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Indomethacin(CAS No. 53-86-1)

Indomethacin C19H16ClNO4 (cas 53-86-1) Molecular Structure

53-86-1 Structure

Identification and Related Records

【Name】
Indomethacin
【CAS Registry number】
53-86-1
【Synonyms】
indomethacin methanol solution
indomethacin crystalline
indomethacin usp
indometacin
1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-ylacetic acid
【EINECS(EC#)】
200-186-5
【Molecular Formula】
C19H16ClNO4 (Products with the same molecular formula)
【Molecular Weight】
357.79
【Inchi】
InChI=1/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
【InChIKey】
CGIGDMFJXJATDK-UHFFFAOYSA-N
【Canonical SMILES】
CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)O
【MOL File】
53-86-1.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.32g/cm3
【Melting Point】
155-162℃
【Boiling Point】
499.4 °C at 760 mmHg
【Flash Point】
255.8 °C
【Water】
Insoluble
【Solubilities】
Insoluble
【Color/Form】
PALE-YELLOW TO YELLOW-TAN, CRYSTALLINE POWDER
CRYSTALS EXHIBIT POLYMORPHISM
【Stability】
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
【Spectral properties】
MAX ABSORPTION (ETHANOL): 230, 260, 319 NM (E= 20,800, 16,200, 6,290)
Intense mass spectral peaks: 111 m/z, 139 m/z, 313 m/z
【Computed Properties】
Molecular Weight:357.78764 [g/mol]
Molecular Formula:C19H16ClNO4
XLogP3:4.3
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:4
Exact Mass:357.076786
MonoIsotopic Mass:357.076786
Topological Polar Surface Area:68.5
Heavy Atom Count:25
Formal Charge:0
Complexity:506
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Anion Count:1
Feature 3D Ring Count:3
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:25

Safety and Handling

【Hazard Codes】
T+:Verytoxic;
【Risk Statements】
R28
【Safety Statements 】
S28;S36/37;S45
【HazardClass】
6.1
【Safety】

A poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: aplastic anemia, changes in kidney tubules, decreased urine volume, diarrhea, fibrous hepatitis, hemorrhage, hypermotility, liver changes, necrotic stomach changes, retinal changes. Human teratogenic effects by ingestion and intravenous routes: developmental abnormalities of the respiratory system and urogenital system, homeostasis, other neonatal effects. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic Cl? and NOx.
Hazard Codes of Indomethacin (CAS NO.53-86-1):?T+,Xi
Risk Statements: 28-36/37/38?
R28: Very toxic if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 28-36/37-45-26?
S28: After contact with skin, wash immediately with plenty of soap-suds.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
F: 8-10
HazardClass:? 6.1
PackingGroup:? I

【PackingGroup 】
I
【Transport】
UN 2811
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

?Synonyms of Indomethacin (CAS NO.53-86-1) are (1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-yl)acetic acid ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure ; 1-(p-Chlorbenzoyl)-5-methoxy-2-methylindol-3-essigsaeure [German] ; 1-(p-Chlorobenzoyl)-2-methyl-5-methoxyindole-3-acetic acid ; 1-(p-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid ; 1-p-Cloro-benzoil-5-metoxi-2-metilindol-3-acido acetico ; 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl- ; Indole-3-acetic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl- .

【Octanol/Water Partition Coefficient】
LogP= 4.27 at pH 2.0
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

p-Anisidine + ethyl levulinate + p-chlorobenzoyl chloride (diazotisation/hydrogenation/Fischer indole synthesis/amide formation/saponification).
Acylation of sodium 2-(4-methoxy-phenyl)hydrazine-1-sulfonate with 4-chlorobenzoyl chloride followed by heating yields 1-(4- chlorobenzoyl)-1-(4-methoxyphenyl)hydrazine. Condensation with levulinic acid in a Fischer indole synthesis affords indomethacin.
【Usage】
Inhibits cyclooxygenase (IC50=0.1uM) selectively over liposygenases (IC50=100uM for 5-,12- and 15-LO). A clinically useful NAISD

