Desogestrel

Names

[ Name ]:
Desogestrel

[Synonym ]:
(8S,9S,10R,13S,14S,17R)-13-éthyl-17-éthynyl-11-méthylidène-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-17-ol
Desogestrel
(8S,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-11-methyliden-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
(17α)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
DESOGESTRAL
13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol
17a-Ethynyl-18-methyl-11-methyl-ene-D4-estren-17b-ol
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol (non-preferred name)
13-ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-ol
org2969
(17a)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
Marvelon 150/320
Cerazette
(8S,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
Dicromil
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
Cyclosa

Biological Activity

[Description]:

Desogestrel(Org-2969) is a third-generation 19-nortestosterone derivative progestogen; is contained in many oral contraceptive preparations, both combined (COCs) to ethinyl-estradiol (EE) or alone in a progestin-only pill (POP).

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Others

[References]

[1]. Gassen DT, et al. Evaluation of hormonal suppression with two contraceptive regimens using ethinyl estradiol and desogestrel. Arch Gynecol Obstet. 2013 Feb;287(2):289-94.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
428.3±45.0 °C at 760 mmHg

[ Melting Point ]:
109-110ºC

[ Molecular Formula ]:
C₂₂H₃₀O

[ Molecular Weight ]:
310.473

[ Flash Point ]:
187.9±21.7 °C

[ Exact Mass ]:
310.229675

[ PSA ]:
20.23000

[ LogP ]:
6.59

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.566

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JF7975000

CHEMICAL NAME :: 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17-alpha)-

CAS REGISTRY NUMBER :: 54024-22-5

LAST UPDATED :: 198910

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C22-H30-O

MOLECULAR WEIGHT :: 310.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 ug/kg

SEX/DURATION :: female 20 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: 16,51,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 ug/kg

SEX/DURATION :: female 20 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - other measures of fertility

REFERENCE :: ACENA7 Acta Endocrinologica (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) V.1- 1948- Volume(issue)/page/year: 83,429,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6300 ng/kg

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

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

REFERENCE :: EXMDA4 International Congress Series--Excerpta Medica. (Excerpta Medica, Inc., POB 3085, Princeton, NJ 08540) No.1- 1952- Volume(issue)/page/year: (396),252,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 28 mg/kg

SEX/DURATION :: male 7 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 :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,231,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6250 ug/kg

SEX/DURATION :: female 5 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: 33,231,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 125 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: 33,231,1983

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
24/25

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
JF7975000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Changes in the size of rectovaginal endometriotic nodules infiltrating the rectum during hormonal therapies.

Arch. Gynecol. Obstet. 287(3) , 447-53, (2013)

To evaluate the changes in the volume of rectovaginal endometriotic nodules infiltrating the rectum during 12-month treatment with hormonal therapies.This prospective, non-randomized, self-controlled ...

The risk of venous thrombosis in women over 50 years old using oral contraception or postmenopausal hormone therapy.

J. Thromb. Haemost. 11(1) , 124-31, (2013)

Oral contraception (OC) and postmenopausal hormone therapy (HT) can be used to alleviate menopausal symptoms. However, the risk of venous thrombosis (VT) associated with OC use in women over 50 years ...

Progestogen-only contraceptive pill compared with combined oral contraceptive in the treatment of pain symptoms caused by endometriosis in patients with migraine without aura.

Eur. J. Obstet. Gynecol. Reprod. Biol. 179 , 63-8, (2014)

Evaluate patient satisfaction at 6-month treatment in women with symptomatic rectovaginal endometriosis and migraine without aura with (progestogen-only contraceptive pill, POP versus sequential combi...