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Chemistry

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Also known as: 52-21-1, Prednisolone 21-acetate, Omnipred, Econopred, Pricortin, Cormalone
Molecular Formula
C23H30O6
Molecular Weight
402.5  g/mol
InChI Key
LRJOMUJRLNCICJ-JZYPGELDSA-N
FDA UNII
8B2807733D

Prednisolone Acetate
Prednisolone Acetate is the acetate salt form of prednisolone, a synthetic glucocorticoid with anti-inflammatory and immunomodulating properties. As a glucocorticoid receptor agonist, prednisolone acetate binds to specific intracellular glucocorticoid receptors, and causes the ligand-receptor complex to be translocated to the nucleus where it initiates the transcription of glucocorticoid-responsive genes such as various cytokines and lipocortins. Lipocortins inhibit phospholipase A2, thereby blocking the release of arachidonic acid from membrane phospholipids and preventing the synthesis of prostaglandins and leukotrienes, both potent mediators of inflammation. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cell populations.
1 2D Structure

Prednisolone Acetate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
2.1.2 InChI
InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
2.1.3 InChI Key
LRJOMUJRLNCICJ-JZYPGELDSA-N
2.1.4 Canonical SMILES
CC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)O
2.1.5 Isomeric SMILES
CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)O
2.2 Other Identifiers
2.2.1 UNII
8B2807733D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Pred Forte

2. Prednisolone 21-acetate

3. Scherisolone-kristall Suspension

2.3.2 Depositor-Supplied Synonyms

1. 52-21-1

2. Prednisolone 21-acetate

3. Omnipred

4. Econopred

5. Pricortin

6. Cormalone

7. Cortipred

8. Deltilen

9. Durapred

10. Predicort

11. Prednidoren

12. Supercortyl

13. Prenema

14. Meticortelone Acetate

15. Prednelan-n

16. Delcort-e

17. Pred Mild

18. Pred Forte

19. Flo-pred

20. Prediacortine

21. Nisolone

22. Prednisolone-21-acetate

23. Predalone 50

24. Predonine Injection

25. Nsc-10966

26. Mls000028512

27. Chebi:8380

28. [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

29. Prednisolone (21-acetate)

30. Smr000058326

31. Econopred Plus

32. 8b2807733d

33. Nsc 10966

34. Dsstox_cid_3502

35. Dsstox_rid_77056

36. Dsstox_gsid_23502

37. Prednisoloneacetate

38. 21-acetoxy-1,4-pregnadiene-11beta,17alpha-diol-3,20-dione

39. Pred-forte

40. Cetapred Ointment

41. Pred-g Liquifilm

42. Vasocidin Ointment

43. Cas-52-21-1

44. Blephamide Liquifilm

45. Einecs 200-134-1

46. Prednisolone Acetate (omnipred)

47. Brn 3111798

48. Prednisolone Acetate [usp:jan]

49. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-

50. Econopred (tn)

51. Prednisoloni Acetas

52. Unii-8b2807733d

53. Ncgc00094765-01

54. Prednisolone-acetate

55. Pred Forte (tn)

56. Component Of Metimyd

57. Mfcd00037710

58. Sterane Im And Ia

59. Blephamide S.o.p.

60. Component Of Composone

61. Pred Forte Tm 1%

62. Opera_id_332

63. Pred-g S.o.p.

64. 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

65. Schembl7999

66. Chembl1152

67. Component Of Isopto Cetapred

68. 4-08-00-03468 (beilstein Handbook Reference)

