Tafluprost

Names
Trade names| Saflutan, Taflotan, Tapros, Zioptan, others

IUPAC name

* Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate

Clinical data
Drug class| Prostaglandin analogue[1]
Main uses| Open-angle glaucoma, ocular hypertension[1]
Side effects| Eye redness, itchiness, eyelash growth, blurry vision[1]
Pregnancy
category|

* US: C (Risk not ruled out)

Routes of
use| Topical (eye drops)
Onset of action| 2–4 hrs
Duration of action| ≥ 24 hrs
External links
AHFS/Drugs.com| Multum Consumer Information
Legal
Legal status|

* US: ℞-only

Pharmacokinetics
Metabolism| Activation by ester hydrolysis, deactivation by beta oxidation
Chemical and physical data
Formula| C25H34F2O5
Molar mass| 452.539 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CC(C)OC(=O)CCC\C=C/CC(C(O)CC1O)C1\C=C\C(F)(F)COc2ccccc2

InChI

* InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1

* Key:WSNODXPBBALQOF-VEJSHDCNSA-N

Tafluprost, sold under the brand name Zioptan among others, is a medication used to treat open-angle glaucoma and ocular hypertension.[1] It is used as an eye drop.[1] It may be used alone or with other medications.[1]

Common side effects include eye redness, itchiness, eyelash growth, and blurry vision.[1] Other side effects may include iritis and macular edema.[1] It is a prostaglandin analogue which is believed to work by increasing the outflow of aqueous fluid from the eye.[1]

Tafluprost was approved for medical use in the United States in 2012 and Canada in 2014.[1][2] In the United States it costs about 150 USD per month as of 2021.[3] In Canada it was less cost effective as compared to bimatoprost in 2020.[4]

## Contents

* 1 Medical uses
* 1.1 Dosage
* 2 Side effects
* 3 Interactions
* 4 Pharmacology
* 4.1 Mechanism of action
* 4.2 Pharmacokinetics
* 5 References
* 6 External links

## Medical uses[edit | edit source]

It is used to treat open-angle glaucoma and ocular hypertension.[1]

### Dosage[edit | edit source]

It is used as one drop once per day of a 0.0015% solution.[1]

## Side effects[edit | edit source]

The most common side effect is conjunctival hyperemia, which occurs in 4 to 20% of patients. Less common side effects include stinging of the eyes, headache, and respiratory infections. Rare side effects are dyspnoea (breathing difficulties), worsening of asthma, and macular oedema.[5][6][7]

## Interactions[edit | edit source]

Nonsteroidal anti-inflammatory drugs (NSAIDs) can either reduce or increase the effect of tafluprost.[5] Timolol eye drops, a common kind of glaucoma medication, does not negatively interact with this drug.[6]

No interactions with systemic (for example, oral) drugs are expected because tafluprost does not reach relevant concentrations in the bloodstream.[6][7]

## Pharmacology[edit | edit source]

### Mechanism of action[edit | edit source]

Tafluprost is a prodrug of the active substance, tafluprost acid, a structural and functional analogue of prostaglandin F2α (PGF2α). Tafluprost acid is a selective agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eyes and thus lowering intraocular pressure.[6][7]

Other PGF2α analogues with the same mechanism include latanoprost and travoprost.[6]

### Pharmacokinetics[edit | edit source]

Tafluprost, as a lipophilic ester, easily penetrates the cornea and is then activated to the carboxylic acid, tafluprost acid. Onset of action is 2 to 4 hours after application, the maximal effect is reached after 12 hours, and ocular pressure remains lowered for at least 24 hours.[6][7]

Tafluprost acid is inactivated by beta oxidation to 1,2-dinortafluprost acid, 1,2,3,4-tetranortafluprost acid, and its lactone, which are subsequently glucuronidated or hydroxylated. The cytochrome P450 liver enzymes play no role in the metabolism.[7]

An analogous pathway (at least up to the tetranor-metabolites) has been found for latanoprost and travoprost.

