Norfloxacin

Modify Date: 2024-01-02 19:06:13

Norfloxacin Structure
Norfloxacin structure
Common Name Norfloxacin
CAS Number 70458-96-7 Molecular Weight 319.331
Density 1.3±0.1 g/cm3 Boiling Point 555.8±50.0 °C at 760 mmHg
Molecular Formula C16H18FN3O3 Melting Point 220°C
MSDS Chinese USA Flash Point 289.9±30.1 °C

 Use of Norfloxacin


Norfloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria, which functions by inhibiting DNA gyrase.Target: DNA gyrase; AntibacterialNorfloxacin is a synthetic chemotherapeutic antibacterial agent occasionally used to treat common as well as complicated urinary tract infections. Norfloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division.There are currently three approved uses in the adult population (one of which is restricted) and the other ineffective due to bacterial resistance. Chibroxin (ophthalmic) is approved for use in children older than one year of age.Norfloxacin is associated with a number of rare serious adverse reactions as well as spontaneous tendon ruptures and irreversible peripheral neuropathy. Tendon problems may manifest long after therapy had been completed and in severe cases may result in lifelong disabilities. Hepatoxicity resulting in fatalities has also been reported with the use of norfloxacin.

 Names

Name norfloxacin
Synonym More Synonyms

 Norfloxacin Biological Activity

Description Norfloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria, which functions by inhibiting DNA gyrase.Target: DNA gyrase; AntibacterialNorfloxacin is a synthetic chemotherapeutic antibacterial agent occasionally used to treat common as well as complicated urinary tract infections. Norfloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division.There are currently three approved uses in the adult population (one of which is restricted) and the other ineffective due to bacterial resistance. Chibroxin (ophthalmic) is approved for use in children older than one year of age.Norfloxacin is associated with a number of rare serious adverse reactions as well as spontaneous tendon ruptures and irreversible peripheral neuropathy. Tendon problems may manifest long after therapy had been completed and in severe cases may result in lifelong disabilities. Hepatoxicity resulting in fatalities has also been reported with the use of norfloxacin.
Related Catalog
References

[1]. Nelson JM, et al. Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story. Clin Infect Dis. 2007 Apr 1;44(7):977-80. Epub 2007 Feb 14.

[2]. Pade?skaia EN. Norfloxacin: more than 20 years of clinical use, the results and place among fluoroquinolones in modern chemotherapy for infections. Antibiot Khimioter. 2003;48(9):28-36.

[3]. Rafalsky V, et al. Quinolones for uncomplicated acute cystitis in women. Cochrane Database Syst Rev. 2006 Jul 19;(3):CD003597.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 555.8±50.0 °C at 760 mmHg
Melting Point 220°C
Molecular Formula C16H18FN3O3
Molecular Weight 319.331
Flash Point 289.9±30.1 °C
Exact Mass 319.133209
PSA 74.57000
LogP 0.82
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.595

 MSDS


Section I.Chemical Product and Company Identification
Chemical Name Norfloxacin
Portland OR
Synonym3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-
dihydro-4-oxo-7-(1-piperazinyl)- (CA INDEX NAME);
1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
3-quinolinecarboxylic Acid
Chemical FormulaC16H18FN3O3
CAS Number70458-96-7

Section II.Composition and Information on Ingredients
Toxicology Data
Chemical NameCAS Number Percent (%)TLV/PEL
Min. 98.0 Not available.Rat LD50 (oral) >4 gm/kg
Norfloxacin70458-96-7
(HPLC,T)Mouse LD50 (intraperitoneal) 1064
mg/kg
Rat LD50 (intravenous) 245 mg/kg

Section III. Hazards Identification
No specific information is available in our data base regarding the toxic effects of this material for humans. However,
Acute Health Effects
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive effects.
Rat TDLo Oral 1375 mg/kg, female 7-17 days of pregnancy
Toxic Effects:
Specific Developmental Abnormalities - Musculoskeletal system
Effects on Newborn - Behavioral
Rabbit Oral 1300 mg/kg, female 6-18 days of pregnancy
Toxic Effects:
Effects on Fertility - Litter size
Effects on Embryo or Fetus - Fetotoxicity
Effects on Embryo or Fetus - Fetal death
Rabbit Oral 1625 mg/kg, female 13 days prior to mating
Toxic Effects:
Maternal Effects - Ovaries, fallopian tubes
Maternal Effects - Uterus, cervix, vagina
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

Section IV.First Aid Measures
Eye ContactCheck for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin ContactIn case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
InhalationIf the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.
Continued on Next Page
Norfloxacin

Section V.Fire and Explosion Data
Not available.
FlammabilityMay be combustible at high temperature.Auto-Ignition
Flammable LimitsNot available.
Flash PointsNot available.
Combustion ProductsThese products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2), halogenated compounds.
WARNING: Highly toxic HF gas is produced during combustion.
Fire HazardsNot available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.

Section VI.Accidental Release Measures
Spill CleanupHygroscopic material.
Use a shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
Instructions
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

Section VII. Handling and Storage
HYGROSCOPIC. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store
Handling and Storage
in a dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents, moisture.

