Heterocyclic compounds with 3 rings

Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, explosives, and rubber additives. The compound is also used medically for certain conditions. It sublimes in vacuum at 280°C. It has a tetrahedral cage-like structure similar to adamantane. The four vertices are occupied by nitrogen atom

Praziquantel, sold under the brandname Biltricide among others, is a medication used to treat a number of types of parasitic worm infections in mammals, birds, amphibians, reptiles, and fish. In humans specifically, it is used to treat schistosomiasis, clonorchiasis, opisthorchiasis, tapeworm infections, cysticercosis, echinococcosis, paragonimiasis, fasciolopsiasis, and fasciolosis. It should not be used for worm infections of the eye. It is taken by mouth.

Adamsite or DM is an organic compound; technically, an arsenical diphenylaminechlorarsine, that can be used as a riot control agent. DM belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases. First synthesized in Germany by Heinrich Otto Wieland in 1915, it was independently developed by the US chemist Roger Adams (for whom it is named) at the University of Illinois in 1918.

Saxitoxin (STX) is a potent neurotoxin and the best-known paralytic shellfish toxin. Ingestion of saxitoxin by humans, usually by consumption of shellfish contaminated by toxic algal blooms, is responsible for the illness known as paralytic shellfish poisoning (PSP).

Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent, poisonous in large doses. It has been historically used as an aphrodisiac (in preparations sold under the name "Spanish fly"). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators.

chemical compound

Cytisine, also known as baptitoxine, cytisinicline, or sophorine, is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been used medically to help with smoking cessation. It has been found effective in several randomized clinical trials, including in the United States and New Zealand, and is being investigated in additional trials in the United States and a non-inferiority trial in Australia in which it is being compared head-to-head with the smoking cessation aid varenicline (sold in the United States as Chantix). It has als

Nedocromil sodium is a medication considered a mast cell stabilizer which acts to prevent wheezing, shortness of breath, and other breathing problems caused by asthma. It is administered by an inhaler under the brand name Tilade, and as an eye drop under the brand name Alocril. The effects of nedocromil versus asthma are gradual rather than fast-acting and it is not indicated for acute respiratory distress compared to fast acting bronchodilators like albuterol or other well-known inhaler medications. Liquid preparations of nedocromil are available in the UK under the name Rapitil for use for a

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.

chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

Santonin is a drug which was widely used in the past as an anthelminthic. It is a terpenoid and an organic compound consisting of colorless flat prisms, turning slightly yellow from the action of light and soluble in alcohol, chloroform and boiling water.

thumb|upright=1.25|Four steps of molybdenum cofactor (Moco) biosynthetic pathway occurring in bacteria and humans: (i) radical-mediated cyclization guanosine 5'-triphosphate (GTP) to (8S)‑3,8‐cyclo‑7,8‑dihydroguanosine-5́‑triphosphate (3,8‑cH2GTP), (ii) formation of cyclic pyranopterin monophosphate (cPMP) from the 3,8‑cH2GTP, (iii) conversion of cPMP into molybdopterin (MPT), (iv) insertion of molybdate into MPT to form Moco (human enzymes in parentheses). Molybdopterins are a class of cofactors found in most molybdenum-containing and all tungsten-containing enzymes. Synonyms for molybdopteri

Cabotegravir, sold under the brand name Vocabria among others, is an antiretroviral medication used for the treatment and prevention of HIV/AIDS. It is available in the form of tablets and as an intramuscular injection, as well as in an injectable combination with rilpivirine under the brand name Cabenuva.

Terpyridine (2,2';6',2"-terpyridine, often abbreviated to Terpy or Tpy) is a heterocyclic compound derived from pyridine. It is a white solid that is soluble in most organic solvents. The compound is mainly used as a ligand in coordination chemistry.

Flumequine is a synthetic fluoroquinolone antibiotic used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed. The marketing authorization of flumequine has been suspended throughout the EU. It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of

Ambroxide, widely known by the brand name Ambroxan, is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris. It is an autoxidation product of ambrein. Ambroxide is used in perfumery for creating ambergris notes and as a fixative. Ambroxide has a scent with woody, musky and slightly salty nuances. Another name for ambroxan is ambrocenide. Small amounts (< 0.01 ppm) are used as a flavoring in food.

Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris (Senecio jacobaea). It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.

Bromo-DragonFLY, also known as DOB-DragonFLY (DOB-DFLY), is a psychedelic drug of the phenethylamine, DOx, and FLY families. It is taken orally. The drug has a delayed onset of up to 6hours and a very long duration of up to 1 to 3days.

