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Synopsis

Synopsis

Chemistry

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Also known as: Beclometasone dipropionate, 5534-09-8, Beclovent, Beconase, Vancenase, Sanasthmax
Molecular Formula
C28H37ClO7
Molecular Weight
521.0  g/mol
InChI Key
KUVIULQEHSCUHY-XYWKZLDCSA-N
FDA UNII
5B307S63B2

Beclomethasone Dipropionate
An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA.
1 2D Structure

Beclomethasone Dipropionate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
2.1.2 InChI
InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
2.1.3 InChI Key
KUVIULQEHSCUHY-XYWKZLDCSA-N
2.1.4 Canonical SMILES
CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
2.1.5 Isomeric SMILES
CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)OC(=O)CC
2.2 Other Identifiers
2.2.1 UNII
5B307S63B2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aerobec

2. Aerobec Forte

3. Aldecin

4. Apo-beclomethasone

5. Ascocortonyl

6. Asmabec Clickhaler

7. Beclamet

8. Beclazone

9. Beclazone Easy Breathe

10. Beclo Asma

11. Beclo Azu

12. Beclocort

13. Becloforte

14. Beclomet

15. Beclometasone

16. Beclomethasone

17. Beclorhinol

18. Becloturmant

19. Beclovent

20. Becodisk

21. Becodisks

22. Beconase

23. Beconase Aq

24. Becotide

25. Bemedrex Easyhaler

26. Bronchocort

27. Dipropionate, Beclomethasone

28. Ecobec

29. Filair

30. Filair Forte

31. Junik

32. Nasobec Aqueous

33. Prolair

34. Propaderm

35. Qvar

36. Respocort

37. Sanasthmax

38. Sanasthmyl

39. Vancenase

40. Vanceril

41. Ventolair

42. Viarin

2.3.2 Depositor-Supplied Synonyms

1. Beclometasone Dipropionate

2. 5534-09-8

3. Beclovent

4. Beconase

5. Vancenase

6. Sanasthmax

7. Beclazone

8. Beclomet

9. Vanceril

10. Becloforte

11. Beclorhinol

12. Entyderma

13. Korbutone

14. Propaderm

15. Sanasthmyl

16. Aerobec

17. Aldecin

18. Qvar

19. Beclacin

20. Ventolair

21. Viarox

22. Propaderm Forte

23. Rino-clenil

24. Inalone R

25. Clenil-a

26. Beclometasone 17,21-dipropionate

27. Qnasl

28. Becotide

29. Sch 18020w

30. Beconase Aq

31. Beclate

32. Becodisks

33. Benconase

34. Chebi:3002

35. (11beta,16beta)-9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione

36. Inalone O

37. Sch 8020w

38. Sgx-201

39. Sgx-202

40. Sgx-203

41. Sch-18020w

42. 9-chloro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

43. 9-chloro-11beta-hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

44. 5b307s63b2

45. Nsc-755901

46. Becloturmant

47. Respocort

48. Belchlorhinol

49. Sanasthymyl

50. Anceron

51. Becloval

52. [2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Propanoate

53. Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-

54. Viarex

55. Vancenase Aq

56. Alanase

57. Aldecina

58. Aldecine

59. Atomase

60. Rhinosol

61. Turbinal

62. Clenil

63. Spir

64. Beclocort Nasel

65. Beclomet Nasal

66. Rhino Clenil

67. (8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl Propionate

68. 9-chloro-11.beta.,17,21-trihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

