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Identification
- Summary
Tafluprost is 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
A prostaglandin analogue ester prodrug used topically (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
Structure for Tafluprost (DB08819)
- Weight
- Average: 452.5313
Monoisotopic: 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Elevated intraocular pressure •••••••••••• Management of Elevated intraocular pressure •••••••••••• Used in combination to treat Ocular hypertension Combination Product in combination with: Timolol (DB00373) •••••••••••• •••••••• Used in combination to treat Ocular hypertension Combination Product in combination with: Timolol (DB00373) •••••••••••• •••••••• - Contraindications & Blackbox Warnings
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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 agonistHumans - 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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Most common ocular adverse reaction is conjunctival hyperemia (range 4% – 20%).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Integrate drug-drug
interactions in your softwareAceclofenac The therapeutic efficacy of Tafluprost can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Tafluprost can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Tafluprost can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Tafluprost can be decreased when used in combination with Alclofenac. Aminophenazone The therapeutic efficacy of Tafluprost can be decreased when used in combination with Aminophenazone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 
Zioptan Solution 0.0045 mg/0.3mL Ophthalmic Merck Sharp & Dohme B.V. 2012-02-10 2016-06-30 US 
Zioptan Solution / drops 0.0045 mg/0.3mL Ophthalmic Akorn 2014-11-26 Not applicable US Zioptan Solution / drops 0.015 mg/1mL Ophthalmic Thea Farma S.P.A. 2022-10-28 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Tafluprost Solution / drops 0.0045 mg/0.3mL Ophthalmic Sandoz S.P.A. 2022-12-05 Not applicable US Tafluprost Solution / drops 0.015 mg/1mL Ophthalmic Ingenus Pharmaceuticals, LLC 2024-04-05 Not applicable US Tafluprost Solution / drops 0.0045 mg/0.3mL Ophthalmic Micro Labs Limited 2022-11-18 Not applicable US Tafluprost Solution 0.0045 mg/0.3mL Ophthalmic The Ritedose Corporation 2022-12-05 Not applicable US Tafluprost Ophthalmic Solution / drops 0.0045 mg/0.3mL Ophthalmic Prasco Laboratories 2022-11-18 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image LOYADA Tafluprost (15 µg/ml) + Timolol (5 MG/ML) Solution / drops Ophthalmic Santen Oy 2015-04-08 Not applicable Italy 
LOYADA Tafluprost (15 µg/ml) + Timolol (5 MG/ML) Solution / drops Ophthalmic Santen Oy 2015-04-08 Not applicable Italy TAPCOM ophthalmic solution Tafluprost (15 µg/mL) + Timolol maleate (5 mg/mL) Solution / drops Ophthalmic SANTEN PHARMA MALAYSIA SDN. BHD. 2020-09-08 2024-06-28 Malaysia 
TAPCOM-S OPHTHALMIC SOLUTION Tafluprost (0.015 mg/ml) + Timolol maleate (5.00 mg/ml) Solution Ophthalmic SANTEN PHARMA MALAYSIA SDN. BHD. 2016-02-08 Not applicable Singapore 
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 
Categories
- ATC Codes
- S01EE05 — Tafluprost
- Drug Categories
- Antiglaucoma Preparations and Miotics
- Autacoids
- Biological Factors
- Eicosanoids
- Fatty Acids
- Fatty Acids, Unsaturated
- Increased Prostaglandin Activity
- Inflammation Mediators
- Lipids
- Ophthalmics
- Ophthalmologicals
- Prostaglandin analogs reducing intraocular pressure (IOP)
- Prostaglandin Receptor Agonists
- Prostaglandins
- Prostaglandins, Synthetic
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- 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
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: ZIOPTAN (tafluprost) ophthalmic [Link]
- External Links
- Human Metabolome Database
- HMDB0015704
- KEGG Drug
- D06274
- PubChem Compound
- 9868491
- PubChem Substance
- 175427102
- ChemSpider
- 8044182
- 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 Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 1 somestatus stop reason just information to hide Not Available Completed Not Available Ocular Hypertension, Primary Open-angle Glaucoma (POAG) / Ocular Surface Disease 1 somestatus stop reason just information to hide Not Available Completed Treatment Ocular Hypertension, Primary Open-angle Glaucoma (POAG) 1 somestatus stop reason just information to hide 4 Completed Treatment Glaucoma 1 somestatus stop reason just information to hide 4 Completed Treatment Glaucoma / Ocular Hypertension 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 15.000 mcg 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 Solution / drops Ophthalmic 0015 MG/ML Solution / drops; suspension / drops Ophthalmic 15 UG/ML Solution Ophthalmic 0.015 mg Solution Ophthalmic Solution / drops Ophthalmic Solution / drops; 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 US9999593 No 2018-06-19 2029-05-28 US US10864159 No 2020-12-15 2029-05-28 US
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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-052f-4439700000-5f902e96f572f76cc593 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05o3-0009200000-57e5650afc06b8ef9365 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udl-3006900000-d9e3c2f668ee28744afd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-3019000000-7f23f368b49615e2d7ab Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00mo-1019400000-aecd74fa7227cbdbe538 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9123000000-e5f513d87ac7705df216 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fb9-3960100000-314446c2b5d734f9c56d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.7165607 predictedDarkChem Lite v0.1.0 [M-H]- 216.11147 predictedDeepCCS 1.0 (2019) [M+H]+ 229.4990607 predictedDarkChem Lite v0.1.0 [M+H]+ 218.00685 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.5501607 predictedDarkChem Lite v0.1.0 [M+Na]+ 223.66032 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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 in the corpus luteum (By similarity). Isoforms 2 to 7 do not bind PGF2-alpha but are proposed to modulate signaling by participating in variant receptor complexes; heterodimers between isoform 1 and isoform 5 are proposed to be a receptor for prostamides including the synthetic analog bimatoprost
- Specific Function
- prostaglandin F receptor activity
- Gene Name
- PTGFR
- Uniprot ID
- P43088
- Uniprot Name
- Prostaglandin F2-alpha receptor
- Molecular Weight
- 40054.1 Da
References
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
- Specific Function
- enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- 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 October 13, 2024 00:22