NAV

Tafluprost

Identification

Summary

Tafluprostis an ophthalmic prostaglandin analog used to lower intraocular pressure in patients with ocular hypertension or open-angle glaucoma.

Brand Names
Zioptan
Generic Name
Tafluprost
DrugBank Accession Number
DB08819
Background

前列腺素类似物酯前体药物局部药使用lly (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Chemically, tafluprost is a fluorinated analog of prostaglandin F2-alpha. Tafluprost was approved for use in the U.S. on February 10, 2012.

Type
Small Molecule
Groups
Approved
Structure
 3D
Similar Structures
Weight
Average: 452.5313
单一同位素的:452.237430608
Chemical Formula
C25H34F2O5
Synonyms
  • Tafluprost
External IDs
  • AFP-168
  • MK-2452

Pharmacology

Indication

Tafluprost is indicated for reducing elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

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Associated Conditions
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Pharmacodynamics

Tafluprost is a novel prostaglandin analog with a high affinity for the fluoroprostaglandin (FP) receptor PGF2α. Tafluprost has an affinity for the FP receptor that is approximately 12 times higher than that of the carboxylic acid of latanoprost, but with almost no potential to bind to other receptors.

Mechanism of action

Tafluprost acid is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and humans suggest that the main mechanism of action is increased uveoscleral outflow.

Target Actions Organism
AProstaglandin F2-alpha receptor
agonist
 Humans
Absorption

Following instillation, tafluprost is absorbed through the cornea and is hydrolyzed to the biologically active acid metabolite, tafluprost acid. Tafluprost is an ester which makes the drug lipophillic enough to be quickly absorbed through. When administered to the eye, the peak plasma concentration (Cmax) and time to peak plasma concentration (Tmax) of tafluprost acid in healthy subjects was 26 pg/mL and 10 minutes respectively. a AUC, tafluprost acid = 394 pgmin/mL - 432 pgmin/mL.

Volume of distribution

The highest concentration of tafluprost acid was found in the cornea and conjunctiva.

Protein binding

Not Available

Metabolism

Tafluprost is an ester prodrug which is rapidly hydrolyzed by corneal esterases to form its biologically active acid metabolite. Tafluprost acid is further metabolized via fatty acid β-oxidation and phase II conjugation into 1,2,3,4-tetranor acid.

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Route of elimination

Mean plasma tafluprost acid concentrations were below the limit of quantification of the bioanalytical assay (10 pg/mL) at 30 minutes following topical ocular administration of tafluprost 0.0015% ophthalmic solution. In male rats, it was observed that tafluprost was excreted into the feces.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Most common ocular adverse reaction is conjunctival hyperemia (range 4% – 20%).

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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interactions in your software
Aceclofenac Tafluprost可以12月的治疗效果eased when used in combination with Aceclofenac.
Acemetacin Tafluprost可以12月的治疗效果eased when used in combination with Acemetacin.
Acetylsalicylic acid Tafluprost可以12月的治疗效果eased when used in combination with Acetylsalicylic acid.
Alclofenac Tafluprost可以12月的治疗效果eased when used in combination with Alclofenac.
Aminophenazone Tafluprost可以12月的治疗效果eased when used in combination with Aminophenazone.
Antipyrine Tafluprost可以12月的治疗效果eased when used in combination with Antipyrine.
Antrafenine Tafluprost可以12月的治疗效果eased when used in combination with Antrafenine.
Balsalazide Tafluprost可以12月的治疗效果eased when used in combination with Balsalazide.
Benorilate Tafluprost可以12月的治疗效果eased when used in combination with Benorilate.
Benoxaprofen Tafluprost可以12月的治疗效果eased when used in combination with Benoxaprofen.
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Food Interactions
No interactions found.

