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CAS 139481-59-7
Also known as: 139481-59-7, Blopress, Cv-11974, 1-((2'-(1h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylic acid, Cv 11974, 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
Molecular Formula
C24H20N6O3
Molecular Weight
440.5  g/mol
InChI Key
HTQMVQVXFRQIKW-UHFFFAOYSA-N
FDA UNII
S8Q36MD2XX

Candesartan is a synthetic, benzimidazole-derived angiotensin II receptor antagonist prodrug with antihypertensive activity. Candesartan selectively competes with angiotensin II for the binding of the angiotensin II receptor subtype 1 (AT1) in vascular smooth muscle, blocking angiotensin II-mediated vasoconstriction and inducing vasodilatation. In addition, antagonism of AT1 in the adrenal gland inhibits angiotensin II-stimulated aldosterone synthesis and secretion by the adrenal cortex; sodium and water excretion increase, followed by a reduction in plasma volume and blood pressure.
Candesartan is an Angiotensin 2 Receptor Blocker. The mechanism of action of candesartan is as an Angiotensin 2 Receptor Antagonist.
1 2D Structure

CAS 139481-59-7

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
2.1.2 InChI
InChI=1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)
2.1.3 InChI Key
HTQMVQVXFRQIKW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
S8Q36MD2XX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-ethoxy-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1h-benzimidazole-7-carboxylic Acid

2. 2-ethoxy-7-carboxy-1-(2'-(1h-tetrazol-5-yl)biphenyl-4-yl)methylbenzimidazole

3. Cv 11974

4. Cv-11974

5. Cv11974

2.3.2 Depositor-Supplied Synonyms

1. 139481-59-7

2. Blopress

3. Cv-11974

4. 1-((2'-(1h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylic Acid

5. Cv 11974

6. 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic Acid

7. 2-ethoxy-1-(p-(o-1h-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic Acid

8. Nsc-759858

9. Candesartan Cilexetil Related Compound G

10. Chembl1016

11. S8q36md2xx

12. Chebi:3347

13. Ncgc00167474-01

14. Dsstox_cid_2725

15. Dsstox_rid_75453

16. Dsstox_gsid_22725

17. 1-((2'-(2h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylic Acid

18. 1h-benzimidazole-7-carboxylic Acid, 2-ethoxy-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-

19. [3h]candesartan

20. 1-((2'-(1h-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylic Acid

21. 2-(ethyloxy)-1-{[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl}-1h-benzimidazole-7-carboxylic Acid

22. 2-ethoxy-1-({2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl)-1h-benzimidazole-7-carboxylic Acid

23. Candesartan [inn]

24. Cas-139481-59-7

25. Sr-05000001447

26. Candesartan (usan/inn)

27. Unii-s8q36md2xx

28. Candesartan [usan:inn:ban]

29. Hsdb 7520

30. 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic Acid

31. 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-4-benzimidazolecarboxylic Acid

32. Candesartan-[d5]

33. 2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1h-benzimidazole-7-carboxylic Acid

34. 2-ethoxy-3-[[4-[2-(2h-1,2,3,4-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic Acid

35. Candesartan- Bio-x

36. Candemore

37. Celexetil

38. Candesartan (atacand)

39. Ks-5003

40. Candesartan - Atacand

41. Candesartan [mi]

42. Tcv-116 (prodrug)

43. Candesartan [hsdb]

44. Candesartan [usan]

45. Candesartan [vandf]

46. Ec 604-138-8

47. Schembl3938

48. 2-ethoxy-1-{[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl}-1h-benzimidazole-7-carboxylic Acid

49. 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]-3h-benzoimidazole-4-carboxylic Acid

50. Candesartan [who-dd]

51. Gtpl587

52. Mls003915631

53. Mls004774041

54. Bidd:gt0350

55. Gtpl6907

56. Dtxsid0022725

57. Bcpp000302

58. Hms2089m22

59. Hms3651c13

60. Hms3715f13

61. Pharmakon1600-01502288

62. Act02607

63. Bcp01137

64. Hy-b0205

65. Str09609

66. Zinc3782818

67. Tox21_112478

68. Bdbm50240609

69. Mfcd00864463

70. Nsc755311

71. Nsc759858

72. S1578

73. Akos015888154

74. Akos025117340

75. Tox21_112478_1

76. Ab07470

77. Am84369

78. Bcp9000479

79. Ccg-213059

80. Ccg-269122

81. Db13919

82. Nsc 759858

83. Nsc-755311

84. Ncgc00167474-02

85. Ncgc00167474-04

86. Ncgc00167474-06

87. 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl] Methyl]-3h-benzoimidazole-4-carboxylic Acid

