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3-BETA-HYDROXY-5-ANDROSTEN-17-ONE


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Chemical Component Summary

Name3-BETA-HYDROXY-5-ANDROSTEN-17-ONE
Identifiers(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
FormulaC19 H28 O2
Molecular Weight288.424
TypeNON-POLYMER
Isomeric SMILESC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C
InChIInChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
InChIKeyFMGSKLZLMKYGDP-USOAJAOKSA-N

Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count6
Bond Count52
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01708 
NamePrasterone
Groups
  • approved
  • investigational
  • nutraceutical
DescriptionPrasterone, also known as dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (DHEA) can be converted to testosterone; androstenedione; estradiol; and estrone. Most of DHEA is sulfated (dehydroepiandrosterone sulfate) before secretion. In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements. In November 2016, DHEA was approved (as Intrarosa) to treat women experiencing moderate to severe pain during sexual intercourse (dyspareunia), a symptom of vulvar and vaginal atrophy (VVA), due to menopause. In Canada, a prescription is required to buy DHEA.
Synonyms
  • 3β-hydroxyandrost-5-en-17-one
  • Prasterone
  • Dehydroepiandrosterone
  • Dehydroisoandrosterone
  • DHEA
Brand Names
  • Intrarosa
  • Prastera
IndicationDHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older people’s skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial “age spots” in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids). DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.
Categories
  • 17-Ketosteroids
  • Adjuvants, Immunologic
  • Adrenal Cortex Hormones
  • Alimentary Tract and Metabolism
  • Anabolic Agents for Systemic Use
ATC-Code
  • G03EA03
  • G03XX01
  • A14AA07
CAS number53-43-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownbinder
Estrogen receptor betaMDIKNSPSSLNSPSSYNCSQSILPLEHGSIYIPSSYVDSHHEYPAMTFYS...unknownactivator
GABA(A) ReceptorMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownantagonist
NMDA receptorMSTMRLLTLALLFSCSVARAACDPKIVNIGAVLSTRKHEQMFREAVNQAN...unknownagonist
Androgen receptorMEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL90593
PubChem 5881
ChEMBL CHEMBL90593
ChEBI CHEBI:28689
CCDC/CSD VEFPUR, ZOYMOP07, VEFPUR02, ZOYMOP06, ZOYMOP04, ZOYMOP, VEFPUR01, ZOYMOP03, ZOYNAC, ZOYMOP01, ZOYMUV, ZOYMOP08