69. 9-chloro-16beta-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionate

70. Qvar 80

71. Vanceril Double Strength

72. Beconasol

73. Inalone

74. Menaderm

75. Qvar 40

76. Orbec

77. Beclovent (tn)

78. Ncgc00094596-03

79. Beclomethasone Dipropionate [usan]

80. Vanceril (tn)

81. Beclazone 250

82. Prestwick_990

83. Einecs 226-886-0

84. Kw-053

85. Mfcd00135613

86. Nasobec

87. Orbeshield

88. Topster

89. Qnasl (tn)

90. Clenil A

91. Beclometasone Dipropionato

92. Prestwick0_000855

93. Prestwick1_000855

94. Prestwick2_000855

95. Prestwick3_000855

96. Beclomethasone-dipropionate

97. Schembl6890

98. Dsstox_cid_28656

99. Dsstox_rid_82926

100. Propionic Acid Beclomethasone

101. Dsstox_gsid_48730

102. Bspbio_000869

103. Mls002154034

104. Spbio_002790

105. Bpbio1_000957

106. Gtpl5894

107. Chembl1200500

108. Dtxsid3048730

109. Unii-5b307s63b2

110. Beclomethasone Dipropionate (usp)

111. Hms1570l11

112. Hms2097l11

113. Hms2235o23

114. Hms3259h03

115. Hms3714l11

116. Beclometasone Dipropionate (jp17)

117. Beclomethasone Dipropionate Anhydrous

118. Zinc3938744

119. Tox21_113168

120. Hy-13571a

121. S3078

122. Akos015951275

123. Ac-2159

124. Ccg-220855

125. Cs-1503

126. Db00394

127. Nc00610

128. Nsc 755901

129. Beclometasone Dipropionate [jan]

130. Beclomethasone Dipropionate [mi]

131. Beclomethasone Dipropionate [usan:usp]

132. Ncgc00179392-01

133. (11beta,16beta)-9-chloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl Dipropanoate

134. Cpd001233361

135. Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11beta,16beta)-

136. Pregna-1,4-diene-3,20-dione, 9-chloro-16-beta-methyl-11-beta,17,21-trihydroxy-, 17,21-dipropionate

137. Smr001233361

138. Beclometasone Dipropionate [who-dd]

139. Beclometasone Dipropionate [who-ip]

140. Beclometasone Dipropionate Anhydrous

141. Beclomethasone 17,21-dipropionate

142. Beclomethasone Dipropionate [vandf]

143. Cas-5534-09-8

144. Beclometasone Dipropionate, Anhydrous

145. Beclomethasone 17,21-diproprionate

146. Beclomethasone Dipropionate [usp-rs]

147. Betamethasone Dipropionate Impurity E

148. B4464

149. C07813

150. D00689

151. D89082

152. Beclometasone Dipropionate [ep Monograph]

153. Beclometasoni Dipropionas [who-ip Latin]

154. Beclomethasone Dipropionate [orange Book]

155. 534b098

156. Beclomethasone Dipropionate [usp Impurity]

157. Beclomethasone Dipropionate [usp Monograph]

158. Q421475

159. Trimbow Component Beclomethasone Dipropionate

160. Brd-k97810537-001-03-7

161. Brd-k97810537-001-13-6

162. Beclometasone Dipropionate, Anhydrous [ep Impurity]

163. Beclomethasone Dipropionate, Analytical Standard, For Drug Analysis

164. Beclometasone (beclomethasone) Dipropionate, British Pharmacopoeia (bp) Assay Standard

165. Beclomethasone Dipropionate, Anhydrous, European Pharmacopoeia (ep) Reference Standard

166. Beclomethasone Dipropionate, Pharmaceutical Secondary Standard; Certified Reference Material

167. Beclomethasone Dipropionate, United States Pharmacopeia (usp) Reference Standard

168. [(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] Propanoate

169. 2-[(1r,2s,10s,11s,13s,14r,15s,17s)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl Propanoate

170. 9alpha-chloro-16beta-methyl-3,20-dioxo-1,4-pregnadiene-11beta,17,21-triol 17,21-dipropionate

171. Beclometasone Dipropionate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

172. Beclometasone Dipropionate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 521.0 g/mol
Molecular Formula C28H37ClO7
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass520.2227812 g/mol
Monoisotopic Mass520.2227812 g/mol
Topological Polar Surface Area107 Ų
Heavy Atom Count36
Formal Charge0
Complexity1050
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameQnasl
PubMed HealthBeclomethasone
Drug ClassesAnti-Inflammatory
Drug LabelBeclomethasone dipropionate USP, the active component of QNASL Nasal Aerosol, is an anti-inflammatory steroid having the chemical name 9-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17, 21-dipropionate and the following chemica...
Active IngredientBeclomethasone dipropionate
Dosage FormAerosol, metered
RouteNasal
Strength0.08mg/actuation
Market StatusPrescription
CompanyTeva Branded Pharm

2 of 4  
Drug NameQvar 40
Active IngredientBeclomethasone dipropionate
Dosage FormAerosol, metered
RouteInhalation
Strength0.04mg/inh
Market StatusPrescription
CompanyTeva Branded Pharm

