Unoprostone - Misplaced Pages

Chemical compound Pharmaceutical compound

Unoprostone
Clinical data

Trade names	Rescula
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Topical (eye drops)
ATC code	S01EE02 (WHO)
Legal status
Legal status	US: Discontinued
Pharmacokinetic data
Elimination half-life	14 min
Excretion	Renal
Identifiers
IUPAC name (Z)-7-hept-5-enoic acid
CAS Number	120373-36-6 120373-24-2 (isopropyl ester)
PubChem CID	5311236
DrugBank	DB06826
ChemSpider	4470755
UNII	6X4F561V3W
KEGG	D08661
ChEMBL	ChEMBL1201407
CompTox Dashboard (EPA)	DTXSID80905120
ECHA InfoCard	100.227.145
Chemical and physical data
Formula	C₂₂H₃₈O₅
Molar mass	382.541 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(O)CCC/C=C\C1(O)C(O)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 Key:TVHAZVBUYQMHBC-SNHXEXRGSA-N
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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.

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

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

In 2015, the drug was discontinued in the U.S.

References

Micromedex Detailed Consumer Information
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.
"Drug Approval Package". Food and Drug Administration.
"Sucampo Pharmaceuticals, Inc. Acquires Rights to Rescula for U.S. and Canada" (Press release). Business Wire. April 24, 2009.

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine
muscarinic/nicotinic	Acetylcholine Carbachol
acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon

Carbonic anhydrase inhibitors/
(sulfonamides)

Beta blocking agents

Prostaglandin analogues (F_2α)

Other agents

Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG)

Precursor

H₂

Active

D/J

D₂

E/F

E₂ (Dinoprostone)

E₁ (Alprostadil)

F_2α (Dinoprost):

I₂ (Prostacyclin/Epoprostenol):

Thromboxanes (TX)

A₂
B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide
Initial	A₄ B₄
SRS-A	C₄ D₄ E₄

Eoxins (EX)

Precursor	Arachidonic acid 15-hydroperoxide
Eoxins	A₄ C₄ D₄ E₄

Nonclassic

Lipoxins (LX) (A₄, B₄)
Virodhamine

By function

bronchoconstriction
- PGD₂
- TXA₂
- LTC₄
- LTD₄
- LTE₄

vasoconstriction
- PGF_2α
- TXA₂
- TXB₂
vasodilation
- PGE₂
- PGI₂
- LTC₄
- LTD₄
- LTE₄

platelets: induce
- TXA₂
inhibit
- PGD₂
- PGI₂
leukocytes: induce
- TXA₂
- LTB₄
inhibit
- PGD₂
- PGE₂

fever stimulation:
- PGE₂

labor stimulation:
- PGE₂ (Dinoprostone)
- PGF_2α (Dinoprost)

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1

Agonists: Prostaglandin D₂
Treprostinil

DP₂Tooltip Prostaglandin D2 receptor 2

Agonists: Indometacin
Prostaglandin D₂

EP (E₂)Tooltip Prostaglandin E2 receptor

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

IP (I₂)Tooltip Prostacyclin receptor

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

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