Basic information
- CAS
5635-50-7- Standard SMILES
CC[C@H](c1ccc(O)cc1)[C@@H](CC)c1ccc(O)cc1- InChIKey
PBBGSZCBWVPOOL-HDICACEKSA-N- Molecular formula
- C18H22O2
- Average molar mass
- 270.4 g/mol
- Monoisotopic mass
- 270.16197994
Overview
A synthetic estrogen that has been used as a hormonal antineoplastic agent.
Names & identifiers
- Preferred name
- Hexestrol
- IUPAC
- 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
- English name
- HEXESTROL
- Molecular formula
- C18H22O2
- Molecular weight
- 270.37
Names & synonyms
Show more names
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 235
Experimental & physicochemical properties
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/
Physicochemical properties
- Melting point
- 186 °C · 186 °C
- Boiling point
- 353.48 °C · 353.48°C (rough estimate)
- Density
- 1.093 · 1.093
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- almost transparency in Methanol
- pka
- 9.8 · 9.80±0.26(Predicted)
- form
- Solid
- color
- White to Almost white
- Merck
- 14 · 14,4701
- BRN
- 3209460 · 3209460
- Major Application
- forensics and toxicologypharmaceutical (small molecule)veterinary
- 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 DataBase Reference
- 84 · 84-16-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 10 BI795R7D · 10BI795R7D
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 350 · H350
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T
- Risk Statements
- 45 · 45
- Safety Statements
- 53 · 53-45
- WGK Germany
- 2 · 2
- RTECS
- 560850 · SL0560850
- HS Code
- 2907.29 · 2907.29.9000
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 B · Carc. 1B
- Hazardous Substances Data
- 84 · 84-16-2(Hazardous Substances Data)
Safety & regulation
GHS classification
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.
Hazard information
Toxicology
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%.
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- rtecs
- SL0560850
- hs_code
- 2907.29.9000
- risk_code
- 45
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- T
- safety_code
- 53-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H350
- Hazard Classifications
- Carc. 1B
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
- Hazardous Substances Data
- 84-16-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
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/
Uses & manufacturing
Uses
MEDICATION
MEDICATION (VET)
Hexestrol is a synthetic estrogen that has been used as a hormonal antineoplastic agent.
Applications
UsesNonsteroidal synthetic estrogen
UsesEstrogen; antineoplastic (hormonal).
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
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