Dienestrol
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Dienestrol
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CAS No:
84-17-3
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Formula:
C18H18O2
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Chemical Name:
Dienestrol
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Synonyms:
Phenol,4,4′-(1,2-diethylidene-1,2-ethanediyl)bis-;Phenol,4,4′-(diethylideneethylene)di-;4,4′-(1,2-Diethylidene-1,2-ethanediyl)bis[phenol];3,4-Bis(p-hydroxyphenyl)-2,4-hexadiene;Cycladiene;Dienestrol;Dienol;p,p′-(Diethylideneethylene)diphenol;4,4′-(Diethylideneethylene)diphenol;4,4′-Dihydroxy-γ,δ-diphenyl-β,δ-hexadiene;Dinovex;Di-(p-oxyphenyl)-2,4-hexadiene;Estroral;Gynefollin;Oestrasid;Oestrodiene;Oestroral;Restrol;Retalon;Sexadien;3,4-Di-p-(hydroxyphenyl)hexa-2,4-diene;2,4-Hexadiene,3,4-bis(4-hydroxyphenyl)-;Estrodienol;Teserene;Follidiene;Follormon;Dienesterol;Synestrol;Hormofemin;DV;Dienoestrol;NSC 59809;Dehydrostilbestrol
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Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System
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CAS No:
Description
Dienestrol is a synthetic, non-steroidal estrogen, is an estrogen receptor agonist, for the treatment of menopausal and postmenopausal symptoms.
Solid
Dienestrol Basic Attributes
266.33
266.33
201-519-7
DTXSID7022382|DTXSID10746003
MINUTE NEEDLES FROM DILUTE ALC|WHITE NEEDLES FROM ETHANOL|COLORLESS OR WHITE, OR PRACTICALLY WHITE NEEDLE-LIKE CRYSTALS OR AS A WHITE, CRYSTALLINE POWDER
Characteristics
40.5
5.4
1.184 g/cm3
227-228 °C
181.4ºC
1.4800 (estimate)
SOL IN FIXED OILS.
2-8°C
Odorless
Safety Information
Ⅲ
2811
3
40-48-62-45
22-24/25-45-36/37-53
SL0580000
Xn,T
Sensitive to light
P201-P280-P308 + P313
H350-H361
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).|The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl dienestrol, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
Gray LE Jr; Delayed Reproductive Effects Following Exposure to Toxic Chemicals During Critical Developmental Periods. NTIS Technical Report NTIS/PB90-112830 (1989). The studies presented in this review indicate that perinatal exposure of the fetal or neonatal rodent to a toxicant can adversely affect reproductive development, reduce fertility and accelerate reproductive senescence. In rodents and humans exposure to diethylstilbestrol, estrogens, androgens and progestins during critical developmental periods produce morphological and pathological alterations of the reproductive tract of males and females. Diethylstilbestrol treatment causes cancer, infertility and serious morphological abnormalities of the reproductive tract in all species examined.
|Danger|H350 (100%): May cause cancer [Danger Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Concurrent use with estrogens may alter the metabolism and protein binding of glucocorticoids, leading to decreased clearance, increased elimination half-life, and increased therapeutic and toxic effects of the glucocorticoids.|Estrogens may cause amenorrhea, interfering with effects of bromocriptine. /Estrogen/|Calcium supplements: concurrent use with estrogens may increase calcium absorption. /Estrogen/|Concurrent use with estrogens may potentiate the anti-inflammatory effects of endogenous cortisol induced by corticotropin. /Estrogen/|For more Interactions (Complete) data for DIENESTROL (9 total), please visit the HSDB record page.
Drug Information
Estrogens, Non-Steroidal|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.|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.|MEDICATION (VET): INCREASES FATTY LIVERS & SERUM CALCIUM, WHILE DECR BONE FRAGILITY IN CHICKENS. CAN BE USED INTRAVAGINALLY & INTRAUTERINE TO HELP RESTORE NORMAL EPITHELIAL GROWTH.|For more Therapeutic Uses (Complete) data for DIENESTROL (10 total), please visit the HSDB record page.
DIENESTROL IS CONTRAINDICATED DURING PREGNANCY.|... 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/|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.|Dienestrol shares the toxic potentials of other estrogens, and the usual cautions, precautions, and contraindications associated with estrogen therapy should be observed.|For more Drug Warnings (Complete) data for DIENESTROL (18 total), please visit the HSDB record page.
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/|IN FACTORY WORKERS GYNECOMASTIA HAS FOLLOWED HANDLING OF DIETHYLSTIBESTROL WITHOUT GLOVES. /DIETHYLSTILBESTEROL/|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/|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/|For more Absorption, Distribution and Excretion (Complete) data for DIENESTROL (10 total), please visit the HSDB record page.
