Guanidines

thumb|Arginine ball and stick model spinning Arginine is the amino acid with the formula (H2N)(HN)CN(H)(CH2)3CH(NH2)CO2H. The molecule features a guanidino group appended to a standard amino acid framework. At physiological pH, the carboxylic acid is deprotonated (−CO2−) and both the amino and guanidino groups are protonated, resulting in a cation. Only the L-arginine (symbol Arg or R) enantiomer is found naturally. Arg residues are common components of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. The guanidine group in arginine is the precursor for the biosynthesis

Streptomycin is an antibiotic medication used to treat a number of bacterial infections, including tuberculosis, Mycobacterium avium complex, endocarditis, brucellosis, Burkholderia infection, plague, tularemia, and rat bite fever. For active tuberculosis it is often given together with isoniazid, rifampicin, and pyrazinamide. It is administered by injection into a vein or muscle.

thumb|Creatine monohydrate powder

Metformin, sold under the brand name Glucophage, among others, is the main first-line medication for the treatment of type2 diabetes, particularly in people who are overweight. It is also used in the treatment of polycystic ovary syndrome, and is sometimes used as an off-label adjunct to lessen the risk of metabolic syndrome in people who take antipsychotic medication. It has been shown to inhibit inflammation, and is not associated with weight gain. Metformin is taken by mouth.

Creatinine (; ) is a breakdown product of creatine phosphate from muscle and protein metabolism. It is released at a constant rate by the body (depending on muscle mass).

Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experiencing renal failure. A guanidine moiety also appears in larger organic molecules, including on the side chain of arginine.

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.

Clonidine, sold under the brand name Catapres, Javadin, Kapvay among others, is an α2-adrenergic receptor agonist, hypotensive and anxiolytic drug used to treat high blood pressure, attention deficit hyperactivity disorder, perioperative pain, drug withdrawal (e.g., alcohol, opioids, or nicotine), and menopausal flushing. Clonidine is often prescribed off-label for tics. It is used orally (by mouth), by injection, or as a transdermal skin patch. Onset of action is typically within an hour with the effects on blood pressure lasting for up to eight hours. Xylazine is a structural analog of cloni

Famotidine, sold under the brand name Pepcid among others, is a histamine H2 receptor antagonist medication that decreases stomach acid production. It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome. It is taken by mouth or by injection into a vein. It begins working within an hour.

Zanamivir, sold under the brand name Relenza among others, is an anti-viral medication used to treat and prevent influenza caused by influenza A and influenza B viruses. It is a neuraminidase inhibitor and was developed by the Australian biotech firm Biota Holdings. It was licensed to Glaxo Wellcome in 1990 and approved in the US in 1999, only for use as a treatment for influenza. In 2006, it was approved for prevention of influenza A and B. Zanamivir is the first neuraminidase inhibitor commercially developed. It was developed by GlaxoSmithKline.

Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated form of creatine that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recycle adenosine triphosphate (ATP), the energy currency of the cell.

Prazosin, sold under the brand name Minipress among others, is a medication used to treat high blood pressure, symptoms of an enlarged prostate, and nightmares related to post-traumatic stress disorder (PTSD). It is an α1 blocker. It is a less preferred treatment of high blood pressure. Other uses may include heart failure and Raynaud syndrome. It is taken by mouth.

Biguanide () is the organic compound with the formula HN(C(NH)NH2)2. It is a colorless solid that dissolves in water to give a highly basic solution. These solutions slowly hydrolyse to ammonia and urea.

Agmatine, also known as 4-aminobutyl-guanidine, was discovered in 1910 by Albrecht Kossel. It is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple molecular targets, notably: neurotransmitter systems, ion channels, nitric oxide (NO) synthesis, and polyamine metabolism and this provides bases for further research into potential pharmacological applications.

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Guanethidine is an antihypertensive drug that reduces the release of catecholamines, such as norepinephrine. Guanethidine is transported across the sympathetic nerve membrane by the same mechanism that transports norepinephrine itself (NET, uptake 1), and uptake is essential for the drug's action. Once guanethidine has entered the nerve, it is concentrated in transmitter vesicles, where it replaces norepinephrine. It may also inhibit the release of granules by decreasing norepinephrine.

2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared.

