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1. 4,4'-(diethylideneethylene)diphenol
2. Dienestrol, (e,e)-isomer
3. Dienestrol, (z,e)-isomer
4. Dienestrol, (z,z)-isomer
5. Dienoestrol
6. Oestrasid
7. Ortho Dienestrol
8. Synestrol
1. Dienoestrol
2. Dehydrostilbestrol
3. Cycladiene
4. E,e-dienestrol
5. Restrol
6. Dienol
7. Estraguard
8. Estroral
9. Follidiene
10. Oestrasid
11. Oestrodiene
12. 13029-44-2
13. 84-17-3
14. Estragard
15. Gynefollin
16. Oestroral
17. Dinovex
18. Retalon
19. (e,e)-dienestrol
20. Estrodienol
21. Hormofemin
22. Dehydrostilboestrol
23. Oestrodienol
24. Dienesterol
25. Dinestrol
26. Follormon
27. Oestrovis
28. Teserene
29. Willnestrol
30. Agaldog
31. Para-dien
32. Dienoestrol Bp
33. P,p'-(diethylideneethylene)diphenol
34. Di(p-oxyphenyl)-2,4-hexadiene
35. Dienestrol [inn]
36. 3,4-bis(4-hydroxyphenyl)-2,4-hexadiene
37. Sexadien
38. 4,4'-(diethylideneethylene)diphenol
39. 4-[(2e,4e)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
40. Mls000069528
41. 3,4-bis(p-hydroxyphenyl)-2,4-hexadiene
42. Dienestrol, .alpha.-
43. 4,4'-hydroxy-gamma,delta-diphenyl-beta,delta-hexadiene
44. Nsc 59809
45. 4,4'-(1,2-diethylidene-1,2-ethanediyl)bisphenol
46. .alpha.-dienestrol Diacetate
47. Rrw32x4u1f
48. Phenol, 4,4'-(diethylideneethylene)di-
49. Smr000058597
50. 4,4'-((2e,4e)-hexa-2,4-diene-3,4-diyl)diphenol
51. Dienestrol Diacetate, .alpha.-
52. 2,4-hexadiene, 3,4-bis(4-hydroxyphenyl)-
53. Alpha-dienestrol
54. Nsc-59809
55. Dv
56. Dienestrol (e,e)
57. Dienestrolo
58. Dienestrolum
59. (e,e)-4,4'-(diethylideneethylene)diphenol
60. Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (e,e)-
61. Dsstox_cid_2382
62. Dsstox_rid_76566
63. Dsstox_gsid_22382
64. Dienestrolo [dcit]
65. Phenol, 4,4'-((1e,2e)-1,2-diethylidene-1,2-ethanediyl)bis-
66. Phenol, 4,4'-[(1e,2e)-1,2-diethylidene-1,2-ethanediyl]bis-
67. Dienestrolum [inn-latin]
68. 4,4'-hexa-2,4-diene-3,4-diyldiphenol
69. Di(para-oxyphenyl)-2,4-hexadiene
70. Dienestrol (usp/inn)
71. Sr-01000003032
72. Chebi:4518
73. Unii-rrw32x4u1f
74. Dienestrol [usp:inn:ban]
75. Dv (tn)
76. Para,para'-(diethylideneethylene)diphenol
77. Ccris 9121
78. 3,4-bis(para-hydroxyphenyl)-2,4-hexadiene
79. Hsdb 3313
80. Cas-84-17-3
81. Prestwick_52
82. Ncgc00016335-01
83. Einecs 201-519-7
84. Dienoestrol [nonsteroidal Oestrogens]
85. Dienestrol Trans-form
86. 4,4'-dihydroxy-gamma,delta-diphenyl-beta,delta-hexadiene
87. Dienestrol [mi]
88. Opera_id_421
89. 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
90. Alpha-dienestrol Diacetate
91. Prestwick2_000798
92. Prestwick3_000798
93. Spectrum5_000875
94. Dienestrol [hsdb]
95. Dienestrol [vandf]
96. Dienestrol [mart.]
97. Chembl1018
98. Dienestrol [who-dd]
99. Schembl52170
100. Bspbio_000936
101. Bspbio_002177
102. Mls001077274
103. Mls002207222
104. Mls002222156
105. Spectrum1500241
106. 4,4'-(2e,4e)-hexa-2,4-diene-3,4-diyldiphenol
107. Bpbio1_001030
108. Cid_667476
109. Gtpl7160
110. Schembl2896853
111. Zinc1283
112. Dienestrol [ep Impurity]
113. Dienestrol [orange Book]
114. Bdbm40491
115. Hms502g13
116. Dienestrol [usp Impurity]
117. Dtxsid20873495
118. Phenol, 4,4'-(diethylideneethylene)di-, Trans-, (e,e)-
119. Hms1570o18
120. Hms1920g04
121. Hms2091m14
122. Hms2097o18
123. Hms2232m11
124. Hms3714o18
125. Pharmakon1600-01500241
126. Dienestrol Trans-form [mi]
127. Hy-b1403
128. Tox21_110378
129. Ccg-40189
130. Mfcd00050983
131. Nsc756734
132. S1858
133. Akos015902490
134. Tox21_110378_1
135. Cs-4911
136. Db00890
137. Nsc-756734
