Imidazoles

Histamine or histamin is an organic nitrogenous compound involved in local immune responses communication, as well as regulating physiological functions in the gut and acting as a neurotransmitter for the brain, spinal cord, and uterus. Discovered in 1910, histamine has been considered a local hormone (autocoid) because it is produced without involvement of the classic endocrine glands; however, in recent years, histamine has been recognized as a central neurotransmitter. Histamine is involved in the inflammatory response and has a central role as a mediator of itching. As part of an immune re

thumb|Histidine ball and stick model spinning Histidine or histidin (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adult

Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole.

Ondansetron, sold under the brand name Zofran among others, is a medication used to prevent nausea and vomiting caused by chemotherapy, radiation therapy, migraines, or surgery. It is also effective for treating gastroenteritis. It can be given orally (by mouth), intramuscularly (injection into a muscle), or intravenously (injection into a vein).

Losartan, sold under the brand name Cozaar among others, is a medication used to treat high blood pressure (hypertension). It is in the angiotensin receptor blocker (ARB) family of medication, and is considered protective of the kidneys. Besides hypertension, it is also used in diabetic kidney disease, heart failure, and left ventricular enlargement. It comes as a tablet that is taken by mouth. It may be used alone or in addition to other blood pressure medication. Up to six weeks may be required for the full effects to occur.

Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production. It is mainly used in the treatment of heartburn and peptic ulcers.

Pilocarpine is a lactone alkaloid originally extracted from plants of the Pilocarpus genus. It is used as a medication to reduce pressure inside the eye and treat dry mouth. As an eye drop it is used to manage angle closure glaucoma until surgery can be performed, ocular hypertension, primary open angle glaucoma, and to constrict the pupil after dilation. However, due to its side effects, it is no longer typically used for long-term management. Onset of effects with the drops is typically within an hour and lasts for up to a day. By mouth it is used for dry mouth as a result of Sjögren's disea

Dacarbazine, also known as imidazole carboxamide and sold under the brand name DTIC-Dome, is a chemotherapy medication used in the treatment of melanoma and Hodgkin's lymphoma. For Hodgkin's lymphoma, it is often used together with vinblastine, bleomycin, and doxorubicin. It is given by injection into a vein.

Thiamazole, also known as methimazole, is a medication used to treat hyperthyroidism. This includes Graves' disease, toxic multinodular goiter, and thyrotoxic crisis. It is taken by mouth. Full effects may take a few weeks to occur.

Olmesartan, sold under the brand name Benicar among others, is a medication used to treat high blood pressure (hypertension). It is taken orally (swallowed by mouth). Versions are available as the combination olmesartan/hydrochlorothiazide and olmesartan/amlodipine. It is available as a prodrug, olmesartan medoxomil.

chemical compound

Ledipasvir is a drug for the treatment of hepatitis C that was developed by Gilead Sciences. After completing Phase III clinical trials, on February 10, 2014, Gilead filed for U.S. approval of a ledipasvir/sofosbuvir fixed-dose combination tablet for genotype 1 hepatitis C. The ledipasvir/sofosbuvir combination is a direct-acting antiviral agent that interferes with HCV replication and can be used to treat patients with genotypes 1a or 1b without PEG-interferon or ribavirin.

Eprosartan, sold under the brand name Teveten among others, is an angiotensin II receptor antagonist used for the treatment of high blood pressure.

Daclatasvir, sold under the brand name Daklinza, is an antiviral medication used in combination with other medications to treat hepatitis C (HCV). The other medications used in combination include sofosbuvir, ribavirin, and interferon, vary depending on the virus type and whether the person has cirrhosis. It is taken by mouth.

Nilotinib, sold under the brand name Tasigna among others, is an anti-cancer medication used to treat chronic myelogenous leukemia (CML) which has the Philadelphia chromosome. It may be used both in initial cases of chronic phase CML as well as in accelerated and chronic phase CML that has not responded to imatinib. It is taken by mouth.

