Estriol dipropionate

Estriol dipropionate
Clinical data
Other names	Oestriol dipropionate; Estriol 3,17β-dipropionate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dipropanoate
Routes of; administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
	IUPAC name [(8R,9S,13S,14S,16R,17R)-16-hydroxy-13-methyl-3-propanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] propanoate;
CAS Number	104202-88-2 ;
PubChem CID	128508;
ChemSpider	113905;
UNII	AYW6G49M3S;
Chemical and physical data
Formula	C24H32O5
Molar mass	400.515 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=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)CC)C)O;
	InChI InChI=1S/C24H32O5/c1-4-21(26)28-15-7-9-16-14(12-15)6-8-18-17(16)10-11-24(3)19(18)13-20(25)23(24)29-22(27)5-2/h7,9,12,17-20,23,25H,4-6,8,10-11,13H2,1-3H3/t17-,18-,19+,20-,23+,24+/m1/s1; Key:QKLDCEYHDKPVDK-PRIYMHJNSA-N;

Estriol dipropionate, or estriol 3,17β-dipropionate, is a synthetic estrogen and estrogen ester – specifically, the C3 and C17β dipropionate ester of estriol – which was first described in 1963 and was never marketed.^[1]^[2]^[3] Following a single intramuscular injection of 6.94 mg estriol dipropionate (equivalent to 5.0 mg estriol) in an oil solution, peak levels of estriol occurred after 0.83 days, an elimination half-life of 12.7 hours was observed, and estriol levels remained elevated for up to 4 days.^[1]^[3] For comparison, the duration of estriol was much shorter, while that of estriol dihexanoate was much longer.^[1]^[3]

References

^ ^a ^b ^c Kuhnz W, Blade H, Zimmermann H (6 December 2012). "Pharmacokinetics and 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 dipropionate; Estriol 3,17β-dipropionate; 16α-Hydroxyestra-1,3,5(10)-triene-3,17β-diyl dipropanoate
Routes of administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name [(8R,9S,13S,14S,16R,17R)-16-hydroxy-13-methyl-3-propanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] propanoate
CAS Number	104202-88-2^Y
PubChem CID	128508
ChemSpider	113905
UNII	AYW6G49M3S
Chemical and physical data
Formula	C₂₄H₃₂O₅
Molar mass	400.515 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(=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)CC)C)O
InChI InChI=1S/C24H32O5/c1-4-21(26)28-15-7-9-16-14(12-15)6-8-18-17(16)10-11-24(3)19(18)13-20(25)23(24)29-22(27)5-2/h7,9,12,17-20,23,25H,4-6,8,10-11,13H2,1-3H3/t17-,18-,19+,20-,23+,24+/m1/s1 Key:QKLDCEYHDKPVDK-PRIYMHJNSA-N