Products

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International/Other Brands
Taflotan (Regeneron Pharmaceuticals)
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Saflutan Solution 4.5 mcg / 0.3 mL Ophthalmic Purdue Pharma Not applicable Not applicable Canada flag
Zioptan Solution / drops 0.0045 mg/0.3mL Ophthalmic Akorn 2014-11-26 Not applicable US flag
Zioptan Solution / drops 0.015 mg/1mL Ophthalmic Thea Pharma Inc. 2022-10-28 Not applicable US flag
Zioptan Solution 0.0045 mg/0.3mL Ophthalmic Merck Sharp & Dohme Limited 2012-02-10 2016-06-30 US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Tafluprost Solution / drops 0.0045 mg/0.3mL Ophthalmic Micro Labs Limited 2022-11-18 Not applicable US flag
Tafluprost Solution 0.0045 mg/0.3mL Ophthalmic The Ritedose Corporation 2022-12-05 Not applicable US flag
Tafluprost Solution / drops 0.0045 mg/0.3mL Ophthalmic Sandoz Inc 2022-12-05 Not applicable US flag
Tafluprost Ophthalmic Solution / drops 0.0045 mg/0.3mL Ophthalmic Prasco Laboratories 2022-11-18 Not applicable US flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
TAPCOM-S OPHTHALMIC SOLUTION Tafluprost(0.015 mg/ml)+Timolol maleate(5.00 mg/ml) Solution Ophthalmic SANTEN PHARMACEUTICAL ASIA PTE. LTD. 2016-02-08 Not applicable
Taptiqom 15 Mikrogramm/ml + 5 mg/ml Augentropfen, Lösung im Einzeldosisbehältnis Tafluprost(15 mcg/ml)+Timolol(5 mg/ml) Solution / drops Ophthalmic Santen Oy 2015-02-24 Not applicable Austria flag
TAPTIQOM 15UG/ML+5MG/ML Tafluprost(15 μg/ml)+Timolol maleate(5 mg/ml) 解决方案/下降;暂停/滴 Ophthalmic 2017-01-01 Not applicable Germany flag
TAPTIQOM 15UG/ML+5MG/ML Tafluprost(15 μg/ml)+Timolol maleate(5 mg/ml) 解决方案/下降;暂停/滴 Ophthalmic 2017-01-01 Not applicable Germany flag
แทพคอม Tafluprost(1.5 mg/100mL)+Timolol(500 mg/100mL) Solution / drops Ophthalmic บริษัท ซันเท็น (ประเทศไทย) จำกัด 2018-11-06 Not applicable Thailand flag
แทพคอม-เอส Tafluprost(1.5 mg/100mL)+Timolol(500 mg/100mL) Solution / drops Ophthalmic บริษัท ซันเท็น (ประเทศไทย) จำกัด 2018-11-06 Not applicable Thailand flag

Categories

ATC Codes
S01EE05 — Tafluprost
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Phenoxy compounds/Phenol ethers/Fatty acid esters/Alkyl aryl ethers/Cyclopentanols/Cyclic alcohols and derivatives/Carboxylic acid esters/Monocarboxylic acids and derivatives/Organofluorides/Organic oxides
show 3 more
Substituents
Alcohol/Alkyl aryl ether/Alkyl fluoride/Alkyl halide/Aromatic homomonocyclic compound/Benzenoid/Carbonyl group/Carboxylic acid derivative/Carboxylic acid ester/Cyclic alcohol
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, carboxylic ester, prostaglandins Falpha (CHEBI:66899)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
1O6WQ6T7G3
CAS number
209860-87-7
InChI Key
WSNODXPBBALQOF-VEJSHDCNSA-N
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
IUPAC Name
propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl]hept-5-enoate
SMILES
CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\C(F)(F)COC1=CC=CC=C1

References

General References
  1. Papadia M, Bagnis A, Scotto R, Traverso CE: Tafluprost for glaucoma. Expert Opin Pharmacother. 2011 Oct;12(15):2393-401. doi: 10.1517/14656566.2011.606810. [Article]
  2. Pantcheva MB, Seibold LK, Awadallah NS, Kahook MY: Tafluprost: a novel prostaglandin analog for treatment of glaucoma. Adv Ther. 2011 Sep;28(9):707-15. doi: 10.1007/s12325-011-0055-8. Epub 2011 Aug 18. [Article]
  3. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [Article]
  4. Fukano Y, Kawazu K: Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. Drug Metab Dispos. 2009 Aug;37(8):1622-34. doi: 10.1124/dmd.108.024885. Epub 2009 May 28. [Article]
  5. FDA Approved Drug Products: ZIOPTAN (tafluprost) ophthalmic [Link]
Human Metabolome Database
HMDB0015704
KEGG Drug
D06274
PubChem Compound
9868491
PubChem Substance
175427102
ChemSpider
8044182
RxNav
1244607
ChEBI
66899
ChEMBL
CHEMBL1963683
ZINC
ZINC000013912394
PharmGKB
PA165958432
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tafluprost
FDA label
Download (274 KB)
MSDS
Download (22.7 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Treatment Glaucoma 1
4 Completed Treatment Glaucoma/Ocular Hypertension 1
4 Completed Treatment Glaucoma/Ocular Hypertension/Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 1
4 Completed Treatment Glaucoma/Ocular Surface Disease 1
4 Completed Treatment Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 1
4 Completed Treatment Ocular Hypertension/Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 2
4 Completed Treatment Ocular Hypertension/Open Angle Glaucoma (OAG) 2
4 Completed Treatment Open Angle Glaucoma (OAG) 1
4 Recruiting Supportive Care Ocular Hypertension/Open Angle Glaucoma (OAG) 1
4 Unknown Status Treatment Glaucoma 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Form Route Strength
Solution Ophthalmic 4.5 mcg / 0.3 mL
Solution / drops Ophthalmic 15 MICROGRAMMI/ML
Solution / drops Ophthalmic 15 mcg/ml
Solution / drops Ophthalmic
Solution Ophthalmic 0.015 mg/mL
解决方案/下降;suspension / drops Ophthalmic 15 UG/ML
Solution Ophthalmic 0.015 mg
Solution Ophthalmic
Solution / drops Ophthalmic
解决方案/下降;suspension / drops Ophthalmic
Solution Ophthalmic 0.0045 mg/0.3mL
Solution / drops Ophthalmic 0.0045 mg/0.3mL
Solution / drops Ophthalmic 0.015 mg/1mL
Liquid Ophthalmic 15 mcg/1ml
Prices
Not Available
Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region
US5886035 No 1999-03-23 2017-12-18 US flag
US9999593 No 2018-06-19 2029-05-28 US flag
US10864159 No 2020-12-15 2029-05-28 US flag

