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Chemical Compound Review

Benovocylin     (17-hydroxy-13-methyl- 6,7,8,9,11,12,14,15...

Synonyms: Progynon-beta, Ovasterol-beta, AGN-PC-00HSGS, BSPBio_002755, KBioGR_001082, ...
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Disease relevance of estradiol benzoate

  • Treatment with low doses of estrogen (2 or 8 micrograms of estradiol benzoate (EB) 48 hr before sacrifice) was slightly but not significantly more effective in elevating hypothalamic progestin receptor content in age-matched females than in males despite the 40% greater body weights of males [1].
  • When an additional dose of P was given up to 24 h prior to or 24 h after the EB, EB-P facilitation of lordosis was inhibited [2].
  • While these data show that EB treatment does reduce the severity of some metabolic disturbances in a genetic model of type II diabetes, long-term estrogens do not appear to offer substantial advantages in the treatment of obesity or diabetes when compared with the effects of caloric restriction alone [3].
  • Whereas precocious puberty resulted from the implantation of EB into the MPOA, a delay of puberty onset was induced by medial preoptic implants of the antiestrogen clomiphene citrate which also enhanced the LH-suppressing effect of s.c. administered EB in prepubertal females [4].
  • In two subsequent experiments, nine of 26 cows were induced to have follicular cysts by follicular aspiration followed by 5 mg of EB [5].

Psychiatry related information on estradiol benzoate

  • Ovariectomized rats fed the HF diet and given both EB and haloperidol exhibited significantly greater tumor number per rat, increased average tumor size, and reduced tumor latency period when compared to similarly treated rats fed the CF diet [6].
  • Measures of EMG activity, response latency, and spike count were altered in castrates, but maintained in EB-treated castrates to the levels of intact males [7].
  • In contrast, maternal behavior latencies were reduced by E/P/EB only among Sham-HYPX females [8].
  • Gonadectomized male rats were submitted to REM sleep deprivation (REMd) for 120 hr and their hetero and homotypical sexual response to estradiol benzoate (EB) was tested [9].
  • Feeding behavior was continuously monitored with photodetectors and recorded on an Esterline Angus event marker before and after a single SC injection of 6 micrograms of EB [10].

High impact information on estradiol benzoate

  • A combined prenatal and neonatal regime of EB injections resulted in the abnormal presence of columnar epithelium in the vaginal fornices of some of the mice from each strain or stock [11].
  • Sham-operated intact rats and bilaterally ovariectomized rats were given daily injections of haloperidol to increase prolactin secretion, bromocryptine to decrease prolactin secretion, and/or estradiol benzoate (EB) [6].
  • Both EB and HAL significantly raised blood prolactin levels [12].
  • Treatment for 8 days with EB produced a significant increase in mammary tumor incidence despite underfeeding, whereas underfed rats given the combination of HAL EB, and GH showed development and growth of mammary tumors equal to that of full-fed controls [12].
  • In vitro one-point binding analyses of estradiol benzoate (EB)-induced cellular PRs and immunohistochemistry of PR in the mediobasal hypothalamus demonstrated a reduction in binding in the homozygous females, equivalent to background levels seen in EB-unresponsive tissue [13].

Chemical compound and disease context of estradiol benzoate

  • Ovariectomized hamsters were administered estradiol benzoate (EB) and 44 h later, progesterone (P.) Lordosis behavior was induced [2].
  • In Experiment 2, we tested the maternal behavior and measured estrogen receptor concentrations in OVX, steroid-primed, nulliparous rats after hysterectomy (H) and EB treatment [14].
  • Conversely, PHEN infused into the MPOA of EB + P primed females transiently increased the number of seconds females held lordosis from 15 min to 2.0 h after infusion (maximum difference 64%; p < 0.005).(ABSTRACT TRUNCATED AT 250 WORDS)[15]
  • A dose of cordycepin that decreased lordosis when infused 1 h before injection of 0.5 microgram EB did not affect the behavior when infused 1 h before injection of 500 micrograms P [16].
  • Conversely, HPA, which elevates endogenous GABA levels, was effective in facilitating lordosis behavior in sham-operated rats treated with EB only [17].

Biological context of estradiol benzoate

  • Protein binding was eliminated by E2Bz [18].
  • These data support the hypothesis that neonatal EB treatment may directly inhibit the synthesis or replenishment of the 8S estradiol "receptor" prior to the development of the persistent estrus syndrome (persistent vaginal estrus, anovulation and polycystic ovaries) [19].
  • Injection of estradiol benzoate (EB, 5 mug/rat) 2 hr prior to, together with or following P treatment at 0300 hr of proestrus restored ovulation and the surge of LH [20].
  • The ability of exogenous P to advance and amplify the LH surge on proestrus and in EB-primed ovariectomized rats appears to result in part from a reduction in the EOP inhibitory influence on LH secretion and may indicate a role for EOP in mediating the stimulatory effects of endogenous steroids on LH secretion in the female rat [21].
  • However, blockade of ovulation was not reversed if EB was administered at 0500 or 0800 hr of proestrus following P treatment on diestrus II [20].