Dexmedetomidine, sold under the brand name Precedex among others, is a medication used for sedation. Veterinarians use dexmedetomidine for similar purposes in treating cats, dogs, and horses. It is also used in humans to treat acute agitation associated with schizophrenia or bipolar disorder. It is administered as an intravenous solution or as a buccal or sublingual film.

Alosetron, sold under the brand name Lotronex among others, is a 5-HT3 antagonist used for the management of severe diarrhea-predominant irritable bowel syndrome (IBS) in females only.

4-Methylimidazole (4-MeI or 4-MEI) is a heterocyclic organic chemical compound with molecular formula – or . It is formally derived from imidazole through replacement of the hydrogen in position 4 by a methyl group. It is a slightly yellowish solid.

Telithromycin is the first ketolide antibiotic to enter clinical use and is sold under the brand name of Ketek. It is used to treat community acquired pneumonia of mild to moderate severity. After significant safety concerns, the US Food and Drug Administration sharply curtailed the approved uses of the drug in early 2007.

Carbimazole (brand names Neo-Mercazole, Anti-Thyrox, etc.) is used to treat hyperthyroidism. Carbimazole is a pro-drug as after absorption it is converted to the active form, methimazole. Methimazole prevents thyroid peroxidase enzyme from iodinating and coupling the tyrosine residues on thyroglobulin, hence reducing the production of the thyroid hormones T3 and T4 (thyroxine).

Bombesin is a 14-amino acid peptide originally isolated from the skin of the European fire-bellied toad (Bombina bombina)

pair of isomers

Medetomidine is a veterinary anesthetic medication with potent sedative effects. , it is an emerging illicit drug adulterant.

'''1,1'-Carbonyldiimidazole (CDI''') is an organic compound with the molecular formula . It is a white crystalline solid. It is often used for the coupling of amino acids for peptide synthesis and as a reagent in organic synthesis.

Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).

chemical compound

Elbasvir is a drug approved by the FDA in January 2016 for the treatment of hepatitis C. It was developed by Merck and completed Phase III trials, used in combination with the NS3/4A protease inhibitor grazoprevir under the trade name Zepatier, either with or without ribavirin.

1-Methylimidazole or '''N-methylimidazole''' is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.

Detomidine is an imidazole derivative and α2-adrenergic receptor agonist, used as a large animal sedative, primarily used in horses. It is usually available as the salt detomidine hydrochloride. It is a prescription medication available to veterinarians sold under various trade names.

Immepip is a histamine H3 receptor agonist.

Atipamezole, sold under the brand name Antisedan among others, is a synthetic α2 adrenergic receptor antagonist used for the reversal of the sedative and analgesic effects of dexmedetomidine and medetomidine in dogs. Its reversal effect works by competing with the sedative for α2-adrenergic receptors and displacing them. It is mainly used in veterinary medicine, and while it is only licensed for dogs and for intramuscular use, it has been used intravenously, as well as in cats and other animals (intravenous use in cats and dogs is not recommended due to the potential for cardiovascular collaps

Burimamide is an antagonist at the H2 and H3 histamine receptors. At physiological pH, it is largely inactive as an H2 antagonist, but its H3 affinity is 100x higher. It is a thiourea derivative.

Netropsin (also termed congocidine or sinanomycin) is a polyamide with antibiotic and antiviral activity. Netropsin was discovered by Finlay et al., and first isolated from the actinobacterium Streptomyces netropsis. It belongs to the class of pyrrole-amidine antibiotics.

Cefpimizole (INN) is a third-generation cephalosporin antibiotic.

chemical compound

Osilodrostat, sold under the brand name Isturisa, is a medication used for the treatment of adults with Cushing's disease who either cannot undergo pituitary gland surgery or have undergone the surgery but still have the disease. Osilodrostat is an orally active (taken by mouth), nonsteroidal corticosteroid biosynthesis inhibitor which was developed by Novartis for the treatment of Cushing's syndrome and pituitary hypersecretion (a specific subtype of Cushing's syndrome). It specifically acts as a potent and selective inhibitor of 11beta-hydroxylase (CYP11B1).