88. Bc164271

89. Smr002203608

90. Smr003500711

91. C-266

92. Ft-0602912

93. Sw199612-2

94. C07468

95. D00522

96. Ab01275447-01

97. Ab01275447_02

98. Ab01275447_03

99. 481c597

100. A807545

101. A808309

102. L000156

103. Q415970

104. Candesartan 100 Microg/ml In Acetonitrile:methanol

105. J-007281

106. Sr-05000001447-1

107. Sr-05000001447-2

108. Sr-05000001447-5

109. Candesartan Cilexetil Impurity G [ep Impurity]

110. Candesartan Cilexetil Related Compound G [usp-rs]

111. 2-ethoxy-1-[[2'-(1 H-tetrazol-5-yl)biphenyl-4-yl]methyl]-benzimidazole-7-carboxylic Acid

112. 2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl]-benzimidazole-7-carboxylic Acid

113. 2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic Acid

114. 2-ethoxy-1-{[2'-(1h-tetrazol-5-yl)biphenyl-4ethyl]}-1h-benzimidazole-7-carboxylic Acid

115. 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic Acid.

116. 2-ethoxy-3-[2'-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzimidazole-4-carboxylic Acid

117. 1-((2'-(2h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylicacid

118. 2-ethoxy-1-((2-(1h-tetrazole-5-yl)biphenyl-4-yl)methyl)-1h-benzamidazole-7-carboxylic Acid.

119. 2-ethoxy-1-({4-[2-(2h-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1h-1,3-benzodiazole-7-carboxylic Acid

120. 2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl]-1h-benzimidazole-7-carboxylic Acid (candesartan)

121. 2-ethoxy-1-[[2'-(2h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1h-benzimidazole-7-carboxylic Acid

122. 2-ethoxy-1-{[2'-(2h-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1h-1,3-benzodiazole-7-carboxylic Acid

123. 2-ethoxy-3-[2''-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid

124. 2-ethoxy-3-[2''-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid(cv-11974)

125. 2-ethoxy-3-[2''-(2h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid

126. 2-ethoxy-3-[2'-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 440.5 g/mol
Molecular Formula C24H20N6O3
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass440.15968852 g/mol
Monoisotopic Mass440.15968852 g/mol
Topological Polar Surface Area119 Ų
Heavy Atom Count33
Formal Charge0
Complexity660
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Angiotensin II Type 1 Receptor Blockers; Antihypertensive Agents

National Library of Medicine's Medical Subject Headings. Candesartan. Online file (MeSH, 2014). Available from, as of September 2, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html


Atacand is indicated for the treatment of hypertension in adults and children 1 to < 17 years of age. It may be used alone or in combination with other antihypertensive agents. /Included in US product labeling/

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Atacand is indicated for the treatment of heart failure (NYHA class II-IV) in adults with left ventricular systolic dysfunction (ejection fraction = 40%) to reduce cardiovascular death and to reduce heart failure hospitalizations. Atacand also has an added effect on these outcomes when used with an ACE inhibitor. /Included in US product labeling/

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Both angiotensin II receptor antagonists and ACE inhibitors have been shown to slow the rate of progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy, and use of a drug from either class is recommended in such patients. /NOT included in US product label/

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014, p. 2059


For more Therapeutic Uses (Complete) data for CANDESARTAN (7 total), please visit the HSDB record page.


4.2 Drug Warning

/BOXED WARNING/ WARNING: FETAL TOXICITY. When pregnancy is detected, discontinue Atacand as soon as possible. Drugs that act directly on the renin-angiotensin system can cause injury and death to the developing fetus.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Use of drugs that act on the renin-angiotensin system during the second and third trimesters of pregnancy reduces fetal renal function and increases fetal and neonatal morbidity and death. Resulting oligohydramnios can be associated with fetal lung hypoplasia and skeletal deformations. Potential neonatal adverse effects include skull hypoplasia, anuria, hypotension, renal failure, and death. When pregnancy is detected, discontinue Atacand as soon as possible. These adverse outcomes are usually associated with use of these drugs in the second and third trimester of pregnancy. Most epidemiologic studies examining fetal abnormalities after exposure to antihypertensive use in the first trimester have not distinguished drugs affecting the renin-angiotensin system from other antihypertensive agents. Appropriate management of maternal hypertension during pregnancy is important to optimize outcomes for both mother and fetus.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Neonates with a history of in utero exposure to Atacand: If oliguria or hypotension occurs, direct attention toward support of blood pressure and renal perfusion. Exchange transfusions or dialysis may be required as a means of reversing hypotension and/or substituting for disordered renal function.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


