Estriol dihexanoate

Estriol dihexanoate
Clinical data
Other names	Oestriol dihexanoate; Estriol 3,17β-dihexanoate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dihexanoate
Routes of; administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
	IUPAC name [(8R,9S,13S,14S,16R,17R)-3-hexanoyloxy-16-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hexanoate;
CAS Number	104202-96-2 ;
PubChem CID	128509;
ChemSpider	113906;
UNII	J2K5XW8K72;
CompTox Dashboard (EPA)	DTXSID90908869 ;
Chemical and physical data
Formula	C30H44O5
Molar mass	484.677 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC(=O)O[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)CCCCC)C)O;
	InChI InChI=1S/C30H44O5/c1-4-6-8-10-27(32)34-21-13-15-22-20(18-21)12-14-24-23(22)16-17-30(3)25(24)19-26(31)29(30)35-28(33)11-9-7-5-2/h13,15,18,23-26,29,31H,4-12,14,16-17,19H2,1-3H3/t23-,24-,25+,26-,29+,30+/m1/s1; Key:ZOVABFBGAYSQTL-AECPDVIXSA-N;

Estriol dihexanoate, or estriol 3,17β-dihexanoate, is a synthetic estrogen and estrogen ester – specifically, the C3 and C17β dihexanoate ester of estriol – which was first described in 1963 and was never marketed.^[1]^[2]^[3] Following a single intramuscular injection of 8.90 mg estriol dihexanoate (equivalent to 5.0 mg estriol) in an oil solution, peak levels of estriol occurred after 2.1 to 3.4 days, an elimination half-life of 187 to 221 hours was observed, and estriol levels remained elevated for up to 20 to 50 days.^[1]^[3] For comparison, the durations of estriol and estriol dipropionate were far shorter.^[1]^[3]

References edit

^ ^a ^b ^c Kuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of exogenous natural and synthetic estrogens and antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 273–. ISBN 978-3-642-60107-1.
^ Tsuneda K, Yamada J, Yasuda K, Mori H (April 1963). "Preparation of some estriol esters". Chemical & Pharmaceutical Bulletin. 11 (4): 510–514. doi:10.1248/cpb.11.510. PMID 13994597.
^ ^a ^b ^c Heithecker R, Aedo AR, Landgren BM, Cekan SZ (1991). "Plasma estriol levels after intramuscular injection of estriol and two of its esters". Hormone Research. 35 (6): 234–238. doi:10.1159/000181911. PMID 1819548.

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Clinical data

Other names	Oestriol dihexanoate; Estriol 3,17β-dihexanoate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dihexanoate
Routes of administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name [(8R,9S,13S,14S,16R,17R)-3-hexanoyloxy-16-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] hexanoate
CAS Number	104202-96-2^Y
PubChem CID	128509
ChemSpider	113906
UNII	J2K5XW8K72
CompTox Dashboard (EPA)	DTXSID90908869
Chemical and physical data
Formula	C₃₀H₄₄O₅
Molar mass	484.677 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC(=O)O[C@H]1[C@@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)CCCCC)C)O
InChI InChI=1S/C30H44O5/c1-4-6-8-10-27(32)34-21-13-15-22-20(18-21)12-14-24-23(22)16-17-30(3)25(24)19-26(31)29(30)35-28(33)11-9-7-5-2/h13,15,18,23-26,29,31H,4-12,14,16-17,19H2,1-3H3/t23-,24-,25+,26-,29+,30+/m1/s1 Key:ZOVABFBGAYSQTL-AECPDVIXSA-N