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14-September-2008 18:02:48 - Pregnenolone Pregnenolone Systematic IUPAC name 3β-hydroxypregn-5-en-20-one Identifiers CAS number 145-13-1 ATC code ? PubChem 8955 DrugBank EXPT02608 Chemical data Formula C21H32O2 Mol. mass 316.483 g/mol Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAB antagonist and increases neurogenesis in the hippocampus.1 Contents 1 Chemistry 2 Synthesis 3 Prohormone 4 Neurosteroid 5 Additional images 6 References Chemistry Like other steroids, pregnenolone consists of four interconnected cyclic hydrocarbons. It contains ketone and hydroxyl functional groups, two methyl branches, and a double bond at C5, in the B cyclic hydrocarbon ring. Like all steroid hormones, it is hydrophobic. Its esterified version, pregnenolone sulfate, is water-soluble. Synthesis Production of Pregnenolone from Cholesteol and further metabolism Production of Pregnenolone from Cholesteol and further metabolism Reaction: Pregnenolone-Progesterone Reaction: Pregnenolone-Progesterone Pregnenolone is synthesized from cholesterol. This conversion involves hydroxylation at the side-chain at C20 and C22 positions, with cleavage of the side-chain. The enzyme performing this task is cytochrome P450scc, located in the mitochondria, and controlled by pituitary tropic hormones, such as ACTH, FSH, LH. Prohormone Pregnenolone undergoes further steroid metabolism in one of three ways. Pregnenolone can be converted to progesterone. The critical enzyme step is two-fold using a 3-beta-hydroxysteroid dehydrogenase and a delta 4-5 isomerase. The latter transfers the double bond from C5 to C4 on the A ring. Progesterone is the entry into the delta-4-pathway, resulting in production of 17-hydroxy progesterone and androstenedione, precursor to testosterone and estrone. Aldosterone and corticosteroids are also derived from progesterone or its derivatives. Pregnenolone can be converted to 17-hydroxy-pregnenolone by the enzyme 17α-hydroxylase CYP17A1. Using this pathway, termed delta-5 pathway, the next step is conversion to dehydroepiandrosterone DHEA using a desmolase. DHEA is the precursor of androstenedione. Pregnenolone can be converted to androsta-5,16-dien-3 beta-ol by 16-ene synthetase. Neurosteroid Pregnenolone and its sulfate, like dehydroepiandrosterone and its sulfate and progesterone, belong to the group of neurosteroids that are found in high concentrations in certain areas in the brain, and are synthesized there. Neurosteroids affect synaptic functioning, are neuroprotective, and enhance myelinization. Pregnenolone and its sulfate ester are under investigation for their potential to improve cognitive and memory functioning.2 Additional images Steroidogenesis Cholesterol Progesterone References ^ Mayo, W; Lemaire, V; Malaterre, J; Rodriguez, Jj; Cayre, M; Stewart, Mg; Kharouby, M; Rougon, G; Le, Moal, M; Piazza, Pv; Abrous, Dn Jan 2005. Pregnenolone Sulfate Enhances Neurogenesis and Psa-Ncam in Young and Aged Hippocampus. Neurobiology of Aging 26 1: 103-14. doi:10.1016/j.neurobiolaging.2004.03.013. PMID 15585350. ^ Vallée M, Mayo W, Le Moal M 2001. Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging.. Brain Res Brain Res Rev 37 1-3: 301-12. doi:10.1016/S0165-01730100135-7. PMID 11744095. v d e Types of Steroids Precursors: Squalene | Lanosterol Common: Cholesterol | Pregnenolone | 17-Hydroxypregnenolone | DHEA | Androstenedione | Androstanediol Estrogens: Estradiol | Estriol | Estrone Androgens: Testosterone | Dihydrotestosterone | Androsterone Progestagens: Progesterone | 17-Hydroxyprogesterone | Progestins Glucocorticoids: Cortisol | Prednisone Mineralocorticoids: Aldosterone Phytosterols: Stigmasterol | Brassicasterol Ergosterols: Ergosterol | Ergocalciferol Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Pregnenolone Categories: Steroid hormones | Neurosteroids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français עברית 日本語 This page was last modified on 1 July 2008, at 09
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