1,8-Diazafluoren-9-one (DFO) is an aromatic ketone first synthesized in 1950. It is used to find fingerprints and blood on porous surfaces. It makes fingerprints glow when they are lit by blue-green light.

Conivaptan, sold under the brand name Vaprisol, is a non-peptide inhibitor of the receptor for anti-diuretic hormone, also called vasopressin. It was approved in 2004 for hyponatremia (low blood sodium levels). Additionally, conivaptan is used for the treatment of syndrome of inappropriate antidiuretic hormone secretion.

Galaxolide (trade name; also known as Abbalide, Pearlide, Astrolide, Musk 50, Polarlide; chemical name 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8,-hexamethyl-cyclopenta[g]benzopyran or HHCB, hexamethylindanopyran) is a synthetic musk with a clean sweet musky floral woody odor used in fragrances. It is one of the musk components that perfume and cologne manufacturers use to add a musk odor to their products. Galaxolide was first synthesized in 1956, and used in the late 1960s in some fabric softeners and detergents. High concentrations were also incorporated in fine fragrances.

chemical compound

Pyoverdines (alternatively, and less commonly, spelled as pyoverdins) are fluorescent siderophores produced by certain pseudomonads. Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient (i.e., iron), regulation of other virulence factors (including exotoxin A and the protease PrpL), supporting the formation of biofilms, and are increasingly recognized for having toxicity themselves.

chemical compound

NBQX (2,3-dioxo-6-nitro-7-sulfamoyl-benzo[f]quinoxaline) is an antagonist of the AMPA receptor.

Iprindole, sold under the brand names Prondol, Galatur, and Tertran, is an atypical tricyclic antidepressant (TCA) that has been used in the United Kingdom and Ireland for the treatment of depression but appears to no longer be marketed. It was developed by Wyeth and was marketed in 1967. The drug has been described by some as the first "second-generation" antidepressant to be introduced. However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

Isoalloxazine is the structural foundation of flavins such as riboflavin (vitamin B2) and is a heterocyclic compound. It has a tricyclic structure which means it has three interconnected rings of atoms and is a tautomer of alloxazine. The structure is formed by primary-secondary aromatic o-diamines and they are a high-melting crystalline substance. The R-group is used to attach various flavin groups It has a similar structure to pteridines which has two interconnected rings. Isoalloxazine was first obtained in 1934 by Richard Kuhn an Austrian-German biochemist and lab mates. thumb|Isoalloxazin

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.

chemical compound

Riddelliine is a chemical compound classified as a pyrrolizidine alkaloid. It was first isolated from Senecio riddellii and is also found in a variety of plants including Jacobaea vulgaris, Senecio vulgaris, and others plants in the genus Senecio.

Sclareolide is a sesquiterpene lactone natural product derived from various plant sources including Salvia sclarea, Salvia yosgadensis, and cigar tobacco. It is a close analog of sclareol, a plant antifungal compound.

Prulifloxacin is an older synthetic antibiotic of the fluoroquinolone class undergoing clinical trials prior to a possible NDA (New Drug Application) submission to the U.S. Food and Drug Administration (FDA). It is a prodrug which is metabolized in the body to the active compound ulifloxacin. It was developed over two decades ago by Nippon Shinyaku Co. and was patented in Japan in 1987 and in the United States in 1989.

chemical compound

Carpaine is the major piperidine alkaloid component of papaya leaves which has been studied for potential medicinal effects. Carpaine extracted from Carica papaya trees has been reported to have diverse biological properties, such as anti-malarial, anti-inflammatory, anti-oxidant, and vasodilatory effects. Especially, Carpaine possessed significant anti-plasmodial activity in vitro (IC50 of 0.2 μM) and high selectivity towards the parasites.

chemical compound, pesticide synergist

Marbofloxacin is a carboxylic acid derivative third generation fluoroquinolone antibiotic. It is used in veterinary medicine under the brand names Marbocyl, Forcyl, Marbo vet and Zeniquin. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon (CAS number 115550-35-1).

Pazufloxacin (INN) is a fluoroquinolone antibiotic. It is sold in Japan under the brand names Pasil and Pazucross.

Epsiprantel (trade name Cestex) is a veterinary drug which is used as an anthelmintic against tapeworms such as Echinococcus granulosus.

chemical compound

Heptazine, or 'tri-s-triazine or cyamelurine', is a chemical compound with formula , that consists of a planar triangular core group or three fused triazine rings, with three hydrogen atoms at the corners. It is a yellow, weakly fluorescent solid with melting point over . It is soluble in organic solvents such as acetonitrile, but is decomposed by water and light.

