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Chemistry

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Also known as: Naganol, Suramine, Fourneau, Farma, 145-63-1, Germanin
Molecular Formula
C51H40N6O23S6
Molecular Weight
1297.3  g/mol
InChI Key
FIAFUQMPZJWCLV-UHFFFAOYSA-N
FDA UNII
6032D45BEM

Suramin
A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.
1 2D Structure

Suramin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid
2.1.2 InChI
InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80)
2.1.3 InChI Key
FIAFUQMPZJWCLV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C=C(C=C1)C(=O)NC2=C3C(=CC(=CC3=C(C=C2)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)NC(=O)C4=CC(=CC=C4)NC(=O)NC5=CC=CC(=C5)C(=O)NC6=C(C=CC(=C6)C(=O)NC7=C8C(=CC(=CC8=C(C=C7)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
6032D45BEM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Germanin

2. Hexasodium Salt Suramin

3. Monosodium Salt Suramin

4. Moranil

5. Naganin

6. Naganol

7. Naphuride

8. Salt Suramin, Hexasodium

9. Salt Suramin, Monosodium

10. Sodium, Suramin

11. Suramin Sodium

12. Suramin, Hexasodium Salt

13. Suramin, Monosodium Salt

2.3.2 Depositor-Supplied Synonyms

1. Naganol

2. Suramine

3. Fourneau

4. Farma

5. 145-63-1

6. Germanin

7. Belganyl

8. Naphuride

9. Sodium Suramin

10. Naganin

11. Farma 939

12. Antrypol

13. Moranyl

14. Metaret

15. Naganine

16. Suramine Sodium

17. Bayer 205

18. Nsc-34936

19. Farma-939

20. M,m'-ureylen-bis-(8-(m-(benzamido)-p-toluamido)naphthalin-1,3,5-trisulfonsaeure)

21. Chembl265502

22. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic Acid

23. Harnstoff, Symmetischer Der 3-aminobenzoyl-3-amino-4-methylbenzoyl-1-naphthylamin-4,6,8-trisulfonsaeure

24. Svr

25. Chebi:45906

26. Nsc 34936

27. 6032d45bem

28. Nsc34936

29. Carbanilide, 3,3'-bis((5-((4,6,8-trisulfo-1-naphthyl)carbamoyl)-o-tolyl)carbamoyl)-

30. Naphuride Sodium

31. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bis-

32. Ncgc00163318-01

33. Naganil

34. Dsstox_cid_26344

35. Dsstox_rid_81548

36. Dsstox_gsid_46344

37. 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bisnaphthalene-1,3,5-trisulphonic Acid

38. Bay 205

39. Naganol 6 Na

40. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-

41. 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-1,3,5-naphthalenetrisulfonic Acid

42. 8-[(4-methyl-3-{[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzene]amido}benzene)amido]naphthalene-1,3,5-trisulfonic Acid

43. Cas-145-63-1

44. Sk 24728

45. Einecs 205-658-4

46. 309 F

47. Brn 3230873

48. Sgcto-001

49. Unii-6032d45bem

50. 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bis-1,3,5-naphthalenetrisulfonic Acid

51. 8,8'-(ureylenebis(m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino))di-1,3,5-naphthalenetrisulfonic Acid

52. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfon Ic Acid

53. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic Acid

54. Spectrum_001877

55. 5,5'',5''''-[1,3,6-naphthalenetriyltris(sulfonylimino)]tris[1,3-benzenesulfonate Analogue

56. Specplus_000662

57. Spectrum3_000724

58. Spectrum4_001247

59. Suramin [who-dd]

60. Schembl3161

61. Lopac0_001182

62. Us8835659, Suramin

63. Bspbio_002248

64. Kbiogr_001774

65. Kbioss_002402

66. 3-14-00-02267 (beilstein Handbook Reference)

67. 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic Acid

68. Divk1c_006758

69. Gtpl1728

70. Dtxsid1046344

71. Kbio1_001702

72. Kbio2_002397

73. Kbio2_004965

74. Kbio2_007533

75. Kbio3_001468

76. Hy-b0879

77. Tox21_112045

78. Bdbm50336799

79. Ccg-36173

80. Mmv637953

81. Tox21_112045_1

82. Cs-4444

83. Db04786

84. Sym-bis(m-aminobenzoyl-m-amino-p-methylbenzoyl-1-napthylamino-4,6,8-trisulfonate) Carbamide

85. Ncgc00025177-08

86. Ncgc00163318-02

87. Ncgc00163318-03

88. 1,3,5-naphthylenetrisulfonic Acid, 8,8'-(ureylenebis(m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino))di-

89. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-naphthalenetrisulfonic Acid

90. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-napthalenetrisulfonic Acid

91. 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic Acid

92. C07974

93. L000585

94. Q425946

95. Brd-k70327167-348-01-9

96. Brd-k70327167-348-09-2

97. Sr-01000075238-10

98. 1-(3-benzamido-4-methylbenzamido)naphthalene-4,8-trisulfonic Acid Sym-3''-urea Sodium Salt

99. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis- (9ci)

100. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di- (8ci)

101. 1,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-, Hexasodium Salt

102. 1,5-naphthalenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-, Hexasodium Salt

103. 1,5-naphthylenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-, Hexasodium Salt

104. 8,8''-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bisnaphthalene-1,3,5-trisulphonic Acid

105. 8,8''-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-naphthalenetrisulfonic Acid(suramin)

106. 8,8''-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic Acid

107. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfon

108. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulphonic Acid

109. 8,8-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic Acid

110. 8-[(4-methyl-3-{[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzoyl]amino}benzoyl)amino]naphthalene-1,3,5-trisulfonic Acid

111. Wln: L66j Bswq Dswq Gswq Jmvr D1 Cmvr Cmvmr Cvmr B1 Evm-jl66j Bswq Dswq Gswq &-na-6

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 1297.3 g/mol
Molecular Formula C51H40N6O23S6
XLogP31.5
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count23
Rotatable Bond Count16
Exact Mass1296.0469086 g/mol
Monoisotopic Mass1296.0469086 g/mol
Topological Polar Surface Area534 Ų
Heavy Atom Count86
Formal Charge0
Complexity3020
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 Drug Indication

For treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Trypanocidal Agents

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)


Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)


5.2 Absorption, Distribution and Excretion

Absorption

Poorly absorbed from the gastrointestinal tract.


5.3 Metabolism/Metabolites

Little or no metabolism


5.4 Biological Half-Life

Approximately 36 to 60 days


5.5 Mechanism of Action

The mechanism is unknown, but the trypanocidal activity may be due to the inhibition of enzymes involved with the oxidation of reduced nicotinamide-adenine dinucleotide (NADH), which functions as a co-enzyme in many cellular reactions, such as respiration and glycolysis, in the trypanosome parasite. Suramin's action in the treatment of onchocerciasis is macrofilaricidal and partially microfilaricidal. It may also act as an antagonist of P2 receptors and as an agonist of Ryanodine receptors. It also can inhibit follicle-stimulating hormone receptors.


Drugs in Development

read-more
read-more

Details:

PAX-101 (suramin sodium) is a intravenous formulation, company is preparing to file a New Drug Application (NDA) with the FDA for its use in treating human african trypanosomiasis.


Lead Product(s): Suramin

Therapeutic Area: Infections and Infectious Diseases Brand Name: PAX-101

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 07, 2024

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01

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101 (suramin sodium) is a intravenous formulation, company is preparing to file a New Drug Application (NDA) with the FDA for its use in treating human african trypanosomiasis.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 07, 2024

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Details:

PAX-101, if approved by the FDA will be the potential first and only intravenous form of suramin for the treatment of Stage 1 Human African Trypanosomiasis, caused by Trypanosoma brucei rhodesiense.


Lead Product(s): Suramin

Therapeutic Area: Infections and Infectious Diseases Brand Name: PAX-101

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable April 11, 2024

blank

02

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101, if approved by the FDA will be the potential first and only intravenous form of suramin for the treatment of Stage 1 Human African Trypanosomiasis, caused by Trypanosoma brucei rhodesiense.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

April 11, 2024

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Details:

The Company intends to use the net proceeds to advance the Company's development programs, including PAX-101 (suramin sodium), an antipurinergic agent delivered as an IV infusion.


Lead Product(s): Suramin

Therapeutic Area: Neurology Brand Name: PAX-101

Study Phase: Phase I/ Phase IIProduct Type: Small molecule

Sponsor: H.C. Wainwright & Co.

