Etanidazole

Last updated
Etanidazole
Etanidazole.svg
Names
Preferred IUPAC name
N-(2-Hydroxyethyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.363 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H10N4O4/c12-4-2-8-6(13)5-10-3-1-9-7(10)11(14)15/h1,3,12H,2,4-5H2,(H,8,13) Yes check.svgY
    Key: WCDWBPCFGJXFJZ-UHFFFAOYSA-N Yes check.svgY
  • O=[N+]([O-])c1nccn1CC(=O)NCCO
Properties
C7H10N4O4
Molar mass 214.181 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Etanidazole is a nitroimidazole drug that was investigated in clinical trials for its radiosensitizing properties in cancer treatment. Administration of etanidazole results in a decrease of glutathione concentration and inhibits glutathione S-transferase. [1] [2] The result is that tissues become more sensitive to the ionizing radiation. [3]

See also

Related Research Articles

Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals and chain reactions that may damage the cells of organisms. Antioxidants such as thiols or ascorbic acid may act to inhibit these reactions. To balance oxidative stress, plants and animals maintain complex systems of overlapping antioxidants, such as glutathione.

Leukemia Group of blood cancers that usually begin in the bone marrow

Leukemia, also spelled leukaemia, is a group of blood cancers that usually begin in the bone marrow and result in high numbers of abnormal blood cells. These blood cells are not fully developed and are called blasts or leukemia cells. Symptoms may include bleeding and bruising, fatigue, fever, and an increased risk of infections. These symptoms occur due to a lack of normal blood cells. Diagnosis is typically made by blood tests or bone marrow biopsy.

Glutathione chemical compound

Glutathione (GSH) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by reactive oxygen species such as free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and cysteine. The carboxyl group of the cysteine residue is attached by normal peptide linkage to glycine.

The therapeutic index is a quantitative measurement of the relative safety of a drug. It is a comparison of the amount of a therapeutic agent that causes the therapeutic effect to the amount that causes toxicity. The related terms therapeutic window or safety window refer to a range of doses which optimize between efficacy and toxicity, achieving the greatest therapeutic benefit without resulting in unacceptable side-effects or toxicity.

Reactive oxygen species Class of compounds

Reactive oxygen species (ROS) are highly reactive chemical molecules formed due to the electron receptivity of O2. Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen.

Small-cell carcinoma Type of malignant cancer

Small-cell carcinoma is a type of highly malignant cancer that most commonly arises within the lung, although it can occasionally arise in other body sites, such as the cervix, prostate, and gastrointestinal tract. Compared to non-small cell carcinoma, small cell carcinoma has a shorter doubling time, higher growth fraction, and earlier development of metastases.

Glutathione <i>S</i>-transferase

Glutathione S-transferases (GSTs), previously known as ligandins, are a family of eukaryotic and prokaryotic phase II metabolic isozymes best known for their ability to catalyze the conjugation of the reduced form of glutathione (GSH) to xenobiotic substrates for the purpose of detoxification. The GST family consists of three superfamilies: the cytosolic, mitochondrial, and microsomal—also known as MAPEG—proteins. Members of the GST superfamily are extremely diverse in amino acid sequence, and a large fraction of the sequences deposited in public databases are of unknown function. The Enzyme Function Initiative (EFI) is using GSTs as a model superfamily to identify new GST functions.

Gingerol Chemical compound

Gingerol, properly as [6]-gingerol, is a phenol phytochemical compound found in fresh ginger that activates spice receptors on the tongue. Molecularly, gingerol is a relative of capsaicin and piperine, the compounds which are alkaloids, though the bioactive pathways are unconnected. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.

Chlorambucil

Chlorambucil, sold under the brand name Leukeran among others, is a chemotherapy medication used to treat chronic lymphocytic leukemia (CLL), Hodgkin lymphoma, and non-Hodgkin lymphoma. For CLL it is a preferred treatment. It is given by mouth.

Dose fractionation effects are utilised in the treatment of cancer with radiation therapy. When the total dose of radiation is divided into several, smaller doses over a period of several days, there are fewer toxic effects on healthy cells. This maximizes the effect of radiation on cancer and minimizes the negative side effects. A typical fractionation scheme divides the dose into 30 units delivered every weekday over six weeks. Hypofractionation is a treatment regimen that delivers higher doses of radiation in fewer visits, which tends to lower the effects of accelerated tumor growth that typically occurs during the later stages of radiotherapy. Hyperfractionation is dividing the same total dose into more deliveries, so that treatments are given more than once a day. Hyperfractionated radiation therapy is given over the same period of time as standard radiation therapy. Accelerated fractionation has also been investigated.