CGS-15943 is a drug which acts as a potent and reasonably selective antagonist for the adenosine receptors A1 and A2A, having a Ki of 3.3nM at A2A and 21nM at A1. It was one of the first adenosine receptor antagonists discovered that is not a xanthine derivative, instead being a triazoloquinazoline. Consequently, CGS-15943 has the advantage over most xanthine derivatives that it is not a phosphodiesterase inhibitor, and so has more a specific pharmacological effects profile. It produces similar effects to caffeine in animal studies, though with higher potency.

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. The structure has been shown by X-ray crystallography to be (1,3,4,5-tetrahydro-5,5-dimethylpyrrolo-[4,3,2-de]quinolinio)-6-sulfate. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad, Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.

2CBFly-NBOMe, also known as NBOMe-2C-B-FLY or as Cimbi-31, is a serotonin receptor modulator of the phenethylamine, DOx, and FLY families. It was indirectly derived from the phenethylamine hallucinogen 2C-B is and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25B-NBOMe.

Camphorsultam, also known as bornanesultam, is a crystalline solid primarily used as a chiral auxiliary in the synthesis of other chemicals with a specific desired stereoselectivity. Camphorsultam is commercially available in both enantiomers of its exo forms: (1R)-(+)-2,10-camphorsultam and (1S)-(−)-2,10-camphorsultam.

11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed.

Lucimycin (INN, also known as lucensomycin and etruscomycin) is a macrolide antibiotic synthesized by the bacterium Streptomyces lucensis. It belongs to the group of polyene antimycotics and was first isolated in the 1960s. It has seen only limited clinical use.

Lophophorine, also known as '''N-methylanhalonine', is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora'' family. It has been found to lack hallucinogenic effects in humans. Arthur Heffter tried lophophorine at a dose of 20mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour. It has also been said to produce nausea in humans. Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.

chemical compound

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda, after which it is named. It is additionally found in Peganum harmala.

Streptazolin is an antibiotic and antifungal substance isolated in 1981 from Streptomyces viridochromogenes.

Pirolate (CP-32,387) is an antihistamine drug with a tricyclic chemical structure which was patented as an "antiallergen". It was never marketed and there are very few references to it in the literature.

Julolidine is a heterocyclic aromatic organic compound. It has the formula C12H15N.

Zilpaterol is a synthetic β2 adrenergic agonist. Under its brand name, Zilmax, it is used to increase the size of cattle and the efficiency of feeding them. Zilmax is produced by Intervet, a subsidiary of Merck & Co., and marketed as a "beef-improvement technology". Zilpaterol is typically fed in the last three to six weeks of cattle's lives, with a brief period (three days in the US) before death for withdrawal, which allows the drug to mostly leave the animal's tissues.

Quizartinib, sold under the brand name Vanflyta, is an anti-cancer medication used for the treatment of acute myeloid leukemia.

Artemisin is a sesquiterpene lactone, similar in structure to α-santonin.

Himbacine is an alkaloid isolated from the bark of Australian magnolias. Himbacine has been synthesized using a Diels-Alder reaction as a key step. Himbacine's activity as a muscarinic receptor antagonist, with specificity for the muscarinic acetylcholine receptor M2, made it a promising starting point in Alzheimer's disease research. The development of a muscarinic antagonist based on himbacine failed, but an analog, vorapaxar, has been approved by the FDA as a thrombin receptor antagonist.

Zosurabalpin (RG6006, Abx-MCP, Ro7223280) is an experimental antibiotic developed in a collaboration between the pharmaceutical company Roche and scientists from Harvard University, for the treatment of carbapenem-resistant Acinetobacter baumannii (CRAB). It targets a lipopolysaccharide transporter. It works by recognizing a composite binding site made up of both the Lpt transporter and its LPS substrate. The chemical family to which it belongs was first disclosed in 2019, but the particular structure of RG6006 remained confidential until publication of the testing results in 2023.

THC-O-acetate (THC acetate ester, O-acetyl-THC, THC-O, AcO-THC) is the acetate ester of THC. The term THC-O-acetate is commonly used for two different isomers of this substance, dependent on which isomer of THC it is synthesized from. The difference between Δ8-THC and Δ9-THC is the location of the double bond within the cyclohexene ring system. In naming the esters of THC, the "-O-" is superfluous.

Nabitan (nabutam, benzopyranoperidine, SP-106, Abbott 40656) is a synthetic cannabinoid analog of dronabinol (Δ9-tetrahydrocannabinol) and dimethylheptylpyran. It exhibits antiemetic and analgesic effects, most likely by binding to and activating the CB1 and CB2 cannabinoid receptors, and reduced intraocular pressure in animal tests, making it potentially useful in the treatment of glaucoma.