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SUSPENSION;ORAL - 40MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, SUSPENSION;ORAL - 125MG/ML

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SUSPENSION;ORAL - 40MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
SUSPENSION;ORAL - 125MG/ML

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Synopsis

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Chemistry

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Also known as: 595-33-5, Megace, Megace es, Niagestin, Megestryl acetate, Megeron

Molecular Formula

C₂₄H₃₂O₄

Molecular Weight

384.5 g/mol

InChI Key

RQZAXGRLVPAYTJ-GQFGMJRRSA-N

FDA UNII

TJ2M0FR8ES

Megestrol acetate is a progestogen with actions and uses similar to those of the progestogens in general. It also has anti-androgenic properties. It is given by mouth in the palliative treatment or as an adjunct to other therapy in endometrial carcinoma and in breast cancer. Megestrol acetate has been approved to treat anorexia and cachexia. (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995)

1 2D Structure

Megestrol Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

2.1.2 InChI

InChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1

2.1.3 InChI Key

RQZAXGRLVPAYTJ-GQFGMJRRSA-N

2.1.4 Canonical SMILES

CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C

2.1.5 Isomeric SMILES

CC1=C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C

2.2 Other Identifiers

2.2.1 UNII

TJ2M0FR8ES

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetate, Megestrol

2. Apo Megestrol

3. Apo-megestrol

4. Apomegestrol

5. Borea

6. Lin Megestrol

7. Lin-megestrol

8. Linmegestrol

9. Maygace

10. Megace

11. Megefren

12. Megestat

13. Megostat

14. Mestrel

15. Nu Megestrol

16. Nu-megestrol

17. Numegestrol

2.3.2 Depositor-Supplied Synonyms

1. 595-33-5

2. Megace

3. Megace Es

4. Niagestin

5. Megestryl Acetate

6. Megeron

7. Megestat

8. Ovaban

9. Ovarid

10. Maygace

11. Pallace

12. Bdh 1298

13. Magestin

14. Sc 10363

15. Nsc-71423

16. Volidan

17. Sc10363

18. 17alpha-hydroxy-6-methylpregna-4,6-diene-3,20-dione Acetate

19. Megesterol Acetate

20. 17alpha-acetoxy-6-dehydro-6-methylprogesterone

21. 6-dehydro-6-methyl-17alpha-acetoxyprogesterone

22. 6-methyl-6-dehydro-17alpha-acetoxyprogesterone

23. 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione 17-acetate

24. 17-acetoxy-6-methylpregna-4,6-diene-3,20-dione

25. Sc-10363

26. 17-(acetyloxy)-6-methylpregna-4,6-diene-3,20-dione

27. Bdh-1298

28. 6-methyl-17alpha-hydroxy-delta(sup 6)-progesterone Acetate

29. Tj2m0fr8es

30. [(8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl] Acetate

31. Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-methyl-

32. 6-methyl-3,20-dioxopregna-4,6-dien-17-yl Acetate

33. Megestrol 17.alpha.-acetate

34. Mls000028633

35. 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione Acetate

36. Bdh1298

37. Smr000058691

38. Dsstox_cid_20683

39. Dsstox_rid_79539

40. Dsstox_gsid_40683

41. Megestil

42. 6-methyl-17alpha-acetoxypregna-4,6-diene-3,20-dione

43. Ovaban (veterinary)

44. 6-methyl-delta(sup 6)-dehydro-17alpha-acetoxyprogesterone

45. Megestrolacetate

46. 6-methyl-delta(sup 4,6)-pregnadien-17alpha-ol-3,20-dione Acetate

47. Megestrol Acetate [usan]

48. (8xi,9xi,10xi,13xi,14xi)-6-methyl-3,20-dioxopregna-4,6-dien-17-yl Acetate

49. Ccris 372

50. Pregna-4,6-diene-3,20-dione, 17-hydroxy-6-methyl-, Acetate

51. Megestrol-17-acetate

