Meclofenamic acid
Identification
- Name
- Meclofenamic acid
- Accession Number
- DB00939 (APRD01090)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Description
A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.
- Structure
Structure for Meclofenamic acid (DB00939)
- Synonyms
- Acide méclofénamique
- ácido meclofenámico
- Acidum meclofenamicum
- Meclofenamate
- Meclofenamic acid
- N-(2,6-dichloro-3-methylphenyl)anthranilic acid
- N-(2,6-dichloro-m-tolyl)anthranilic acid
- N-(3-methyl-2,6-dichlorophenyl)anthranilic acid
- External IDs
- CI 583 / CI-583 / Cl 583 / INF 4668 / INF-4668
- Product Ingredients
Ingredient UNII CAS InChI Key Meclofenamate sodium 94NJ818U2W 67254-91-5 QHJLLDJTVQAFAN-UHFFFAOYSA-M - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataMeclofenamate Sodium Capsule 50 mg/1 Oral Mylan Pharmaceuticals Inc. 1986-09-03 Not applicable US 
Meclofenamate Sodium Capsule 50 mg/1 Oral Physicians Total Care, Inc. 1986-09-03 2002-06-30 US Meclofenamate Sodium Capsule 100 mg/1 Oral Mylan Pharmaceuticals Inc. 1986-09-03 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- International/Other Brands
- Ethos (Yung Shin) / Eucome (U-Liang) / Meclomen (Pfizer)
- Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amines
- Aminobenzoates
- Analgesics
- Analgesics, Non-Narcotic
- Aniline Compounds
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antirheumatic Agents
- Benzene Derivatives
- Benzoates
- Central Nervous System Agents
- Cyclooxygenase Inhibitors
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Fenamates
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OAT1/SLC22A6 inhibitors
- ortho-Aminobenzoates
- Peripheral Nervous System Agents
- Sensory System Agents
- Thyroxine-binding globulin substrates
- Topical Products for Joint and Muscular Pain
- UNII
- 48I5LU4ZWD
- CAS number
- 644-62-2
- Weight
- Average: 296.149
Monoisotopic: 295.016684015 - Chemical Formula
- C14H11Cl2NO2
- InChI Key
- SBDNJUWAMKYJOX-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)
- IUPAC Name
- 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
- SMILES
- CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1
Pharmacology
- Indication
For the relief of mild to moderate pain, for the treatment of primary dysmenorrhea and for the treatment of idiopathic heavy menstrual blood loss. Also for relief of the signs and symptoms of acute and chronic rheumatoid arthritis and osteoarthritis.
- Associated Conditions
- Pharmacodynamics
Meclofenamic acid is a nonsteroidal agent which has demonstrated anti-inflammatory, analgesic, and antipyretic activity in laboratory animals.
- Mechanism of action
The mode of action, like that of other nonsteroidal anti-inflammatory agents, is not known. Therapeutic action does not result from pituitary-adrenal stimulation. In animal studies, meclofenamic acid was found to inhibit prostaglandin synthesis and to compete for binding at the prostaglandin receptor site. In vitro meclofenamic acid was found to be an inhibitor of human leukocyte 5-lipoxygenase activity. These properties may be responsible for the anti-inflammatory action of meclofenamic acid. There is no evidence that meclofenamic acid alters the course of the underlying disease.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans AArachidonate 5-lipoxygenase inhibitorHumans UPotassium voltage-gated channel subfamily KQT member 2 otherHumans UPotassium voltage-gated channel subfamily KQT member 3 otherHumans - Absorption
Rapidly absorbed in man following single and multiple oral doses with peak plasma concentrations occurring in 0.5 to 2 hours. The concomitant administration of antacids (aluminum and magnesium hydroxides) does not interfere with absorption of meclofenamic acid. Unlike most NSAIDs, which when administered with food have a decrease in rate but not in extent of absorption, meclofenamic acid is decreased in both. It has been reported that following the administration of meclofenamic acid capsules one-half hour after a meal, the average extent of bioavailability decreased by 26%, the average peak concentration (Cmax) decreased fourfold and the time to Cmax was delayed by 3 hours.
- Volume of distribution
- 9.1 to 43.2 L
- Protein binding
Greater than 99% bound to plasma proteins over a wide drug concentration range.
- Metabolism
Hepatic. Meclofenamic acid is extensively metabolized to an active metabolite (Metabolite I; 3-hydroxymethyl metabolite of meclofenamic acid) and at least six other less well characterized minor metabolites. Only Metabolite I has been shown in vitro to inhibit cyclooxygenase activity with approximately one fifth the activity of meclofenamic acid.