Biomedical Effects and Toxicity

【Biological Activity】
Cyclooxgenase (COX) inhibitor; displays selectivity for COX-1 (IC 50 values are 230 and 630 nM for human COX-1 and COX-2 respectively). Widely used anti-inflammatory agent.
【Pharmacological Action】
- Anti-inflammatory agents that are not steroids. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They are used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. Certain NSAIDs also may inhibit lipoxygenase enzymes or TYPE C PHOSPHOLIPASES or may modulate T-cell function. (AMA Drug Evaluations Annual, 1994, p 1814-5)
- Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.
- Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
- Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout.
- Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete.
【Therapeutic Uses】
Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase Inhibitors; Gout Suppressants; Tocolytic Agents
THE PHARMACOKINETICS OF INDOMETHACIN (0.2 MG/KG IV) WERE STUDIED IN 35 PREMATURE INFANTS WITH SYMPTOMATIC PATENT DUCTUS ARTERIOSUS. THE INEFFECTIVE INDOMETHACIN INFUSIONS WERE ASSOC WITH FASTER CLEARANCE, A SHORTER HALF-LIFE, AND LOWER PLASMA LEVELS. IT WAS SUGGESTED THAT MEASUREMENT OF THE PLASMA INDOMETHACIN LEVEL COULD BE OF VALUE IN INFANTS WITH NO RESPONSE TO A FIRST DOSE. [BRASH AR ET AL; N ENGL J MED 305 (JUL 9): 67 (1981)]
【Biomedical Effects and Toxicity】
INDOMETHACIN READILY ENTERS SYNOVIAL FLUID, & CONCN OF DRUG THEREIN EXCEEDS THAT IN PLASMA FROM 4 HR AFTER ADMIN.../ORALLY/; THIS SUGGESTS AN ACTIVE TRANSPORT MECHANISM.
PLASMA CONCN OF INDOMETHACIN WERE STUDIED IN 5 HEALTHY VOLUNTEERS AFTER SINGLE & MULTIPLE DOSES (25 MG IV, 25, 50 & 100 MG ORALLY, 100 MG RECTALLY & 25 MG ORALLY 3 TIMES DAILY). IT WAS RAPIDLY & WELL ABSORBED AFTER ORAL DOSING WITH PEAK PLASMA CONCN WITHIN 2 HR. FROM ORAL & RECTAL DOSES PLASMA DECAY OF INDOMETHACIN WAS BIPHASIC & DATA INTERPRETED ACCORDING TO 2-COMPARTMENT OPEN MODEL. HALF-LIFE OF BETA-PHASE VARIED BETWEEN 2.6 & 11.2 HR. VOL OF DISTRIBUTION RANGED FROM 0.34 TO 1.57 L/KG & PLASMA CLEARANCE FROM 0.44-0.109 L/KG/HR.
AVAILABILITY OF DRUG TO SYSTEMIC CIRCULATION IN 41 INFANTS PRETERM WAS SIMILAR FROM ORAL & RECTAL DOSES, & THERE WERE NO DIFFERENCES IN PEAK PLASMA LEVELS OF DRUG IN RESPONDING & NON-RESPONDING PATIENTS. ELIMINATION HALF-LIFE...IS PROLONGED TO AS MUCH AS 20 HR OR 24 HR IN PREMATURE INFANTS. HALF-LIFE IS INVERSELY RELATED TO GESTATIONAL AGE, APPROACHING NORMAL VALUES AT GESTATIONAL AGE OF 36 WEEKS.
ACCUMULATIVE BILIARY SECRETION RANGES APPROX 30-FOLD FROM 13% OF DOSAGE IN RABBITS TO 362% IN DOGS, & PROVIDES A QUANTITATIVE CORRELATION TO WIDE SPECIES VARIATION IN SENSITIVITY TO INDOMETHACIN RELATED INTESTINAL LESIONS.
Indomethacin is rapidly and almost completely absorbed from the gastrointestinal tract after oral ingestion. The peak concentrations in plasma is attained within 2 hours in the fasting subject but may be somewhat delayed when the drug is taken after meals.
Steady state concentrations in plasma after long term administration are approximately 0.5 ug/ml.
Indomethacin is 90% bound to plasma proteins and also extensively bound to tissues. The concentration of the drug in the CSF is low, but its concentration in synovial fluid is equal to that in plasma within 5 hours of administration.
Between 10% and 20% of the drug is excreted unchanged in the urine, in part by tubular secretion.
The synthesis and in vitro and in vivo assessment of the usefulness of indomethacin polyoxyethylene esters as indomethacin dermal prodrugs are reported; anti-inflammatory activity of indomethacin ester 5 was investigated in 6 healthy human volunteers, ages 25-35 yr, whose forearm sites, after subjected to methyl nicotinate induced inflammation, were treated with controls applying 50 mg of gel without active drug and with 50 mg of indomethacin ester 5 gel. Esters 1-5 showed good water stability and rapid enzymatic cleavage and their hydrolysis rates, both chemical and enzymatic, were not significantly affected by the length of the polyoxyethylenic chain used as promoiety. Results from in vitro percutaneous absorption studies showed that only esters 4 and 5 significantly incr indomethacin cumulative amount penetrated through excised human skin compared to the parent drug. In vivo results showed an interesting delayed and sustained activity of ester 5 compared to the parent drug. /Indomethacin polyoxyethylene esters/
