Nitrosoprodenafil is a synthetic

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

found in "herbal"

aphrodisiac An aphrodisiac is a substance that increases libido, sexual desire, sexual attraction, sexual pleasure, or sexual behavior. These substances range from a variety of plants, spices, and foods to synthetic chemicals. Natural aphrodisiacs, such as ...

products, which is a novel nitrosated analogue of

sildenafil Sildenafil, sold under the brand name Viagra among others, is a medication used to treat erectile dysfunction and pulmonary hypertension, pulmonary arterial hypertension. It is also sometimes used off-label for the treatment of certain sym ...

(Viagra). It has an innovative structure which acts as a

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

, breaking down in the body to release both the PDE₅ inhibitor aildenafil as well as free

nitric oxide Nitric oxide (nitrogen oxide, nitrogen monooxide, or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes den ...

, which have powerfully synergistic effects. This dual mechanism of action has never been exploited by conventional pharmaceutical companies because of the risks involved; usually combining PDE₅ inhibitors with nitric oxide releasers like

amyl nitrite Amyl nitrite is a chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrite functional group. The alkyl group (the amyl in this case) is unreactive and the chemical ...

is contraindicated as it can cause a precipitous drop in blood pressure that can potentially result in death.

Nitrosamine Nitrosamines (or more formally ''N''-nitrosamines) are organic compounds produced by industrial processes. The chemical structure is , where R is usually an alkyl group. Nitrosamines have a nitroso group () that are "probable human carcinogens", ...

s are also generally avoided in drug development as they can often be

hepatotoxic Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

and carcinogenic, so while the combined mechanisms of action are likely to be effective, this drug also has severe risks of toxicity. Shortly after Venhuis et al. published the suggested structure for nitrosoprodenafil, it was contested by Demizu et al. who suggested the structure was an

azathioprine Azathioprine, sold under the brand name Imuran, among others, is an immunosuppressive medication. It is used for the treatment of rheumatoid arthritis, granulomatosis with polyangiitis, Crohn's disease, ulcerative colitis, and systemic lupus er ...

/aildenafil hybrid. This newly suggested structure was dubbed 'mutaprodenafil' because of the structural similarity with the

mutagenic In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in ...

immunosuppressive drug

. The final confirmation of the azathioprine/aildenafil hybrid was provided by Sakamoto et al. who prepared crystals for X-ray analysis. Although Sakamoto et al. support the name 'mutaprodenafil', they prefer to use 'nitrosoprodenafil' instead.

References

{{Phosphodiesterase inhibitors Designer drugs Nitroso compounds PDE5 inhibitors Phenol ethers Piperazines Pyrazolopyrimidines Thiazoles Propyl compounds

See also

References