3 of 4  
Drug NameQnasl
PubMed HealthBeclomethasone
Drug ClassesAnti-Inflammatory
Drug LabelBeclomethasone dipropionate USP, the active component of QNASL Nasal Aerosol, is an anti-inflammatory steroid having the chemical name 9-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17, 21-dipropionate and the following chemica...
Active IngredientBeclomethasone dipropionate
Dosage FormAerosol, metered
RouteNasal
Strength0.08mg/actuation
Market StatusPrescription
CompanyTeva Branded Pharm

4 of 4  
Drug NameQvar 40
Active IngredientBeclomethasone dipropionate
Dosage FormAerosol, metered
RouteInhalation
Strength0.04mg/inh
Market StatusPrescription
CompanyTeva Branded Pharm

4.2 Drug Indication

Indicated for oral inhalation use in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. The aerosol form of beclomethasone diproprionate is not indicated for the relief of acute bronchospasm. Indicated for intranasal use to relieve the symptoms of seasonal or perennial allergic and nonallergic (vasomotor) rhinitis and prevent the recurrence of nasal polyps following surgical removal. Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients 13 years of age and older. Corticosteroid-responsive dermatoses include psoriasis, contact dermatitis (dermatitis venenata), atopic dermatitis (infantile eczema, allergic dermatitis), neurodermatitis (lichen simplex chronicus, lichen planus, eczema, eczematous dermatitis), intertrigo, dyshidroses (pompholyx), seborrheic dermatitis, exfoliative dermatitis, solar dermatitis, stasis dermatitis, and anogenital and senile pruritus.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Inflammatory conditions, including asthma, dermatoses, and allergic rhinitis, involve the activation of cascades by inflammatory mediators. Inflammation is a primary defense mechanism and the homeostatic response of the immune system; however, a prolonged inflammatory response in certain disorders may lead to tissue damage, pain, and swelling. Beclomethasone dipropionate works by attenuating the inflammatory responses associated with asthma, allergic rhinitis, nasal polyps, and corticosteroid-responsive dermatoses. It suppresses the actions of inflammatory cells, such as mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils. It also inhibits the release of inflammatory mediators, such as histamine, eicosanoids, leukotrienes, and cytokines. Beclomethasone dipropionate is reported to exhibit potent topical activity while possessing low systemic effects. Beclomethasone dipropionate is a corticosteroid drug with anti-inflammatory and vasoconstrictive effects used to treat chronic inflammatory processes such as asthma, allergic rhinitis, corticosteroid-responsive dermatoses. When inhaled, it improves lung function, decreases airway hyper-reactivity, and reduces the severity of asthmatic symptoms. Although inhaled corticosteroids, including beclomethasone dipropionate, are reported to mainly act locally in the lungs, systemic effects such as disruption of hypothalamic-pituitary-adrenal (HPA) axis function, bone turnover, osteoporosis, and growth suppression may still be observed with chronic use or high dose administration. There were varying findings from clinical studies examining the effect of beclomethasone dipropionate on growth suppression in pediatric patients. It was shown to suppress the hypothalamo-pituitary-adrenal (HPA) axis in a dose-dependent manner. HPA axis is a central hormonal response system to stress and activation of HPA axis leads to the production of endogenous steroid hormone production. Long-term use of high-dose systemic corticosteroids, including those inhaled, was often associated with signs and symptoms of adrenal insufficiency when exposed to stress conditions, such as trauma, surgery, or infections. As corticosteroids work by suppressing the immune system, there may be an increased risk for developing infections. Cases of _Candida albicans_ infection of the mouth and throat have been reported with inhaled beclomethasone dipropionate therapy.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


Anti-Asthmatic Agents

Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 Absorption, Distribution and Excretion

Absorption

Following oral inhalation of 320 mcg of beclomethasone dipropionate (BDP), the Cmax was 88 pg/mL and it was reached after 0.5 at post-administration. The mean Cmax of the major and most active metabolite, beclomethasone-17-monopropionate (17-BMP), was 1419 pg/mL at 0.7 hour post-dosing. In another pharmacokinetic study, the AUC of BDP and 17-BMP were 6660 and 6185 pgxh/mL, respectively. The Cmax was 35356 pg/mL for BDP and 2633 pg/mL for 17-BMP, and and the median time to reach these concentrations (Tmax) was 0.2 hours. In the same study, the AUC of 17-BMP following oral and intranasal administration were 10158 and 3660 pgxh/mL, respectively. The Cmax of 17-BMP following oral and intranasal administration were 703 and 310 pg/mL, respectively, and the Tmax was 4 hours. The total bioavailability of 17-BMP following oral and intranasal administration were 41% and 44%, respectively.