FDA Pregnancy Risk Category: D /POSITIVE EVIDENCE OF RISK. Studies in humans, or investigational or post-marketing data, have demonstrated fetal risk. Nevertheless, potential benefits from the use of the drug may outweigh the potential risk. For example, the drug may be acceptable if needed in a life-threatening situation or serious disease for which safer drugs cannot be used or are ineffective./

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


For more Drug Warnings (Complete) data for CANDESARTAN (19 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


Angiotensin II Type 1 Receptor Blockers

Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
CANDESARTAN
5.2.2 FDA UNII
S8Q36MD2XX
5.2.3 Pharmacological Classes
Angiotensin 2 Receptor Blocker [EPC]; Angiotensin 2 Receptor Antagonists [MoA]
5.3 ATC Code

C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09C - Angiotensin ii receptor blockers (arbs), plain

C09CA - Angiotensin ii receptor blockers (arbs), plain

C09CA06 - Candesartan


5.4 Absorption, Distribution and Excretion

The volume of distribution of candesartan is 0.13 L/kg. Candesartan is highly bound to plasma proteins (>99%) and does not penetrate red blood cells. The protein binding is constant at candesartan plasma concentrations well above the range achieved with recommended doses. In rats, it has been demonstrated that candesartan crosses the blood-brain barrier poorly, if at all. It has also been demonstrated in rats that candesartan passes across the placental barrier and is distributed in the fetus.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Following administration of candesartan cilexetil, the absolute bioavailability of candesartan was estimated to be 15%. After tablet ingestion, the peak serum concentration (Cmax) is reached after 3 to 4 hours. Food with a high fat content does not affect the bioavailability of candesartan after candesartan cilexetil administration.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Total plasma clearance of candesartan is 0.37 mL/min/kg, with a renal clearance of 0.19 mL/min/kg. When candesartan is administered orally, about 26% of the dose is excreted unchanged in urine. Following an oral dose of (14)C-labeled candesartan cilexetil, approximately 33% of radioactivity is recovered in urine and approximately 67% in feces. Following an intravenous dose of (14)C-labeled candesartan, approximately 59% of radioactivity is recovered in urine and approximately 36% in feces. Biliary excretion contributes to the elimination of candesartan.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


It is not known whether candesartan is excreted in human milk, but candesartan has been shown to be present in rat milk.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


5.5 Metabolism/Metabolites

Candesartan cilexetil is rapidly and completely bioactivated by ester hydrolysis during absorption from the gastrointestinal tract to candesartan, a selective AT1 subtype angiotensin II receptor antagonist. Candesartan is mainly excreted unchanged in urine and feces (via bile). It undergoes minor hepatic metabolism by O-deethylation to an inactive metabolite.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


Candesartan has known human metabolites that include (2S,3S,4S,5R)-6-[2-Ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid and 3-[[4-[2-[2-[(3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]tetrazol-5-yl]phenyl]phenyl]methyl]-2-ethoxy-1H-benzimidazol-3-ium-4-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

The elimination half-life of candesartan is approximately 9 hours.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


5.7 Mechanism of Action

Although these agents /angiotensin II receptor antagonists/ are similar to ACE inhibitors in that they decrease the effects of angiotensin II, rather than decreasing the formation of angiotensin II, drugs antagonize angiotensin II at the type I angiotensin receptor. This allows the drugs to inhibit the vasoconstrictive and aldosterone promoting effects of angiotensin II without interfering with bradykinin degradation, significantly reducing the adverse effects of cough and angioedema seen with ACE inhibitor therapy. ... /Angiotensin II receptor antagonists/

Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 782


Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme (ACE, kininase II). Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Candesartan blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in many tissues, such as vascular smooth muscle and the adrenal gland. Its action is, therefore, independent of the pathways for angiotensin II synthesis. There is also an AT2 receptor found in many tissues, but AT2 is not known to be associated with cardiovascular homeostasis. Candesartan has much greater affinity (>10,000-fold) for the ATI receptor than for the AT2 receptor. Blockade of the renin-angiotensin system with ACE inhibitors, which inhibit the biosynthesis of angiotensin II from angiotensin I, is widely used in the treatment of hypertension. ACE inhibitors also inhibit the degradation of bradykinin, a reaction also catalyzed by ACE. Because candesartan does not inhibit ACE (kininase II), it does not affect the response to bradykinin. Whether this difference has clinical relevance is not yet known. Candesartan does not bind to or block other hormone receptors or ion channels known to be important in cardiovascular regulation. Blockade of the angiotensin II receptor inhibits the negative regulatory feedback of angiotensin II on renin secretion, but the resulting increased plasma renin activity and angiotensin II circulating levels do not overcome the effect of candesartan on blood pressure.

NIH; DailyMed. Current Medication Information for Atacand (Candesartan Cilexetil) Tablet (Revised: April 2013). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=a73e1339-9643-4eea-2cbe-e879c88fb50e


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