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Substance Name: Prasterone [USAN:INN]
RN: 53-43-0
UNII: 459AG36T1B
InChIKey: FMGSKLZLMKYGDP-USOAJAOKSA-N

Notes

  • 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.
  • 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.

Molecular Formula

  • C19-H28-O2

Molecular Weight

  • 288.4282
 

Classification Codes

  • Adjuvants, Immunologic
  • Hormone
  • Human Data
  • Immunologic Factors
  • Mutation Data
  • Reproductive Effect
  • Treatment of Moderate to Severe Dyspareunia (or Pain at Sexual Activity), a Symptom of Vulvovaginal Atrophy due to Menopause
  • Tumor Data

Names and Synonyms

Name of Substance

  • Prasterone
  • Prasterone [USAN:INN]

MeSH Heading

  • Dehydroepiandrosterone

Synonyms

  • (3-beta)-3-Hydroxyandrost-5-en-17-one
  • 17-Chetovis
  • 17-Hormoforin
  • 3-beta-Hydroxy-5-androsten-17-one
  • 3beta-Hydroxyandrost-5-en-17-one
  • 4-08-00-00994 (Beilstein Handbook Reference)
  • 5,6-Dehydroisoandrosterone
  • 5,6-Dehydroisoandrostorone
  • 5,6-Didehydroisoandrosterone
  • 5-Dehydroepiandrosterone
  • Andrestenol
  • Androstenolone
  • BRN 2058110
  • Caswell No. 051F
  • CCRIS 3277
  • Dehydro-epi-androsterone
  • Dehydroepiandrosterone
  • Dehydroisoandrosterone
  • DHEA
  • Diandron
  • Diandrone
  • EC 200-175-5
  • EINECS 200-175-5
  • EM-760
  • EPA Pesticide Chemical Code 126510
  • Epiandrosterone, 5-dehydro-
  • GL 701
  • Gynodian
  • Intrarosa
  • NSC 9896
  • Prasterona
  • Prasterona [INN-Spanish]
  • Prasterone
  • Prasteronum
  • Prasteronum [INN-Latin]
  • Prestara
  • Psicosterone
  • Siscelar plus
  • trans-Dehydroandrosterone
  • UNII-459AG36T1B

Systematic Names

  • 3beta-Hydroxyandrost-5-en-17-one
  • Androst-5-en-17-one, 3-beta-hydroxy-
  • Androst-5-en-17-one, 3-hydroxy-, (3-beta)- (9CI)
  • Androst-5-en-17-one, 3-hydroxy-, (3beta)-
  • Androst-5-en-17-one, 3beta-hydroxy- (8CI)
  • Dehydroepiandrosterone
  • Prasterone

Registry Numbers

CAS Registry Number

  • 53-43-0

FDA UNII

  • 459AG36T1B

Other Registry Numbers

  • 105597-37-3
  • 108673-53-6
  • 9013-35-8

System Generated Number

  • 0000053430

Structure Descriptors

InChI

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

InChIKey

FMGSKLZLMKYGDP-USOAJAOKSA-N

Smiles

C1[C@@H]2[C@@H]([C@@]3(C(C[C@@H](O)CC3)=C1)C)CC[C@@]1([C@H]2CCC1=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 10mg/kg/2W-I (10mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Annals of Internal Medicine. Vol. 129, Pg. 588, 1998.
mouse LD50 oral > 10gm/kg (10000mg/kg)   British UK Patent Application. Vol. #2208473,
mouse LD50 subcutaneous 900mg/kg (900mg/kg)   British UK Patent Application. Vol. #2208473,
rat LD50 oral > 10gm/kg (10000mg/kg)   British UK Patent Application. Vol. #2208473,
rat LD50 subcutaneous 1gm/kg (1000mg/kg)   British UK Patent Application. Vol. #2208473,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 140-141 deg C   EXP
log P (octanol-water) 3.23 (none)   EXP
Water Solubility 63.5 mg/L 25 EXP
Vapor Pressure 2.23E-08 mm Hg 25 EST
Henry's Law Constant 6.62E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.27E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.