Orforglipron, sold under the brand name Foundayo, is an oral, non-peptide, small-molecule GLP-1 receptor agonist developed as a weight loss drug by Eli Lilly and Company. It was discovered by Chugai Pharmaceutical Co., then was licensed to Lilly in 2018.

Imidafenacin (INN) is a urinary antispasmodic of the anticholinergic class. It is used for the treatment of urinary incontinence and related bladder issues, especially in patients with benign prostatic hyperplasia or who have had prostate surgery. Unlike most related drugs, it is orally active but still shows a rapid onset of action, which makes it more convenient to administer.

2-Methylimidazole is an organic compound that is structurally related to imidazole with the chemical formula CH3C3H2N2H. It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry.

Capravirine was a non-nucleoside reverse transcriptase inhibitor which reached phase II trials before development was discontinued by Pfizer. Both phase IIb trials which were conducted failed to demonstrate that therapy with capravirine provided any significant advantage over existing triple-drug HIV therapies, and pharmacology studies showed that capravirine may interact with other HIV drugs.

'''1,1'-Thiocarbonyldiimidazole (TCDI''') is a thiourea containing two imidazole rings. It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).

chemical compound

Cimicoxib (UR-8880 trade name Cimalgex) is a nonsteroidal anti-inflammatory drug (NSAID) used in veterinary medicine to treat dogs for pain and inflammation associated with osteoarthritis and for the management of pain and inflammation associated with surgery. It acts as a COX-2 inhibitor.

Metiamide is a histamine H2 receptor antagonist developed from another H2 antagonist, burimamide. It was an intermediate compound in the development of the successful anti-ulcer drug cimetidine (Tagamet).

4-Methylhistamine is a histamine agonist selective for the H4 subtype.

Cilansetron is an experimental drug that is a 5-HT3 antagonist under development by Solvay Pharmaceuticals.

Methimepip is a histamine agonist which is highly selective for the H3 subtype. It is the N-methyl derivative of immepip.

3-Methylhistidine (3-MH) is a post-translationally modified amino acid which is excreted in human urine. Urinary concentration of 3-methylhistidine is a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury. Urinary 3-methylhistidine concentrations are also elevated from consumption of soy-based products and meat, particularly chicken.

Impentamine is a histamine antagonist selective for the H3 subtype.

SB-431542 is a drug candidate developed by GlaxoSmithKline (GSK) as an inhibitor of the activin receptor-like kinase (ALK) receptors, ALK5, ALK4 and ALK7. However, it is not an inhibitor of anaplastic lymphoma kinase (which are commonly known as ALK inhibitors).

Cenicriviroc (INN, code names TAK-652, TBR-652, commonly abbreviated as CVC) is an experimental drug candidate for the treatment of HIV infection and in combination with Tropifexor for non-alcoholic steatohepatitis. It is being developed by Takeda and Tobira Therapeutics.

Azalanstat (INN, codenamed RS-21607) is an anti-obesity drug acting as a lanosterol 14α-demethylase inhibitor.

Dazoxiben is an orally active thromboxane synthase inhibitor. It has shown a significant clinical improvement in patients with Raynaud's syndrome.

Iodophenpropit is a histamine antagonist which binds selectively to the H3 subtype. Its 125I radiolabelled form has been used for mapping the distribution of H3 receptors in animal studies.

SCH-79687 is a histamine antagonist selective for the H3 subtype.

chemical compound

Imafen (R25540) is an antidepressant which was patented in the mid-1970s by Janssen, but was never marketed.

Flumizole is an antiinflammatory agent. More specifically, it is a nonsteroidal anti-inflammatory drug (NSAID) that acts via inhibition of the enzyme cyclooxygenase (COX).

Mivazerol is an α2-adrenergic receptor agonist.

chemical compound