Gestodene

Names

[ Name ]:
Gestodene

[Synonym ]:
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one
SH B 331
GESTOGENE
(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
SH B 33
Femodene
EINECS 262-145-8
Gestodene
GESTODONE
17a-Ethynyl-13-ethyl-17b-hydroxy-4,15-gonadien-3-one
SHG 415 G
17a-Ethynyl-17b-hydroxy-18-methyl-4,15-estradien-3-one
Gynovin
MFCD00867858

Biological Activity

[Description]:

Gestodene(SHB 331;WL 70) is a progestogen hormonal contraceptive.Target: Estrogen Receptor/ERRGestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel. When 40 micrograms of gestodene was taken, six out of seven women did not ovulate, and one out of seven had a cycle with luteal insufficiency. These data indicate that 40 micrograms of gestodene is the borderline dose for inhibition of ovulation. A combination of 75 micrograms gestodene with 30 micrograms ethinyl estradiol was found to inhibit ovulation in ten subjects, and no follicular maturation was noted [1]. gestodene bound with high affinity to the progesterone receptor, as did other synthetic and natural progestogens. However, gestodene did not bind to the estradiol receptor. The relative binding affinities of all tested synthetic and natural ligands showed no organ-specific differences and no differences between neoplastically transformed and normal tissues [2].Clinical indications: Female contraception

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Endocrinology

[References]

[1]. Spona, J. and J. Huber, Pharmacological and endocrine profiles of gestodene. Int J Fertil, 1987. 32 Suppl: p. 6-14.

[2]. Pollow, K., et al., Lack of binding of gestodene to estrogen receptor in human breast cancer tissue. Eur J Cancer, 1990. 26(5): p. 608-10.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
462.7±45.0 °C at 760 mmHg

[ Melting Point ]:
190-192°C

[ Molecular Formula ]:
C₂₁H₂₆O₂

[ Molecular Weight ]:
310.430

[ Flash Point ]:
196.9±21.3 °C

[ Exact Mass ]:
310.193268

[ PSA ]:
37.30000

[ LogP ]:
3.65

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JF7956000

CHEMICAL NAME :: 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-

CAS REGISTRY NUMBER :: 60282-87-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H26-O2

MOLECULAR WEIGHT :: 310.47

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 12 ug/kg

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

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,459,1985

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361

[ Precautionary Statements ]:
P280

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
62

[ Safety Phrases ]:
S22-S36/37

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Progestins in preventive hormone therapy. Including pharmacology of the new progestins, desogestrel, norgestimate, and gestodene: are there advantages?

Obstet. Gynecol. Clin. North Am. 21(2) , 299-319, (1994)

Clofarabine was the latest new drug to be approved, in 2004, for relapsed or refractory acute lymphoblastic leukaemia (ALL). To investigate its value in the frontline treatment of ALL we applied clofa...

Activation of NF-kappaB and COX-2 expression is associated with breakthrough bleeding in patients using oral contraceptives in extended regimens.

Gynecol. Endocrinol. 26(4) , 265-9, (2010)

The objective of the present study was to determine whether there is an increase in endometrial inflammation associated with the occurrence of breakthrough bleeding in patients using an oral contracep...

17-Hydroxysteroid dehydrogenase type 5 gene polymorphism (-71A/G HSD17B5 SNP) and treatment with oral contraceptive pills in PCOS women without metabolic comorbidities.

Gynecol. Endocrinol. 28(8) , 606-10, (2012)

We studied (1) the effects of oral contraceptive pills (OCPs) on hirsutism, hormonal and metabolic variables in 49 polycystic ovary syndrome patients without metabolic comorbidities and (2) the effect...