25908-76-3

Usage

General Description

21-fluoro-16-ethyl-19-norprogesterone, also known as flunorprogesterone, is a synthetic progestin that exhibits strong progestational activity. This chemical compound is characterized by the presence of a fluoro group at position 21, an ethyl group at position 16, and removal of the methyl group at position 19 of the steroid nucleus. Flunorprogesterone is a potent and selective agonist of the progesterone receptor, and it is used in gynecology and endocrinology for various therapeutic purposes, such as contraception, hormone replacement therapy, and treatment of menstrual disorders. Its modified structure and enhanced stability make it a valuable pharmaceutical agent with improved bioavailability and efficacy compared to natural progesterone. Overall, 21-fluoro-16-ethyl-19-norprogesterone is an important synthetic progestin with a wide range of clinical applications.

InChI:InChI=1/C22H31FO2/c1-3-13-11-19-18-6-4-14-10-15(24)5-7-16(14)17(18)8-9-22(19,2)21(13)20(25)12-23/h10,13,16-19,21H,3-9,11-12H2,1-2H3/t13?,16-,17+,18+,19-,21+,22-/m0/s1

Upstream product

• 113975-10-3 21-<<(trifluoromethyl)sulfonyl>oxy>-16α-ethyl-19-norpregn-4-ene-3,20-dione 
• 24320-06-7 16α-ethyl-21-hydroxy-19-nor-pregn-4-ene-3,20-dione 

Relevant academic research and scientific papers

21-[18F]fluoro-16 alpha-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography.

We have synthesized 21-[18F]fluoro-16 alpha-ethyl-19-norprogesterone (FENP), a high affinity ligand for the progesterone receptor, labeled with the positron-emitting radionuclide fluorine-18 (t1/2 = 110 min). The synthesis proceeds in two steps from 21-hydroxy-16 alpha-ethyl-19-norprogesterone and involves [18F]fluoride ion displacement of the 21-trifluoromethanesulfonate (21-triflate). This material is purified by HPLC and is obtained in 4-30% overall yield (decay corrected) within 40 min after the end of bombardment to produce [18F]fluoride ion. The effective specific activity, determined by competitive radioreceptor binding assays, is 700-1400 Ci/mmol. In vivo, [18F]FENP demonstrates highly selective, receptor-mediated uptake by the uterus of estrogen-primed rats; the uterus to blood and uterus to muscle ratios were respectively 26 and 16 at 1 h and 71 and 41 at 3 h after injection. The high target tissue selectivity of this uptake suggests that this compound may be useful for the in vivo imaging of progestin target tissues and receptor-rich tumors (such as human breast tumors) by positron emission tomography.