Systematic (IUPAC) name
[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] (Z)-octadec-9-enoate
Clinical data
Pregnancy cat.  ?
Legal status  ?
ATC code None
PubChem CID 6918373
ChemSpider 20153369 YesY
Chemical data
Formula C36H54O3 
Mol. mass 534.812 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Oleoyl-estrone (OE) is a fatty acid ester of estrone. It is a naturally circulating hormone in animals including humans. It was first reported in 1996 to cause a body fat loss effect in rats in the International Journal of Obesity and Related Metabolic Disorders.[1] The animal research has all been conducted by the Nitrogen-Obesity Research Group of the University of Barcelona.

The compound was found to potently induce body-fat loss while preserving protein stores in animals which is the ultimate goal of an anti-obesity agent as body protein loss is an undesired but inevitable (to some degree) side effect of fat loss via calorie restriction.



Oleoyl-estrone functions by reducing energy-intake without prescribed dietary restriction (forced dietary restriction in addition to OE actually led to protein losses) while maintaining energy expenditure (which normally falls as part of the adaptations to calorie restriction). The partitioning effects of this hormone leads to adipose stores being the source of energy that makes up for the energy deficit rather than protein stores.


The molecule has been widely studied in various strains of animals and shown to be effective in virtually all studies. A surprising result that came out of the animal studies was that OE treated animals maintained their fat loss after treatment was stopped. Weight loss maintenance is one of the most difficult aspects of obesity treatment and so this effect is promising. This led to the postulation that oleoyl-estrone can reduce the body's bodyfat setpoint which would allow the body to maintain a reduced bodyfat without experiencing a hormonal milieu that aims to regain the lost bodyfat by reducing energy expenditure and increasing energy intake.

The research group discovered that oleoyl-estrone levels correlated with bodyfat stores except for obese organisms where there was less oleoyl-estrone circulating than would be predicted based on bodyfat levels. This led to the theory that administering oleoyl-estrone to bring plasma OE levels up to normal would signal to the body that there is an excess amount of bodyfat and therefore there would be a bodyfat loss.

Recent research shows that corticosterone inhibits the fat mobilizing effects of oleoyl-estrone in female rats that had their adrenal glands removed. [2]

The research group set up a company called Oleoyl-Estrone Developments in 2001 which included as a founder Dr. Marià Alemany, one of the principal researches, who is also the holder of a 1998 U.S. patent (U.S. Patent 5,798,348) for fatty acid esters of estrone, including OE, in relation to fat loss.

The group studied the effects of oral OE on Dr. Marià Alemany who was morbidly obese. It was shown for the first time to be effective at producing fat loss in a human and also a maintenance (and increase) of weight loss in two-month rest periods in between three-week dosing periods. This was achieved with no prescribed dietary restrictions.[3]

Clinical development

OE was licensed in an exclusive worldwide deal to Manhattan Pharmaceuticals in 2002. An Investigational New Drug application was accepted by the U.S. Food and Drug Administration (FDA) in 2005 and a Phase I trial was conducted in Switzerland. The results showed OE to be safe and to lead to weight loss after just 7 days of dosing, and this weight loss was maintained for three further weeks after treatment had stopped.

In June 2006 a Phase IIa trial of 100 patients began which included two 14-day dosing periods each followed by 28 days of no treatment which was designed to elucidate the best dosing methods and in particular the maintenance of weight loss that had been shown. This trial was originally a single-centre trial in Switzerland, but in November 2006 it was announced that the trial had been expanded to two additional clinical sites in the USA.[4] The results from this trial are expected in the first half of 2007.

An additional trial was commenced in October 2006 that is designed to investigate the efficacy of the drug in morbidly obese patients who had been designated as bariatric patient candidates.[5] This trial, taking place in the USA, will recruit 24 patients and will dose OE for 30 days, without any break, and then have a follow-up 30 days after dosing has been completed. The results from this trial are also expected in the first half of 2007.

On July 10, 2007 Manhattan Pharmaceuticals announced that its phase 2a studies for oral oleoyl-estrone failed. The two studies demonstrated no clinically meaningful or statistically significant placebo adjusted weight loss.[6]


  1. ^ Sanchis D, Balada F, del Mar Grasa M, et al. (June 1996). "Oleoyl-estrone induces the loss of body fat in rats". Int. J. Obes. Relat. Metab. Disord. 20 (6): 588–94. PMID 8782737. 
  2. ^ del Mar Grasa M, Serrano M, Fernández-López JA, Alemany M (August 2007). "Corticosterone inhibits the lipid-mobilizing effects of oleoyl-estrone in adrenalectomized rats". Endocrinology 148 (8): 4056–63. doi:10.1210/en.2007-0331. PMID 17510239. http://endo.endojournals.org/cgi/pmidlookup?view=long&pmid=17510239. 
  3. ^ Marià Alemany PhD et al. (pdf). Oleoyl-estrone-induced weight loss in an obese man. Manhattan Pharmaceuticals Inc.. Archived from the original on 2007-03-16. http://web.archive.org/web/20070316040624/http://www.manhattanpharma.com/oe-ma6.pdf. Retrieved 2007-04-04. 
  4. ^ "Manhattan Pharmaceuticals Expands Phase 2a Obesity Clinical Trial Sites to US" (Press release). Manhattan Pharmaceuticals, Inc.. November 8, 2006. http://www.manhattanpharma.com/pr_110806.html. Retrieved 2007-04-04. 
  5. ^ "Manhattan Pharmaceuticals Expanding Oral Oleoyl-Estrone Clinical Program To Include Morbidly Obese" (Press release). Manhattan Pharmaceuticals, Inc.. October 12, 2006. http://www.manhattanpharma.com/pr_101206.html. Retrieved 2007-04-04. 
  6. ^ http://www.emaxhealth.com/95/13821.html

External links

Wikimedia Foundation. 2010.

Игры ⚽ Нужно решить контрольную?

Look at other dictionaries:

  • Oleoyl-estrone — Général PubChem 6918373 …   Wikipédia en Français

  • Oléoyl-estrone — Général PubChem 6918373 …   Wikipédia en Français

  • Amphetamine — For other uses, see Amphetamine (disambiguation). Amphetamine Systematic (IUPAC) name …   Wikipedia

  • Stimulant — Ritalin Slow Release (SR) 20 mg tablets. Stimulants (also referred to as psychostimulants) are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include… …   Wikipedia

  • Benzphetamine — Systematic (IUPAC) name (2S) N benzyl N methyl 1 phenylpropan 2 amine …   Wikipedia

  • Orlistat — Packaging of orlistat (Xenical) 120 mg capsules, as sold in Canada. Systematic (IUPAC) name …   Wikipedia

  • Cathine — Not to be confused with caffeine, a compound found in coffee and tea. Cathine Systematic ( …   Wikipedia

  • Anorectic — An anorectic or anorexic (from the Greek an = without and orexis = appetite ), also known as anorexigenic or appetite suppressant, is a dietary supplement and/or drug which reduces appetite, food consumption, and as a result, causes weight loss… …   Wikipedia

  • Phenylpropanolamine — Systematic (IUPAC) name 2 …   Wikipedia

  • 5-Hydroxytryptophan — Not to be confused with serotonin (5 hydroxytryptamine, 5 HT). 5 Hydroxytryptophan …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”