CAS 16320-04-0|Gestrinone

Introduction：Basic information about CAS 16320-04-0|Gestrinone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Gestrinone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Synonyms

Common Name	Gestrinone
CAS Number	16320-04-0	Molecular Weight	308.414
Density	1.2±0.1 g/cm3	Boiling Point	507.6±50.0 °C at 760 mmHg
Molecular Formula	C₂₁H₂₄O₂	Melting Point	154ºC
MSDS	/	Flash Point	214.9±22.7 °C

Names

Name	Gestrinone
Synonym	More Synonyms

Gestrinone BiologicalActivity

Description	Gestrinone (R2323) is a synthetic steroid hormone used to treat endometriosis. It inhibits leiomyoma cells with an IC50 of 43.67 μM.
Related Catalog	Signaling Pathways >>Others >>Estrogen Receptor/ERRResearch Areas >>Inflammation/Immunology
Target	IC50: 43.67 μM (leiomyoma cells)[2]
In Vitro	Gestrinone binds to endometrial receptors for estrogen, progesterone and androgen, occupies all specific binding sites of steroids in the steroid target cells despite the presence of endogenous steroids[1]. Gestrinone exhibits stronger inhibitory effects on the growth of leiomyoma cells at 60 h than that at 20 and 40 h. Leiomyoma cells appears less dense, the cytoplasm is atrophic, the intercellular connections dwindled and nuclear aggregations are observed with more than 10 μM gestrinone treatment. Gestrinone treatment reduces the relative mRNA levels of estrogen α in a concentration dependent manner at concentrations of 0.1-3.0 μM[2].
In Vivo	The estrogen-sensitive endpoints, vaginal keratinization and uterine progesterone receptor concentration, are enhanced by treatment with a combination of flutamide and either danazol or gestrinone. These data indicate that danazol and gestrinone have estrogenic activity that is masked by the androgenic component of these drugs[3]. The mean hormone binding globulin treated with gestrinone fell from 56.4 nM to 28.1 nM after one week’s treatment and to 7.1 nM after 4 weeks respectively[4].
Cell Assay	Gestrinone is dissolved in DMSO and diluted in cell culture media. The final concentration of DMSO in the culture media is 0.5%. The cells are cultured in 96-well plates and treated with DMSO or graded concentrations of gestrinone (0.1, 0.5, 1.0, 5.0, 10, 50 or 100 μM) for 20, 40 and 60 h. The absorbance (OD) at 450 nm is read to determine the cell viability in each well[2].
References	[1]. Tamaya T, et al. Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol. Acta Obstet Gynecol Scand. 1986;65(5):439-41. [2]. Zhu Y, et al. Gestrinone inhibits growth of human uterine leiomyoma may relate to activity regulation of ERα, Src and P38 MAPK. Biomed Pharmacother. 2012 Dec;66(8):569-77. [3]. Snyder BW, et al. Studies on the mechanism of action of danazol and gestrinone (R2323) in the rat: evidence for a masked estrogen component. Fertil Steril. 1989 Apr;51(4):705-10. [4]. Dowsett M, et al. A comparison of the effects of danazol and gestrinone on testosterone binding to sex hormone binding globulin in vitro and in vivo. Clin Endocrinol (Oxf). 1986 May;24(5):555-63.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	507.6±50.0 °C at 760 mmHg
Melting Point	154ºC
Molecular Formula	C₂₁H₂₄O₂
Molecular Weight	308.414
Flash Point	214.9±22.7 °C
Exact Mass	308.177643
PSA	37.30000
LogP	3.27
Vapour Pressure	0.0±3.0 mmHg at 25°C
Index of Refraction	1.607
InChIKey	BJJXHLWLUDYTGC-ANULTFPQSA-N
SMILES	C#CC1(O)CCC2C3CCC4=CC(=O)CCC4=C3C=CC21CC
Storage condition	-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JF7964000

CHEMICAL NAME :: 18,19-Dinor-17-alpha-pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-

CAS REGISTRY NUMBER :: 16320-04-0

LAST UPDATED :: 199612

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C21-H24-O2

MOLECULAR WEIGHT :: 308.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - other changes

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,701,1988

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - visual field changes Behavioral - altered sleep time (including change in righting reflex) Nutritional and Gross Metabolic - other changes

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,701,1988

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - other changes

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,701,1988 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 ug/kg

SEX/DURATION :: female 8 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 14,275,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1200 ug/kg

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

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

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 31,278,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 1800 ug/kg

SEX/DURATION :: female 48 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 11,625,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 185 ug/kg

SEX/DURATION :: female 28 day(s) pre-mating

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

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 14,671,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 2600 ug/kg

SEX/DURATION :: female 26 week(s) pre-mating

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

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 49,418,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,713,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 500 ug/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,713,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 15-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,737,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1200 mg/kg

SEX/DURATION :: female 15-18 day(s) after conception lactating female 20 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 16,737,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 2486 ug/kg

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

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

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 15,335,1977

Synonyms

D-GESTRINONE

Dimetriose

TridoMose

13b-Ethyl-17a-ethynyl-D4,9,11-gonatriene-17b-ol-3-one

(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one

13b-Ethyl-17a-ethynyl-17b-hydroxy-4,9,11-gonatrien-3-one

Dimetrose

MFCD00865561

gestrigone

(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one

18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-

Gestrinone

(8S,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

13-ETHYL-17α-ETHYNYL-17β-HYDROXY-4,9,11-GONATRIENE-3-ONE

NeMestran

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