Route of Elimination

Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine.


Volume of Distribution

Following intravenous administration, the steady-state volume of distribution was 20 L for beclomethasone dipropionate and 424 L for the active metabolite, beclomethasone-17-monopropionate.


Clearance

Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.


5.5 Metabolism/Metabolites

During absorption, beclomethasone dipropionate is undergoes rapid and extensive hydrolysis mediated by esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH). 17-BMP is the major active metabolite with the most potent anti-inflammatory activity. About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.


5.6 Biological Half-Life

Following intravenous administration, the half life of beclomethasone dipropionate was 0.5 hours while the half life of the active metabolite 17-BMP was 2.7 hours. Following oral and intranasal administration, the half life of 17-BMP was 8.8 and 5.7 hours, respectively.


5.7 Mechanism of Action

Beclomethasone dipropionate is a corticosteroid and prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP), which mediates anti-inflammatory actions. 17-BMP has been shown _in vitro_ to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 13 times that of dexamethasone and 25 times that of beclomethasone dipropionate. Upon binding of the ligand, the glucocorticoid receptors dimerize and translocate into the nucleus, where they subsequently bind to glucocorticoid response elements (GRE) on glucocorticoid-responsive genes, leading to changes in transcription. There are several proposed mechanisms for the anti-inflammatory action of corticosteroids. Corticosteroids may work by increasing the transcription of genes coding for anti-inflammatory proteins, including lipocortin-1 and interleukin-10. Corticosteroids were also shown to inhibit the expression of multiple genes that encode pro-inflammatory factors, such as cytokines, chemokines, and adhesion molecules, that are activated during the chronic inflammatory process. This is thought to be due to the direct inhibitory interaction between activated glucocorticoid receptors and activated pro-inflammatory transcription factors, such as nuclear factor-kappa B and activator protein-1. Chronic inflammation is often characterized by enhanced expression of these transcription factors that bind to and activate coactivator molecules, which then acetylate core histones to switch on gene transcription to further amplify the inflammatory process. Corticosteroids suppress the multiple inflammatory gene expression by promoting histone deacetylation, resulting in tighter coiling of DNA and reduced access of transcription factors to their binding sites.


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ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"AXPLORA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"1.35","actualQuantity":"1350","unit":"GMS","unitRateFc":"5.5","totalValueFC":"7513.7","currency":"USD","unitRateINR":"463.9","date":"22-May-2024","totalValueINR":"626299","totalValueInUsd":"7513.7","indian_port":"Indore-EPZ\/SEZ","hs_no":"29372200","bill_no":"1003585","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Micronized","supplierPort":"N\/A","supplierAddress":"VIA PAVIA 1 27027 GROPELLO CAIROLI ITALY","customerAddress":"159, C.S.T. ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716748200,"product":"BECLOMETHASONE DIPROPIONATE MICRONIZED","address":"159, C.S.T. ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"AXPLORA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"48.00","actualQuantity":"48000","unit":"GMS","unitRateFc":"5.5","totalValueFC":"267154","currency":"USD","unitRateINR":"463.9","date":"27-May-2024","totalValueINR":"22268400","totalValueInUsd":"267154","indian_port":"Indore-EPZ\/SEZ","hs_no":"29372200","bill_no":"1003739","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Micronized","supplierPort":"N\/A","supplierAddress":"VIA PAVIA 1 27027 GROPELLO CAIROLI ITALY","customerAddress":"159, C.S.T. ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1720809000,"product":"BECLOMETHASONE DIPROPIONATE MICRONIZED","address":"159, C.S.T. ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"AXPLORA","supplierCountry":"ITALY","foreign_port":"MALPENSA APT\/MILANO","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"22.00","actualQuantity":"22000","unit":"GMS","unitRateFc":"5.5","totalValueFC":"122243.3","currency":"USD","unitRateINR":"464.5","date":"13-Jul-2024","totalValueINR":"10218450","totalValueInUsd":"122243.3","indian_port":"Indore-EPZ\/SEZ","hs_no":"29372200","bill_no":"1005146","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Micronized","supplierPort":"MALPENSA APT\/MILANO","supplierAddress":"VIA PAVIA 1 27027 GROPELLO CAIROLI ITALY","customerAddress":"159, C.S.T. ROAD,"}]
19-Jan-2021
26-Jul-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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