Metabolism. From left to right: tafluprost, tafluprost acid (the active metabolite), 1,2-dinortafluprost acid, 1,2,3,4-tetranortafluprost acid, 1,2,3,4-tetranortafluprost acid lactone[8][9]

A tafluprost/timolol combination ophthalmic solution

## References[edit | edit source]

1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 "Tafluprost Monograph for Professionals". Drugs.com. Archived from the original on 4 March 2021. Retrieved 20 September 2021.
2. ↑ Canada, Health (2 July 2014). "Notice: Prescription Drug List (PDL): Multiple additions". www.canada.ca. Archived from the original on 8 July 2021. Retrieved 20 September 2021.
3. ↑ "Tafluprost Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 1 May 2016. Retrieved 20 September 2021.
4. ↑ "Prostaglandin Analogues for Ophthalmic Use: A Review of Comparative Clinical Effectiveness, Cost-Effectiveness, and Guidelines | CADTH". www.cadth.ca. Archived from the original on 22 September 2021. Retrieved 20 September 2021.
5. ↑ 5.0 5.1 Tafluprost Professional Drug Facts.
6. ↑ 6.0 6.1 6.2 6.3 6.4 6.5 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.`{{cite book}}`: CS1 maint: unrecognized language (link)
7. ↑ 7.0 7.1 7.2 7.3 7.4 Dinnendahl V, Fricke U, eds. (2011). Arzneistoff-Profile (in German). Vol. 9 (25 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.`{{cite book}}`: CS1 maint: unrecognized language (link)
8. ↑ Fukano Y, Kawazu K (August 2009). "Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats". Drug Metabolism and Disposition. 37 (8): 1622–34. doi:10.1124/dmd.108.024885. PMID 19477946. S2CID 12425702.
9. ↑ Fukano Y, Kawazu K, Akaishi T, Bezwada P, Pellinen P (June 2011). "Metabolism and ocular tissue distribution of an antiglaucoma prostanoid, tafluprost, after ocular instillation to monkeys". Journal of Ocular Pharmacology and Therapeutics. 27 (3): 251–9. doi:10.1089/jop.2010.0178. PMID 21491995.

## External links[edit | edit source]

Identifiers:|

* ATC code:

* S01EE05 (WHO)

* CAS Number: 209860-87-7
* PubChem CID: 6433101
* DrugBank:

* DB08819

* ChemSpider:

* 8044182

* UNII:

* 1O6WQ6T7G3

* KEGG:

* D06274

* ChEBI:

* CHEBI:66899

* ChEMBL:

* ChEMBL1963683

|

* v
* t
* e

Eicosanoids

Precursor|

* Arachidonic acid

Prostanoids|

| Prostaglandins (PG)|

| Precursor|

* H2

|

Active|

| D/J|

* D2

|

E/F|

* E2 (Dinoprostone)

* E1 (Alprostadil)

* F2α (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
* PGF2α
* 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)
* PGF2α (Dinoprost)

* v
* t
* e

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics|

* Apraclonidine
* Brimonidine (+timolol)
* Clonidine
* Dipivefrine
* Epinephrine

Parasympathomimetics|

| muscarinic|

* Aceclidine
* Pilocarpine

|

muscarinic/nicotinic|

* Acetylcholine
* Carbachol

acetylcholinesterase inhibitors|

* Demecarium
* Ecothiopate
* Stigmine (Fluostigmine
* Neostigmine
* Physostigmine)
* Paraoxon

Carbonic anhydrase inhibitors/
(sulfonamides)|

* Acetazolamide
* Brinzolamide (+timolol, +brimonidine)
* Diclofenamide
* Dorzolamide (+timolol)
* Methazolamide

Beta blocking agents|

* Befunolol
* Betaxolol
* Carteolol
* Levobunolol
* Metipranolol
* Timolol
* Mepindolol

