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디에틸스틸베스트롤

디에틸스틸베스트롤
디에틸스틸베스트롤 구조식 이미지
카스 번호:
56-53-1
한글명:
디에틸스틸베스트롤
동의어(한글):
다이에틸스틸베스트롤;디에틸스틸베스트롤
상품명:
Diethylstilbestrol
동의어(영문):
DES;Stil;CSM1;CSM2;-PVT;Sibol;Bufon;Cyren;Desma;CMD1I
CBNumber:
CB9751457
분자식:
C18H20O2
포뮬러 무게:
268.35
MOL 파일:
56-53-1.mol

디에틸스틸베스트롤 속성

녹는점
170-172 °C(lit.)
끓는 점
351.51°C (rough estimate)
밀도
1.1096 (rough estimate)
굴절률
1.4800 (estimate)
저장 조건
2-8°C
용해도
methanol: 0.1 g/mL, clear, faintly yellow
물리적 상태
Crystalline Powder
산도 계수 (pKa)
pKa 9.02(H2O t=25 I=0.025) (Uncertain)
색상
White to almost white
수용성
PRACTICALLY INSOLUBLE
Merck
13,3155
BRN
2056095
안정성
Isomerizes rapidly in Benzene, Chloroform, and Ether. Keep Shielded from light.
CAS 데이터베이스
56-53-1(CAS DataBase Reference)
NIST
Diethylstilbesterol(56-53-1)
IARC
1 (Vol. 21, Sup 7, 100A) 2012
EPA
Diethylstilbestrol (56-53-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N
위험 카페고리 넘버 45-61-36/37/38-51/53-40
안전지침서 53-36/37/39-45-60-61-36/37
유엔번호(UN No.) UN 3077 9/PG 3
WGK 독일 3
RTECS 번호 WJ5600000
F 고인화성물질 10
위험 등급 6.1(b)
포장분류 III
HS 번호 29072990
유해 물질 데이터 56-53-1(Hazardous Substances Data)
독성 LD50 oral in rat: > 3gm/kg
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H360 태아 또는 생식능력에 손상을 일으킬 수 있음 생식독성 물질 구분 1A, 1B 위험
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

디에틸스틸베스트롤 MSDS


Diethylstilbestrol

디에틸스틸베스트롤 C화학적 특성, 용도, 생산

개요

Diethylstilbestrol (DES) is a nonsteroidal, synthetic stilbene derivative with estrogenic activity. It is an odorless, white crystalline powder, with a molecular weight of 268.36. Its cisisomer tends to revert to the trans-form.

개요

Diethylstilbestrol (DES) is a synthetic estrogen receptor agonist that was prescribed to pregnant women in the late 1930s. It was banned in 1971 because of possible links to increased risk of breast cancer in mothers along with congenital abnormalities and increased risk of cancer in offspring. DES is structurally related to, and is as potent as, estradiol in most assays, with a longer half-life. It has a relative binding affinity to sex hormone binding globulin (SHBG) of 0.2 compared to estradiol which has a relative binding affinity of 100. A concentration of 20 μM DES, displaces 30 ± 13% of 3H-estradiol from SHBG in serum.

화학적 성질

White Solid

Originator

DES,Amfre-Grant,US,1946

용도

A synthetic, nonsteroidal estrogen. Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.

용도

Diethylstilbestrol is a synthetic nonsteroidal estrogen that was formerly used in estrogenic hormone therapy (for menstrual disorders, postpartum breast engorgement, postcoital contraceptive, prevention of spontaneous abortion) and in chemotherapy of various cancers, including postmenopausal breast cancer and prostate cancer. It was also used in biomedical research and veterinary medicine (growth promoter for cattle and sheep; veterinary drug to treat estrogen deficiency disorders).

Indications

Diethylstilbestrol is one of the older synthetic estrogens in use. It was used to treat prostate cancer but is now rarely used for this purpose because of its adverse effects,although it is occasionally used in postmenopausal women with breast cancer. It is taken orally in tablet form.

Manufacturing Process

50 parts by weight of p-hydroxypropiophenone are dissolved in 200 parts by weight of a 12.5% solution of caustic soda and shaken with 350 parts by weight of 3% sodium amalgam. The sodium salt of the pinacol thereby precipitating is reacted with glacial acetic acid, whereby the free pinacol is obtained (MP 205°C to 210°C, after purification 215°C to 217°C). The yield amounts to 95% of the theoretical. The pinacol is suspended in ether and gaseous hydrogen chloride introduced, whereby water separates and the pinacolin formed is dissolved in the ether, from which it is obtained by evaporation as a viscous oil (diacetateof MP 91°C). The yield is quantitative.
40 parts by weight of pinacolin are dissolved in ethyl alcohol and gradually treated with 80 parts by weight of sodium under reflux. The solution is decomposed with water and the pinacolin alcohol formed extracted from the neutralized solution with ether. The pinacolin alcohol is a viscous oil which is characterized by a dibenzoate of MP 172°C. The yield is 95% of the theoretical.
A solution of 30 parts by weight of pinacolin alcohol in ether is saturated with hydrogen chloride at room temperature and the ether solution then agitated with bicarbonate. After concentration by evaporation it leaves behind the crude diethylstilbestrol [α,β-(p,p'-dihydroxydiphenyl)-α,β-diethylethylene] which, when recrystallized from benzene, melts at 170°C to 171°C. The yield amounts to 75% of the calculated. The total yield of diethylstilbestrol, calculated on p-hydroxypropiophenone, is 68% of the theoretical.