Indometacin farnesil was compared with indomethacin and loxoprofen in rats to ascertain whether it caused less gastric mucosal damage than the two older drugs. Damage was evaluated in terms of the size of ulcers that formed after oral admin and the changes in concn of prostaglandins E2 and I2 in the mucosa. Indometacin farnesil caused less damage than indomethacin and tended to cause less damage than loxoprofen. Indometacin farnesil was less potent than indomethacin in inhibiting prostaglandin generation by gastric mucosa. This property of indometacin farnesil may contribute to the low ulcerogenicity of this cmpd. [Arakawa T, et al; Drugs Exp Clin Res 21 (3): 85-8 (1995)] PubMed Abstract
The enhancing effects of various phospholipids on the percutaneous penetration of indomethacin through the dorsal skin of guinea pigs were studied in vitro. Phosphatidylglycerol had the greatest enhancing effect on drug penetration. Pretreatment of skin with phosphatidylethanolamine, lecithin (phosphatidylcholine), and phosphatidylglycerol significantly enhanced percutaneous penetration of indomethacin. In skin without stratum corneum, percutaneous penetration was not significantly affected by the phospholipids. The results suggested that phospholipids had a direct influence on the lipid bilayer of the cell membrane in the stratum corneum and the enhancement of drug penetration was due to the alteration of permeability by the interaction of the cell membrane with phospholipids in the skin.
Five indomethacin oligoethylene ester derivatives (3-7) were synthesized and evaluated for their anti-inflammatory, analgesic, and ulcerogenic activity after oral admin. The molecular weight of the oligoethylene glycols used for synthesizing esters 3-7 ranged from 106 to 282. The chemical and enzymatic stabilities of esters 3-7 were evaluated in pH 7.4 and 2.0 buffers and in human plasma, respectively. All the prodrugs showed a good stability both in pH 7.4 phosphate buffer and in pH 2.0 buffer, and they were readily hydrolyzed by human plasma. Esters 3-7 showed an anti-inflammatory activity, determined as the percent inhibition of carrageenan induced edema, similar to that of indomethacin, although at higher doses. From writhing test results, /it was/ observed that all the prodrugs exhibited better or similar analgesic activity compared to indomethacin. Esters 3-7 were significantly less irritating to the gastric mucosa than indomethacin, after oral admin, and esters 3-5 did not show any ulcerogenic activity, although they were admin at higher doses than indomethacin. /Indomethacin oligoethylene ester derivatives/ [De Caprariis P, et al; J Pharm Sci 83 (11): 1578-81 (1994)] PubMed Abstract
Sustained release hydrogel suppositories prepared with water soluble dietary fibers, xanthan gum and locust bean gum, were evaluated as a vehicle for rectal admin of indomethacin (IMC) in rabbits. The drug plasma levels were compared with those after rectal admin of commercial suppositories. When the commercial suppositories were given to rabbits, the plasma concn reached the maximum level at 30 min after admin followed by a quick reduction, while no sharp peak of plasma levels was seen with the hydrogel suppositories. In particular, the plasma levels observed with the hydrogel suppositories of 1% (w/v) gum concn were sustained much longer than those after dosing with the commercial suppositories; the mean residence times had higher values without a decr in the area under the plasma concn vs time curves. Histopathological study showed good biological safety of the hydrogel suppositories to the rectal mucosa. These results suggested that the IMC hydrogel suppositories prepared with xanthan gum and locust bean gum were a practical rectal preparation with prolonged action and reduced side effects. /Indomethacin hydrogel/ [Watanabe K, et al; Biol Pharm Bull 16 (4): 391-4 (1993)] PubMed Abstract