- Route of elimination
Other metabolites, whose excretion rates are unknown, account for the remaining 35% to 62% of the dose excreted in the urine. The remainder of the administered dose (approximately 30%) is eliminated in the feces (apparently through biliary excretion). Trace amounts of meclofenamate sodium are excreted in human breast milk.
- Half life
In a study in 10 healthy subjects following a single oral dose the apparent elimination half-life ranged from 0.8 to 5.3 hours. Metabolite I (3-hydroxymethyl metabolite of meclofenamic acid) has a mean half-life of approximately 15 hours.
- Clearance
- Oral cl=206 mL/min
- Toxicity
After a massive overdose, CNS stimulation may be manifested by irrational behavior, marked agitation and generalized seizures. Following this phase, renal toxicity (falling urine output, rising creatinine, abnormal urinary cellular elements) may be noted with possible oliguria or anuria and azotemia. A 24 year-old male was anuric for approximately one week after ingesting an overdose of 6 to 7 grams of meclofenamate sodium. Spontaneous diuresis and recovery subsequently occurred.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
Drug Interaction Unlock Additional Data(R)-warfarin The risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with (R)-warfarin. (S)-Warfarin The risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with (S)-Warfarin. 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Meclofenamic acid is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid. 1-benzylimidazole The risk or severity of hypertension can be increased when Meclofenamic acid is combined with 1-benzylimidazole. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of hypertension can be increased when Meclofenamic acid is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of hypertension can be increased when Meclofenamic acid is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of hypertension can be increased when Meclofenamic acid is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-hydroxycoumarin The risk or severity of gastrointestinal bleeding can be increased when Meclofenamic acid is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine The risk or severity of hypertension can be increased when Meclofenamic acid is combined with 4-Methoxyamphetamine. 5-fluorouridine The therapeutic efficacy of Meclofenamic acid can be decreased when used in combination with 5-fluorouridine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Not Available
References
- Synthesis Reference
U.S. Patent 3,313,848.
- General References
- Not Available
- External Links
- ATC Codes
- M01AG04 — Meclofenamic acid
- M01AG — Fenamates
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- PDB Entries
- 3r6i / 4n6p / 4qkn / 5ikq
- MSDS
- Download (74.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Bipolar Disorder (BD) / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders 1 Not Available Active Not Recruiting Treatment Progressive Brain Metastases / Recurrent Brain Metastases 1
Pharmacoeconomics
- Manufacturers
- Quantum pharmics ltd
- American therapeutics inc
- Barr laboratories inc
- Mylan pharmaceuticals inc
- Par pharmaceutical inc
- Sandoz inc
- Usl pharma inc
- Vitarine pharmaceuticals inc
- Watson laboratories inc
- Parke davis div warner lambert co
- Packagers
- Dispensing Solutions
- Mylan
- Nucare Pharmaceuticals Inc.
- Pharmedix
- Physicians Total Care Inc.
- Sandhills Packaging Inc.
- Dosage forms
Form Route Strength Capsule Oral 100 mg/1 Capsule Oral 50 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 248-250 U.S. Patent 3,313,848. water solubility 30 mg/L MERCK INDEX (1996) logP 5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00366 mg/mL ALOGPS logP 5.11 ALOGPS logP 6.09 ChemAxon logS -4.9 ALOGPS pKa (Strongest Acidic) 3.79 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 49.33 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 76.45 m3·mol-1 ChemAxon Polarizability 28.44 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9393 Blood Brain Barrier + 0.8668 Caco-2 permeable + 0.8398 P-glycoprotein substrate Non-substrate 0.806 P-glycoprotein inhibitor I Non-inhibitor 0.8943 P-glycoprotein inhibitor II Non-inhibitor 0.9474 Renal organic cation transporter Non-inhibitor 0.9094 CYP450 2C9 substrate Non-substrate 0.6402 CYP450 2D6 substrate Non-substrate 0.9164 CYP450 3A4 substrate Non-substrate 0.6566 CYP450 1A2 substrate Inhibitor 0.9236 CYP450 2C9 inhibitor Inhibitor 0.9106 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.8271 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.558 Ames test Non AMES toxic 0.8633 Carcinogenicity Non-carcinogens 0.5329 Biodegradation Not ready biodegradable 0.9709 Rat acute toxicity 3.0345 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9502 hERG inhibition (predictor II) Non-inhibitor 0.872
