Unoprostone

Chemical compound
  • S01EE02 (WHO)
Legal statusLegal status
  • US: Discontinued
Pharmacokinetic dataElimination half-life14 minExcretionRenalIdentifiers
  • (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)
    cyclopentyl]hept-5-enoic acid
CAS Number
  • 120373-36-6 checkY 120373-24-2 (isopropyl ester)
PubChem CID
  • 5311236
DrugBank
  • DB06826 ☒N
ChemSpider
  • 4470755 ☒N
UNII
  • 6X4F561V3W
KEGG
  • D08661 checkY
ChEMBL
  • ChEMBL1201407 ☒N
CompTox Dashboard (EPA)
  • DTXSID80905120 Edit this at Wikidata
ECHA InfoCard100.227.145 Edit this at WikidataChemical and physical dataFormulaC22H38O5Molar mass382.541 g·mol−13D model (JSmol)
  • Interactive image
  • O=C(O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CCC(=O)CCCCCCC
InChI
  • InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1 ☒N
  • Key:TVHAZVBUYQMHBC-SNHXEXRGSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Unoprostone (INN) is a prostaglandin analogue. Its isopropyl ester, unoprostone isopropyl, was marketed under the trade name Rescula for the management of open-angle glaucoma and ocular hypertension.[1][2]

It was approved by the Food and Drug Administration in 2000.[3]

In 2009, Sucampo Pharmaceuticals acquired the rights to the drug in the U.S. and Canada.[4]

In 2015, the drug was discontinued in the U.S.[citation needed]

References

  1. ^ Micromedex Detailed Consumer Information
  2. ^ Fung DS, Whitson JT (2014). "An evidence-based review of unoprostone isopropyl ophthalmic solution 0.15% for glaucoma: place in therapy". Clinical Ophthalmology. 8. Auckland, N.Z.: 543–54. doi:10.2147/OPTH.S41562. PMC 3958522. PMID 24648719.
  3. ^ "Drug Approval Package". Food and Drug Administration.
  4. ^ "Sucampo Pharmaceuticals, Inc. Acquires Rights to Rescula for U.S. and Canada" (Press release). Business Wire. April 24, 2009.
  • v
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Drugs used for glaucoma preparations and miosis (S01E)
SympathomimeticsParasympathomimetics
muscarinic
muscarinic/nicotinic
acetylcholinesterase inhibitors
Carbonic anhydrase inhibitors/
(sulfonamides)Beta blocking agentsProstaglandin analogues (F)Other agents
  • v
  • t
  • e
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
  • H2
Active
D/J
  • D2
E/F
  • E2 (Dinoprostone)
  • E1 (Alprostadil)
  • F (Dinoprost):
I
  • I2 (Prostacyclin/Epoprostenol):
Thromboxanes (TX)
  • A2
  • B2
Leukotrienes (LT)
Precursor
Initial
  • A4
  • B4
SRS-A
  • C4
  • D4
  • E4
Eoxins (EX)
Precursor
  • Arachidonic acid 15-hydroperoxide
Eoxins
  • A4
  • C4
  • D4
  • E4
Nonclassic
By function
  • labor stimulation:
    • PGE2 (Dinoprostone)
    • PGF (Dinoprost)
  • v
  • t
  • e
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
  • Antagonists: AH-6809
  • ONO-8130
  • SC-19220
  • SC-51089
  • SC-51322
EP2Tooltip Prostaglandin EP2 receptor
  • Antagonists: AH-6809
  • PF-04418948
  • TG 4-155
EP3Tooltip Prostaglandin EP3 receptor
  • Antagonists: L-798106
EP4Tooltip Prostaglandin EP4 receptor
  • Antagonists: Grapiprant
  • GW-627368
  • L-161982
  • ONO-AE3-208
Unsorted
  • Agonists: 16,16-Dimethyl Prostaglandin E2
  • Aganepag
  • Carboprost
  • Evatanepag
  • Gemeprost
  • Nocloprost
  • Omidenepag
  • Prostaglandin F (dinoprost)
  • Simenepag
  • Taprenepag
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
  • Antagonists: RO1138452
TP (TXA2)Tooltip Thromboxane receptor
  • Agonists: Carbocyclic thromboxane A2
  • I-BOP
  • Thromboxane A2
  • U-46619
  • Vapiprost
Unsorted
  • Arbaprostil
  • Ataprost
  • Ciprostene
  • Clinprost
  • Cobiprostone
  • Delprostenate
  • Deprostil
  • Dimoxaprost
  • Doxaprost
  • Ecraprost
  • Eganoprost
  • Enisoprost
  • Eptaloprost
  • Esuberaprost
  • Etiproston
  • Fenprostalene
  • Flunoprost
  • Froxiprost
  • Lanproston
  • Limaprost
  • Luprostiol
  • Meteneprost
  • Mexiprostil
  • Naxaprostene
  • Nileprost
  • Nocloprost
  • Ornoprostil
  • Oxoprostol
  • Penprostene
  • Pimilprost
  • Piriprost
  • Posaraprost
  • Prostalene
  • Rioprostil
  • Rivenprost
  • Rosaprostol
  • Spiriprostil
  • Tiaprost
  • Tilsuprost
  • Tiprostanide
  • Trimoprostil
  • Viprostol
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
HQL-79
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators
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