Quinestrol

Names

[ CAS No. ]:
152-43-2

[ Name ]:
Quinestrol

[Synonym ]:
3-(Cyclopentyloxy)-19-nor-17a-pregna-1,3,5(10)-trien-20-yn-17-ol
17a-Ethinylestradiol 3-Cyclopentyl Ether
19-Norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, (17α)-
MFCD00079189
Quinestrol
(8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
Estra-1(10),2,4-trien-17-ol, 3-(cyclopentyloxy)-17-ethynyl-, (17β)-
17α-Ethynylestradiol 3-Cyclopentyl Ether
(17α)-3-(Cyclopentyloxy)-19-norpregna-1(10),2,4-trien-20-yn-17-ol
EINECS 205-803-1

Biological Activity

[Description]:

Quinestrol is a synthetic estrogen, used in hormone replacement therapy, and occasionally to treat breast cancer and prostate cancer

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Endocrinology

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
502.5±50.0 °C at 760 mmHg

[ Melting Point ]:
107 - 108ºC

[ Molecular Formula ]:
C₂₅H₃₂O₂

[ Molecular Weight ]:
364.520

[ Flash Point ]:
218.8±24.4 °C

[ Exact Mass ]:
364.240234

[ PSA ]:
29.46000

[ LogP ]:
6.67

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.596

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC8948000

CHEMICAL NAME :: 19-Nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-

CAS REGISTRY NUMBER :: 152-43-2

LAST UPDATED :: 199603

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C25-H32-O2

MOLECULAR WEIGHT :: 364.57

WISWESSER LINE NOTATION :: L E5 B666TTT&J E1 FQ F1UU1 OO- AL5TJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 80 ug/kg

SEX/DURATION :: female 2 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 14,295,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 ug/kg

SEX/DURATION :: lactating female 4 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - postpartum

REFERENCE :: INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 12,261,1967

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 9,132,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 ug/kg

SEX/DURATION :: female 12 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 20,239,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 60 ug/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 22,49,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12 ug/kg

SEX/DURATION :: female 12 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

REFERENCE :: INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 20,239,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 600 ug/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 22,49,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 12 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: STEDAM Steroids. (Holden-Day Inc., 4432 Telegraph Ave., Oakland, CA 94609) V.1- 1963- Volume(issue)/page/year: 10,687,1967

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H312-H332-H350-H360

[ Precautionary Statements ]:
P201-P280-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R46;R61;R20/21/22

[ Safety Phrases ]:
S53-S22-S36/37/39-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RC8948000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

The bioaccumulation and biotransformation of synthetic estrogen quinestrol in crucian carp.

Aquat. Toxicol. 155 , 84-90, (2014)

The occurrence and fate of endocrine disrupting chemicals (EDCs) in aquatic species have attracted close attention during the last decades. In this study, the bioaccumulation and biotransformation of ...

Photodegradation of quinestrol in waters and the transformation products by UV irradiation.

Chemosphere 89(11) , 1419-25, (2012)

Quinestrol is synthetic estrogen used in contraceptive and hormone replacement therapy and occasionally for treating breast cancer and prostate cancer. It can make its way into the environment through...

Effects of quinestrol on reproductive hormone expression, secretion, and receptor levels in female Mongolian gerbils (Meriones unguiculatus).

Theriogenology 77(6) , 1223-31, (2012)

Quinestrol, a synthetic estrogen with marked estrogenic effects and prolonged activity, has potential as a contraceptive for Mongolian gerbils. The objective of this study was to describe the effects ...