To investigate the effects of diethyl-beta-cyclodextrin on drug release from ointments, 4 indomethacin gel ointments were prepared using indomethacin alone, with diethyl-beta-cyclodextrin, or with other polymers; the gels underwent in vitro release studies, as well as in vivo release studies using hamster cheek pouch and abdominal rat skin. Results indicated that diethyl-beta-cyclodextrin accelerated indomethacin release from gel ointment. The amount of drug released from cheek pouch was highest in the case of the indomethacin-diethyl-beta-cyclodextrin ointment. In addition, absorption of drug from the ointment with diethyl-beta-cyclodextrin, in rat skin, was accelerated. It was concluded that diethyl-beta-cyclodextrin might be applicable for enhanced-release preparations from ointments. /Indomethacin gel ointments/
The effects of 100 and 787 mcg/sq cm 2-n-nonyl-1,3-dioxolane on the percutaneous absorption of indomethacin were studied in vitro and in vivo across hairless rat skin. Regardless of the quantity used, the addition of 2-n-nonyl-1,3-dioxolane strongly enhanced indomethacin absorption. The degree of absorption enhancement was nonlinear as a function of 2-n-nonyl-1,3-dioxolane in the range of 0-20%. A double labeling study suggested that the absorption enhancer penetrated the stratum corneum barrier first, facilitating the diffusion of the vehicle containing indomethacin. It was concluded that 2-n-nonyl-1,3-dioxolane incr the percutaneous absorption of indomethacin in vitro and in vivo.
The effects of low versus high molecular weight (MW) alginate on the absorption of indomethacin and gastric damage induced by the drug were examined by comparing the dissolution rates of indomethacin from low MW alginate dispersions with those of indomethacin alone in beagle dogs and in 4 healthy male volunteers, ages 23 to 38 yr. Dissolution rates of indomethacin from the alginate dispersions were significantly enhanced in comparison with that of the drug alone. The dispersion with lower MW alginate exhibited a more rapid dissolution rate than that of the dispersion with higher MW alginate. These enhanced dissolution rates of indomethacin by alginate may be due to the improvement of wettability and the decr of crystallinity and crystal size. The absorption rate from alginate dispersions was enhanced in comparison with that from indomethacin alone indicating enhanced bioavailability in dogs and volunteers. In addition, indomethacin induced gastric lesions were reduced by dispersing indomethacin in alginate. /Indomethacin alginates/ [Shiraishi S, et al; J Pharm Pharmacol 43: 615-20 (1991)] PubMed Abstract
The gastroduodenal absorption kinetics of indomethacin were studied in 7 subjects (aged 22-34 yr) by comparing oral indomethacin, admin in a pH 6.8 buffered solution, with an iv indomethacin. The 7 subjects showed evidence of rapid absorption at an average rate constant of 2.848/hr. The extent of absorption correlated with the quotients of the area under the curve as regards to the plasma concn as a function of time. Volumetric measurements and pH taken from gastric juice after oral admin of a pH 6.8 buffer solution revealed that on an empty stomach, gastric emptying was about 10 min. It was concluded that because of rapid gastric emptying and solubility of indomethacin, absorption may take place in the duodenum after oral admin.
A pharmacokinetic model with 2 parallel absorption processes from 2 fractions was derived for the percutaneous absorption of indomethacin (I) which included first order rate constants for: 1) rapid absorption, 2) slow absorption through skin, 3) distribution into tissue, and 4) subsequent elimination from the body. The model, applied to data obtained after percutaneous dosing of indomethacin ointments to the skin of rats under occlusion, successfully described the plasma profile observed in the presence and absence of laurocapram (Azone) and sorbitan monooleate. Penetration characteristics through stripped skin were also well described by the model. Laurocapram and sorbitan monooleate incr the fraction absorbed via the rapid absorption pathway by about 3 times without a significant alteration of either absorption rate constant, while the enhancers had no significant effect on either absorption pathway in the stripped skin. It was concluded that the results suggest that the model is simple yet adaptable enough to prove of general use for the interpretation of percutaneous absorption data. [Ogiso T, et al; J Pharm Sci 78: 319-23 (1989)] PubMed Abstract
