11-Deoxycortisol

The absence of this enzyme in sea lampreys indicates the existence of a complex and highly specific corticosteroid signaling pathway that emerged at least 500 million years ago with the advent of early vertebrates.It's important to note that these mechanisms may be relevant not only for cortisol-induced hypertension but also for conditions such as Cushing's syndrome (excess cortisol production), apparent mineralocorticoid excess (related to defects in 11β-hydroxylase enzymes), licorice abuse (glycyrrhetinic acid affecting glycyrrhetinic acid receptor),[18] chronic renal failure (prolonged half-life of cortisol due to reduced 11β-hydroxylase activity), and even essential hypertension where there may be abnormalities with 11β-hydroxylase activity or glucocorticoid receptor variations.Low cortisol levels can disrupt this system, leading to altered angiotensin production, reduced aldosterone secretion, and subsequently lower blood pressure.[24] In 1934, biochemist Tadeus Reichstein, working in Switzerland, began research on extracts from animal adrenal glands in order to isolate physiologically active compounds.[27] In 1949, American research chemist Percy Lavon Julian, in looking for ways to produce cortisone, announced the synthesis of the Compound S, from the cheap and readily available pregnenolone (synthesized from the soybean oil sterol stigmasterol).[28][29] On 5 April 1952, biochemist Durey Peterson and microbiologist Herbert Murray at Upjohn, published the first report of a breakthrough fermentation process for the microbial 11α-oxygenation of steroids (e.g. progesterone) in a single step by common molds of the order Mucorales.
Cortodoxone chemical structure
Cortodoxone 3D ball molecule view
Steroidogenesis , showing 11-deoxycortisol in the pathway from cholesterol to cortisol . [ 9 ]
IUPAC nameCAS NumberChEMBLChemSpiderECHA InfoCardIUPHAR/BPSPubChemCompTox DashboardSMILESChemical formulaMolar massMelting pointstandard stateendogenousglucocorticoidsteroid hormonemetabolic intermediatecortisolTadeusz ReichsteinSteroidogenesischolesterol17α-hydroxyprogesterone21-hydroxylase11β-hydroxylasebiological activitysea lampreysmetamorphosisseawaterCYP11B111-deoxycorticosteronecorticosterone11β-hydroxylase deficiencymineralocorticoidhypertension21-hydroxylase deficiencylow blood pressuremineralocorticoidselectrolytesCushing's syndromelicoriceglycyrrhetinic acidvascular toneandrostenedionebiochemistTadeus ReichsteinSwitzerlandadrenal glandsphysiologically activePercy Lavon JuliancortisonepregnenolonestigmasterolmicrobiologistUpjohnfermentationprogesteroneMucoralesCortexolone 17α-propionateBibcodeChicago TribuneChemical & Engineering NewsJ Am Chem SocHormonesEndocrineglandsHypothalamic–pituitaryHypothalamusDopamineSomatostatin (GHIH)Posterior pituitaryOxytocinVasopressinAnterior pituitaryProlactinEndorphinsLipotropinAdrenal axisAldosteroneDHEA-SAdrenalineNorepinephrineThyroidThyroid hormonesCalcitoninThyroid axisParathyroidGonadal axisTestisTestosteroneInhibinEstradiolActivinRelaxinPlacentaEstrogenPancreasGlucagonInsulinAmylinSomatostatinPancreatic polypeptidePineal glandMelatoninN,N-Dimethyltryptamine5-Methoxy-N,N-dimethyltryptamineThymusThymosinsThymosin α1Beta thymosinsThymopoietinThymulinDigestive systemStomachGastrinGhrelinDuodenumSecretinMotilinEnteroglucagonPeptide YYInsulin-like growth factorAdipose tissueLeptinAdiponectinResistinSkeletonOsteocalcinKidneyCalcitriolProstaglandinNatriuretic