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Aminobenzoic acids
- Alternative Parents
- Benzoic acids / Aminotoluenes / Aniline and substituted anilines / Dichlorobenzenes / Benzoyl derivatives / Aryl chlorides / Vinylogous amides / Amino acids / Secondary amines / Monocarboxylic acids and derivatives show 6 more
- Substituents
- Aminobenzoic acid / Benzoic acid / Benzoyl / 1,3-dichlorobenzene / Aniline or substituted anilines / Aminotoluene / Toluene / Chlorobenzene / Halobenzene / Aryl chloride show 19 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- organochlorine compound, secondary amino compound, aminobenzoic acid (CHEBI:6710)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Perez-Vizcaino F, Lopez-Lopez JG, Santiago R, Cogolludo A, Zaragoza-Arnaez F, Moreno L, Alonso MJ, Salaices M, Tamargo J: Postnatal maturation in nitric oxide-induced pulmonary artery relaxation involving cyclooxygenase-1 activity. Am J Physiol Lung Cell Mol Physiol. 2002 Oct;283(4):L839-48. [PubMed:12225961]
- Shiels IA, Whitehouse MW: Lyprinol: anti-inflammatory and uterine-relaxant activities in rats, with special reference to a model for dysmenorrhoea. Allerg Immunol (Paris). 2000 Sep;32(7):279-83. [PubMed:11094641]
- Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222]
- Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181]
- Meade EA, Smith WL, DeWitt DL: Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1993 Mar 25;268(9):6610-4. [PubMed:8454631]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181]
- Traupe T, Lang M, Goettsch W, Munter K, Morawietz H, Vetter W, Barton M: Obesity increases prostanoid-mediated vasoconstriction and vascular thromboxane receptor gene expression. J Hypertens. 2002 Nov;20(11):2239-45. [PubMed:12409963]
- Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222]
- Narsinghani T, Chaturvedi SC: QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors. Bioorg Med Chem Lett. 2006 Jan 15;16(2):461-8. Epub 2005 Nov 14. [PubMed:16290292]
- Smith WL, Meade EA, DeWitt DL: Interactions of PGH synthase isozymes-1 and -2 with NSAIDs. Ann N Y Acad Sci. 1994 Nov 15;744:50-7. [PubMed:7825862]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Iron ion binding
- Specific Function
- Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
- Gene Name
- ALOX5
- Uniprot ID
- P09917
- Uniprot Name
- Arachidonate 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
References
- Yu XY, Hubbard W, Spannhake EW: Inhibition of canine tracheal smooth muscle by mediators from cultured bronchial epithelial cells. Am J Physiol. 1992 Feb;262(2 Pt 1):L229-34. [PubMed:1539679]
- Boctor AM, Eickholt M, Pugsley TA: Meclofenamate sodium is an inhibitor of both the 5-lipoxygenase and cyclooxygenase pathways of the arachidonic acid cascade in vitro. Prostaglandins Leukot Med. 1986 Aug;23(2-3):229-38. [PubMed:3020588]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel with essentially identical properties to the channel underlying the native M-current...
- Gene Name
- KCNQ2
- Uniprot ID
- O43526
- Uniprot Name
- Potassium voltage-gated channel subfamily KQT member 2
- Molecular Weight
- 95846.575 Da
References
- Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, Shabat D, Attali B: Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Mol Pharmacol. 2005 Apr;67(4):1053-66. Epub 2004 Dec 14. [PubMed:15598972]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Probably important in the regulation of neuronal excitability. Associates with KCNQ2 or KCNQ5 to form a potassium channel with essentially identical properties to the channel underlying the native ...
- Gene Name
- KCNQ3
- Uniprot ID
- O43525
- Uniprot Name
- Potassium voltage-gated channel subfamily KQT member 3
- Molecular Weight
- 96741.515 Da
References
- Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, Shabat D, Attali B: Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Mol Pharmacol. 2005 Apr;67(4):1053-66. Epub 2004 Dec 14. [PubMed:15598972]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Major thyroid hormone transport protein in serum.
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- CYTOMEL (liothyronine) FDA label [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Thyroid hormone transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-gluc...
- Gene Name
- SLCO1C1
- Uniprot ID
- Q9NYB5
- Uniprot Name
- Solute carrier organic anion transporter family member 1C1
- Molecular Weight
- 78695.625 Da
References
- Westholm DE, Stenehjem DD, Rumbley JN, Drewes LR, Anderson GW: Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs. Endocrinology. 2009 Feb;150(2):1025-32. doi: 10.1210/en.2008-0188. Epub 2008 Oct 9. [PubMed:18845642]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:08