Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: Chemistry and metabolism

Proceedings of the Society for Experimental Biology and Medicine

Volumn 217, Issue 1, 1998, Pages 6-16

  Bhavnani, Bhagu R ^a,b  

^a UNIVERSITY OF TORONTO   (Canada)

^b ST MICHAEL'S HOSPITAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED ESTROGEN;

CARDIOVASCULAR DISEASE; CONFERENCE PAPER; ESTROGEN ACTIVITY; ESTROGEN METABOLISM; ESTROGEN THERAPY; FEMALE; HORSE; HUMAN; OSTEOPOROSIS; POSTMENOPAUSE;

EQUIDAE; EQUUS CABALLUS;

EID: 0031974053     PISSN: 00379727     EISSN: None     Source Type: Journal    
DOI: 10.3181/00379727-217-44199     Document Type: Conference Paper

References (51)

1. 3H]equilin in the pregnant mare. Endocrinology 108:232-238, 1981.
2. Bhavnani BR. The saga of the ring B unsaturated equine estrogens. Endocrine Rev 9:396-416, 1988.
3. Dorfman RI, Dorfman AS. The assay of estrogens in the chick by oral administration. Endocrinology 53:301-305, 1953.
4. Dorfman RI, Dorfman AS. Estrogen assays using the rat uterus. Endocrinology 55:65-69, 1954.
5. Howard RP, Keaty KC. Evaluation of equilin-3-monosulfate and other estrogens. Arch Int Med 128:229-233, 1971.
6. Beek VA, Friedrich F. Equilin sulfate zur substitution beim menopause-syndrom. Wien Klin Wochenschr 87:59-62, 1975.
7. Lobo RL, Nguyen HN, Eggena P, Brenner PF. Biologic effects of equilin sulfate in postmenopausal women. Fertil Steril 49:234-238, 1988.
8. Artner J, Friedrich F. Die behandlung des klimakerichen syndroms mit dihydroequilin. Wien Klin Wochenschr 82:275-277, 1970.
9. Bhavnani BR, Cecutti A, Dey MS. Effect in postmenopausal women of delta-8-estrone sulfate: a novel estrogen component of premarin. J Soc Gynecol Investig 4:(No. 1, Supplement) 177A (Abstract No. 392) 1997.
10. Mashchak CA, Lobo RA, Dozono R, Eggena P, Nakamura RM, Brenner PF, Mikhail G. Comparison of phamacodynamic properties of various estrogens formulations. Am J Obstet Gynecol 144:511-518, 1982.
11. Evans RM. The steroid and thyroid hormone receptor superfamily. Science 240:889-895, 1988.
12. Bhavnani BR, Woolever CA. Interaction of ring B unsaturated estrogens with estrogen receptors of human endometrium and rat uterus. Steroids 56:201-209, 1991.
13. Bhavnani BR, Gerulath A, Cecutti A. Pharmacokinetics and pharmacodynamics of delta-8-estrone. J Soc Gynecol Investig 3(Suppl. 2) (Abstract No. 613), 1996.
14. Yang NN, Venugopalan M, Hardikor S, Glasebrook A. Identification of an estrogen response element activated by metabolites of 17β-estradiol and raloxifene. Science 273:1222-1225, 1996.
15. Pan CC, Woolever CA, Bhavnani BR. Transport of equine estrogens: Binding of conjugated and unconjugated equine estrogens with human serum proteins. J Clin Endocrinol Metab 61:499-507, 1985.
16. Rosenthal H, Pietrzak E, Slaunwhite WR Jr., Sandberg AA. Binding of estrone sulfate in human plasma. J Clin Endocrinol Metab 34:805-813, 1972.
17. Wu CH, Motohashi T, Abdel-Rahman HA, Flickinger GL, Mikhail G. Free and protein bound plasma estradiol 17β during the menstrual cycle. J Clin Endocrinol Metab 43:436-445, 1976.
18. Dunn JF, Nisula BC, Rodbard D. Transport of steroid hormones: Binding of 21 endogenous steroids to both testosterone-binding globulin and corticosteroid binding globulin in human plasma. J Clin Endocrinol Metab 53:58-68, 1981.
19. Bhavnani BR, Sarda IR, Woolever CA. Radioimmunoassay of plasma equilin and estrone in postmenopausal women after the administration of Premarin. J Clin Endocrinol Metab 52:741-747, 1981.
20. Ruder HJ, Loriaux DL, Lipsett MB. Estrone sulfate: Production rate and metabolism in man. J Clin Invest 51:1020-1033, 1972.
21. Anderson ABM, Sklovsky E, Sayers L, Steele P, Turnbull AC. Comparison of serum oestrogen concentrations in postmenopausal women taking estrone sulphate and oestradiol. BMJ 1:140-142, 1978.
22. 3H]equilin sulfate after oral and intravenous administration in normal postmenopausal women and men. J Clin Endocrinol Metab 68:757-765, 1989.
23. Longcope C. The metabolism of estrone sulfate in normal males. J Clin Endocrinol Metab 34:113-122, 1972.
24. Tait JF, Burstein S. In vivo studies of steroid dynamics in man. In: Pincus G, Thimann KV, Astwood EB, Eds. The Hormones. New York: Academic Press, pp 441-557, 1964.
25. Bhavnani BR, Woolever CA, Benoit H, Wong T. Pharmacokinetics of equilin and equilin sulfate in normal postmenopausal women and men. J Clin Endocrinol Metab 56:1048-1056, 1983.
26. Bhavnani BR, Cecutti A. Pharmacokinetics of 17β-dihydroequilin sulfate and 17β-dihydroequilin in normal postmenopausal women. J Clin Endocrinol Metab 78:197-204, 1994.
