Norgestimate

Bezeichnung:Norgestimate

CAS-Nr35189-28-7

Englisch Name:Norgestimate

CBNumberCB2110884

SummenformelC23H31NO3

Molgewicht369.5

MOL-Datei35189-28-7.mol

Norgestimate physikalisch-chemischer Eigenschaften

Schmelzpunkt	216°C
alpha	D25 +110°
Siedepunkt	497.9±45.0 °C(Predicted)
Dichte	1.22±0.1 g/cm3(Predicted)
storage temp.	Hygroscopic, -20°C Freezer, Under Inert Atmosphere
Löslichkeit	DMSO: soluble5mg/mL (clear solution)
Aggregatzustand	powder
pka	12.21±0.60(Predicted)
Farbe	white to beige
Optische Aktivität	[α]/D 43±3°, c = 1 in chloroform
BRN	6440219
Stabilität	Hygroscopic
CAS Datenbank	35189-28-7
EPA chemische Informationen	18,19-Dinorpregn-4-en-20-yn-3-one, 17-(acetyloxy)-13-ethyl-, 3-oxime, (17.alpha.)- (35189-28-7)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	63-22-36/38-62
S-Sätze:	26-36/37
WGK Germany	3
RTECS-Nr.	JF7976000
HS Code	2937230000
Giftige Stoffe Daten	35189-28-7(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Norgestimate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Norgestimate is an orally-effective progestogen, recently launched in combination with ethinyl estradiol as an oral contraceptive.
Chemische Eigenschaften
White Crystalline Solid
Originator
Ortho (USA)
Verwenden
Progestogen. In combination with estrogen as oral contraceptive.
Verwenden
antifungal
Definition
ChEBI: Norgestimate is a steroid ester, a ketoxime 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 4.5 g of D-17β-acetoxy-13β-ethyl-17α-ethynyl-gon-4-en-3-one in 15 ml of pyridine and 2.0 g of hydroxylamine hydrochloride hydroxylamine hydrochloride is heated on a steam bath for 45 min. It is then cooled and poured into a large amount of ice-water, after which the solid which is thus produced is filtered off and air dried. Recrystallization from methylene chloride-ethanol gives D-17β-acetoxy-13α-ethyl-17α-ethynyl-gon-4-en-one oxime, m.p. 214-218°C; [α]D25 = +41°.
Trademarks
CILEST
Therapeutic Function
Progestin
Allgemeine Beschreibung
Norgestimate, (17α)-17-acetyloxy-13-ethyl-18,19-dinor-pregn-4-en-20yn-3-one oxime, is a 19-nortestosterone, 3-oxime prodrug that is orally active andused with an estrogen in oral contraceptive products. It hasminimal androgenic action. Norgestimate is metabolized to17-deacetylnorgestimate (norelgestromin) and norgestrel,which provide the progestational action.
in vitro
norgestimate was found that, unlike other 19-nortestosterone derivatives, showed high selectivity for the progesterone receptor and low androgenic activity. moreover, norgestimate and its main active metabolite norelgestromin could not bind to or occupy sex hormone-binding globulin [1].
in vivo
the androgenic and the progestational activity of norgestimate were compared in two animal studies. it was found the difference in the pharmacological response in norgestimate treated rats was equivalent to the difference in the exposure of the animals to either directly administered or metabolically derived levonorgestrel [2].
Stoffwechsel
Norgestimate is considered to be a pro-proges tin (prodrug), because it rapidly undergoes a two-s tep m etabolic transformation to form two active products, norelgestromine (levonorgestrel 3-oxime) and levonorgestrel. Deacetylation occurs in the intestine and liver, whereas convers ion of the 3-oxime to the corresponding ketone occurs primarily in the liver. Unlike the other progestins mentioned, norgestimate and its metabolites are not bound to SHBG.
Einzelnachweise
[1] thomas l. lemke; david a. williams (2008). foye's principles of medicinal chemistry. lippincott williams & wilkins. pp. 1316–. isbn 978-0-7817-6879-5.
[2] kuhnz w, beier s. comparative progestational and androgenic activity of norgestimate and levonorgestrel in the rat. contraception. 1994 mar;49(3):275-89.
[3] https://en. wikipedia.org/wiki/norgestimate

Norgestimate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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