1.0 2011-09-21 00:29:08 UTC 2015-07-21 06:57:40 UTC FDB023385 Tetrahydrogestrinone The identification of tetrahydrogestrinone (THG), the first true "designer androgen," as a sports doping agent reflects both an alarmingly sophisticated illicit manufacturing facility and an underground network of androgen abusers in elite sports, as well as the still untapped potential for designer androgens in medicine. Never marketed, THG was apparently developed as a potent androgen that was undetectable by conventional International Olympic Committee-mandated urinary sports doping tests. As a potent androgen and progestin with unspecified contaminants, its distribution for use at high doses without any prior biological or toxicological evaluation poses significant health risks. Yet this diversion of science also highlights the prospect of designer androgens for use in human medicine. Designer androgens also offer the possibility of tissue-specific effects enhancing the beneficial effects of androgens while mitigating the undesirable ones. Further developments require better understanding of the post receptor tissue selectivity of androgens, comparable to the mechanism underlying that of partial estrogen agonists (SERMs). This experience highlights the ongoing need for vigilance to detect novel drug doping strategies in order to maintain fairness and safety in elite sports. This will require the deployment of generic catch-all tests, such as sensitive and specific in vitro androgen bioassays, coupled with the development of mass spectrometry-based tests for specific doping agents. Starting from gestrinone, chemists can synthesize THG in one reaction step. (PMID: 15934041, 15292520) [HMDB] (17a)-13-ethyl-17-hydroxy-18,19-Dinorpregna-4,9,11-trien-3-one THG C21H28O2 312.4458 312.20893014 (10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one tetrahydrogestrinone 618903-56-3 [H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h9,11,13,18-19,23H,3-8,10,12H2,1-2H3/t18-,19+,20+,21+/m1/s1 OXHNQTSIKGHVBH-ANULTFPQSA-N belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Estrogens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Estrane steroids Aliphatic homopolycyclic compounds 17-hydroxysteroids 3-oxosteroids Cyclic alcohols and derivatives Cyclohexenones Hydrocarbon derivatives Organic oxides Tertiary alcohols 17-hydroxysteroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Tertiary alcohol Solid logp 3.95 ALOGPS logs -4.20 ALOGPS solubility 1.99e-02 g/l ALOGPS logp 3.5 ChemAxon pka_strongest_acidic 18.9 ChemAxon pka_strongest_basic -0.14 ChemAxon iupac (10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one ChemAxon average_mass 312.4458 ChemAxon mono_mass 312.20893014 ChemAxon smiles [H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] ChemAxon formula C21H28O2 ChemAxon inchi InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h9,11,13,18-19,23H,3-8,10,12H2,1-2H3/t18-,19+,20+,21+/m1/s1 ChemAxon inchikey OXHNQTSIKGHVBH-ANULTFPQSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 95.42 ChemAxon polarizability 37.02 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18060 Specdb::CMs 38772 Specdb::CMs 151617 Specdb::MsMs 245271 Specdb::MsMs 245272 Specdb::MsMs 245273 Specdb::MsMs 265218 Specdb::MsMs 265219 Specdb::MsMs 265220 Specdb::MsMs 3045040 Specdb::MsMs 3045041 Specdb::MsMs 3045042 Specdb::MsMs 3094600 Specdb::MsMs 3094601 Specdb::MsMs 3094602 HMDB04626 17H #<Reference:0x000055ce32f6c830> #<Reference:0x000055ce32f6c678>