Estradiol distearate

Estradiol distearate (EDS), also known as estradiol dioctadecanoate, is an estrogen and an estrogen ester, which was never marketed.^[1][2] It is a long-acting prodrug of estradiol in the body.^[2]

Estradiol distearate

Clinical data
Other names	EDS; Estradiol 3,17β-distearate; Estradiol dioctadecanoate; Estra-1,3,5(10)-triene-3,17β-diol 3,17β-dioctadecanoate
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-13-methyl-3-octadecanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] octadecanoate
CAS Number	126144-03-4^Y
PubChem CID	53672832
UNII	B8HEM55UGK
Chemical and physical data
Formula	C54H92O4
Molar mass	805.326 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)CCCCCCCCCCCCCCCCC)C
InChI InChI=1S/C54H92O4/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-52(55)57-46-37-39-47-45(44-46)36-38-49-48(47)42-43-54(3)50(49)40-41-51(54)58-53(56)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h37,39,44,48-51H,4-36,38,40-43H2,1-3H3/t48-,49-,50+,51+,54+/m1/s1 Key:BBBPCTNBNYFUOV-NXCWIAOISA-N

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Structural properties of selected estradiol esters

Estrogen	Structure	Ester(s)				Relative mol. weight	Relative E2 content^b	log P^c
		Position(s)	Moiet(ies)	Type	Length^a
Estradiol		–	–	–	–	1.00	1.00	4.0
Estradiol acetate		C3	Ethanoic acid	Straight-chain fatty acid	2	1.15	0.87	4.2
Estradiol benzoate		C3	Benzoic acid	Aromatic fatty acid	– (~4–5)	1.38	0.72	4.7
Estradiol dipropionate		C3, C17β	Propanoic acid (×2)	Straight-chain fatty acid	3 (×2)	1.41	0.71	4.9
Estradiol valerate		C17β	Pentanoic acid	Straight-chain fatty acid	5	1.31	0.76	5.6–6.3
Estradiol benzoate butyrate		C3, C17β	Benzoic acid, butyric acid	Mixed fatty acid	– (~6, 2)	1.64	0.61	6.3
Estradiol cypionate		C17β	Cyclopentylpropanoic acid	Cyclic fatty acid	– (~6)	1.46	0.69	6.9
Estradiol enanthate		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.41	0.71	6.7–7.3
Estradiol dienanthate		C3, C17β	Heptanoic acid (×2)	Straight-chain fatty acid	7 (×2)	1.82	0.55	8.1–10.4
Estradiol undecylate		C17β	Undecanoic acid	Straight-chain fatty acid	11	1.62	0.62	9.2–9.8
Estradiol stearate		C17β	Octadecanoic acid	Straight-chain fatty acid	18	1.98	0.51	12.2–12.4
Estradiol distearate		C3, C17β	Octadecanoic acid (×2)	Straight-chain fatty acid	18 (×2)	2.96	0.34	20.2
Estradiol sulfate		C3	Sulfuric acid	Water-soluble conjugate	–	1.29	0.77	0.3–3.8
Estradiol glucuronide		C17β	Glucuronic acid	Water-soluble conjugate	–	1.65	0.61	2.1–2.7
Estramustine phosphate^d		C3, C17β	Normustine, phosphoric acid	Water-soluble conjugate	–	1.91	0.52	2.9–5.0
Polyestradiol phosphate^e		C3–C17β	Phosphoric acid	Water-soluble conjugate	–	1.23^f	0.81^f	2.9^g
Footnotes: ^a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic or cyclic fatty acids. ^b = Relative estradiol content by weight (i.e., relative estrogenic exposure). ^c = Experimental or predicted octanol/water partition coefficient (i.e., lipophilicity/hydrophobicity). Retrieved from PubChem, ChemSpider, and DrugBank. ^d = Also known as estradiol normustine phosphate. ^e = Polymer of estradiol phosphate (~13 repeat units). ^f = Relative molecular weight or estradiol content per repeat unit. ^g = log P of repeat unit (i.e., estradiol phosphate). Sources: See individual articles.

See also

• Estradiol dienantate
• List of estrogen esters § Estradiol esters

References

1. Deb S, Wähälä K (October 2010). "Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: expedient one-pot procedure for estradiol monoesters". Steroids. 75 (10): 740–4. doi:10.1016/j.steroids.2010.03.005. PMID 20347856. S2CID 1695106.
2. Vazquez-Alcantara MA, Menjivar M, Garcia GA, Díaz-Zagoya JC, Garza-Flores J (December 1989). "Long-acting estrogenic responses of estradiol fatty acid esters". Journal of Steroid Biochemistry. 33 (6): 1111–8. doi:10.1016/0022-4731(89)90417-2. PMID 2515394.