Benznidazole

Benznidazole is an antiparasitic medication used in the treatment of Chagas disease. While it is highly effective in early disease this decreases in those who have long-term infection. It is the first-line treatment given its moderate side effects compared to nifurtimox. It is taken by mouth.

Nasopharyngeal carcinoma Medical condition

Nasopharyngeal carcinoma (NPC), or nasopharynx cancer, is the most common cancer originating in the nasopharynx, most commonly in the postero-lateral nasopharynx or pharyngeal recess, accounting for 50% of cases. NPC occurs in children and adults. NPC differs significantly from other cancers of the head and neck in its occurrence, causes, clinical behavior, and treatment. It is vastly more common in certain regions of East Asia and Africa than elsewhere, with viral, dietary and genetic factors implicated in its causation. It is most common in males. It is a squamous cell carcinoma of an undifferentiated type. Squamous epithelial cells are a flat type of cell found in the skin and the membranes that line some body cavities. Differentiation means how different the cancer cells are from normal cells. Undifferentiated cells are cells that do not have their mature features or functions.

Lactalbumin, also known as "whey protein", is the albumin contained in milk and obtained from whey. Lactalbumin is found in the milk of many mammals. There are alpha and beta lactalbumins; both are contained in milk.

18F-EF5 Chemical compound

EF5 is a nitroimidazole derivative used in oncology research. Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia.

GSTP1

Glutathione S-transferase P is an enzyme that in humans is encoded by the GSTP1 gene.

GPX1

Glutathione peroxidase 1, also known as GPx1, is an enzyme that in humans is encoded by the GPX1 gene on chromosome 3. This gene encodes a member of the glutathione peroxidase family. Glutathione peroxidase functions in the detoxification of hydrogen peroxide, and is one of the most important antioxidant enzymes in humans.

GPX4

Glutathione peroxidase 4, also known as GPX4, is an enzyme that in humans is encoded by the GPX4 gene. GPX4 is a phospholipid hydroperoxidase that protects cells against membrane lipid peroxidation.

Mitotic catastrophe refers to a mechanism of delayed mitosis-linked cell death, a sequence of events resulting from premature or inappropriate entry of cells into mitosis that can be caused by chemical or physical stresses. Mitotic catastrophe is unrelated to programmed cell death or apoptosis and is observed in cells lacking functional apoptotic pathways. It has been observed following delayed DNA damage induced by ionizing radiation. It can also be triggered by agents influencing the stability of microtubule spindles, various anticancer drugs and mitotic failure caused by defective cell cycle checkpoints. This mechanism can activate after detection of imperfections in the segregation of genetic material between daughter cells. Mitotic catastrophe is the primary mechanism underlying reproductive cell death in cancer cells treated with ionizing radiation.

Treatment of cancer Overview of various treatment possibilities for cancer

Cancer can be treated by surgery, chemotherapy, radiation therapy, hormonal therapy, targeted therapy and synthetic lethality. The choice of therapy depends upon the location and grade of the tumor and the stage of the disease, as well as the general state of the patient. Cancer genome sequencing helps in determining which cancer the patient exactly has for determining the best therapy for the cancer. A number of experimental cancer treatments are also under development. Under current estimates, two in five people will have cancer at some point in their lifetime.

GPX3 enzyme in humans

Glutathione peroxidase 3 (GPx-3), also known as plasma glutathione peroxidase (GPx-P) or extracellular glutathione peroxidase is an enzyme that in humans is encoded by the GPX3 gene.

References

  1. Definition of etanidazole, National Cancer Institute Drug Dictionary.
  2. DrugBank DB12736 . Accessed 27 April 2021.
  3. Inanami, O.; Sugihara, K.; Okui, T.; Hayashi, M.; Tsujitani, M.; Kuwabara, M. (2002). "Hypoxia and etanidazole alter radiation-induced apoptosis in HL60 cells but not in MOLT-4 cells". International Journal of Radiation Biology. 78 (4): 267–274. doi:10.1080/09553000110105695. PMID   12020438. S2CID   37923448.