1.0 2011-09-21 00:24:16 UTC 2015-10-09 22:33:11 UTC FDB023073 Danazol Danazol is a synthetic steroid with anti-oestrogenic and anti progestogenic activity, and weak androgenic properties. Danazol suppresses oestrogen and progesterone receptors in the endometrium, leading to endometrial atrophy (thinning of the lining of the uterus) and reduced menstrual loss and to amenorrhoea in some women. Danazol significantly lowers the duration of menses when compared with NSAIDs and a progesterone releasing IUD; however, caused more adverse events than NSAIDs and progestogens. The use of Danazol may be limited by its side effect profile, its acceptability to women and the need for continuing treatment. Because danazol is structurally related to the anabolic steroid stanozolol, its use should be questioned. Derivatization methods and GC/MS data are used to implement danazol detection in routine screening and confirmation procedures in doping analysis. Danazol main metabolite ethisterone is excreted relatively fast in urine. (PMID: 17636649, 1640693, 16288903) [HMDB] (17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol 17 alpha-pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol 17a-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol 17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol 1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole- pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv. Bonzol Chronogyn Cyclomen Danazolum Danocrine Danol Danovaol Danzol Ladogal Winobanin C22H27NO2 337.4553 337.204179113 (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol 17230-88-5 [H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3 InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1 POZRVZJJTULAOH-LHZXLZLDSA-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 Acetylides Azacyclic compounds Cyclic alcohols and derivatives Heteroaromatic compounds Hydrocarbon derivatives Isoxazoles Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Tertiary alcohols Ynones 17-hydroxysteroid Acetylide Alcohol Aromatic heteropolycyclic compound Azacycle Azole Cyclic alcohol Estrane-skeleton Heteroaromatic compound Hydrocarbon derivative Hydroxysteroid Isoxazole Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Tertiary alcohol Ynone 17beta-hydroxy steroid terminal acetylenic compound Solid logp 3.62 ALOGPS logs -4.28 ALOGPS solubility 1.76e-02 g/l ALOGPS logp 3.46 ChemAxon pka_strongest_acidic 17.59 ChemAxon pka_strongest_basic 0.25 ChemAxon iupac (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol ChemAxon average_mass 337.4553 ChemAxon mono_mass 337.204179113 ChemAxon smiles [H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3 ChemAxon formula C22H27NO2 ChemAxon inchi InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1 ChemAxon inchikey POZRVZJJTULAOH-LHZXLZLDSA-N ChemAxon polar_surface_area 46.26 ChemAxon refractivity 98.54 ChemAxon polarizability 38.44 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 1908 Specdb::CMs 10837 Specdb::CMs 38485 Specdb::CMs 157250 Specdb::NmrTwoD 1843 Specdb::MsMs 2146 Specdb::MsMs 2147 Specdb::MsMs 2148 Specdb::MsMs 260619 Specdb::MsMs 260620 Specdb::MsMs 260621 Specdb::MsMs 280554 Specdb::MsMs 280555 Specdb::MsMs 280556 Specdb::MsMs 450508 Specdb::MsMs 451669 Specdb::MsMs 2236702 Specdb::MsMs 2238745 Specdb::MsMs 2238832 Specdb::MsMs 2240375 Specdb::MsMs 2240750 Specdb::MsMs 2240958 Specdb::MsMs 2242850 Specdb::MsMs 2242979 Specdb::MsMs 2249158 Specdb::MsMs 2807489 Specdb::MsMs 2807490 Specdb::MsMs 2807491 Specdb::MsMs 2898699 Specdb::MsMs 2898700 HMDB02835 #<Reference:0x000055ce2e9370b8> #<Reference:0x000055ce2e936f00> #<Reference:0x000055ce2e936d48> C-C motif chemokine 2 P13500 CCL2 Estrogen receptor P03372 ESR1 N-acetylated-alpha-linked acidic dipeptidase-like protein Q9UQQ1 NAALADL1 Sex hormone-binding globulin P04278 SHBG