상표명

Stilbestrol (Tablicaps); Stilbetin (Bristol-Myers Squibb);Distilbene;Oestro-gynedron;Stilphostrol.

Therapeutic Function

Estrogen

World Health Organization (WHO)

Diethylstilbestrol, a synthetic estrogen which is a stilbene derivative, was introduced into obstetric practice in the late 1940s and subsequently widely used for the treatment of threatened abortion. This use was later shown to be associated with an increased risk of vaginal cancer in the offspring which resulted in restrictive regulatory action in several countries. Diethylstilbestrol and other stilbenes remain available in many countries, however, for the treatment of certain hormone-dependent neoplasms including carcinoma of the prostate and postmenopausal breast cancer. (Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)

일반 설명

At first glance, it might be surprising that synthetic nonsteroidal molecules such as diethylstilbestrol (DES) could have the same activity as estradiol or other estrogens. DES can be viewed, however, as a form of estradiol with rings B and C open and a six-carbon ring D. The activity of DES analogs was explained in 1946. It was proposed that the distance between the two DES phenol OH groups was the same as the 3-OH to 17-OH distance of estradiol; therefore, they could both fit the same receptor. Medicinal chemists have shown the OH-to-OH distance to be actually 12.1 ? in DES and 10.9 ? in estradiol. In aqueous solution, however, estradiol has two water molecules that are hydrogen bonded to the 17-OH. If one of the two water molecules is included in the distance measurement, there is a perfect fit with the two OH groups of DES. This suggests that water may have an important role for estradiol in its receptor site.
It is now generally accepted that the estrogens must have a phenolic moiety for binding, but some investigators propose that the receptor may be flexible enough to accommodate varying distances between the two key hydroxyls. This point about estrogens needing a phenolic ring for high-affinity binding to the ER is critical. Steroids with a phenolic A ring and related phenolic compounds lack high-affinity binding to the other steroid hormone receptors.

일반 설명

Odorless tasteless white crystalline powder.

공기와 물의 반응

Insoluble in water.

반응 프로필

Diethylstilbestrol is incompatible with strong oxidizing agents, strong bases, acid chlorides and acid anhydrides .

화재위험

Flash point data for Diethylstilbestrol are not available; however, Diethylstilbestrol is probably combustible.

부작용

These include sodium retention and oedema,nausea,gynaecomastia and impotence in men, and venous and arterial thrombosis. It can cause bone pain and hypercalcaemia when used for breast cancer.

Safety Profile

Confirmed carcinogen producing skin, liver, and lung tumors in exposed humans as well as uterine and other reproductive system tumors in the female offspring of exposed women. Experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. A transplacental carcinogen. A human teratogen by many routes. Poison by intraperitoneal and subcutaneous routes. It causes glandular system effects by sktn contact. Human reproductive effects by ingestion: abnormalspermatogenesis; changes in testes, epididymis, and sperm duct; menstrual cycle changes or disorders; changes in female ferulity; unspecified maternal effects; developmental abnormalities of the fetal urogenital system; germ cell effects in offspring; and delayed effects in newborn. Implicated in male impotence and enlargement of male breasts. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also ETHINYL ESTRADIOL.

Carcinogenicity

Diethylstilbestrol is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.

환경귀착

Diethylstilbestrol is a known teratogen and carcinogen. Experimental studies using transgenic estrogen receptor knockout animals suggest that binding and activation of the estrogen receptor is required to elicit diethylstilbestrol toxicity. Hence, diethylstilbestrol lesions primarily appear in tissues enriched with estrogen receptors. Diethylstilbestrol binds to the estrogen receptor with a very high affinity and forms a complex with the target tissue. The complex then internalizes in to the cell and translocates to the nucleus. Once in the nucleus, diethylstilbestrol may directly bind with the cellular DNA and cause mutations and unscheduled DNA synthesis. Diethylstilbestrol is also known to induce aneuploidy.

Toxicity evaluation

Diethylstilbestrol’s production and use in biochemical research, medicine, and veterinary medicine may result in its release to the environment through various waste streams. It may also be released to the environment during transport, storage, or disposal. If released to soil, diethylstilbestrol is predicted to strongly adsorb to the soil. Volatilization from the dry or wet soil surface would probably be unlikely. The extent of biodegradation in soil is not known, although diethylstilbestrol has been shown to be resistant to degradation in activated sludge. If released to water, diethylstilbestrol may bioconcentrate in aquatic organisms and strongly adsorb to suspended solids and sediments. Diethylstilbestrol is expected to be essentially nonvolatile on water surfaces. Diethylstilbestrol would not be susceptible to hydrolysis. The extent of biodegradation in natural waters is not certain, although diethylstilbestrol has been shown to be resistant to degradation in activated sludge. If released to the atmosphere, diethylstilbestrol vapors should rapidly oxidize, primarily by reaction with ozone. It is expected to exist solely in the particulate phase in an ambient atmosphere. Particulatephase diethylstilbestrol may be removed from the air by wet and dry deposition.

디에틸스틸베스트롤 준비 용품 및 원자재

원자재

준비 용품


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