Lugduname (from lat. Lugdunum for Lyon) is one of the most potent sweetening agents known. Lugduname has been estimated to be between 220,000 and 300,000 times as sweet as sucrose (table sugar), with estimates varying between studies. It was developed at the University of Lyon, France in 1996. Lugduname is part of a family of potent sweeteners which contain acetic acid functional groups attached to guanidine.

Epinastine (brand names Alesion, Elestat, Purivist, Relestat) is a second-generation antihistamine and mast cell stabilizer that is used in eye drops to treat allergic conjunctivitis. It is produced by Allergan and marketed by Inspire in the United States. It is highly selective for the H1 receptor and does not cross the blood-brain-barrier.

Argatroban is an anticoagulant that is a small molecule direct thrombin inhibitor. In 2000, argatroban was licensed by the US Food and Drug Administration (FDA) for prophylaxis or treatment of thrombosis in people with heparin-induced thrombocytopenia (HIT). In 2002, it was approved for use during percutaneous coronary interventions in people who have HIT or are at risk for developing it. In 2012, it was approved by the UK Medicines and Healthcare products Regulatory Agency for anticoagulation in people with heparin-induced thrombocytopenia Type II (HIT) who require parenteral antithrombotic t

Benomyl (also marketed as Benlate) is a fungicide introduced in 1968 by DuPont. It is a systemic benzimidazole fungicide that is selectively toxic to microorganisms and invertebrates (especially earthworms), but relatively nontoxic toward mammals.

Camostat is a serine protease inhibitor. Serine protease enzymes have a variety of functions in the body, and so camostat has a diverse range of uses. Camostat is approved in Japan for the treatment of chronic pancreatitis and postoperative reflux esophagitis. The oral proteolytic enzyme inhibitor has been on the market since 1985 under the trade name Foipan Tablets. The manufacturer is Ono Pharmaceutical. The drug is used in the treatment of some forms of cancer and is also effective against some viral infections, as well as inhibiting fibrosis in liver or kidney disease or pancreatitis.

Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of a guanidine group from arginine). In vertebrate organism it is then transformed into creatine by methylation.

Dihydrostreptomycin is semisynthetic aminoglycoside antibiotic with bactericidal properties. It is the dihydro derivative of streptomycin, and was formerly used in the treatment of tuberculosis.

thumb|Exterior of Rapiacta I.V. Bag 300mg (Generic name: Peramivir hydrate). An anti-influenza virus drug administered by intravenous infusion in Japan.

Sulfaguanidine is a sulfonamide.

Eptifibatide (Integrilin, Millennium Pharmaceuticals, also co-promoted by Schering-Plough/Essex), is an antiplatelet drug of the glycoprotein IIb/IIIa inhibitor class. Eptifibatide is a cyclic heptapeptide derived from a disintegrin protein () found in the venom of the southeastern pygmy rattlesnake (Sistrurus miliarius barbouri). It belongs to the class of the arginine-glycine-aspartate-mimetics and reversibly binds to platelets. Eptifibatide has a short half-life. The drug is the third inhibitor of GPIIb/IIIa that has found broad acceptance after the specific antibody abciximab and the non-p

Ambazone is an oral antiseptic.

thumb|Inavir Laninamivir (CS-8958) is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B. It is currently in Phase III clinical trials. It is a long-acting neuraminidase inhibitor administered by inhalation.

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.

Apraclonidine (INN), also known under the brand name Iopidine, is a sympathomimetic used in glaucoma therapy. It is an α2 adrenergic receptor agonist and a weak α1 adrenergic receptor agonist.

Tetramethylguanidine is an organic compound with the formula HNC(N(CH)). This colourless liquid, while technically a "weak base," is a relatively strong base, as judged by the high pK of its conjugate acid.

Guanabenz (pronounced GWAHN-a-benz, sold under the trade name Wytensin) is an alpha agonist that is selective to the alpha-2 adrenergic receptor. Guanabenz is used as an antihypertensive drug used in the treatment of high blood pressure (hypertension).

Leonurine (also known as SCM-198 in research) is a pseudoalkaloid that has been isolated from Leonotis leonurus, Leonotis nepetifolia, Leonurus japonicus, Leonurus cardiaca (motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. Leonurine is easily extracted into water.

Triazabicyclodecene (1,5,7-triazabicyclo[4.4.0]dec-5-ene or TBD) is an organic compound consisting of a bicyclic guanidine. For a charge-neutral compound, it is a relatively strong base that is effective for a variety of organic transformations. TBD is colorless solid that is soluble in a variety of solvents.

