Ethynodiol diacetate

Names

[ CAS No. ]:
297-76-7

[ Name ]:
Ethynodiol diacetate

[Synonym ]:
Metrodiol diacetate
Ethinodiol diacetate
Ovulen
Continuin
Metrodiol
Estr-4-ene-3,17-diol, 17-ethynyl-, diacetate
Femulen
Cervicundin
ETHYNODIOL DIACETATE
MFCD00083326
3β,17β-Diacetoxy-17α-ethynyl-4-estrene
EINECS 206-044-9
19-Norpregn-4-en-20-yne-3,17-diyl diacetate
17a-Ethynyl-4-estren-3b,17-diol diacetate
[(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Luto-metrodiol
Ovulen 50
Ethynodiol (diacetate)

Biological Activity

[Description]:

Ethynodiol diacetate is a steroidal progestin which is used as a hormonal contraceptive, it has relatively little or no potency as an androgen,has significant estrogenic effects.

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Endocrinology

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
461.1±45.0 °C at 760 mmHg

[ Melting Point ]:
128 - 131ºC

[ Molecular Formula ]:
C₂₄H₃₂O₄

[ Molecular Weight ]:
384.509

[ Flash Point ]:
221.8±27.1 °C

[ Exact Mass ]:
384.230072

[ PSA ]:
52.60000

[ LogP ]:
5.44

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.546

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC8963000

CHEMICAL NAME :: 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol diacetate

CAS REGISTRY NUMBER :: 297-76-7

LAST UPDATED :: 199510

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C24-H32-O4

MOLECULAR WEIGHT :: 384.56

WISWESSER LINE NOTATION :: L E5 B666 MUTJ E1 FOV1 F1UU1 OOV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 840 ug/kg

SEX/DURATION :: female 21 day(s) pre-mating

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 840 ug/kg

SEX/DURATION :: female 24 week(s) pre-mating

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 ug/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

DOSE :: 240 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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 16500 ug/kg

SEX/DURATION :: male 60 day(s) pre-mating

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 48 mg/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1400 ug/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 140 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 120 ug/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1560 ug/kg

SEX/DURATION :: female 1-3 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5 mg/kg

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

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

TYPE OF TEST :: Mutation test systems - not otherwise specified

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Mammal - cattle Cells - not otherwise specified

DOSE/DURATION :: 10 mg/L

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 120,390,1974 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 21,387,1979

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332-H351

[ Precautionary Statements ]:
P280

[ 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 ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
22-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RC8963000

Articles

Suppressive effect of neonatal treatment with a phytoestrogen, coumestrol, on lordosis and estrous cycle in female rats.

Brain Res. Bull. 64(5) , 449-54, (2005)

The neural control systems for the ovulatory cycle and lordosis behavior are sexually differentiated by estrogen during the perinatal period in rats. In the present study, the effects of a single neon...

New observations on endometrial physiology after transcervical injection of methylene blue dye.

Fertil. Steril. 82(6) , 1700-4, (2004)

We describe the in vivo features of endometrium stained with methylene blue dye and observed via microhysteroscopy, showing the patterns of endometrial glands and superficial cell changes during the m...

Membrane-initiated steroid signaling (MISS): genomic steroid action starts at the plasma membrane.

J. Steroid Biochem. Mol. Biol. 85(1) , 9-23, (2003)

Plasma membrane (PM) steroid recognition sites are thought to be responsible only for rapid, non-genomic responses without any link to the nuclear receptor-mediated genomic effects of steroids. We foc...