The effects of benzyl nicotinate (nicotinic acid benzyl ester; or lecithin on the percutaneous absorption of indomethacin were studied by using radiolabeled indomethacin ointment preparations containing benzyl nicotinate or lecithin. Slight incr in absorption were noted with the addition of benzyl nicotinate or lecithin, but significant incr occurred with a combination of the compounds. Pharmacokinetic parameters and urinary and fecal excretion of indomethacin were significantly affected by lecithin.
Plasma levels and absorption characteristics of indomethacin were studied in dogs following admin of formulations containing glycerin, sucrose or sodium carboxymethylcellulose or a lipid containing capsule. All additives significantly incr plasma indomethacin levels. The rate and extent of dissolution was also significantly higher. Markedly improved absorption and improved availability were obtained.
The in vitro dissolution rates of 3 types of plasters containing indomethacin were determined, and plasma concn after application of the plasters to rat abdomen was studied. Dissolution rate from one type of plaster was higher than others, 70.6% of the initial drug amount for 6 hr. Plasma concn of indomethacin was 10.4 mcg/ml 4 hr after application.
The bioavailabilities of flurbiprofen, ketoprofen and indomethacin following rectal admin in aqueous polyacrylic acid gels to rats were investigated, and factors affecting availability are discussed. Incr absorption was noted at higher gel pH, at lower viscosity of the gel base, and with the addition of oleic acid to indomethacin. In vitro experiments confirmed viscosity effects on drug absorption.
The effects of anatomical site on the percutaneous absorption of indomethacin from an ointment were studied in rabbits. Dorsal sites led to higher levels than abdominal sites which in turn led to higher levels than application to the thigh areas. The absorption incr in direct proportion to the size of the application area in the abdomen. The effects of different pH values of the drug were also studied. At a lower pH (7.07) there was good absorption.
The percutaneous absorption and local anti-inflammatory activity of indomethacin gel were studied in various animal inflammation models. 1% gels were shown to produce local effects, with lower resultant blood levels. Definite effects were observed in adjuvant arthritis in rats and suppression of UV induced erythema in guinea pigs. [Wada Y, et al; J Pharm Pharmacol 34: 467-68 (1982)] PubMed Abstract
The GI absorption of alpha or gamma form of indomethacin polymorphs was studied in rabbits, and their absorption kinetics was analyzed. There was no significant difference between the bioavailabilities of the two polymorphs after oral admin. The absorption kinetics were found to be satisfactorily explained by a 2 compartment model with 2 consecutive first order input steps.
A pharmacokinetic model was developed to st certain concepts regarding the percutaneous absorption of indomethacin (I) from topical ointment bases applied to rabbits. Both the drug release from the ointment bases and absorption from the skin followed first order kinetics, with the exception of the initial period (lag time). The ointment bases selected for study were solution type and suspension bases. I was most effectively, absorbed from absorption bases. The effect of additives on absorption was also investigated. Urea, 0.5%, promoted absorption best in the absorption ointment base.
The absorption of indomethacin (Metindol) from micellar polysorbate 80 solutions was studied in rats and compared to absorption from true solutions, solutions in 60% polyethylene glycol 400, and suspensions. All solutions were tested at different pH values ranging from pH 2 (no ionization), to pH 4 (part ionization), to pH 8 (complete ionization). Surfactant concn was 5% and 10%. The values of the area under the serum concn time curve indicated that the presence of surfactant does not retard absorption, nor does its concn have any effect. The ionized form of the drug was more readily absorbed than the unionized.
The influence of bile flow on the intestinal absorption of indomethacin in control rats with intact bile flow and in rats with a choleretic agent stimulated bile was investigated. Enhanced bile flow incr the plasma levels of the drug about 2.5 times, apparently by incr the solubility and dissolution rate of the drug. [Miyazaki S, et al; Acta Pharm Suec 18 (3): 135-38 (1981)] PubMed Abstract

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