52. Einecs 209-864-5

53. Unii-tj2m0fr8es

54. Megestin

55. Megestrol Acetole [progestins]

56. Megestrol Acetate [usan:usp]

57. Megestrol Acetole

58. Megestrol-acetate

59. 17-alpha-acetoxy-6-dehydro-6-methylprogesterone

60. 6-dehydro-6-methyl-17-alpha-acetoxyprogesterone

61. 6-methyl-6-dehydro-17-alpha-acetoxyprogesterone

62. Ncgc00016516-01

63. (8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl Acetate

64. Cas-595-33-5

65. Megace (tn)

66. 17alpha-acetoxy-6-methylpregna-4,6-diene-3,20-dione

67. 6-methyl-17-alpha-acetoxypregna-4,6-diene-3,20-dione

68. 6-methyl-17-alpha-hydroxy-delta(sup 6)-progesterone Acetate

69. 6-methyl-6-dehydro-17.alpha.-acetylprogesterone

70. 6-methyl-delta(sup 6)-dehydro-17-alpha-acetoxyprogesterone

71. 6-methyl-delta4,6-pregnadien-17alpha-ol-3,20-dione Acetate

72. 17.alpha.-acetoxy-6-dehydro-6-methylprogesterone

73. 6-dehydro-6-methyl-17.alpha.-acetoxyprogesterone

74. 6-methyl-6-dehydro-17.alpha.-acetoxyprogesterone

75. Megestrol Acetate (usp)

76. Opera_id_1511

77. Prestwick0_000956

78. Prestwick1_000956

79. Prestwick2_000956

80. Prestwick3_000956

81. 6-methyl-delta(sup 4,6)-pregnadien-17-alpha-ol-3,20-dione Acetate

82. Schembl745

83. Bspbio_000952

84. Mls000759501

85. Mls001074091

86. Mls001424055

87. Par-100,2

88. Spbio_003101

89. Megestrol Acetate [mi]

90. Bpbio1_001048

91. Chebi:6723

92. Chembl1201139

93. Dtxsid9040683

94. Megestrol Acetate [vandf]

95. Megestrol Acetate [mart.]

96. Bcpp000168

97. Hms1570p14

98. Hms2051i20

99. Hms2090n04

100. Hms2097p14

101. Hms2235d16

102. Hms3714p14

103. Megestrol Acetate [usp-rs]

104. Megestrol Acetate [who-dd]

105. Megestrol Acetate [who-ip]

106. Nia

107. Nsc71423

108. Zinc4097467

109. Tox21_110469

110. Tox21_302360

111. Lmst02030118

112. Mfcd00056470

113. S1304

114. Akos015894927

115. Megestrol Acetate [green Book]

116. Tox21_110469_1

117. Bcp9000904

118. Ccg-100899

119. Cs-2065

120. Db00351

121. Megestrol Acetate [orange Book]

122. Nc00149

123. Megestrol Acetate [ep Monograph]

124. 17-acetoxy-6-methylpregna-4,20-dione

125. Megestrol Acetate [usp Monograph]

126. Ncgc00024196-03

127. Ncgc00024196-05

128. Ncgc00255456-01

129. Ac-24570

130. As-13384

131. Hy-13676

132. 17.alpha.-acetoxy-6-methyl-4,20-dione

133. Ab00490013

134. B1377

135. 17-hydroxy-6-methylpregna-4,20-dione Acetate

136. 17.alpha.-acetoxy-6-methylpregna-4,20-dione

137. C08151

138. D00952

139. D91560

140. Ab00383046-13

141. Ab00383046-14

142. Ab00383046-15

143. Ab00383046_16

144. Pregna-4,20-dione, 17-(acetyloxy)-6-methyl-

145. 595m335

146. A832354

147. Megestrol-17-acetate 1000 Microg/ml In Methanol

148. Sr-01000000258

149. Megestrol-17-acetate 100 Microg/ml In Acetonitrile

150. Pregna-4,20-dione, 17-hydroxy-6-methyl-, Acetate

151. Q-201346

152. Q6808975

153. Sr-01000000258-4

154. Brd-k19507340-001-03-1

155. Medroxyprogesterone Acetate Impurity G [who-ip]

156. Megestrol Acetate, Vetranal(tm), Analytical Standard

157. Megestrol-17-acetate 100 Microg/ml In Methanol/water

158. 17alpha-acetoxy-6-methyl-4,6-pregnadiene-3,20-dione

159. Megestrol Acetate, Analytical Standard, For Drug Analysis

160. Medroxyprogesterone Acetate Impurity G [ep Impurity]

161. Wln: L E5 B666 Ov Ku Mutj A1 E1 Fv1 Fov1 L1

162. 6-methyl-17.alpha.-hydroxy-.delta.(sup 6)-progesterone Acetate

163. Megestrol Acetate, European Pharmacopoeia (ep) Reference Standard

164. 6-methyl-3,20-dioxopregna-4,6-dien-17-yl Acetate [who-ip]

