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Details

Stereochemistry RACEMIC
Molecular Formula C18H18N3O3S.Na
Molecular Weight 379.409
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROSIGLITAZONE SODIUM

SMILES

[Na+].CN(CCOC1=CC=C(CC2SC(=O)[N-]C2=O)C=C1)C3=CC=CC=N3

InChI

InChIKey=XFOHHIYSRDUSCX-UHFFFAOYSA-M
InChI=1S/C18H19N3O3S.Na/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15;/h2-9,15H,10-12H2,1H3,(H,20,22,23);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C18H19N3O3S
Molecular Weight 357.427
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/rosiglitazone.html http://www.rxlist.com/avandia-drug.htm http://www.wikidoc.org/index.php/Rosiglitazone

Rosiglitazone acts as a highly selective and potent agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. It is FDA approved for the treatment of as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Inhibitors of CYP2C8 (e.g., gemfibrozil) may increase rosiglitazone levels; inducers of CYP2C8 (e.g., rifampin) may decrease rosiglitazone levels. Common adverse reactions include edema, weight gain, and headache.

CNS Activity

Originator

Approval Year

1999
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 40.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
AVANDIA

Approved Use

After consultation with a healthcare professional who has considered and advised the patient of the risks and benefits of rosiglitazone, AVANDAMET® is indicated as an adjunct to diet and exercise to improve glycemic control when treatment with both rosiglitazone and metformin is appropriate in adults with type 2 diabetes mellitus who either are: already taking rosiglitazone, or not already taking rosiglitazone and unable to achieve glycemic control on other diabetes medications and, in consultation with their healthcare provider, have decided not to take pioglitazone (ACTOS®) or pioglitazone-containing products (ACTOPLUS MET®, ACTOPLUS MET XR®, DUETACT®) for medical reasons. Other Important Limitations of Use: Due to its mechanism of action, rosiglitazone is active only in the presence of endogenous insulin. Therefore, AVANDAMET should not be used in patients with type 1 diabetes. Coadministration of AVANDAMET with insulin is not recommended [see Warnings and Precautions (5.2, 5.3)

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
432 ng/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
598 ng/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2890 ng × h/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
2971 ng × h/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.59 h
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
3.37 h
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
unhealthy, 53.1
n = 32
Health Status: unhealthy
Condition: Nonalcoholic steatohepatitis
Age Group: 53.1
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
DLT: Headache, Malaise...
Disc. AE: Pain in leg...
Dose limiting toxicities:
Headache (3.1%)
Malaise (3.1%)
Oedema legs (9.4%)
AEs leading to
discontinuation/dose reduction:
Pain in leg (3.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Page: p.73,74
unhealthy, 60
n = 1
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Age Group: 60
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Page: p.73,74
Disc. AE: Macular edema...
AEs leading to
discontinuation/dose reduction:
Macular edema
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Page: p.73,74
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Disc. AE: Congestive heart failure, Myocardial ischemia...
AEs leading to
discontinuation/dose reduction:
Congestive heart failure
Myocardial ischemia (2%)
Fluid retention
Edema
Weight gain
Anemia
Macular edema
Fracture bone
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Headache 3.1%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
unhealthy, 53.1
n = 32
Health Status: unhealthy
Condition: Nonalcoholic steatohepatitis
Age Group: 53.1
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
Malaise 3.1%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
unhealthy, 53.1
n = 32
Health Status: unhealthy
Condition: Nonalcoholic steatohepatitis
Age Group: 53.1
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
Pain in leg 3.1%
Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
unhealthy, 53.1
n = 32
Health Status: unhealthy
Condition: Nonalcoholic steatohepatitis
Age Group: 53.1
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
Oedema legs 9.4%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
unhealthy, 53.1
n = 32
Health Status: unhealthy
Condition: Nonalcoholic steatohepatitis
Age Group: 53.1
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Page: p.105
Macular edema Disc. AE
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Page: p.73,74
unhealthy, 60
n = 1
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Age Group: 60
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Page: p.73,74
Myocardial ischemia 2%
Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Anemia Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Congestive heart failure Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Edema Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Fluid retention Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Fracture bone Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Macular edema Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
Weight gain Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Page: p.1
PubMed

