Promestriene

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 444415121

| IUPAC_name = (8R,9S,13S,14S)-17-methoxy-13-methyl-3-propoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene

| image = Promestriene skeletal.svg

| width = 250px

| tradename = Colpotrofin, Colpotrophine, Delipoderm

| pregnancy_AU =

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| routes_of_administration = Topical

| class = Estrogen; Estrogen ester

| bioavailability =

| protein_bound =

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| CAS_number_Ref =

| CAS_number = 39219-28-8

| CAS_supplemental =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GXM4PER6WZ

| ATC_prefix = G03

| ATC_suffix = CA09

| PubChem = 71717

| DrugBank_Ref =

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64767

| synonyms = Estradiol 3-propyl 17β-methyl diether; 17β-Methoxy-3-propoxyestra-1,3,5(10)-triene

| C=22 | H=32 | O=2

| SMILES = CCCOc1ccc2c(c1)CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4OC)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C22H32O2/c1-4-13-24-16-6-8-17-15(14-16)5-7-19-18(17)11-12-22(2)20(19)9-10-21(22)23-3/h6,8,14,18-21H,4-5,7,9-13H2,1-3H3/t18-,19-,20+,21?,22+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IUWKNLFTJBHTSD-QIKJAYGVSA-N

}}

Promestriene ({{abbrlink|INN|International Nonproprietary Name}}) (brand names Colpotrofin, Colpotrophine, Delipoderm), also known as estradiol 3-propyl 17β-methyl diether, is a synthetic estrogen which is used topically in a 1% cream formulation for the treatment of vaginal atrophy in women.{{cite journal | vauthors = Del Pup L, Di Francia R, Cavaliere C, Facchini G, Giorda G, De Paoli P, Berretta M | title = Promestriene, a specific topic estrogen. Review of 40 years of vaginal atrophy treatment: is it safe even in cancer patients? | journal = Anti-Cancer Drugs | volume = 24 | issue = 10 | pages = 989–998 | date = November 2013 | pmid = 24080714 | doi = 10.1097/CAD.0b013e328365288e | s2cid = 3458356 }}{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents|url=https://books.google.com/books?id=A0THacd46ZsC&pg=PA1671|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=1671–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1561|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1248, 1266, 1318, 1557}}{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA449|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=270–271}}{{cite book|author=Muller|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=HiSdvzs2pPAC&pg=PA332|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=289, 33 2}} It is the 3-propyl and 17β-methyl diether of estradiol and does not appear to convert into estradiol in the body.{{cite journal | vauthors = Santos I, Clissold S | title = Urogenital disorders associated with oestrogen deficiency: the role of promestriene as topical oestrogen therapy | journal = Gynecological Endocrinology | volume = 26 | issue = 9 | pages = 644–651 | date = September 2010 | pmid = 20374067 | doi = 10.3109/09513591003767948 | s2cid = 243338 }} Promestriene is minimally absorbed and appears to have negligible systemic estrogenic effect. The drug has been described as a tropic agent and antiseborrheic. It has not been found to be effective in the treatment of pattern hair loss or other conditions of cutaneous androgenization.{{cite book| vauthors = Orfanos CE, Montagna W, Stüttgen G |title=Hair Research: Status and Future Aspects; Proceedings of the First International Congress on Hair Research, Hamburg, March 13th–16, 1979|url=https://books.google.com/books?id=4gBJCAAAQBAJ&pg=PT553|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-81650-5|pages=553–}}{{cite book| vauthors = Beylot C | chapter = Menopause, Skin, and Cosmetology | veditors = Baran R, Maibach HI |title=Textbook of Cosmetic Dermatology| chapter-url = https://books.google.com/books?id=yIVfq5Lpl2EC&pg=PA493 |date=1 October 1998|publisher=CRC Press|isbn=978-1-85317-478-0|pages=493–}} Promestriene was first introduced in France in 1974 and has been marketed in 34 countries worldwide. It has been used in millions of women.