165. Megestrol Acetate, United States Pharmacopeia (usp) Reference Standard

166. Megesgtrol Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

167. Megestrol Acetate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

168. Megestrol Acetate For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₂O₄
Molecular Weight	384.5 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	384.23005950 g/mol
Monoisotopic Mass	384.23005950 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	821
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Megace
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	MEGACE (megestrol acetate, USP) Oral Suspension contains megestrol acetate, a synthetic derivative of the naturally occurring steroid hormone, progesterone. Megestrol acetate is a white, crystalline solid chemically designated as 17-(acetyloxy)-6...
Active Ingredient	Megestrol acetate
Dosage Form	Suspension
Route	Oral
Strength	40mg/ml
Market Status	Prescription
Company	Bristol Myers Squibb

2 of 6
Drug Name	Megace es
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Megace ES oral suspension contains megestrol acetate, a synthetic derivative of the naturally occurring steroid hormone, progesterone. Megestrol acetate is a white, crystalline solid chemically designated as 17-Hydroxy-6-methyl pregna-4,6-diene-3...
Active Ingredient	Megestrol acetate
Dosage Form	Suspension
Route	Oral
Strength	125mg/ml
Market Status	Prescription
Company	Par Pharm

3 of 6
Drug Name	Megestrol acetate
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Megestrol acetate is a synthetic, antineoplastic and progestational drug. Megestrol acetate is a white, crystalline solid chemically designated as 17(alpha)-(acetyloxy)-6-methylpregna-4,6-diene-3,20-dione. Solubility at 37C in water is 2 mcg per mL...
Active Ingredient	Megestrol acetate
Dosage Form	Tablet; Suspension
Route	Oral
Strength	125mg/ml; 40mg/ml; 40mg; 20mg
Market Status	Prescription
Company	Twi Pharms; Wockhardt; Par Pharm; Roxane; Teva Pharms; Barr

4 of 6
Drug Name	Megace
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	MEGACE (megestrol acetate, USP) Oral Suspension contains megestrol acetate, a synthetic derivative of the naturally occurring steroid hormone, progesterone. Megestrol acetate is a white, crystalline solid chemically designated as 17-(acetyloxy)-6...
Active Ingredient	Megestrol acetate
Dosage Form	Suspension
Route	Oral
Strength	40mg/ml
Market Status	Prescription
Company	Bristol Myers Squibb

5 of 6
Drug Name	Megace es
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Megace ES oral suspension contains megestrol acetate, a synthetic derivative of the naturally occurring steroid hormone, progesterone. Megestrol acetate is a white, crystalline solid chemically designated as 17-Hydroxy-6-methyl pregna-4,6-diene-3...
Active Ingredient	Megestrol acetate
Dosage Form	Suspension
Route	Oral
Strength	125mg/ml
Market Status	Prescription
Company	Par Pharm

6 of 6
Drug Name	Megestrol acetate
PubMed Health	Megestrol Acetate (By mouth)
Drug Classes	Endocrine-Metabolic Agent
Drug Label	Megestrol acetate is a synthetic, antineoplastic and progestational drug. Megestrol acetate is a white, crystalline solid chemically designated as 17(alpha)-(acetyloxy)-6-methylpregna-4,6-diene-3,20-dione. Solubility at 37C in water is 2 mcg per mL...
Active Ingredient	Megestrol acetate
Dosage Form	Tablet; Suspension
Route	Oral
Strength	125mg/ml; 40mg/ml; 40mg; 20mg
Market Status	Prescription
Company	Twi Pharms; Wockhardt; Par Pharm; Roxane; Teva Pharms; Barr

4.2 Drug Indication

For the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). Also used for the palliative management of recurrent, inoperable, or metastatic breast cancer, endometrial cancer, and prostate cancer in Canada and some other countries.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Megestrol is a synthetic progestin and has the same physiologic effects as natural progesterone. These effects include induction of secretory changes in the endometrium, increase in basal body temperature, pituitary inhibition, and production of withdrawal bleeding in the presence of estrogen. Mestrogel has slight glucocorticoid activity and very slight mineralocorticoid activity. This drug has no estrogenic, androgenic, or anabolic activity. The precise mechanism of megestrol’s antianorexic and anticachetic effects is unknown. Initially developed as a contraceptive, it was first evaluated in breast cancer treatment in 1967.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

Appetite Stimulants

Agents that are used to stimulate appetite. These drugs are frequently used to treat anorexia associated with cancer and AIDS. (See all compounds classified as Appetite Stimulants.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Progestin [EPC]; Progesterone Congeners [CS]

5.4 Absorption, Distribution and Excretion

Absorption

Variable, but well absorbed orally.

