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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 235
実験および物理化学的性質
Color/Form
NEEDLES FROM BENZENE, THIN PLATES FROM DIL ALC
WHITE CRYSTALLINE POWDER
Melting Point
185-188 °C
CRYSTALS; MP: 137-139 °C /DIACETATE/
CRYSTALS FROM PETROLEUM ETHER; MP: 127-128 °C /DIPROPIONATE/
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
- 酸解離定数(Pka)
- 9.8 · 9.80±0.26(Predicted)
- 外見
- Solid
- 色
- White to Almost white
- Merck
- 14 · 14,4701
- BRN
- 3209460 · 3209460
- 主な用途
- 法医学と毒物学医薬品(低分子化合物)獣医
- InChI
- InChI=1/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+
- InChIKey
- PBBGSZCBWVPOOL-HDICACEKNA-N
- SMILES
- [C@@H](C1=CC=C(O)C=C1)(CC)[C@@H](C1=CC=C(O)C=C1)CC |&1:0,10,r|
- CAS データベース
- 84 · 84-16-2(CAS DataBase Reference)
化学的性質
化学的特性Crystalline Solid
安全と法規制
GHS分類
GHS Classification
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
毒性情報
Interactions
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
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.
Non-Human Toxicity Excerpts
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%.
安全データ
- wgk
- 2
- rtecs
- SL0560850
- hs_code
- 2907.29.9000
- risk_code
- 45
- hazard_code
- T
- safety_code
- 53-45
- Hazard Classifications
- Carc. 1B
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 84-16-2(Hazardous Substances Data)
化学と産業
薬理情報
Mechanism of Action
...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/
MeSH Pharmacological Classification
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
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
MEDICATION
MEDICATION (VET)
Hexestrol is a synthetic estrogen that has been used as a hormonal antineoplastic agent.
応用分野
使用Estrogen; antineoplastic (hormonal).
調製方法
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.]
上流・下流製品情報
上流原料
サプライヤー50 社
関連反応
関連ノート
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