Anatomical context of estradiol benzoate

  • One day after EB treatment, rats were bilaterally cannulated in the anterior ventromedial preoptic area (POA) [22].
  • In a futher experiment in rats ovariectomized at 9 days of age, those treated neonatally with EB had significantly smaller uteri than their untreated ovariectomized controls, thus providing indirect evidence for an extravarian factor affected by neonatal treatment [19].
  • These results demonstrate that the activation of cAMP phosphodiesterase after an injection of EB and the subsequent decrease in oviduct cAMP concentration are necessary for the epithelial cells to achieve their proliferative cycle [23].
  • There was no significant effect of sex or EB treatment on ER mRNA levels in medial amygdala [24].
  • Ovariectomized (OVX) ewes (n = 4/group) were given either 50 micrograms of estradiol benzoate (EB) or oil and were killed 16 h later for collection of the pituitary glands for immunohistochemistry and confocal microscopy [25].

Associations of estradiol benzoate with other chemical compounds


Gene context of estradiol benzoate

  • In addition, while DPN lacked an agonistic action on peripheral tissue and serum pituitary reproductive hormones concentration, EB, PPT and PPT+DPN induced similar uterine ballooning and vaginal cornification, and increased and decreased, respectively, serum concentrations of PRL and gonadotropins [29].
  • To this end, 2-week-old ovariectomized (OVX) rats were injected over 3 days with 25 microg estradiol benzoate (EB), 1.5 mg of propylpyrazole triol (PPT), a selective ERalpha agonist, 1.5 mg of the selective ERbeta agonist diarylpropionitrile (DPN) or a combination of PPT and DPN [29].
  • EB, PPT and PPT+DPN treatments increased PR mRNA and the number and intensity of nuclei immunoreactive (IR) for PR in gonadotropes, and reduced the number of gonadectomy cells [29].
  • Progesterone and NET significantly increased GnRH concentrations and reversed the EB-induced changes [30].
  • Normal parthenogens did not increase ER mRNA in response to EB in either age group, in contrast to the strong response of 1-day-old males and females of the sexual species and 30-day-old created males [31].

Analytical, diagnostic and therapeutic context of estradiol benzoate

  • Five days after ovariectomy, rats received oil or EB (30 micrograms/rat) at 1000 h on day 0 [32].
  • Isotopic in situ hybridization histochemistry revealed that within the limbic-hypothalamic nuclei, levels of CCK and preproenkephalin (PPE) mRNA levels were significantly higher in EB and EB + T4-treated animals compared with T4 or oil-treated animals [33].
  • In postnatal Week 16, subjects were gonadectomized, and blood samples were collected after treatment with 10 micrograms estradiol benzoate (EB), used to elicit an LH surge; subjects were subsequently treated with GnRH to test pituitary responsiveness [34].
  • No treatment, EB only, and EB plus P served as control groups [35].
  • In a separate group of acyclic, tumor-bearing females 42--56 days after transplantation, a single s.c. injection of 20 micrograms estradiol benzoate (EB) at 1030 h elicited significant increases in both serum LH and FSH values between 1700 and 1830 h on the next day [36].


