ヘキセストロール

Hexestrol

HCID 192197CAS 5635-50-7

基本情報

標準SMILES
CC[C@H](c1ccc(O)cc1)[C@@H](CC)c1ccc(O)cc1
InChIKey
PBBGSZCBWVPOOL-HDICACEKSA-N
分子式
C18H22O2
平均分子量
270.4 g/mol
単同位体質量
270.16197994

概要

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

名称と識別子

優先名称
Hexestrol
IUPAC
4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
現地名
ヘキセストロール
英語名
HEXESTROL
分子式
C18H22O2
分子量
270.37

名称と別名

hexestrol84-16-2meso-HexestrolHexoestrolHexanoestrolMesohexestrolErythrohexestrolHormoestrolCycloestrolEstronalHexestrofenSynthovo
名称をさらに表示
ヘキセストロールシントロゲンホルモエストロールエストロナール4,4'-[(1S,2R)-1,2-ジエチルエチレン]ビスフェノールヘキスロンヘキサノエストロール(3R,4S)-3,4-ビス(p-ヒドロキシフェニル)ヘキサンmeso-ヘキソエストロールヘキソエストロールシントーボシクロエストロールmeso-ヘキセストロールシネストロールメソヘキソエストロールヘキセストロール標準品HexronNSC-9894SinestrolSynestrolVitestrolEstra-Plex
SyntrogeneEstrifarExtra-plexmeso-3,4-Di(p-hydroxyphenyl)-n-hexaneDihydrostilbestrolSynoestrolumDTXSID2022381meso-3,4-Bis(p-hydroxyphenyl)-n-hexane

データベース識別子

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

物性

構造計算による物性

XLogP
5.2
極性表面積
40.5 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
5
重原子数
20

実験および物理化学的性質

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

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 · 3 件

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)

物理化学的性質

融点
186 °C · 186 °C
沸点
353.48 °C · 353.48°C (rough estimate)
比重(密度)
1.093 · 1.093
屈折率
1.48 · 1.4800 (estimate)
貯蔵温度
Sealed in dry,Room Temperature
溶解性
almost transparency in Methanol

化学的性質

化学的特性Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesCarc. 1B (100%)

毒性情報

Interactions · 2 件

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 · 5 件

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 · 4 件

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/

安全データ

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

化学と産業

薬理情報

Mechanism of Action · 3 件

...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 · 2 件

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 · 4 件

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/

用途と製造

Uses · 3 件

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...

応用分野

使用Estrogen; antineoplastic (hormonal).

調製方法 · 1 件

純化方法Crystallise meso-Hexestero from *benzene or aqueous EtOH (m 185-188o). The meso-dibenzoyl derivative has m 236-237o. The 3RS,4RS(±)-racemate [5776-72-7] crystallises from pet ether, *C6H6/pet ether, Et2O/pet ether, or MeOH/H2O and has m 128-129o . The (±)-dibenzoyl derivative has m 123-124o . The 3R,4R(+)-isomer [26614-21-1] and 3S,4S(-)-isomer [26614-22-2] crystallise from Et2O/pet ether with m 80 -80.5o and have [] D (+) and (-) 17.7o (c 5, EtOH). Their dibenzoyl derivatives have m 116.5o .[Beilstein 6 III 5503, 6 IV 6761.] They have estrogenic activity where optically active forms are more potent and they have antineoplastic activity. [Aboul-Enein et al. Anal Profiles Drug Subst 11 347 1982, J Am Chem Soc 65 4911941.]

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