The predictedlog P of oxilofrine ranges from -0.13 to 0.6.[12][1][13] It is morehydrophilic than ephedrine, which has an experimental log P of 1.13 and a predicted log P of 0.9 to 1.32.[14][15][16]
Oxilofrine was originally developed in the 1930s as acardiac stimulant. Trade names included Suprifen (Bayer) and, combined with anadenosine-containing standardized organ extract, Carnigen (Hoechst AG).[9]
In combination withnormethadone, it was marketed as acough suppressant under the trade name Ticarda. As of 2021, this formulation was still manufactured in Canada byValeant and sold as Cophylac.[17]
Oxilofrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name.[4][7][10] It is also known by synonyms includingmethylsynephrine,oxyphedrine, andhydroxyephedrine.[4][10] Brand names of oxilofrine includeCarnigen,Cophylac (withnormethadone),Suprifen, andTicarda (also with normethadone), among others.[4][10][9]
Oxilofrine is currently aWorld Anti-Doping Agency (WADA) prohibited substance when used in competition.[20] It has been found as anadulterant in some dietary supplements.[9][21] Even after receiving warning letters from the FDA,[22] some sports and weight loss supplement companies continue to use oxilofrine as an undeclared ingredient in their products despite it being prohibited.[23]
Severaldoping cases involving oxilofrine have been publicized, including:
In 2009, Brazilian/American cyclistFlávia Oliveira was suspended for 2 years after taking a supplement known as "HyperDrive 3.0+" which contained methylsynephrine, a chemical equivalent of oxilofrine, among other substances.[24] Her sentence was eventually reduced to 18 months after an appeal as there was enough evidence that she had unknowingly consumed said substance as the old label did not list methylsynephrine.[25]
On 18 September 2010, Vietnamese weightlifterHoàng Anh Tuấn, silver medalist in2008 Summer Olympics was handed a four-year ban, later reduced to two years, for testing positive with the substance. It was found out that the substance came from unlabeled drinks he consumed during his training in China.[26]
On July 14, 2013, Jamaican runnersAsafa Powell andSherone Simpson tested positive for oxilofrine prior to the2013 World Athletics Championships.[27] Powell, however, maintained that he did not take any banned supplements knowingly or willfully.[28] Powell voluntarily withdrew as a result of the test. On 10 April 2014, both athletes received an 18-month suspension from competing, which was set to expire in December that year.[29] However, after appealing to theCourt of Arbitration for Sport (CAS), both athletes' suspensions were lifted on 14 July 2014.[30]
On July 16, 2015,Red Sox pitching prospectMichael Kopech was suspended without pay for 50 games after testing positive for oxilofrine, which is a banned substance under the Minor League Drug Prevention and Treatment Program. Kopech denied knowingly taking the substance.[31]
In October 2018, theWBO stripped boxerBilly Joe Saunders of its middleweight world title after he tested positive for oxilofrine, as a result of a drug test administered by the Voluntary Anti-Doping Association (VADA). In his defense, Saunders held that while the substance was proscribed by VADA it was not banned "out of competition" byUK Anti-Doping, or theBritish Boxing Board of Control, but this appeal was rejected.[32]
^Fourcroy JL (2008).Pharmacology, doping and sports: a scientific guide for athletes, coaches, physicians, scientists and administrators. Taylor & Francis.ISBN978-0-415-42845-3.
^Külz F, Schneider M (1950). "Über neue gefäßerweiternde Sympathomimetika" [On new vasodilating sympathomimetics].Klin Wochenschr (in German).28 (31–32):535–537.doi:10.1007/BF01481535.PMID14775050.