PubMed

TitleDatePubMed
Regulation of gene expression by activation of the peroxisome proliferator-activated receptor gamma with rosiglitazone (BRL 49653) in human adipocytes.
1999 Nov
v- and t-SNARE protein expression in models of insulin resistance: normalization of glycemia by rosiglitazone treatment corrects overexpression of cellubrevin, vesicle-associated membrane protein-2, and syntaxin 4 in skeletal muscle of Zucker diabetic fatty rats.
2000 Apr
Differential activation of peroxisome proliferator-activated receptor-gamma by troglitazone and rosiglitazone.
2000 Apr
Asymmetry in the PPARgamma/RXRalpha crystal structure reveals the molecular basis of heterodimerization among nuclear receptors.
2000 Mar
Activation of peroxisome proliferator-activated receptor gamma suppresses nuclear factor kappa B-mediated apoptosis induced by Helicobacter pylori in gastric epithelial cells.
2001 Aug 17
Troglitazone and rosiglitazone induce apoptosis of vascular smooth muscle cells through an extracellular signal-regulated kinase-independent pathway.
2001 Feb
Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists.
2001 Jan 15
A novel potent antagonist of peroxisome proliferator-activated receptor gamma blocks adipocyte differentiation but does not revert the phenotype of terminally differentiated adipocytes.
2001 Jul
Suppression of inducible cyclooxygenase and nitric oxide synthase through activation of peroxisome proliferator-activated receptor-gamma by flavonoids in mouse macrophages.
2001 May 4
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.
2002 Jan 11
Troglitazone inhibits both post-glutamate neurotoxicity and low-potassium-induced apoptosis in cerebellar granule neurons.
2002 Jan 11
Peroxisome proliferator-activated receptor agonists inhibit inflammatory edema and hyperalgesia.
2002 Jun
Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation.
2002 Jun
Evaluation of liver function in type 2 diabetic patients during clinical trials: evidence that rosiglitazone does not cause hepatic dysfunction.
2002 May
Rosiglitazone-induced granulomatous hepatitis.
2002 May-Jun
Lipid metabolome-wide effects of the PPARgamma agonist rosiglitazone.
2002 Nov
Accelerated hypertension due to rosiglitazone therapy.
2002 Nov-Dec
PPAR gamma-dependent anti-inflammatory action of rosiglitazone in human monocytes: suppression of TNF alpha secretion is not mediated by PTEN regulation.
2003 Apr 11
15d-PGJ2 and rosiglitazone suppress Janus kinase-STAT inflammatory signaling through induction of suppressor of cytokine signaling 1 (SOCS1) and SOCS3 in glia.
2003 Apr 25
Rosiglitazone reduces blood pressure and urinary albumin excretion in type 2 diabetes: G Bakris et al.
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Rosiglitazone and retinoic acid induce uncoupling protein-1 (UCP-1) in a p38 mitogen-activated protein kinase-dependent manner in fetal primary brown adipocytes.
2003 Jan 3
Effects of rosiglitazone and linoleic acid on human preadipocyte differentiation.
2003 Jul
PPARgamma ligands induce prostaglandin production in vascular smooth muscle cells: indomethacin acts as a peroxisome proliferator-activated receptor-gamma antagonist.
2003 Oct
Rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2, ligands of the peroxisome proliferator-activated receptor-gamma (PPAR-gamma), reduce ischaemia/reperfusion injury of the gut.
2003 Sep
Effects of rosiglitazone and metformin on liver fat content, hepatic insulin resistance, insulin clearance, and gene expression in adipose tissue in patients with type 2 diabetes.
2004 Aug
Decreased expression of peroxisome proliferator activated receptor gamma in cftr-/- mice.
2004 Aug
[Anti-hypertensive effect of rosiglitazone in non-diabetic essential hypertension].
2004 Dec
A yeast two-hybrid technology-based system for the discovery of PPARgamma agonist and antagonist.
2004 Dec 15
Reduction of intracellular cholesterol accumulation in THP-1 macrophages by a combination of rosiglitazone and atorvastatin.
2004 Jul 1
Evidence for a potent antiinflammatory effect of rosiglitazone.
2004 Jun
Rosiglitazone induction of Insig-1 in white adipose tissue reveals a novel interplay of peroxisome proliferator-activated receptor gamma and sterol regulatory element-binding protein in the regulation of adipogenesis.
2004 Jun 4
PPAR(gamma) agonist rosiglitazone improves vascular function and lowers blood pressure in hypertensive transgenic mice.
2004 Mar
Rosiglitazone facilitates angiogenic progenitor cell differentiation toward endothelial lineage: a new paradigm in glitazone pleiotropy.
2004 Mar 23
Rosiglitazone improves insulin sensitivity, glucose tolerance and ambulatory blood pressure in subjects with impaired glucose tolerance.
2004 May
Transactivation of the PPAR-responsive enhancer module in chemopreventive glutathione S-transferase gene by the peroxisome proliferator-activated receptor-gamma and retinoid X receptor heterodimer.
2004 May 15
Mitochondrial remodeling in adipose tissue associated with obesity and treatment with rosiglitazone.
2004 Nov
Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism.
2004 Nov
Chronic heart failure-related interventions after starting rosiglitazone in patients receiving insulin.
2004 Oct
Altered adipokine response in murine 3T3-F442A adipocytes treated with protease inhibitors and nucleoside reverse transcriptase inhibitors.
2005
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
2005 Aug
Rosiglitazone, PPAR-gamma receptor ligand, decreases the viability of rat prolactin-secreting pituitary tumor cells in vitro.
2005 Feb
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury.
2005 Feb
The effects of rosiglitazone on fatty acid and triglyceride metabolism in type 2 diabetes.
2005 Jan
The peroxisome proliferator-activated receptor gamma ligand rosiglitazone delays the onset of inflammatory bowel disease in mice with interleukin 10 deficiency.
2005 Mar
Development of a complex scintillation proximity assay for high-throughput screening of PPARgamma modulators.
2005 Mar
Comparison of pioglitazone with other antidiabetic drugs for associated incidence of liver failure: no evidence of increased risk of liver failure with pioglitazone.
2005 Mar
Rosiglitazone causes bone loss in mice by suppressing osteoblast differentiation and bone formation.
2005 Mar
Fatty acids and expression of adipokines.
2005 May 30
Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.
2005 Oct
Patents

