unoprostone isopropyl

Trade name: rescula

Small moleculeapproved

Approved

Aug 3, 2000

Unoprostone Isopropyl is a synthetic docosanoid and a structural analogue of an inactive biosynthetic cyclic derivative of arachidonic acid, 13,14-dihydro-15-keto-prostaglandin F 2a. Although the mechanism of action is unknown, unoprostone isopropyl is believed to reduce elevated intraocular pressure by increasing the outflow of aqueous humor through the trabecular meshwork. Unoprostone isopropyl (UI) may have a local effect on Big Potassium channels and ClC-2 chloride channels, but the exact mechanism is unknown at this time. Unoprostone is used for the management of open-angle glaucoma and ocular hypertension. The therapeutic efficacy of Unoprostone can be decreased when used in combination with Celecoxib, Diclofenac, Diflunisal, Etodolac and some other drugs. Unoprostone isopropyl ophthalmic solution may gradually increase the pigmentation of the iris, cause pigment changes (darkening) to periorbital pigmented tissues and eyelashes, exacerbate active intraocular inflammation (e.g., uveitis), and cause macular edema. In clinical studies, the most common ocular adverse reactions with use of Rescula were burning/stinging, burning/stinging upon drug instillation, dry eyes, itching, increased length of eyelashes, and injection. These were reported in approximately 10–25% of patients. Ocular adverse reactions occurring in approximately 5–10% of patients were abnormal vision, eyelid disorder, foreign body sensation, and lacrimation disorder. Other adverse reactions occurred more rarely. — NCATS

Clinical trial activity

2 trials · 2 clinical orgs · 2 marketing orgs

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

Earliest trial started May 1, 2011 (NCT01379560)

Timeline

2000s

  1. Aug 3, 2000

    Ciba — Earliest FDA Approval

  2. Aug 3, 2000

    Sucampo — NDA Secondary Org

  3. Aug 3, 2000

    Ciba — NDA Organization

2010s

  1. Jan 1, 2011

    Sucampo — Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2013

    Earliest Phase 3 Sponsor(trial)

Indications

Mechanism of action

  • Unspecified targetOTHER

    Unknown

Approval history

  • approvedPriority reviewAug 3, 2000

Chemistry & pharmacology

Loading structure…

SMILES

CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
Mol. weight
382.5341 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Discontinued

Oral

No

Parenteral

No

Topical

Yes

Prodrug

Sources

Also known as

  • eescula
  • isopropyl 20-ethyl-9alpha,11alpha-dihydroxy-15-keto-cis-delta-5-prostanoate
  • isopropyl unoprostone
  • isopropyl unoprostone
  • isopropyl z-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)hept-5-enoate, d-
  • rescula
  • rescula
  • rescula
  • rescula
  • rescula
  • uf 021
  • uf-021
  • uf-021
  • uf-021
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl
  • unoprostone isopropyl ester
  • unoprostone isopropyl ester
  • unoprostone isopropyl ester
  • unoprostone isopropyl ester
  • unoprostone isopropyl ester

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT01786395Phase 3Mar 1, 2013R-Tech Ueno
NCT01379560Phase 2May 1, 2011Sucampo
Showing 2 of 2 trials
Page 1 / 1

Organizations

Research & Development (2)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
R-Tech UenoFor profit1112013
SucampoFor profit1112011
2 organizations
Page 1 / 1

Marketing (2)

OrganizationOrg typeRelationshipDate
CibaFor profitNDAAug 3, 2000
SucampoFor profitNDA2Aug 3, 2000