138. Idi1_000771
139. Ncgc00018153-03
140. Ncgc00018153-04
141. Ncgc00018153-05
142. Ncgc00018153-06
143. Ncgc00018153-07
144. Ncgc00018153-10
145. Ncgc00022210-03
146. Ncgc00022210-04
147. Ncgc00178779-01
148. Ncgc00178779-02
149. Ac-13162
150. Bs-17610
151. Sbi-0051344.p003
152. 4,4'-(hexa-2,4-diene-3,4-diyl)diphenol
153. D0449
154. C08090
155. D00898
156. D81865
157. Dienestrol, Vetranal(tm), Analytical Standard
158. Ab00051967_16
159. A936711
160. J-005782
161. Q5274949
162. Sr-01000003032-2
163. Sr-01000003032-4
164. 4,4'-[(2e,4e)-2,4-hexadiene-3,4-diyl]diphenol
165. Brd-k55106630-001-01-0
166. Brd-k95309561-001-05-6
167. Brd-k95309561-001-15-5
168. Dienestrol, European Pharmacopoeia (ep) Reference Standard
169. Dienestrol, United States Pharmacopeia (usp) Reference Standard
170. 4,4'-dihydroxy-.gamma.,.delta.-diphenyl-.beta.,.delta.-hexadiene
171. Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (e,e)
| Molecular Weight | 266.3 g/mol |
|---|---|
| Molecular Formula | C18H18O2 |
| XLogP3 | 5.4 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Exact Mass | 266.130679813 g/mol |
| Monoisotopic Mass | 266.130679813 g/mol |
| Topological Polar Surface Area | 40.5 Ų |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Complexity | 318 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Estrogens, Non-Steroidal
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
DIENESTROL, LIKE STILBESTROL, IS A NON-STEROIDAL ESTROGEN DERIVED FROM STILBENE. IT MAY BE ADMIN ORALLY OR APPLIED TOPICALLY. ITS USE ORALLY HAS NO ADVANTAGES OVER OTHER ORAL ESTROGENS, & NO ORAL PREPN ARE MARKETED. DIENESTROL IS PRIMARILY USED AS AN INTRAVAGINAL CREAM FOR ATROPHIC VAGINITIS OR PREPUBERTAL VULVOVAGINITIS.
Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 867
MEDICATION (VET): SYNTHETIC ESTROGEN. THE DIACETATE FORM IS USED IN FEEDING TRIALS. PARENTERALLY, IN FUNCTIONAL STERILITY WHERE ADEQUATE ESTROGENS ARE LACKING FOR STIMULATION & MATURATION OF OVARIAN FOLLICLE IN CATTLE & OCCASIONALLY IN HORSES. ORALLY, FOR CHICKENS & TURKEYS TO IMPROVE TENDERNESS & APPEARANCE BY PROPER FAT DISTRIBUTION.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 167
MEDICATION (VET): INCREASES FATTY LIVERS & SERUM CALCIUM, WHILE DECR BONE FRAGILITY IN CHICKENS. CAN BE USED INTRAVAGINALLY & INTRAUTERINE TO HELP RESTORE NORMAL EPITHELIAL GROWTH.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 167
For more Therapeutic Uses (Complete) data for DIENESTROL (10 total), please visit the HSDB record page.
DIENESTROL IS CONTRAINDICATED DURING PREGNANCY.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 943
... DISADVANTAGE OF SOME SYNTHETIC ESTROGENIC CMPD IS THAT NAUSEA FOLLOWS USE OF ... MINIMUM EFFECTIVE DOSE IN SOME WOMEN, BUT ... NOT OVER 20% OF THOSE WHO USE MATERIALS CAREFULLY. IN SUCH WOMEN SYNTHETIC MATERIALS MUST BE REPLACED BY NATURAL PRODUCTS. /SYNTHETIC ESTROGEN/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 917
Dienestrol has not been shown to be effective for any purpose during pregnancy, and use of the drug in pregnant women may cause severe harm to the fetus.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1939
Dienestrol shares the toxic potentials of other estrogens, and the usual cautions, precautions, and contraindications associated with estrogen therapy should be observed.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 1939
For more Drug Warnings (Complete) data for DIENESTROL (18 total), please visit the HSDB record page.
