD data, showing that the pentamidine portion of 2 induces a significant decrease in the fluorescence of the Ub residues Phe4 and Phe45 located on the beta-cluster of the molecule, but not of Tyr59 on the alpha-cluster. These data indicate that pentamidine specifically modifies the beta-cluster, i.e., the 'basic face' of ubiquitin. ... /The/ results suggest that the biochemical mechanism of action of pentamidine may be a consequence of its dual binding to DNA and proteins., In this work pentamidine is shown to exhibit characteristics of a cationic uncoupler of oxidative phosphorylation in isolated rat liver mitochondria: it released respiratory control, enhanced the latent ATPase activity, and released the inhibition of State 3 respiration by oligomycin. Maximal stimulation of respiration and ATPase activity was observed at a concentration of pentamidine of 200-300 microM. Higher concentrations had an inhibitory effect on mitochondrial respiration. As it happens with other cationic uncouplers, the uncoupling effect of pentamidine required inorganic phosphate. Pentamidine-induced uncoupling of oxidative phosphorylation was accompanied by an efflux of Ca2+ from the mitochondria and partial collapse of the mitochondrial membrane potential. |
Source
|
| Record name | Pentamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00738 | |
| 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 | PENTAMIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7474 | |
| 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 |
Crystallizes as colorless plates from water | |
CAS No. |
100-33-4 |
Source
|
| Record name | Pentamidine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=100-33-4 | |
| 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. | |
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| Record name | Pentamidine [INN:BAN:DCF] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000100334 | |
| 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 | Pentamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00738 | |
| 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 | pentamidine | |
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| Record name | Pentamidine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID7023431 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Pentamidine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.002.583 | |
| 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. | |
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| Record name | PENTAMIDINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/673LC5J4LQ | |
| 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. | |
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| Record name | PENTAMIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7474 | |
| 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 | Pentamidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014876 | |
| 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. | |
Melting Point |
Decomposes at 186 °C, 186.0 °C (decomposes) |
Source
|
| Record name | Pentamidine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00738 | |
| 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 | PENTAMIDINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7474 | |
| 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 | Pentamidine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014876 | |
| 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. | |
Synthesis routes and methods
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Retrosynthesis Analysis
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