Patents

06515132
8
JP2002543077A
8
JP2004536047A
24
JP2008195625A
8
JP2011252007A
8
JP4365554B2
22
JP4741458B2
8

Sample Use Guides

In Vivo Use Guide
Start at 4 mg daily in single or divided doses; do not exceed 8 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Rosiglitazone treatment (5 uM) prevents NO and prostacyclin overproduction by inhibiting microparticles-induced iNOS and COX-2 expression.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:24:17 GMT 2023
Edited
by admin
on Sat Dec 16 11:24:17 GMT 2023
Record UNII
YR4MBO751R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROSIGLITAZONE SODIUM
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(METHYL-2-PYRIDINYLAMINO)ETHOXY)PHENYL)METHYL)-, SODIUM SALT
Common Name English
Rosiglitazone sodium [WHO-DD]
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(METHYL-2-PYRIDINYLAMINO)ETHOXY)PHENYL)METHYL)-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000176334
Created by admin on Sat Dec 16 11:24:17 GMT 2023 , Edited by admin on Sat Dec 16 11:24:17 GMT 2023
PRIMARY
PUBCHEM
23692351
Created by admin on Sat Dec 16 11:24:17 GMT 2023 , Edited by admin on Sat Dec 16 11:24:17 GMT 2023
PRIMARY
FDA UNII
YR4MBO751R
Created by admin on Sat Dec 16 11:24:17 GMT 2023 , Edited by admin on Sat Dec 16 11:24:17 GMT 2023
PRIMARY
CAS
316371-83-2
Created by admin on Sat Dec 16 11:24:17 GMT 2023 , Edited by admin on Sat Dec 16 11:24:17 GMT 2023
PRIMARY
Related Record Type Details
Structure of ROSIGLITAZONE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ROSIGLITAZONE
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