For use in the treatment of atrophic vaginitis and kraurosis vulvae.
Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
Estrogens, Non-Steroidal
Non-steroidal compounds with estrogenic activity. (See all compounds classified as Estrogens, Non-Steroidal.)
G - Genito urinary system and sex hormones
G03 - Sex hormones and modulators of the genital system
G03C - Estrogens
G03CB - Synthetic estrogens, plain
G03CB01 - Dienestrol
G - Genito urinary system and sex hormones
G03 - Sex hormones and modulators of the genital system
G03C - Estrogens
G03CC - Estrogens, combinations with other drugs
G03CC02 - Dienestrol
Absorption
Systemic absorption and mode of action of dienestrol are undetermined.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
ESTROGENS USED IN THERAPY ARE ... READILY ABSORBED THROUGH SKIN, MUCOUS MEMBRANES, AND GI TRACT. WHEN THEY ARE APPLIED FOR LOCAL ACTION, ABSORPTION IS OFTEN SUFFICIENT TO CAUSE SYSTEMIC EFFECTS. /ESTROGENS/
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1391
IN FACTORY WORKERS GYNECOMASTIA HAS FOLLOWED HANDLING OF DIETHYLSTIBESTROL WITHOUT GLOVES. /DIETHYLSTILBESTEROL/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1429
URINARY EXCRETION RATE OF ESTROGENS IS QUITE SIMILAR WHETHER AGENTS ARE GIVEN ORALLY OR INTRAVENOUSLY, WHICH SUGGESTS THAT ABSORPTION OF MOST ESTROGENS FROM GI TRACT IS PROMPT & QUITE COMPLETE. /ESTROGENS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1429
ESTROGENS ARE PRACTICALLY INSOLUBLE IN WATER. WHEN DISSOLVED IN OIL AND INJECTED, THEY ARE RAPIDLY ABSORBED & QUICKLY METABOLIZED. ... INACTIVATION OF ESTROGEN IS CARRIED OUT MAINLY IN THE LIVER. /ESTROGENS/
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1391
For more Absorption, Distribution and Excretion (Complete) data for DIENESTROL (10 total), please visit the HSDB record page.
Hepatic.
DIENESTROL YIELDS DIENESTROL-BETA-D-GLUCURONIDE IN RABBITS.
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. D-27
DIENESTROL IS A KNOWN METABOLITE OF DIETHYLSTILBESTROL IN PRIMATES & MICE; IT IS CONVERTED TO OMEGA-HYDROXY-DIENESTROL, WHICH IS EXCRETED IN CONJUGATED FORM ... RABBITS GIVEN ORAL DOSES OF DIENESTROL EXCRETED DIENESTROL GLUCURONIDE IN THEIR URINE ... .
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 166 (1979)
RABBITS GIVEN ORAL DOSES OF DIENESTROL EXCRETED DIENESTROL GLUCURONIDE IN THEIR URINE ... .
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V21 166 (1979)
Dienestrol is a synthetic, non-steroidal estrogen. Estrogens passively diffuse into target cells of responsive tissues, complex with the estrogen receptors, and enter the cell's nucleus to initiate or enhance gene transcription of protein synthesis after binding to DNA.
ESTROGENS ARE FIRST BOUND WITH VERY HIGH AFFINITY TO A CYTOPLASMIC 8 S RECEPTOR PROTEIN, WHICH THEN DISSOCIATES INTO A 4 S WITH ESTROGEN ATTACHED. ... THE ESTROGEN COMPLEX IS CONVERTED TO A 5 S SPECIES THAT IS TRANSPORTED TO THE NUCLEUS, WHERE ULTIMATE BINDING OF ESTROGEN-CONTAINING COMPLEX OCCURS. /ESTROGENS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1429
THE ACTIVITY OF ... SYNTHETIC ... ESTROGENS DEPENDS ON PRESENCE OF HYDROXYL GROUPS @ EXTREMITIES OF THEIR MOLECULES ... HYDROXYLS ... INVOLVED IN BINDING WITH SPECIFIC RECEPTOR PROTEINS, PRESENT IN CYTOSOL OF CELLS IN TARGET ORGANS. /ESTROGENS/
Searle, C. E. (ed.). Chemical Carcinogens. ACS Monograph 173. Washington, DC: American Chemical Society, 1976., p. 662
At the cellular level, estrogens increase the cellular synthesis of DNA, RNA, and various proteins in responsive tissues. Estrogens reduce the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus, leading to a reduction in release of follicle-stimulating hormone and luteinizing hormone from the pituitary. /Estrogen/
US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.1346 (1992)
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