27. Bhavnani BR, Cecutti A. Metabolic clearance rate of equilin sulfate and its conversion to plasma equilin, conjugated and unconjugated equilenin, 17β-dihydroequilin, and 17β-dihydroequilenin in normal postmenopausal women and men under steady state conditions. J Clin Endocrinol Metab 77:1269-1274, 1993.
28. Bhavnani BR, Cecutti A, Gerulath AH. 17β-Dihydroequilin sulfate dynamics in postmenopausal women and men under steady state conditions. J Soc Gynecol Investig 4:No. 1 (Suppl.) 177A (Abstract 391), 1997.
29. Sandberg E, Gurpide E, Lieberman S. Quantitative studies on the metabolism of dehydroisoandrosterone sulfate. Biochemistry 3:1256-1267, 1966.
30. Wang DY, Bulbrook RD, Sheedon A, Hamilton T. The metabolic clearance rates of dehydroepiandrosterone, testosterone and their sulphate esters in man, rat and rabbit. J Endocrinol 38:307-318, 1967.
31. Longcope C, Tait JF. Validity of metabolic clearance rates and interconversion rates and transfer factors. J Clin Endocrinol Metab 32:481-490, 1971.
32. Longcope C. Metabolic clearance and blood production rates of estrogens in postmenopausal women. Amer J Obstet Gynecol 111:778-781, 1971.
33. Longcope C, Layne DS, Tait JF. Metabolic clearance rates and interconversions of estrone and 17β-estradiol in normal males. J Clin Invest 47:93-106, 1968.
34. Hembree WC, Bardin CW, Lipset MB. A study of estrogen metabolic clearance rates and transfer factors. J Clin Invest 48:1809-1813, 1969.
35. 3H]dihydroequilin-dihydroequilin sulfate in normal postmenopausal women. Steroids 59:389-394, 1994.
36. Bhavnani BR, Woolever CA. The metabolism of equilin in normal men. J Steroid Biochem Mol Biol 17:217-223, 1982.
37. 3H]equilin in normal and malignant human endometrium and in endometrial adenocarcinoma transplanted into nude mice. J Steroid Biochem Mol Biol 38:433-439, 1991.
38. Ryan KJ, Engle LL. The interconversion of estrone and estradiol in human tissue slices. Endocrinology 52:287-291, 1953.
39. Tseng L, Gurpide E. Estradiol and 20α-dihydroprogesterone dehydrogenase activities in human endometrium during the menstrual cycle. Endocrinology 94:419-423, 1974.
40. Purdy RH. Active intermediates and carcinogenesis. In: Merriam YR, Ed. Catechol Estrogens. New York: Raven Press, pp 123-140, 1983.
41. Zhu BT, Roy D, Liehr JG. The carcinogenic activity of ethinyl estrogens is determined by both their hormonal characteristics and their conversion to catechol metabolites. Endocrinology 132:577-583, 1993.
42. Li JJ, Li SA. Estrogen carcinogenesis in hamster tissues. Endocrine Rev 11:524-531, 1990.
43. Li JJ, Li SA, Oberley TD, Parson JA. Carcinogenic activities of various steroidal and non-steroidal estrogens in the hamster kidney: Relation to hormonal activity and cell proliferation. Cancer Res 55:4347-4351, 1995.
44. Bhavnani BR, Lau A, Cecutti A, Gerulath A. Demonstration of 2- and 4-hydroxylation of equilin by normal proliferative and secretory human endometrial microsomal preparations. J Soc Gynecol Investig 2:424 (Abstract No. 415), 1995.
45. Reddy VVR, Hanjahi P. Synthesis of catechol estrogens by human uterus and leiomyoma. Steroids 37:195-199, 1981.
46. Bhavnani BR, Cecutti A. Identification of novel 16α-hydroxylated ring B unsaturated estrogens following administration of equilin to postmenopausal women and men. J Soc Gynecol Investig 3(Suppl. 2):365 (Abstract No. 615), 1996.
47. Schneider J, Kinne D, Fracchia A, Pierce V, Anderson KE, Bradlow HL, Fishman J. Abnormal oxidative metabolism of estradiol in women with breast cancer. Proc Natl Acad Sci (USA) 79:3047-3051, 1982.
48. Bradlow HL, Hershcopf RJ, Martucci CP, Fishman J. Estradiol 16α-hydroxylation in the mouse correlates with mammary tumor incidence and presence of marine mammary tumor virus: A possible model for the hormonal etiology of breast cancer in humans. Proc Natl Acad Sci (USA) 82:6295-6299, 1985.
49. Swaneck GE, Fishman J. Covalent binding of the endogenous estrogen 16α-hydroxy estrone to estradiol receptor in human breast cancer cells: Characterization and intranuclear localization. Proc Natl Acad Sci (USA) 85:7831-7835, 1988.
50. Yu SC, Fishman J. Interaction of histones with estrogens: Covalent adduct formation with 16α-hydroxy-estrone. Biochemistry 24:8017-8021, 1985.
51. Miyairi S, Ichikawa T, Nambara T. Structure of the adduct of 16α-hydroxy estrone with a primary amine: Evidence for the Heyns rearrangement of steroidal D-ring-hydroxymines. Steroids 56:361-366, 1991.