Desogestrel Chemical Properties

Melting point:

109-110°C

alpha 

D20 +55° (chloroform)

Boiling point:

390.62°C (rough estimate)

Density 

1.0169 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

-20°C Freezer

solubility 

Practically insoluble in water, very soluble in methanol, freely soluble in anhydrous ethanol and in methylene chloride.

pka

13.07±0.40(Predicted)

color 

White to Almost white

Merck 

14,2926

Safety Information

Safety Statements 

24/25

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

JF7975000

HS Code 

29372390

Hazardous Substances Data

54024-22-5(Hazardous Substances Data)

MSDS

• Language:English Provider:Desogestrel

Desogestrel Usage And Synthesis

Description

Desogestrel is a synthetic progestogen. It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8⁺ T cells in a dose-dependent manner. Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome.

Chemical Properties

White Solid

Originator

Dicromil,Organol ,W. Germany,1981

Uses

A progestogen with low androgenic potency

Definition

ChEBI: Desogestrel is a 17beta-hydroxy steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a progestin and a synthetic oral contraceptive.

Manufacturing Process

A solution of 1.0 g of 11,11-methylene-18-methyl-delta4-estren-17-one in 33 ml tetrahydrofuran was added to a potassium-acetylide solution in tetrahydrofuran.
After 2 hours of stirring at 0°C to 5°C the reaction mixture was acidified with 2N H2SO4and processed further.
By a chromatographic treatment on silica gel and crystallization from pentane 0.7 g of 11,11-methylene-17α-ethynyl-18-methyl-δ4-estren-17β-ol with a melting point of 109°C to 110°C and an [α]D of +55°C (CHCl3) was obtained.

Therapeutic Function

Progestin

General Description

Desogestrel, (17α)-13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol, is a 19-nortestosterone analog with good progestin activity. Likethe other progestins, it is orally active and used in combinationwith an estrogen in oral contraceptives. Desogestrel is aprodrug that must be oxidized to the 3-one in vivo to haveprogestational action. CYPs 2C9 and 2C19 have been implicatedin the initial hydroxylation of desogestrel at C3.

Clinical Use

Desogestrel also is a prodrug and is rapidly metabolized in the intestinal mucosa and on first pass through the liver to its active metabolite, etonogestrel (3-ketodesogestrel). Following oral administration, the relative bioavailability for desogestrel is approximately 84%. Desogestrel also exhibits high selectivity for the progesterone receptor and low and rogenic activity, and it does not diminish the beneficial effects of estrogen on the lipid profile.

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