Hexestrol

HCID 192197CAS 5635-50-7

기본 정보

표준 SMILES
CC[C@H](c1ccc(O)cc1)[C@@H](CC)c1ccc(O)cc1
InChIKey
PBBGSZCBWVPOOL-HDICACEKSA-N
분자식
C18H22O2
평균 분자량
270.4 g/mol
단동위원소 질량
270.16197994

개요

A synthetic estrogen that has been used as a hormonal antineoplastic agent.

이름 및 식별자

우선 이름
Hexestrol
IUPAC
4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
영어명
HEXESTROL
분자식
C18H22O2
분자량
270.37

이름 및 동의어

hexestrol84-16-2meso-HexestrolHexoestrolHexanoestrolMesohexestrolErythrohexestrolHormoestrolCycloestrolEstronalHexestrofenSynthovo
이름 더 보기
HexronNSC-9894SinestrolSynestrolVitestrolEstra-Plex
SyntrogeneEstrifarExtra-plexmeso-3,4-Di(p-hydroxyphenyl)-n-hexaneDihydrostilbestrolSynoestrolumDTXSID2022381meso-3,4-Bis(p-hydroxyphenyl)-n-hexane

데이터베이스 식별자

CAS
5635-50-7、84-16-2
PubChem CID
192197
DTXSID
DTXSID2022381
ChEMBL
CHEMBL9225
UNII
10BI795R7D
EC Number
201-518-1、227-082-2
Nikkaji
J4.893C

물성

구조 계산 물성

XLogP
5.2
극성 표면적
40.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
5
무거운 원자 수
20

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
OdorODORLESS
Color/Form · 2건

NEEDLES FROM BENZENE, THIN PLATES FROM DIL ALC

WHITE CRYSTALLINE POWDER

SolubilityFREELY SOL IN ETHER; SOL IN ACETONE, ALCOHOL, METHANOL, DILUTE SOLN OF ALKALI HYDROXIDES, VEGETABLE OILS UPON SLIGHT WARMING; SLIGHTLY SOL IN BENZENE, CHLOROFORM; PRACTICALLY INSOL IN WATER, DIL MINERAL ACIDS
Melting Point · 3건

185-188 °C

CRYSTALS; MP: 137-139 °C /DIACETATE/

CRYSTALS FROM PETROLEUM ETHER; MP: 127-128 °C /DIPROPIONATE/

Refractive IndexINDEX OF REFRACTION: 1.495 (ALPHA), 1.565 (BETA), 1.687 (GAMMA)

물리화학적 성질

녹는점
186 °C · 186 °C
끓는 점
353.48 °C · 353.48°C (rough estimate)
밀도
1.093 · 1.093
굴절률
1.48 · 1.4800 (estimate)
저장 조건
Sealed in dry,Room Temperature
용해도
almost transparency in Methanol

화학적 성질

Crystalline Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H350 (100%): May cause cancer [Danger Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory.

유해성 정보

Hazard Classes and CategoriesCarc. 1B (100%)

독성 정보

Interactions · 2건

EFFECTS OF ESTROGENS CAN BE BLOCKED BY INHIBITORS OF RNA SYNTHESIS (DACTINOMYCIN) OR PROTEIN SYNTHESIS (CYCLOHEXIMIDE). /ESTROGENS/

ESTROGENS...INHIBIT ORAL ANTICOAGULANT ACTIVITY... OTHER INTERACTIONS INCL POTENTIATION OF TRICYCLIC ANTIDEPRESSANT ACTIVITY & REDUCTION OF BOTH PYRIDOXINE & FOLIC ACID LEVELS. PHENOBARBITAL INCR METABOLISM OF ESTROGENS... /ESTROGENS/

Human Toxicity Excerpts · 5건

BREAST ENLARGEMENT AND NODULARITY OCCURRED IN BOTH MALE AND FEMALE CHILDREN AFTER CONSUMPTION OF VITAMIN CAPSULES CONTAMINATED WITH ESTROGENS. /ESTROGENS/

PROMINENT GYNECOMASTIA AND OTHER FEMINIZING EFFECTS WERE PRODUCED IN MALES OCCUPATIONALLY EXPOSED TO ESTROGENS. ENOUGH MATERIAL CAN BE ABSORBED PERCUTANEOUSLY OR BY RESPIRATORY ROUTE TO PRODUCE THESE EFFECTS. /ESTROGENS/

SIDE EFFECTS NOTED AFTER CLINICAL ADMIN WERE HEADACHE, NAUSEA, VOMITING & SOMETIMES VAGINAL BLEEDING. /ESTROGENS/

...UNPLEASANT SYMPTOM ATTENDING USE OF ESTROGEN IS NAUSEA. WITH LARGE DOSES THERE MAY ALSO BE ANOREXIA & EVEN VOMITING & MILD DIARRHEA. /ESTROGENS/

For more Human Toxicity Excerpts (Complete) data for HEXESTROL (9 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 4건

CHICKEN WASTE CONTAINING SYNTHETIC ESTROGEN CAUSED STERILITY AND PREDISPOSITION TO URINARY TRACT INFECTIONS IN MINK... /ESTROGENS/

WHATEVER FORM IN WHICH ESTROGEN IS ADMINISTERED, SYMPTOMS AND LESIONS OF TOXICITY FOLLOWING PROLONGED EXPOSURE TO ITS ACTION ARE THE SAME. IN LACTATING CATTLE, PROLAPSE OF VAGINA & RECTUM...RECORDED...FOLLOWING ORAL ADMIN OF STILBESTROL. /ESTROGENS/

...SEEMS TO HAVE HAD NO REPORTED ADVERSE EFFECTS ON EYES, & TESTING BY FEEDING AS 0.0001% OF DIET TO WEANLING RATS FOR 12 WK SPECIFICALLY PRODUCED NO CHANGE IN CRYSTALLINE LENSES.