Properties

State
Liquid
Experimental Properties
Property Value Source
melting point (°C) 87.5 °C Not Available
boiling point (°C) 100°C Not Available
water solubility Insoluble FDA label
logP 4.05 Not Available
pKa 5.5-6.7 FDA label
Predicted Properties
Property Value Source
Water Solubility 0.00528 mg/mL ALOGPS
logP 4.46 ALOGPS
logP 4.29 Chemaxon
logS -4.9 ALOGPS
pKa (Strongest Acidic) 14.51 Chemaxon
pKa (Strongest Basic) -2.9 Chemaxon
Physiological Charge 0 Chemaxon
Hydrogen Acceptor Count 4 Chemaxon
Hydrogen Donor Count 2 Chemaxon
Polar Surface Area 75.99 Å2 Chemaxon
Rotatable Bond Count 13 Chemaxon
Refractivity 120.59 m3·mol-1 Chemaxon
Polarizability 47.77 Å3 Chemaxon
Number of Rings 2 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9644
Blood Brain Barrier + 0.8687
Caco-2 permeable + 0.5372
P-glycoprotein substrate Substrate 0.5871
P-glycoprotein inhibitor I Non-inhibitor 0.9015
P-glycoprotein inhibitor II Non-inhibitor 0.7888
Renal organic cation transporter Non-inhibitor 0.8711
CYP450 2C9 substrate Non-substrate 0.8086
CYP450 2D6 substrate Non-substrate 0.854
CYP450 3A4 substrate Substrate 0.6508
CYP450 1A2 substrate Non-inhibitor 0.75
CYP450 2C9 inhibitor Non-inhibitor 0.7344
CYP450 2D6 inhibitor Non-inhibitor 0.9056
CYP450 2C19 inhibitor Non-inhibitor 0.6873
CYP450 3A4 inhibitor Non-inhibitor 0.8038
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7418
Ames test Non AMES toxic 0.7286
Carcinogenicity Non-carcinogens 0.9028
Biodegradation Not ready biodegradable 0.9737
Rat acute toxicity 3.7129 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9787
hERG inhibition (predictor II) Non-inhibitor 0.7362
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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insights and accelerate drug research.
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Details 1.Prostaglandin F2-alpha receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin f receptor activity
Specific Function
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis...
Gene Name
PTGFR
Uniprot ID
P43088
Uniprot Name
Prostaglandin F2-alpha receptor
Molecular Weight
40054.1 Da
References
  1. Pantcheva MB, Seibold LK, Awadallah NS, Kahook MY: Tafluprost: a novel prostaglandin analog for treatment of glaucoma. Adv Ther. 2011 Sep;28(9):707-15. doi: 10.1007/s12325-011-0055-8. Epub 2011 Aug 18. [Article]

Enzymes

Details 1.Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Roh YJ, Park YG, Kang S, Kim SY, Moon JI: Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch Clin Exp Ophthalmol. 2012 Dec;250(12):1765-75. doi: 10.1007/s00417-012-2125-2. Epub 2012 Aug 22. [Article]

Drug created at February 24, 2012 17:29 / Updated at April 30, 2023 03:04