Quinolines

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinol

Mefloquine, sold under the brand name Lariam among others, is a medication used to prevent or treat malaria. When used for prevention it is typically started before potential exposure and continued for several weeks after potential exposure. It can be used to treat mild or moderate malaria but is not recommended for severe malaria. It is taken by mouth.

Montelukast, sold under the brand name Singulair among others, is a medication used in the maintenance treatment of asthma. It is generally less preferred for this use than inhaled corticosteroids. It is not useful for acute asthma attacks. Other uses include allergic rhinitis and hives of long duration. For allergic rhinitis it is a second-line treatment.

Saquinavir, sold under the brand name Invirase among others, is an antiretroviral medication used together with other medications to treat or prevent HIV/AIDS. Typically it is used with ritonavir or lopinavir/ritonavir to increase its effect. It is taken by mouth.

Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.

Amodiaquine (ADQ) is a medication used to treat malaria, including Plasmodium falciparum malaria when uncomplicated. It is recommended to be given with artesunate to reduce the risk of resistance. Due to the risk of rare but serious side effects, it is not generally recommended to prevent malaria. Though, the World Health Organization (WHO) in 2013 recommended use for seasonal preventive in children at high risk in combination with sulfadoxine and pyrimethamine.

Pitavastatin (usually as a calcium salt) is a member of the blood cholesterol lowering medication class of statins.

Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.

Simeprevir, sold under the brand name Olysio among others, is a medication used in combination with other medications for the treatment of hepatitis C. It is specifically used for hepatitis C genotype 1 and 4. Medications it is used with include sofosbuvir or ribavirin and peginterferon-alfa. Cure rates are in 80s to 90s percent. It may be used in those who also have HIV/AIDS. It is taken by mouth once daily for typically 12 weeks.

Elvitegravir (EVG) is an integrase inhibitor used to treat HIV infection. It was developed by the pharmaceutical company Gilead Sciences, which licensed EVG from Japan Tobacco in March 2008. The drug gained approval by the U.S. Food and Drug Administration on 27 August 2012, for use in adult patients starting HIV treatment for the first time as part of the fixed dose combination known as Stribild. On 24 September 2014, the FDA approved Elvitegravir as a single pill formulation under the trade name Vitekta. On 5 November 2015, the FDA approved the drug for use in patients affected with HIV-1 as

chemical compound

Quinaldine or 2-methylquinoline is an organic compound with the formula CH3C9H6N. It is one of the methyl derivatives of the heterocyclic compound quinoline. It is bioactive and is used in the preparation of various dyes. It is a colorless oil but commercial samples can appear colored.

Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest (under commercial names such as "Stop-Scald"). It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments.

Cabozantinib, sold under the brand names Cometriq and Cabometyx among others, is an anti-cancer medication used to treat medullary thyroid cancer, renal cell carcinoma, and hepatocellular carcinoma. It is a small-molecule tyrosine-kinase inhibitor (TKI) of c-Met (HGFR) and VEGFR2, and also inhibits AXL, RET, and FLT3. It was discovered and developed by Exelixis Inc.

Bosutinib, sold under the brand name Bosulif, is a small molecule BCR-ABL and src tyrosine kinase inhibitor used for the treatment of chronic myelogenous leukemia.

Neratinib (INN), sold under the brand name Nerlynx, is a tyrosine kinase inhibitor anti-cancer medication used for the treatment of breast cancer.

4-Aminoquinoline is a form of aminoquinoline with the amino group at the 4-position of the quinoline. The compound has been used as a precursor for the synthesis of its derivatives.

Pyrvinium (Viprynium) is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.

Dequalinium is a quaternary ammonium cation and bolaamphiphile commonly available as the dichloride salt. It is useful as an antiseptic and disinfectant. The bromide, iodide, acetate, and undecenoate salts are known as well. Dequalinium chloride is the active ingredient of several medications.

Lepidine, or 4-methylquinoline, is an organic compound with the formula . It is one of the two commercially important methyl quinolines. It is a colorless liquid, although impure samples can appear yellow.

Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria. With respect to acute malaria, it is used together with other medications to prevent relapse by Plasmodium vivax. It may be used to prevent all types of malaria. It is taken by mouth.

Zavegepant, sold under the brand name Zavzpret, is a medication used for the treatment of migraine. Zavegepant is a calcitonin gene-related peptide receptor antagonist. It is sprayed into the nose. It is sold by Pfizer.

Cefquinome is a fourth-generation cephalosporin with pharmacological and antibacterial properties valuable in the treatment of coliform mastitis and other infections. It is only used in veterinary applications.

chemical compound

Pixantrone (rINN; trade name Pixuvri) is an experimental antineoplastic (anti-cancer) drug, an analogue of mitoxantrone with fewer toxic effects on cardiac tissue. It acts as a topoisomerase II poison and intercalating agent. The code name BBR 2778 refers to pixantrone dimaleate, the actual substance commonly used in clinical trials.

Tivozanib, sold under the brand name Fotivda, is a medication used for the treatment of advanced renal cell carcinoma (kidney cancer). It is an oral VEGF receptor tyrosine kinase inhibitor.

8-Aminoquinoline is the 8-amino derivative of quinoline. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to 8-hydroxyquinoline.

Torcetrapib (CP-529,414, Pfizer) was a drug being developed to treat hypercholesterolemia (elevated cholesterol levels) and prevent cardiovascular disease. Its development was halted in 2006 when phase III studies showed excessive all-cause mortality in the treatment group receiving a combination of atorvastatin (Lipitor) and torcetrapib.

Glafenine is a nonsteroidal anti-inflammatory drug (NSAID). Use of glafenine is limited due to the risk of anaphylaxis and acute kidney failure.

Pamaquine is an 8-aminoquinoline drug formerly used for the treatment of malaria. It is closely related to primaquine.

chemical compound

Cethromycin, trade name Restanza (initially known as ABT-773) is a ketolide antibiotic undergoing research for the treatment of community acquired pneumonia (CAP) and for the prevention of post-exposure inhalational anthrax, and was given an "orphan drug" status for this indication. Originally discovered and developed by Abbott, it was acquired by Advanced Life Sciences Inc. for further development.

Piperaquine is an antiparasitic drug used in combination with dihydroartemisinin to treat malaria. Piperaquine was developed under the Chinese National Malaria Elimination Programme in the 1960s and was adopted throughout China as a replacement for the structurally similar antimalarial drug chloroquine. Due to widespread parasite resistance to piperaquine, the drug fell out of use as a monotherapy, and is instead used as a partner drug for artemisinin combination therapy. Piperaquine kills parasites by disrupting the detoxification of host heme.

Cinchophen (trade names Atophan, Quinophan, and Phenaquin) is an analgesic drug that was first produced by Doebner & Gieskel in 1887, it was commercially introduced in 1908 as a treatment for gout. This drug is still used, in combination with Prednisolone, by veterinarians to treat arthritis in animals. It can be prepared starting from anilin, benzaldehyde and pyruvic acid in absolute ethanol. Use of this drug in humans ceased in the 1930s due to the discovery that cinchophen can cause serious liver damage. There is some evidence that it stimulates C-Fos.

Mitapivat, sold under the brand name Pyrukynd among others, is a medication used to treat different types of anemia. It is taken as the sulfate hydrate salt by mouth. Mitapivat is a pyruvate kinase activator.

Abanoquil (INN) is an α1-adrenergic receptor antagonist.

Faldaprevir was an experimental drug for the treatment of hepatitis C (HCV). It was being developed by Boehringer-Ingelheim and reached Phase III clinical trials in 2011. Boehringer announced in 2014 that it would not pursue approval of the drug any more because of better HCV treatments having become available.

Imazaquin is an imidazolinone herbicide, so named because it contains an imidazolinone core. This organic compound is used to control a broad spectrum of weed species. It is a colorless or white solid, although commercial samples can appear brown or tan.