HEXESTROL ADMIN AFTER CASTRATION OF MALE RATS INCR RATE OF SUCCESSFUL TRANSPLANTATION OF PROSTATE ADENOMA FROM 51.25% TO 60% & RATE OF ADENOCARCINOMA FORMATION TO 20%.

Antidote and Emergency TreatmentCHANGES IN SECONDARY SEXUAL CHARACTERISTICS ARE FULLY REVERSIBLE ON CESSATION OF EXPOSURE. /ESTROGENS/

안전 데이터

wgk
2
rtecs
SL0560850
HS 번호
2907.29.9000
risk_code
45
hazard_code
T
safety_code
53-45

화학 및 산업

약리 정보

Mechanism of Action · 3건

...INCR IN SYNTHESIS OF VARIOUS TYPES OF RNA & PROTEIN...STIMULATION OF DNA SYNTHESIS... IT IS NOT CLEAR WHETHER PROMINENT...STIMULATION OF RNA SYNTHESIS IS RESULT OF INCR RNA POLYMERASE ACTIVITY, INCR CHROMATIN TEMPLATE ACTIVITY, ALTERED NUCLEAR TRANSPORT PHENOMENA, OR COMBINATIONS THEREOF. /ESTROGENS/

...AS RESULT OF...NUCLEAR BINDING...METABOLIC ALTERATIONS ENSUE. ...MRNA & CERTAIN SPECIFIC BUT UNKNOWN PROTEINS ARE APPARENTLY SYNTHESIZED RAPIDLY, PERHAPS BECAUSE OF UNMASKING OF RESTRICTED REGIONS OF DNA. /ESTROGENS/

ESTROGENS ARE LARGELY RESPONSIBLE FOR CHANGES THAT TAKE PLACE @ PUBERTY IN GIRLS, &...FOR TANGIBLE & INTANGIBLE ATTRIBUTES OF FEMININITY. BY DIRECT ACTION, THEY CAUSE GROWTH & DEVELOPMENT OF VAGINA, UTERUS, & FALLOPIAN TUBES. /ESTROGENS/

Metabolism/MetabolitesHEXESTROL YIELDS HEXESTROL-BETA-D-GLUCURONIDE IN RABBIT; JELLINCK PH, BIOCHEM J, 58, 262 (1954). /FROM TABLE/
MeSH Pharmacological Classification · 2건

Non-steroidal compounds with estrogenic activity.

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079)

Absorption, Distribution and Excretion · 4건

ENOUGH MATERIAL CAN BE ABSORBED PERCUTANEOUSLY OR BY RESPIRATORY ROUTE TO PRODUCE...EFFECTS. /ESTROGENS/

STUDIES WITH RADIOACTIVE...HEXESTROL...HAVE CONFIRMED...REPORTS THAT...COMPD ARE RAPIDLY ABSORBED INTO ANIMAL BODY AND...EXCRETED IN FECES AND URINE. PROPORTION EXCRETED...IS...70% IN FECES AND 30% IN URINE...

...TRACES OF...HEXESTROL COULD BE FOUND IN TISSUES 24 HR AFTER...ADMIN TO SHEEP AND GOATS... CONTINUED ADMIN...TO FATTENING STOCK MAY LEAD TO... ACCUMULATION IN EDIBLE PARTS OF CARCASS ALTHOUGH EVIDENCE ON THIS SUBJECT IS CONTROVERSIAL.

ESTROGENS USED IN THERAPY ARE, IN GENERAL, READILY ABSORBED THROUGH SKIN, MUCOUS MEMBRANES, & GI TRACT. WHEN THEY ARE APPLIED FOR LOCAL ACTION, ABSORPTION IS OFTEN SUFFICIENT TO CAUSE SYSTEMIC EFFECTS... /ESTROGENS/

용도 및 제조

Uses · 3건

MEDICATION

MEDICATION (VET)

Hexestrol is a synthetic estrogen that has been used as a hormonal antineoplastic agent.

Methods of ManufacturingFROM ANETHOLE HYDROGEN BROMIDE: CAMPBELL ET AL, PROC ROY SOC B128, 253 (1940)...US PATENT 2,357,985 (1944)... BY REDUCTION OF GRIGNARD COMPD WITH COBALTOUS CHLORIDE: KHARASCH ET AL, J AM CHEM SOC 65, 491 (1943).
Formulations/PreparationsDIACETATE, RETALON-LINGUAL... DIPROPIONATE, RETALON OLEOSUM...

응용 분야

용도Estrogen; antineoplastic (hormonal).

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

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