Pregnenolone

Pregnenolone
Clinical data


AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, transdermal
ATC code	None
Legal status
Legal status	Over-the-counter
Identifiers
IUPAC name 3β-hydroxypregn-5-en-20-one
CAS Number	145-13-1^Y
PubChem (CID)	8955
IUPHAR/BPS	2376
DrugBank	DB02789^N
ChemSpider	8611^N
UNII	73R90F7MQ8^Y
ChEBI	CHEBI:16581^N
ChEMBL	CHEMBL253363^N
ECHA InfoCard	100.005.135
Chemical and physical data
Formula	C₂₁H₃₂O₂
Molar mass	316.483 g/mol
3D model (Jmol)	Interactive image
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
InChI InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1^N Key:ORNBQBCIOKFOEO-QGVNFLHTSA-N^N
^NY (what is this?)

Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.

Pregnenolone is synthesized from cholesterol. This conversion involves hydroxylation of the side chain at the C20 and C22 positions, with cleavage of the side chain. The enzyme performing this task is cytochrome P450scc, located in the , and controlled by anterior pituitary trophic hormones, such as adrenocorticotropic hormone, follicle-stimulating hormone, and luteinizing hormone, in the adrenal glands and gonads. There are two intermediates in the transformation of cholesterol into pregnenolone, 22R-hydroxycholesterol and 20α,22R-dihydroxycholesterol, and all three steps in the transformation are catalyzed by P450scc.

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Wikipedia

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