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  2. The excitation and inhibition of sexual receptivity in female hamsters by progesterone: time and dose relationships, neural localization and mechanisms of action. DE'Bold, J.F., Martin, J.V., Whalen, R.E. Endocrinology (1976) [Pubmed]
  3. Effects of estrogen on food intake, body weight, and temperature of male and female obese mice. Dubuc, P.U. Proc. Soc. Exp. Biol. Med. (1985) [Pubmed]
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  10. Similar effects of estrogen and lateral hypothalamic lesions on feeding behavior of female rats. Nance, D.M., Gorski, R.A. Brain Res. Bull. (1978) [Pubmed]
  11. Adenosis-like lesions and other cervicovaginal abnormalities in mice treated perinatally with estrogen. Plapinger, L., Bern, H.A. J. Natl. Cancer Inst. (1979) [Pubmed]
  12. Relationship of hormones to inhibition of mammary tumor development by underfeeding during the "critical period" after carcinogen administration. Sylvester, P.W., Aylsworth, C.F., Meites, J. Cancer Res. (1981) [Pubmed]
  13. Dopamine requires the unoccupied progesterone receptor to induce sexual behavior in mice. Mani, S.K., Allen, J.M., Lydon, J.P., Mulac-Jericevic, B., Blaustein, J.D., DeMayo, F.J., Conneely, O., O'Malley, B.W. Mol. Endocrinol. (1996) [Pubmed]
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  15. Effects of clonidine and phentolamine infused into the medial preoptic area and medial basal hypothalamus of the guinea pig. Malik, K.F., Morrell, J.I., Feder, H.H. Neuroendocrinology (1993) [Pubmed]
  16. Estrogen induction of sexual behavior in female rats and synthesis of polyadenylated messenger RNA in the ventromedial nucleus of the hypothalamus. Yahr, P., Ulibarri, C. Brain Res. (1986) [Pubmed]
  17. Influence of gamma-aminobutyric acid on lordosis behavior and dopamine activity in estrogen primed spayed female rats. Mcginnis, M.Y., Gordon, J.H., Gorski, R.A. Brain Res. (1980) [Pubmed]
  18. Prolactin augments progesterone-dependent uteroglobin gene expression by modulating promoter-binding proteins. Kleis-SanFrancisco, S., Hewetson, A., Chilton, B.S. Mol. Endocrinol. (1993) [Pubmed]
  19. Neonatal treatment with sex steroids: relationship between the uterotropic response and the estrogen "receptor" in prepubertal rats. Gellert, R.J., Lewis, J., Pétra, P.H. Endocrinology (1977) [Pubmed]
  20. Observations on facilitation of the preovulatory rise of LH by estrogen. Kalra, S.P. Endocrinology (1975) [Pubmed]
  21. Modulation of endogenous opioid influence on luteinizing hormone secretion by progesterone and estrogen. Gabriel, S.M., Simpkins, J.W., Kalra, S.P. Endocrinology (1983) [Pubmed]
  22. In vivo biosynthesis of hypothalamic luteinizing hormone releasing hormone in individual free-running female rats. Krause, J.E., Advis, J.P., McKelvy, J.F. Endocrinology (1982) [Pubmed]
  23. Cyclic nucleotide phosphodiesterase activity in the quail oviduct: hormonal regulation and involvement in estrogen-induced growth. Dumas, M.Y., Fanidi, A., Pageaux, J.F., Courion, C., Nemoz, G., Prigent, A.F., Pacheco, H., Laugier, C. Endocrinology (1988) [Pubmed]
  24. Estrogen receptor messenger RNA expression in rat hypothalamus as a function of genetic sex and estrogen dose. Lauber, A.H., Mobbs, C.V., Muramatsu, M., Pfaff, D.W. Endocrinology (1991) [Pubmed]
  25. The positive feedback action of estrogen mobilizes LH-containing, but not FSH-containing secretory granules in ovine gonadotropes. Thomas, S.G., Clarke, I.J. Endocrinology (1997) [Pubmed]
  26. Evidence for gamma-aminobutyric acid modulation of ovarian hormonal effects on luteinizing hormone secretion and hypothalamic catecholamine activity in the female rat. Adler, B.A., Crowley, W.R. Endocrinology (1986) [Pubmed]
  27. Influence of ovarian steroids on relaxin-induced uterine growth in ovariectomized gilts. Hall, J.A., Cantley, T.C., Galvin, J.M., Day, B.N., Anthony, R.V. Endocrinology (1992) [Pubmed]
  28. Melatonin effects on prolactin secretion in pituitary-grafted male rats. Villanua, M.A., Agrasal, C., Tresguerres, J.A., Vaughan, M.K., Esquifino, A.I. J. Pineal Res. (1989) [Pubmed]
  29. Biological role of pituitary estrogen receptors ERalpha and ERbeta on progesterone receptor expression and action and on gonadotropin and prolactin secretion in the rat. Sánchez-Criado, J.E., Martín De Las Mulas, J., Bellido, C., Tena-Sempere, M., Aguilar, R., Blanco, A. Neuroendocrinology (2004) [Pubmed]
  30. Progestins modulate the action of estrogen on gonadotropin-releasing hormone, luteinizing hormone and prolactin in the rat. Genazzani, A.R., Petraglia, F., Silferi, M., Lattesa, A.M., Coukos, G., Genazzani, A.D., Artini, P., Nappi, C., Volpe, A. Gynecol. Obstet. Invest. (1990) [Pubmed]
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  32. Hypothalamic neuropeptide-Y gene expression increases before the onset of the ovarian steroid-induced luteinizing hormone surge. Sahu, A., Crowley, W.R., Kalra, S.P. Endocrinology (1994) [Pubmed]
  33. Interaction of thyroxine and estrogen on the expression of estrogen receptor alpha, cholecystokinin, and preproenkephalin messenger ribonucleic acid in the limbic-hypothalamic circuit. Holland, K., Norell, A., Micevych, P. Endocrinology (1998) [Pubmed]
  34. Prenatal inhibition of aromatase activity affects luteinizing hormone feedback mechanisms and reproductive behaviors of adult guinea pigs. Choate, J.V., Resko, J.A. Biol. Reprod. (1994) [Pubmed]
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