(R*,S*)-4,4'-(1,2-diethylethylen)bis(phenol)

Hexestrol

HCID 192197CAS 5635-50-7

Grundinformationen

Standard-SMILES
CC[C@H](c1ccc(O)cc1)[C@@H](CC)c1ccc(O)cc1
InChIKey
PBBGSZCBWVPOOL-HDICACEKSA-N
Summenformel
C18H22O2
Durchschnittliche Molmasse
270,4 g/mol
Monoisotopische Masse
270,16197994

Überblick

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

Namen und Bezeichner

Bevorzugter Name
Hexestrol
IUPAC
4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
Lokaler Name
(R*,S*)-4,4'-(1,2-diethylethylen)bis(phenol)
Englischer Name
HEXESTROL
Summenformel
C18H22O2
Molmasse
270.37

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,2
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
20

Experimentelle und physikochemische Eigenschaften

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

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 Einträge

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)

Physikochemische Eigenschaften

Schmelzpunkt
186 °C · 186 °C
Siedepunkt
353.48 °C · 353.48°C (rough estimate)
Dichte
1.093 · 1.093
Brechungsindex
1.48 · 1.4800 (estimate)
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
almost transparency in Methanol

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesCarc. 1B (100%)

Toxikologische Informationen

Interactions · 2 Einträge

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 Einträge

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 Einträge

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/

Sicherheitsdaten

wgk
2
hs_code
2907.29.9000
RTECS-Nr.
SL0560850
risk_code
45
hazard_code
T
safety_code
53-45

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

...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 Einträge

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 Einträge

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/

Verwendung und Herstellung

Uses · 3 Einträge

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...

Anwendungen

VerwendenEstrogen; antineoplastic (hormonal).

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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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