Deal Size: $7.0 million Upfront Cash: Undisclosed

Deal Type: Public Offering November 22, 2023

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03

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : The Company intends to use the net proceeds to advance the Company's development programs, including PAX-101 (suramin sodium), an antipurinergic agent delivered as an IV infusion.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Undisclosed

November 22, 2023

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Details:

Through the acquisition, PaxMedica gains certain suramin research assets to support the submission for the approval of PAX-101 (suramin sodium), specifically for the treatment of African Sleeping Sickness caused by the Trypanosoma brucei rhodesiense parasite.


Lead Product(s): Suramin

Therapeutic Area: Infections and Infectious Diseases Brand Name: PAX-101

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: PaxMedica

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Acquisition October 31, 2023

blank

04

Medlab Asia & Asia Health
Not Confirmed
Medlab Asia & Asia Health
Not Confirmed

Details : Through the acquisition, PaxMedica gains certain suramin research assets to support the submission for the approval of PAX-101 (suramin sodium), specifically for the treatment of African Sleeping Sickness caused by the Trypanosoma brucei rhodesiense para...

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Undisclosed

October 31, 2023

blank

Details:

PAX-101 (suramin sodium) is a intravenous formulation for Autism Spectrum Disorder. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.


Lead Product(s): Suramin

Therapeutic Area: Rare Diseases and Disorders Brand Name: PAX-101

Study Phase: IND EnablingProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable October 27, 2023

blank

05

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101 (suramin sodium) is a intravenous formulation for Autism Spectrum Disorder. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

October 27, 2023

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Details:

Under the agreement, VoxNova will have exclusive access to PaxMedica’s PAX-101 intravenous suramin for the treatment of Autism Spectrum Disorder, in the United States for a period of up to seven years.


Lead Product(s): Suramin

Therapeutic Area: Neurology Brand Name: PAX-101

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Vox Nova

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Agreement July 06, 2023

blank

06

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : Under the agreement, VoxNova will have exclusive access to PaxMedica’s PAX-101 intravenous suramin for the treatment of Autism Spectrum Disorder, in the United States for a period of up to seven years.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Undisclosed

July 06, 2023

blank

Details:

PAX-101 (suramin sodium) is a intravenous formulation for Autism Spectrum Disorder. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.


Lead Product(s): Suramin

Therapeutic Area: Neurology Brand Name: PAX-101

Study Phase: Phase I/ Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 14, 2023

blank

07

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101 (suramin sodium) is a intravenous formulation for Autism Spectrum Disorder. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 14, 2023

blank

Details:

PAX-101 (IV Suramin) is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study and completed a Phase 2B study for ASD in 2021.


Lead Product(s): Suramin

Therapeutic Area: Neurology Brand Name: PAX-101

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 01, 2023

blank

08

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101 (IV Suramin) is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study and completed a Phase 2B study for ASD in 2021.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 01, 2023

blank

Details:

PaxMedica will use the net proceeds for the development of the autism spectrum disorder (ASD) indication for PAX-101. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.


Lead Product(s): Suramin

Therapeutic Area: Neurology Brand Name: PAX-101

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Lind Global Partners

Deal Size: $3.2 million Upfront Cash: Undisclosed

Deal Type: Financing February 03, 2023

blank

09

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PaxMedica will use the net proceeds for the development of the autism spectrum disorder (ASD) indication for PAX-101. Suramin is a broadly acting anti-purinergic therapy and has reported positive results from a dose range study.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Undisclosed

February 03, 2023

blank

Details:

PAX-101 (suramin) Phase 1B Study has been approved by SAHPRA for individuals with documented COVID-19 infections who develop debilitating physical and neuropsychiatric symptoms that persist for more than 12 weeks after the viral infection has passed.


Lead Product(s): Suramin

Therapeutic Area: Infections and Infectious Diseases Brand Name: PAX-101

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable January 07, 2022

blank

10

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

PaxMedica

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : PAX-101 (suramin) Phase 1B Study has been approved by SAHPRA for individuals with documented COVID-19 infections who develop debilitating physical and neuropsychiatric symptoms that persist for more than 12 weeks after the viral infection has passed.

Brand Name : PAX-101

Molecule Type : Small molecule

Upfront Cash : Not Applicable

January 07, 2022

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