Section VIII. Exposure Controls/Personal Protection
Engineering ControlsUse process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Personal ProtectionSplash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Not available.
Exposure Limits

Section IX. Physical and Chemical Properties
Physical state @ 20°CSolid. (Very pale yellow ~ pale yellow,SolubilitySolubility at 25°C (mg/ml): water 0.28;
crystal ~ powder.)
methanol 0.98; ethanol 1.9; acetone 5.1;
chloroform 5.5; diethyl ether 0.1; benzene
Not available.
Specific Gravity
0.15; ethyl acetate 0.94; octyl alcohol 5.1;
glacial acetic acid 340.
Solubility in water is pH dependent,
increasing sharply at pH <5 or at pH >10.
Molecular Weight319.33Partition CoefficientLOG Pow: 0.46
Boiling PointNot available.Not applicable.
Vapor Pressure
Melting Point221°C (429.8°F)Vapor DensityNot available.
Not available.Not available.
Refractive IndexVolatility
Critical TemperatureNot available.OdorNot available.
Not available.Not available.
ViscosityTaste

Section X.Stability and Reactivity Data

This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of InstabilityAvoid excessive heat and light. Hygroscopic; keep container tightly closed.
IncompatibilitiesReactive with oxidizing agents, moisture.
Continued on Next Page
Norfloxacin

Section XI. Toxicological Information
RTECS NumberVB2005000
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Toxicity DataRat LD50 (oral) >4 gm/kg
Mouse LD50 (intraperitoneal) 1064 mg/kg
Rat LD50 (intravenous) 245 mg/kg
Chronic Toxic EffectsCARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Reproductive effects.
Rat TDLo Oral 1375 mg/kg, female 7-17 days of pregnancy
Toxic Effects:
Specific Developmental Abnormalities - Musculoskeletal system
Effects on Newborn - Behavioral
Rabbit Oral 1300 mg/kg, female 6-18 days of pregnancy
Toxic Effects:
Effects on Fertility - Litter size
Effects on Embryo or Fetus - Fetotoxicity
Effects on Embryo or Fetus - Fetal death
Rabbit Oral 1625 mg/kg, female 13 days prior to mating
Toxic Effects:
Maternal Effects - Ovaries, fallopian tubes
Maternal Effects - Uterus, cervix, vagina
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic EffectsNo specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling this
compound.

Section XII.Ecological Information
Not available.
Ecotoxicity
Not available.
Environmental Fate

Section XIII. Disposal Considerations
Waste DisposalRecycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

Section XIV. Transport Information
DOT ClassificationNot a DOT controlled material (United States).
PIN NumberNot applicable.
Proper Shipping NameNot applicable.
Packing Group (PG)Not applicable.
DOT Pictograms

Section XV. Other Regulatory Information and Pictograms
TSCA Chemical InventoryThis product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS ClassificationOn DSL.
(Canada)
EINECS Number (EEC) 274-614-4
EEC Risk StatementsNot available.
Japanese Regulatory Data Not available.
Continued on Next Page


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VB2005000
CHEMICAL NAME :
3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
CAS REGISTRY NUMBER :
70458-96-7
BEILSTEIN REFERENCE NO. :
0567897
LAST UPDATED :
199612
DATA ITEMS CITED :
33
MOLECULAR FORMULA :
C16-H18-F-N3-O3
MOLECULAR WEIGHT :
319.37
WISWESSER LINE NOTATION :
T66 BN EVJ B2 DVQ HF I- DT6M DNTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
94 mg/kg/13D-I
TOXIC EFFECTS :
Musculoskeletal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
48 mg/kg/2D-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), zonal Behavioral - muscle weakness Musculoskeletal - joints
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
245 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1064 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
470 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1400 mg/kg/2W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
9 gm/kg/30D-I
TOXIC EFFECTS :
Musculoskeletal - joints
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1375 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2750 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20 gm/kg
SEX/DURATION :
male 61 day(s) pre-mating female 15 day(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 gm/kg
SEX/DURATION :
male 61 day(s) pre-mating female 15 day(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1250 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2 gm/kg
SEX/DURATION :
female 10-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Endocrine - estrogenic Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
4650 mg/kg
SEX/DURATION :
female 20-50 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1625 mg/kg
SEX/DURATION :
female 13 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1300 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1300 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1300 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
Unscheduled DNA synthesis
TEST SYSTEM :
Rodent - rat Liver
DOSE/DURATION :
310 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 221,263,1989

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases 26-37/39
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS VB2005000
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

Zomxin
1-Ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid
Fulgram
Barazan
NORFLOXACINE
CHIBROXIN
Noflo
Utinor
EINECS 274-614-4
Nolicin
Sebercim
Chibroxol
Zoroxin
4803P
3-Quinolinecarboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
am-715
MFCD08060466
1-ethyl-6-fluoro-4-oxo-7-piperazinyl-1,4-dihydro-quinoline-3-carboxylic acid
Norfloxacin
1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid
Floxacin
1-ethyl-6-fluoro-7-piperazino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
Noroxin
Lexinor
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
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