quinestrol

Trade name: estrovis

Small moleculeapproved

Approved

Apr 26, 1996

Quinestrol is a synthetic estrogen that is effective in hormone replacement therapy. It is a 3-cyclopentyl ether of ethynyl estradiol. After gastrointestinal absorption, it is stored in adipose tissue, where it is slowly released and metabolized in the liver to its active form, ethinyl estradiol. Quinestrol has found limited use in suppressing lactation in postpartum women and, in combination with synthetic progestogens, as contraceptive therapy, although additional studies are needed for both applications. Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 2 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Timeline

1990s

  1. Apr 26, 1996

    Parke-Davis — Earliest FDA Approval

  2. Apr 26, 1996

    Parke-Davis — NDA Organization

  3. Apr 26, 1996

    Warner Lambert — NDA Secondary Org

Indications

Approved for

Mechanism of action

Approval history

  • approvedApr 26, 1996

Chemistry & pharmacology

Loading structure…

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(OC5CCCC5)=CC=C34)[C@@H]1CC[C@@]2(O)C#C
Mol. weight
364.5204 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 17-alpha-ethinylestradiol 3-cyclopentyl ether
  • 17-alpha-ethinylestradiol 3-cyclopentyl ether
  • 17alpha-ethynylestradiol 3-cyclopentyl ether
  • 17alpha-ethynylestradiol 3-cyclopentyl ether
  • eston
  • eston
  • estradiol-17-beta 3-cyclopentyl ether
  • estradiol-17-beta 3-cyclopentyl ether
  • estrovis
  • estrovis
  • estrovis
  • estrovis
  • estrovis
  • estrovis 4000
  • estrovis 4000
  • estrovister
  • estrovister
  • estrovister
  • ethinyl estradiol 3-cyclopentyl ether
  • ethinyl estradiol 3-cyclopentyl ether
  • plestrovis
  • plestrovis
  • plestrovis
  • quilea
  • quilea
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrol
  • quinestrolo
  • quinestrolo
  • quinestrolum
  • quinestrolum
  • w-3566
  • w-3566

Organizations

Marketing (3)

OrganizationOrg typeRelationshipDate
Parke-DavisFor profitSYNApr 26, 1996
Parke-DavisFor profitNDAApr 26, 1996
Warner LambertFor profitNDA2Apr 26, 1996