Route of Elimination

The major route of drug elimination in humans is urine. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces.

5.5 Metabolism/Metabolites

Primarily hepatic. Megestrol metabolites which were identified in urine constituted 5% to 8% of the dose administered. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces. No active metabolites have been identified.

5.6 Biological Half-Life

34 hours

5.7 Mechanism of Action

The precise mechanism by which megestrol acetate produces effects in anorexia and cachexia is unknown at the present time, but its progestin antitumour activity may involve suppression of luteinizing hormone by inhibition of pituitary function. Studies also suggest that the megestrol's weight gain effect is related to its appetite-stimulant or metabolic effects rather than its glucocorticoid-like effects or the production of edema. It has also been suggested that megestrol may alter metabolic pathyways via interferences with the production or action of mediators such as cachectin, a hormone that inhibits adipocyte lipogenic enzymes.

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[{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q4","strtotime":1639074600,"product":"NOMEGESTROL ACETATE (BATCH NO.NB1923","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"NEWCHEM SPA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"VIATRIS","customerCountry":"INDIA","quantity":"9.00","actualQuantity":"9","unit":"KGS","unitRateFc":"14832.7","totalValueFC":"134332.7","currency":"USD","unitRateINR":"1125800","date":"10-Dec-2021","totalValueINR":"10132200","totalValueInUsd":"134332.7","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29372300","bill_no":"1004942","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"VIA EDMONDO DE AMICIS 47 20123 MILANO","customerAddress":"564\/A\/22, ROAD NO.92"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1706293800,"product":"NOMEGESTROL ACETATE (BATCH NO.ND1116)","address":"564\/A\/22, ROAD NO.92","city":"HYDERABAD,ANDHRA PRADESH","supplier":"NEWCHEM SPA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"VIATRIS","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"14267.5","totalValueFC":"72186","currency":"USD","unitRateINR":"1199900","date":"27-Jan-2024","totalValueINR":"5999500","totalValueInUsd":"72186","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29372300","bill_no":"1000339","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"VIA E. DE AMICIS-47 20123 MILANO Italy","customerAddress":"564\/A\/22, ROAD NO.92"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1712341800,"product":"NOMEGESTROL ACETATE (BATCH NO.NE0732)","address":"","city":"","supplier":"NEWCHEM SPA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"SENADOR LABORATORIES PRIVATE LIMITED","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"14186.7","totalValueFC":"71649.4","currency":"USD","unitRateINR":"1196650","date":"06-Apr-2024","totalValueINR":"5983250","totalValueInUsd":"71649.4","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29372300","bill_no":"1001291","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"VIA E. DE AMICIS-47 20123 MILANO Italy","customerAddress":""},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722623400,"product":"NOMEGESTROL ACETATE (FOR R&D PURPOSE ONLY NOT FOR SALE VIDEIMPORT LIC.NO.SW\/OD\/11\/2024\/000003184 DT. 24.06.2024)","address":"D-158-A,OKHLA INDUSTRIAL AREA,","city":"NEW DELHI","supplier":"NEWCHEM SPA","supplierCountry":"ITALY","foreign_port":"MILAN","customer":"KUSUM HEALTHCARE PVT LTD","customerCountry":"INDIA","quantity":"0.10","actualQuantity":"0.1","unit":"KGS","unitRateFc":"19800","totalValueFC":"2177.6","currency":"EUR","unitRateINR":"1826550","date":"03-Aug-2024","totalValueINR":"182655","totalValueInUsd":"2177.6","indian_port":"Delhi Air","hs_no":"29372300","bill_no":"4856876","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN","supplierAddress":"VIA SAN VITTORE 39 - 20123, MILANO,ITALYSDNF ITALY","customerAddress":"D-158-A,OKHLA INDUSTRIAL AREA,"}]

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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INTERMEDIATES SUPPLIERS

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FDF Dossiers

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FDA Orange Book

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Europe

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Canada

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Listed Dossiers

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - SUSPENSION;ORAL - 40MG/ML **Federal ...DOSAGE - SUSPENSION;ORAL - 40MG/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20264

DOSAGE - SUSPENSION;ORAL - 125MG/ML

USFDA APPLICATION NUMBER - 21778

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