Zosuquidar (development code LY-335979) is an experimental antineoplastic drug. Zosquidir inhibits P-glycoproteins. Other drugs with this mechanism include tariquidar and laniquidar. P-glycoproteins are trans-membrane proteins that pump foreign substances out of cells in an ATP dependent fashion. Cancers overexpressing P-glycoproteins are able to pump out therapeutic molecules before they are able to reach their target, effectively making the cancer multi-drug resistant. Zosuquidar inhibits P-glycoproteins, inhibiting the efflux pump and restoring sensitivity to chemotherapeutic agents.

Dihydroquinidine (also called hydroquinidine) is an organic compound, a cinchona alkaloid closely related to quinine. The specific rotation is +226° in ethanol at 2 g/100 ml. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

Viqualine (INN; developmental code PK-5078) is an antidepressant and anxiolytic drug that was never marketed. It acts as a potent and selective serotonin releasing agent (SRA) and serotonin reuptake inhibitor (SRI) similarly to para-chloroamphetamine (PCA). In addition, viqualine displaces diazepam from the GABAA receptor and produces benzodiazepine-like effects, indicating that it is also a positive allosteric modulator of the benzodiazepine site of the GABAA receptor. The drug has mainly been researched as a potential treatment for alcoholism.

Optochin (or ethylhydrocupreine hydrochloride) is a derivative of quinine introduced in 1911 by Morgenroth and Levy with the intention to treat pneumococci infection. In very high dilutions, it inhibits the growth of representatives of all four groups of pneumococci in vitro. That is the main reason it is now used in bacteriology for the differentiation of Streptococcus pneumoniae, which is optochin-sensitive, from the other, resistant alpha-hemolytic streptococci, sometimes called the viridans streptococci because of the green colouration on blood agar around colonies.

Linsitinib is an experimental drug candidate for the treatment of various types of cancer. It is an inhibitor of the insulin receptor and of the insulin-like growth factor 1 receptor (IGF-1R). This prevents tumor cell proliferation and induces tumor cell apoptosis.

Pipequaline (INN; development code PK-8165) is an anxiolytic drug that was never marketed. It possesses a novel chemical structure that is not closely related to other drugs of this type. The drug has a similar pharmacological profile to the benzodiazepine family of drugs, but with mainly anxiolytic properties and very little sedative, amnestic or anticonvulsant effects, and so is classified as a nonbenzodiazepine anxiolytic.

aspect of COVID-19 research

Quinclorac is an organic compound with the formula . A colorless solid, it is soluble in hydrocarbons and alcohols. The compound is the carboxylic acid of 3,7-dichloroquinoline.

Quinmerac is a chemical herbicide first manufactured by BASF in 1993. Its formula is , and it is a quinolinemonocarboxylic acid that includes chlorine and methyl groups as substituents.

SB-215505 is a drug which acts as a potent and selective antagonist at the serotonin 5-HT2B receptor, with good selectivity over the related 5-HT2A and 5-HT2C receptors. It is used in scientific research into the function of the 5-HT2 family of receptors, especially to study the role of 5-HT2B receptors in the heart, and to distinguish 5-HT2B-mediated responses from those produced by 5-HT2A or 5-HT2C.

'''N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ''') is a dopamine-receptor antagonist.

Vabicaserin (codenamed SCA-136) was a novel antipsychotic and anorectic under development by Wyeth. As of 2010 it is no longer in clinical trials for the treatment of psychosis. It was also under investigation as an antidepressant but this indication appears to have been dropped as well.

Dactolisib (codenamed NVP-BEZ235 and BEZ-235, also known as RTB101) is an imidazoquinoline derivative acting as a PI3K inhibitor. It also inhibits mTOR. It is being investigated as a possible cancer treatment.

Floctafenine is a nonsteroidal anti-inflammatory drug (NSAID).

SB-277,011A is a drug which acts as a potent and selective dopamine D3 receptor antagonist, which is around 80–100times selective for D3 over D2, and lacks any partial agonist activity.