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Norgestimate

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Norgestimate Basic information
Product Name:Norgestimate
Synonyms:13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl acetate;(17R)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one oxime;Norgestimate (200 mg);(17α)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-OxiMe;(17a)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-Oxime;D-138;(17-alpha)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one3-oxime;18,19-dinorpregn-4-en-20-yn-3-one,17-(acetyloxy)-13-ethyl-,3-oxime,(17-alpha
CAS:35189-28-7
MF:C23H31NO3
MW:369.5
EINECS:
Product Categories:Metabolite Reference Standard;Isotopically Labeled Pharmaceutical Reference Standard;VAGISTAT;Hormone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
Mol File:35189-28-7.mol
Norgestimate Structure
Norgestimate Chemical Properties
Melting point 216°C
alpha D25 +110°
Boiling point 497.9±45.0 °C(Predicted)
density 1.22±0.1 g/cm3(Predicted)
storage temp. Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility DMSO: soluble5mg/mL (clear solution)
form powder
pka12.21±0.60(Predicted)
color white to beige
optical activity[α]/D 43±3°, c = 1 in chloroform
BRN 6440219
Stability:Hygroscopic
CAS DataBase Reference35189-28-7
EPA Substance Registry System18,19-Dinorpregn-4-en-20-yn-3-one, 17-(acetyloxy)-13-ethyl-, 3-oxime, (17.alpha.)- (35189-28-7)
Safety Information
Hazard Codes Xn
Risk Statements 63-22-36/38-62
Safety Statements 26-36/37
WGK Germany 3
RTECS JF7976000
HS Code 2937230000
Hazardous Substances Data35189-28-7(Hazardous Substances Data)
MSDS Information
Norgestimate Usage And Synthesis
DescriptionNorgestimate is an orally-effective progestogen, recently launched in combination with ethinyl estradiol as an oral contraceptive.
Chemical PropertiesWhite Crystalline Solid
OriginatorOrtho (USA)
UsesProgestogen. In combination with estrogen as oral contraceptive.
Usesantifungal
DefinitionChEBI: 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 ProcessA 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°.
Brand nameCILEST
Therapeutic FunctionProgestin
General DescriptionNorgestimate, (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 vitronorgestimate 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 vivothe 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].
MetabolismNorgestimate 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.
references[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 Preparation Products And Raw materials
Tag:Norgestimate(35189-28-7) Related Product Information
Cefpodoxime proxetil Ethyl cellulose BENORILATE Ethyl acetate CHLOROETHANE Ethyl formate Ethanol Ethyl acrylate Ethylparaben Ethylbenzene Diethyl ether Diphenoxylate Norgestimate Related Compound A DEACETYLNORGESTIMATE (25 MG) ((E)- AND (Z)-17-DEACETYL NORGESTIMATE MIXTURE) 17-DESACETYL NORGESTIMATE NORGESTIMATE-D3 Norgestimate-d6 (major) NORGESTIMATE RELATED COMPOUND A (25 MG) (LEVONORGESTREL ACETATE)