Prostaglandin analogues (F2α)|

* Bimatoprost (+timolol)
* Latanoprost (+timolol)
* Tafluprost
* Travoprost (+timolol)
* Unoprostone

Other agents|

* Dapiprazole
* Guanethidine
* Netarsudil/latanoprost
* Ripasudil

* v
* t
* e

Prostanoid signaling modulators

Receptor
(ligands)|

| DP (D2)|

| DP1|

* Agonists: Prostaglandin D2
* Treprostinil

* Antagonists: Asapiprant
* Laropiprant
* Vidupiprant

|

DP2|

* Agonists: Indometacin
* Prostaglandin D2

* Antagonists: ADC-3680
* AZD-1981
* Bay U3405
* Fevipiprant
* MK-1029
* MK-7246
* QAV-680
* Ramatroban
* Setipiprant
* Timapiprant
* TM30089
* Vidupiprant

EP (E2)|

| EP1|

* 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

|

EP2|

* Agonists: Butaprost
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Treprostinil

* Antagonists: AH-6809
* PF-04418948
* TG 4-155

EP3|

* 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

EP4|

* 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 F2α (dinoprost)
* Simenepag
* Taprenepag

FP (F2α)|

* Agonists: Alfaprostol
* Bimatoprost
* Carboprost
* Cloprostenol
* Enprostil
* Fluprostenol
* Latanoprost
* Prostaglandin D2
* Prostaglandin F2α (dinoprost)
* Sulotroban
* Tafluprost
* Travoprost
* Unoprostone

IP (I2)|

* 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 (TXA2)|

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

* Antagonists: 12-HETE
* 13-APA
* AA-2414
* Argatroban
* Bay U3405
* BMS-180,291
* Daltroban
* Domitroban
* EP-045
* GR-32191
* ICI-185282
* ICI-192605
* Ifetroban
* Imitrodast
* L-655240
* L-670596
* Linotroban
* Mipitroban
* ONO-3708
* ONO-11120
* Picotamide
* Pinane thromboxane A2
* Ramatroban
* Ridogrel
* S-145
* Samixogrel
* Seratrodast
* SQ-28,668
* SQ-29,548
* Sulotroban
* Terbogrel
* Terutroban
* TRA-418

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)|

* Salicylic acids: Aloxiprin
* Aspirin (acetylsalicylic acid)
* Benorilate (benorylate)
* Carbasalate calcium
* Diflusinal
* 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

|

PGD2S|

* Retinoids
* Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGES|

HQL-79

PGFS|

Bimatoprost

PGI2S|

Tranylcypromine

TXAS|

* Camonagrel
* Dazmegrel
* Dazoxiben
* Furegrelate
* Isbogrel
* Midazogrel
* Nafagrel
* Nicogrelate
* Ozagrel
* Picotamide
* Pirmagrel
* Ridogrel
* Rolafagrel
* Samixogrel
* Terbogrel
* U63557A

Others|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* Prostaglandin G2
* Prostaglandin H2

See also
Receptor/signaling modulators
Leukotriene signaling modulators
*[US]: United States
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DP (D2)]: Prostaglandin D2 receptor
*[DP1]: Prostaglandin D2 receptor 1
*[DP2]: Prostaglandin D2 receptor 2
*[EP (E2)]: Prostaglandin E2 receptor
*[EP1]: Prostaglandin EP1 receptor
*[EP2]: Prostaglandin EP2 receptor
*[EP3]: Prostaglandin EP3 receptor
*[EP4]: Prostaglandin EP4 receptor
*[FP (F2α)]: Prostaglandin F receptor
*[IP (I2)]: Prostacyclin receptor
*[TP (TXA2)]: Thromboxane receptor
*[COX]: Cyclooxygenase
*[PTGS]: prostaglandin G/H synthase
*[PGD2S]: Prostaglandin D synthase
*[PGES]: Prostaglandin E synthase
*[PGFS]: Prostaglandin F synthase
*[PGI2S]: Prostacyclin synthase
*[TXAS]: Thromboxane A synthase