peptidesteroidsPrecursors22R-Hydroxycholesterol20α,22R-Dihydroxycholesterol17α-Hydroxypregnenolone21-HydroxypregnenoloneCorticosteroidsGlucocorticoids3α,5α-Tetrahydrocorticosterone5α-Dihydrocorticosterone11-Ketoprogesterone21-Deoxycortisol21-Deoxycortisone5α-Dihydrocortisol5α-Dihydroaldosterone11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)11β-Hydroxyprogesterone (21-deoxycorticosterone)18-Hydroxy-11-deoxycorticosterone18-HydroxycorticosteroneSex steroidsAndrogens11-Ketodihydrotestosterone11-Ketotestosterone7β-Hydroxyepiandrosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione)AndrostenediolAndrosteroneDehydroandrosteroneDHEA sulfateDihydrotestosteroneEpiandrosteroneEpitestosterone16α-Hydroxyandrostenedione16α-Hydroxy-DHEA16α-Hydroxy-DHEA sulfate3α-Androstanediol3α-Androstanediol glucuronide3β-Androstanediol5β-Dihydrotestosterone3α-Etiocholanediol3β-EtiocholanediolAndrostenediol sulfateAndrostenetriolAndrosterone glucuronideAndrosterone sulfateEtiocholanedioneEtiocholanoloneEtiocholanolone glucuronideEpietiocholanoloneTestosterone glucuronideTestosterone sulfateEstrogensEstetrolEstroneEstriol17α-Estradiol16β-Epiestriol (16β-hydroxyestradiol)17α-Epiestriol (16α-hydroxy-17α-estradiol)16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)2-Hydroxyestradiol2-Hydroxyestriol2-Hydroxyestrone4-Hydroxyestradiol4-Hydroxyestriol4-Hydroxyestrone4-Methoxyestradiol4-Methoxyestrone16α-Hydroxyestrone16β-Hydroxyestrone16-Ketoestradiol16-Ketoestrone27-Hydroxycholesterol4-Androstenedione5-Androstenediol7-Keto-DHEA7α-Hydroxy-DHEA2-Methoxyestradiol2-Methoxyestrone2-Methoxyestriol4-MethoxyestriolEstradiol disulfateEstradiol glucuronideEstradiol 3-glucuronideEstradiol 3-glucuronide 17β-sulfateEstradiol sulfateEstradiol 17β-sulfateEstrone glucuronideEstrone sulfateEstriol glucuronideEstriol sulfateLipoidal estradiolestradiol stearateestradiol palmitateProgestogens16α-Hydroxyprogesterone20α-Dihydroprogesterone20β-Dihydroprogesterone5α-Dihydroprogesterone5α-DHDOCAllopregnanediolPregnanediolPregnanediol glucuronidePregnanetriolNeurosteroids24S-Hydroxycholesterol3α-Dihydroprogesterone3β-Dihydroprogesterone5β-DihydroprogesteroneAllopregnanoloneEpipregnanoloneIsopregnanolonePregnanolonePregnenolone sulfate3α-Androstenol7β-Hydroxy-DHEA7α-HydroxyepiandrosteronePheromones3β-AndrostenolAndrostadienolAndrostadienoneAndrostenoneEstratetraenolVitamin D7-DehydrocholesterolCalcidiol/CalcifediolCholecalciferol7α-Hydroxycholesterol11α-Hydroxyprogesterone11β-HydroxyprogesteroneCholesterol sulfateGlucocorticoid receptormodulatorsAgonists9α-Fluorocortisone (alfluorone)11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)Cortifen (cortiphen, kortifen)Δ7-PrednisoloneAmebucortChloroprednisoneChloroprednisone acetateCloprednolhydrocortisoneBenzodrocortisone (hydrocortisone benzoate)Hydrocortamate (hydrocortisone diethylaminoacetate)Cortisone acetateDeprodoneDichlorisoneDifluprednateEndrisone (endrysone)EtiprednolFludrocortisone (fludrocortone)Fludrocortisone acetateFluorometholoneFluorometholone acetateFluperoloneFluperolone acetateFluprednisoloneHalopredoneIsoflupredone (9α-fluoroprednisolone)LoteprednolMazipredone (depersolone)MedrysoneMethylprednisolonePrebediolonePrebediolone acetatePrednisolonePrednazatePrednazolinePrednicarbate (prednisolone ethylcarbonate propionate)PrednimustinePrednisolamate (prednisolone diethylaminoacetate)PrednisonePregnenolone acetatePregnenolone succinate (pregnenolone hemisuccinate)ResocortolTipredaneTixocortolButixocort (tixocortol butyrate)Tixocortol pivalate16α-Methyl-11-oxoprednisoloneAlclometasoneAlclometasone dipropionateAmelometasoneBeclometasone (beclomethasone)Betamethasone (betametasone)Cortobenzolone (betamethasone salicylate)Ciclometasone (ciclomethasone, cyclomethasone)ClobetasolClobetasol propionateClobetasoneClobetasone butyrateClocortoloneCloticasoneCormetasone (cormethasone)DescinoloneDesoximetasone (desoxymethasone)Dexamethasone (dexametasone)DiflorasoneDiflorasone diacetateDiflucortoloneDiflucortolone valerateDimesoneDoxibetasol (doxybetasol)FlucloroloneFlumetasone (flumethasone)Flumetasone pivalateFluocinoloneFluocortinFluocortin butyl (fluocortin butylate)FluocortoloneFluprednidene (fluprednylidene)Fluprednidene acetateFluticasone furoateFluticasone propionateHalocortoloneHalometasoneIcometasoneIsoprednideneLocicortolone (locicortone)MeclorisoneMeprednisone (methylprednisone)MometasoneMometasone furoateParamethasoneParamethasone acetatePrednylideneRimexoloneTicabesoneTimobesoneTriamcinoloneTriamcinolone diacetateUlobetasol (halobetasol)Ulobetasol propionateVamoroloneAcrocinonide (triamcinolone acroleinide)Amcinafal (triamcinolone pentanonide)Amcinafide (triamcinolone acetophenide)Amcinonide (triamcinolone acetate cyclopentanonide)BudesonideCiclesonideCicortonideDeflazacort (azacort)Descinolone acetonideDesonide (hydroxyprednisolone acetonide)DexbudesonideDrocinonideFluazacortFluclorolone acetonide (flucloronide)Fludroxycortide (flurandrenolone, flurandrenolide)FlumoxonideFlunisolideFluocinolone acetonideCiprocinonide (fluocinolone acetonide cyclopropylcarboxylate)Fluocinonide (fluocinolide, fluocinolone acetonide acetate)Procinonide (fluocinolone acetonide propionate)FormocortalHalcinonideItrocinonideRofleponideRofleponide palmitateTralonideTriamcinolone acetonideFlupamesone (triamcinolone acetonide metembonate)Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)TriclonideCortisuzolCortivazolDomoprednateNaflocortNicocortonideNivacortol (nivazol)OxisopredRU-2836215β-Hydroxycyproterone acetateBromoketoprogesteroneChlormadinone acetateCyproteroneCyproterone acetateDanazolDelmadinone acetateDesogestrelDU-41165EtonogestrelFlugestoneFlugestone acetate (flurogestone acetate)Fluoromedroxyprogesterone acetateFluoxymesteroneGestodeneMedrogestoneMedroxyprogesterone acetateMegestrol acetateMetriboloneNorgestometOsaterone acetatePromegestoneRU-2309QuingestroneSegesterone acetate (nestorone)TetrahydrogestrinoneAZD-5423SEGRMsDagrocoratFosdagrocoratMapracoratAntagonists17α-MethylprogesteroneAglepristoneAsoprisnilAsoprisnil ecamateGuggulsteroneKetoconazoleLilopristoneMetapristone (RU-42633)MiconazoleMifepristone (RU-486)Miricorilant (CORT-118335)OnapristonePregnenolone 16α-carbonitrileRelacorilant (CORT-125134)RTI 3021–012TelapristoneTiboloneToripristoneUlipristal acetateIONIS-GCCRRx (ISIS-426115)List of corticosteroidsMineralocorticoid receptor19-Norprogesterone6β-Hydroxy-7α-thiomethylspironolactone7α-Thiomethylspironolactone (SC-26519)7α-Thioprogesterone (SC-8365)7α-Thiospironolactone (SC-24813)17α-Hydroxyprogesterone (hydroxyprogesterone)18-DeoxyaldosteroneCanrenoate potassium (potassium canrenoate)Canrenoic acid (canrenoate)Canrenone (canrenoate y-lactone)DicirenoneDimethisteroneDrospirenoneDydrogesteroneEplerenoneHydroxyprogesterone caproateMespirenoneMexrenoate potassiumMexrenoic acid (mexrenoate)MexrenoneOxprenoic acid (oxprenoate)Oxprenoate potassium (RU-28318)Prorenoate potassiumProrenoic acid (prorenoate)ProrenoneSC-5233 (spirolactone)SC-8109SpirorenoneSpironolactoneSpiroxasoneTrimegestoneAmlodipineApararenoneBenidipineEsaxerenoneFelodipineFinerenoneNifedipineNimodipineNitrendipineOcedurenone