Estropipate (formerly piperazine estrone sulfate), a female sex hormone produced by the ovaries that functions as an agonist for the estrogen receptor and a type of estrogen. The body needs estrogen for a number of functions. Estropipate is used to prevent osteoporosis (bone loss) in menopausal women and to treat menopause symptoms like hot flashes and vaginal changes. It serves a variety of purposes. Menopause symptoms can be relieved by hormone replacement therapy, infertility treatments, conditions that cause female sexual characteristics to underdevelop, prostate cancer treatments, and osteoporosis prevention. The nuclear estrogen receptor, which is present in the breast, pituitary, hypothalamus, liver, and bone, is bound by escropipate as it diffuses across cell membranes. The activated complex binds to the DNA's estrogen response element, triggering the transcription of genes related to the development of secondary sex traits and the operation of the female reproductive system.

Physicochemical Properties

Molecular Formula	C22H32N2O5S
Molecular Weight	436.5649
Exact Mass	436.203
Elemental Analysis	C, 60.53; H, 7.39; N, 6.42; O, 18.32; S, 7.34
CAS #	7280-37-7
Related CAS #	7280-37-7
PubChem CID	5284555
Appearance	White to off-white solid powder
LogP	4.211
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Heavy Atom Count	30
Complexity	650
Defined Atom Stereocenter Count	4
SMILES	S(=O)(=O)(O[H])OC1C([H])=C([H])C2=C(C=1[H])C([H])([H])C([H])([H])[C@]1([H])[C@]2([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C(C([H])([H])C([H])([H])[C@]21[H])=O.N1([H])C([H])([H])C([H])([H])N([H])C([H])([H])C1([H])[H]
InChi Key	HZEQBCVBILBTEP-ZFINNJDLSA-N
InChi Code	InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
Chemical Name	[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate;piperazine
Synonyms	Estropipate; Piperazine estrone sulfate; Piperazine estronesulfate; Harmogen; Ogen
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

Bagdade JD, Subbaiah PV. Effects of estropipate treatment on plasma lipids and lipoprotein lipid composition in postmenopausal women. J Clin Endocrinol Metab. 1991 Feb;72(2):283-6. PubMed PMID: 1991799.

Additional Infomation

Estropipate can cause cancer and developmental toxicity according to state or federal government labeling requirements. Estropipate is a steroid sulfate and a piperazinium salt. It is functionally related to an estrone. Estropipate is a natural estrogenic substance composed of estrone sulfate and piperazine. Estropipate diffuses through the cell membrane and binds to and subsequently activates the nuclear estrogen receptor found in the reproductive tract, breast, pituitary, hypothalamus, liver, and bone. The activated complex binds to the estrogen response element on the DNA and activates the transcription of genes involved in the functioning of the female reproductive system and secondary sex characteristics. See also: Estrone (has active moiety).

Solubility Data

Solubility (In Vitro)

DMSO: 87~110 mg/mL (199.3~252 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.75 mg/mL (6.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (6.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (6.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.2906 mL	11.4532 mL	22.9064 mL
	5 mM	0.4581 mL	2.2906 mL	4.5813 mL
	10 mM	0.2291 mL	1.1453 mL	2.2906 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.