DIENESTROL YIELDS DIENESTROL-BETA-D-GLUCURONIDE IN RABBITS.|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 ... .|RABBITS GIVEN ORAL DOSES OF DIENESTROL EXCRETED DIENESTROL GLUCURONIDE IN THEIR URINE ... .
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/|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/|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/
BREAST ENLARGEMENT & NODULARITY OCCURRED IN BOTH MALE & FEMALE CHILDREN AFTER CONSUMPTION OF VITAMIN CAPSULES CONTAMINATED WITH ESTROGENS. /ESTROGENS/|ONE CASE OF ADENOCARCINOMA OF VAGINA HAS BEEN REPORTED IN YOUNG GIRL, 17 YR OLD, WHOSE MOTHER HAD TAKEN 5 MG/DAY DIENESTROL ORALLY & 2 IM DOSES OF ESTRONE DURING 3RD MONTH OF PREGNANCY ... .|MALAISE, IRRITABILITY, & DEPRESSION ... OCCUR WITH SMALL DOSES & ... WITH LARGE DOSES. EFFECT ON LIBIDO IS ERRATIC, BEING INCR IN SOME & DECR IN OTHERS. ... CHANGES IN CONCN OF SOME OF CLOTTING FACTORS IN BLOOD ... INCR INCIDENCE OF THROMBOPHLEBITIS & THROMBOEMBOLISM IN ... SUPERFICIAL & DEEP VEINS. /ESTROGENS/|PULMONARY EMBOLISM, CEREBRAL EMBOLISM WITH STROKE & MESENTERIC VASCULAR OCCLUSION OCCUR. CORONARY THROMBOSIS ... INCR ... ALTER HEPATIC FUNCTION, WHICH ... ALTER ... TESTS OF LIVER FUNCTION AS WELL AS VARIOUS SYNTHETIC & BIOTRANSFORMATION PROCESSES. ... DECR IN GLUCOSE TOLERANCE, & DIABETES MELLITUS MAY BE EXACERBATED. /ESTROGENS/|For more Human Toxicity Excerpts (Complete) data for DIENESTROL (21 total), please visit the HSDB record page.
Dienestrol Use and Manufacturing
estrogen
FARMACYROL, LIPAMONE, RETALON-ORAL /DIENESTROL DIACETATE/|Grade: National Formulary|Vaginal Cream: 0.01%, DV, Marion Merrall Dow; Ortho Dienestrol, Ortho.|DOSAGE FORMS-- CREAM NF: 0.01%; SUPPOSITORIES: 0.7 MG; TABLETS NF: 100 & 500 MCG.
DIENESTROL IS NOT KNOWN TO OCCUR NATURALLY.|... DO NOT ADMIN TO LAYING BIRDS OR BREEDING FLOCKS. AVOID CONTAMINATION WITH FEED OR WATER SUPPLY TO OTHER LIVESTOCK OR HUMANS.|Dienestrol is a synthetic nonsteroidal estrogen. The drug is structurally similar to diethylstilbestrol but differs structurally from diethylstilbestrol in the substitution of two unsaturated ethylidene groups for the two diethyl groups of diethylstilbestrol.
HPLC ANALYSIS OF DIENESTROL AND ITS DOSAGE FORMS.|GLC DETERMINATION OF DIENESTROL IN DIENESTROL CREAM.|CONFIGURATION OF DIENESTROL BY X-RAY DIFFRACTION.|MASS SPECTRA OF DIENESTROL.|Determination of dienestrol by using a HPLC operated at room temperature. The apparatus is equipped with an UV detector capable of monitoring absorption at 254 nm. The flow rate is about 2 ml/min.
A method was developed for the detection of diethylstilbestrol, together with dienestrol and hexestrol, using extraction with a single immunoaffinity column containing antibodies raised against diethylstilbestrol, followed by GC negative ion chemical ionization MS.|A procedure for the separation and identification of several anabolic substances from bovine urine samples is presented. Chromatographic separations of various group of anabolics in different eluting conditions were carried out in order to provide the possibility of an analytical application as extensive as possible.|A rapid and selective chromatographic method is described for the clean-up of anabolics in bovine urine using group fractionation.|The combination of supercritical fluid extraction/supercritical fluid chromatography-tandem MS was evaluated for the detection of residues of a small group of veterinary drugs in freeze-dried pig kidney.|STABLE DERIVATIVES FOR GC DETERMINATION OF DIENESTROL IN MEAT & ORGANS OF CATTLE.
Computed Properties
Molecular Weight:266.3
XLogP3:5.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:266.130679813
Monoisotopic Mass:266.130679813
Topological Polar Surface Area:40.5
Heavy Atom Count:20
Complexity:318
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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