Iobenguane, or MIBG, is an aralkylguanidine analog of the adrenergic neurotransmitter norepinephrine (noradrenaline), typically used as a radiopharmaceutical. It acts as a blocking agent for adrenergic neurons. When radiolabeled, it can be used in nuclear medicinal diagnostic and therapy techniques as well as in neuroendocrine chemotherapy treatments.

Bethanidine (or betanidine) is a sympatholytic drug.

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.

Vargulin, also called Cypridinid luciferin, Cypridina luciferin, or Vargula luciferin, is the luciferin found in the ostracod Cypridina hilgendorfii, also named Vargula hilgendorfii. These bottom dwelling ostracods emit a light stream into water when disturbed presumably to deter predation. Vargulin is also used by the midshipman fish, Porichthys.

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Debrisoquine is a derivative of guanidine. It is an antihypertensive drug similar to guanethidine. Debrisoquine is frequently used for phenotyping the CYP2D6 enzyme, a drug-metabolizing enzyme.

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Cycloguanil is a dihydrofolate reductase inhibitor, and is a metabolite of the antimalarial drug proguanil; its formation in vivo has been thought to be primarily responsible for the antimalarial activity of proguanil. However, more recent work has indicated that, while proguanil is synergistic with the drug atovaquone (as in the combination Malarone), cycloguanil is in fact antagonistic to the effects of atovaquone, suggesting that, unlike cycloguanil, proguanil may have an alternative mechanism of antimalarial action besides dihydrofolate reductase inhibition.

'''N-Methylarginine''' is an inhibitor of nitric oxide synthase. Chemically, it is a methyl derivative of the amino acid arginine. It is used as a biochemical tool in the study of physiological role of nitric oxide.

Guanadrel is an antihypertensive agent. It is used in the form of its sulfate.

Octopine is a derivative of the amino acids arginine and alanine. It was the first member of the class of chemical compounds known as opines to be discovered. Octopine gets its name from Octopus octopodia from which it was first isolated in 1927.

Kopexil (INCI name diaminopyrimidine oxide, trade name Aminexil) is a chemical compound similar to minoxidil. Minoxidil was originally used to treat high blood pressure; a side effect was increased body hair. Both compounds have been used for therapy of alopecia. Kopexil is not approved for use as a drug in the United States or in Europe.

Trilaciclib, sold under the brand name Cosela, is a medication used to reduce the frequency of chemotherapy-induced bone marrow suppression.

Ebrotidine is an H2 receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage. The antisecretory properties of ebrotidine are similar to those of ranitidine, and approximately 10-fold greater than those of cimetidine. Ebrotidine has anti-Helicobacter pylori activity via inhibition of the urease enzyme and the proteolytic and mucolytic activities of the bacterium. However, its activity is synergistic with a number of antibacterial agents. Ebrotidine counteracts the inhibitory effects of H. pylori lipopolysaccharides. Ebrotidine was wi

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Gusperimus is an immunosuppressive drug. It is a derivative of the naturally occurring HSP70 inhibitor spergualin, and inhibits the interleukin-2-stimulated maturation of T cells to the S and G2/M phases and the polarization of the T cells into IFN-gamma-secreting Th1 effector T cells, resulting in the inhibition of growth of activated naive CD4 T cells.

Ditolylguanidine (DTG) is a sigma receptor agonist. It is somewhat selective for sigma receptors, but non-selective between the two sigma receptor subtypes, binding to both σ1 and σ2 with equal affinity. It has neuroprotective and antidepressant effects, and potentiates the effects of NMDA antagonists.

1-(2-Pyrimidinyl)piperazine (1-PP, 1-PmP) is a chemical compound and piperazine derivative. It is known to act as an antagonist of the α2-adrenergic receptor (Ki = 7.3–40 nM) and, to a much lesser extent, as a partial agonist of the 5-HT1A receptor (Ki = 414 nM; Emax = 54%). It has negligible affinity for the dopamine D2, D3, and D4 receptors (Ki > 10,000 nM) and does not appear to have significant affinity for the α1-adrenergic receptors. Its crystal structure has been determined.

Guanoxabenz is a metabolite of guanabenz.

Guanoxan is a sympatholytic drug that was marketed as Envacar by Pfizer in the UK to treat high blood pressure. It was not widely used and was eventually withdrawn from the market due to liver toxicity.