1.0 2011-09-21 00:24:48 UTC 2018-05-28 18:35:17 UTC FDB023109 Stanozolol Stanozolol was first synthesized by Clinton et al. in 1959, as a heterocyclic anabolic androgenic steroid. The structure of Stan differs from endogenous steroid hormones and most commercially available anabolic steroids. It most closely resembles methyl testosterone. Instead of the 3-ketogroup in methyltestosterone, there is a pyrazole ring fused to the androstane ring system. This slightly different structure has the disadvantage of making extraction and isolation of the molecule from matrices more difficult. Like most other anabolic steroids, Stan has poor gas chromatographic behavior and is difficult to detect in urine, because of renal clearance and low urinary excretion. This is due to the rapid metabolization, leading to low concentration levels of the parent compound found in urine. Therefore, most research studies had focused on the detection of urinary metabolites. Androgens are drugs, derived from the natural male sex hormone testosterone, with high anabolic potential and minimized androgenic activity. Anabolic steroids stimulate protein synthesis, resulting in an acceleration of the food conversion rate and increasing muscle growth, body mass and enhanced performance. Androgens can be used as therapeutics, because they accelerate the recovery of protein deficiency and protein-wasting disorders (e.g. osteoporosis), but they are also widely abused in doping, as well in animals as in men. (PMID: 10404632, 10435307, 11175645, 11284331, 12064656, 12580506, 1448813, 14698206, 15013688, 15458725, 15631866, 15664350, 16040239, 16259046, 16288903, 1640693, 17066372, 17146762, 2306548, 2362445, 2625454, 2663904, 6539197, 9001957, 9300863, 9580049) [HMDB] (5a,17b)-17-methyl-2'H-Androst-2-eno[3,2-c]pyrazol-17-ol 1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethyl-Cyclopenta[7,8]phenanthro[2,3-c]pyrazol-1-ol 17-Methyl-5a-androstano[3,2-c]pyrazol-17b-ol 17-Methyl-pyrazolo[4',3':2,3]-5a-androstan-17b-ol 17a-Methyl-17b-hydroxy-5a-androstano(3,2-c)pyrazole 17b-Hydroxy-17-methyl-5a-androstano[3,2-c]pyrazole 17b-Hydroxy-17a-methyl-5a-androstano[3,2-c]pyrazole 2'H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8CI) Anabol Androstanazol Androstanazole Androstanazolestanazol Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'H-androst-2-eno[3,2-c]pyrazol-17-ol deriv. Estanozolol Estazol Stanazolol Stanozololum Stromba Strombaject Tevabolin Win 14833 Winstroid Winstrol Winstrol Depot Winstrol V C21H32N2O 328.4916 328.251463656 (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol stanozolol 10418-03-8 [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1 LKAJKIOFIWVMDJ-IYRCEVNGSA-N belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. Estrane steroids Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Estrane steroids Aromatic heteropolycyclic compounds 17-hydroxysteroids Azacyclic compounds Cyclic alcohols and derivatives Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Pyrazoles Tertiary alcohols 17-hydroxysteroid Alcohol Aromatic heteropolycyclic compound Azacycle Azole Cyclic alcohol Estrane-skeleton Heteroaromatic compound Hydrocarbon derivative Hydroxysteroid Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrazole Tertiary alcohol 17beta-hydroxy steroid Androstane and derivatives anabolic androgenic steroid organic heteropentacyclic compound tertiary alcohol Solid logp 4.33 ALOGPS logs -5.28 ALOGPS solubility 1.73e-03 g/l ALOGPS logp 3.81 ChemAxon pka_strongest_acidic 16.23 ChemAxon pka_strongest_basic 2.86 ChemAxon iupac (1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol ChemAxon average_mass 328.4916 ChemAxon mono_mass 328.251463656 ChemAxon smiles [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C ChemAxon formula C21H32N2O ChemAxon inchi InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1 ChemAxon inchikey LKAJKIOFIWVMDJ-IYRCEVNGSA-N ChemAxon polar_surface_area 48.91 ChemAxon refractivity 96.8 ChemAxon polarizability 39.22 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13454 Specdb::CMs 38526 Specdb::CMs 150092 Specdb::MsMs 77310 Specdb::MsMs 77311 Specdb::MsMs 77312 Specdb::MsMs 137409 Specdb::MsMs 137410 Specdb::MsMs 137411 Specdb::MsMs 2228263 Specdb::MsMs 2835720 Specdb::MsMs 2835721 Specdb::MsMs 2835722 Specdb::MsMs 2873396 Specdb::MsMs 2873397 Specdb::MsMs 2873398 HMDB03116 #<Reference:0x000055ce32719c00> #<Reference:0x000055ce32719890> #<Reference:0x000055ce32719610> #<Reference:0x000055ce32719458> #<Reference:0x000055ce32718c88> #<Reference:0x000055ce327188c8> #<Reference:0x000055ce32718468> #<Reference:0x000055ce32743e88> #<Reference:0x000055ce32743c30> #<Reference:0x000055ce32743a78> #<Reference:0x000055ce32743820> #<Reference:0x000055ce327435f0> #<Reference:0x000055ce327432a8> #<Reference:0x000055ce32743028> #<Reference:0x000055ce32742df8> #<Reference:0x000055ce32742c40> #<Reference:0x000055ce32742a60> #<Reference:0x000055ce32742858> #<Reference:0x000055ce327426a0> #<Reference:0x000055ce32742420> #<Reference:0x000055ce32741e58> #<Reference:0x000055ce32741980> #<Reference:0x000055ce327414d0> #<Reference:0x000055ce327410c0> #<Reference:0x000055ce32740c88> #<Reference:0x000055ce32740878> #<Reference:0x000055ce32740580> #<Reference:0x000055ce32740238> #<Reference:0x000055ce32740030> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823