69. Mls001148097

70. Mls002207146

71. Mls002548870

72. Component Of Neo-delta-cortef

73. Dtxsid3023502

74. Hms2234f18

75. Hms3259o07

76. Prednisolone Acetate [jan]

77. Prednisolone 21-acetate, >=97%

78. Prednisone Impurity L [ep]

79. 2-((8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Acetate

80. Bcp18958

81. Hy-b1214

82. Nsc10966

83. Zinc3875348

84. Prednisolone Acetate [vandf]

85. Tox21_111328

86. Prednisolone Acetate [mart.]

87. Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-, 21-acetate

88. S2570

89. Prednisolone Acetate [usp-rs]

90. Prednisolone Acetate [who-dd]

91. Prednisolone Acetate [who-ip]

92. Akos007930677

93. Akos015960469

94. Prednisolone 21-acetate [mi]

95. Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-, 21-acetate

96. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11beta)-

97. Tox21_111328_1

98. Ac-2176

99. Ccg-268673

100. Cs-4642

101. Db15566

102. Nc00470

103. Prednisolone Acetate (jp17/usp/inn)

104. Ncgc00021925-03

105. Ncgc00021925-05

106. Prednisolone Acetate [green Book]

107. 2-((1s,10s,11s,15s,17s,2r,14r)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8 .7.0.0<2,7>.0<11,15>]heptadeca-3,6-dien-14-yl)-2-oxoethyl Acetate

108. As-11673

109. Prednisolone Acetate [orange Book]

110. Prednisolone Acetate [ep Monograph]

111. Prednisolone Acetate [usp Impurity]

112. Prednisoloni Acetas [who-ip Latin]

113. Prednisolone Acetate [usp Monograph]

114. Prednisolone Acetate For Peak Identification

115. Metimyd Component Prednisolone Acetate

116. P1283

117. Pred-g Component Prednisolone Acetate

118. Prednisolone Impurity C [ep Impurity]

119. Cetapred Component Prednisolone Acetate

120. Sulphrin Component Prednisolone Acetate

121. Blephamide Component Prednisolone Acetate

122. C08180

123. D00980

124. Poly-pred Component Prednisolone Acetate

125. Predamide Component Prednisolone Acetate

126. Prednisolone Acetate 100 Microg/ml In Methanol

127. Prednisolone Acetate Component Of Pred-g

128. Ab00443788-11

129. Ab00443788_13

130. Prednisolone Acetate 1000 Microg/ml In Methanol

131. Prednisolone Acetate Component Of Cetapred

132. Prednisolone Acetate Component Of Metimyd

133. Prednisolone Acetate Component Of Sulphrin

134. Predsulfair Component Prednisolone Acetate

135. 037p710

136. A828982

137. Prednisolone Acetate Component Of Blephamide

138. Prednisolone Acetate Component Of Poly-pred

139. Prednisolone Acetate Component Of Predamide

140. Prednisolone Acetate Component Of Predsulfair

141. Q-201614

142. Hydrocortisone Acetate Impurity C [ep Impurity]

143. Isopto Cetapred Component Prednisolone Acetate

144. Neo-delta-cortef Component Prednisolone Acetate

145. Q27108063

146. Blephamide S.o.p. Component Prednisolone Acetate

147. Prednisolone Acetate Component Of Isopto Cetapred

148. Prednisolone Acetate Component Of Neo-delta-cortef

149. Methylprednisolone Acetate Impurity E [ep Impurity]

150. Prednisolone 21-acetate, Vetranal(tm), Analytical Standard

151. Prednisolone Acetate Component Of Blephamide S.o.p.

152. 11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

153. Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-, 21-acetate

154. Prednisolone Acetate, British Pharmacopoeia (bp) Reference Standard

155. Prednisolone Acetate, European Pharmacopoeia (ep) Reference Standard

156. (11beta)-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl Acetate

157. 11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

158. 11.beta.,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl Acetate

159. Prednisolone Acetate, United States Pharmacopeia (usp) Reference Standard

160. Pregna-1,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-

161. Prednisolone Acetate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

162. Prednisolone Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

163. [2-[(8s,9s,10r,11s,13s,14s,17r)-10,13-dimethyl-11,17-bis(oxidanyl)-3-oxidanylidene-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxidanylidene-ethyl] Ethanoate

164. Acetic Acid [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Ester

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 402.5 g/mol
Molecular Formula C23H30O6
XLogP32.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass402.20423867 g/mol
Monoisotopic Mass402.20423867 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count29
Formal Charge0
Complexity827
Isotope Atom Count0
Defined Atom Stereocenter Count7
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 10  
Drug NameBlephamide s.o.p.
PubMed HealthPrednisolone
Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
Drug LabelFlo-Pred (prednisolone acetate oral suspension) contains prednisolone which is the acetate ester of the glucocorticoid prednisolone. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from...
Active Ingredientsulfacetamide sodium; Prednisolone acetate
Dosage FormOintment
RouteOphthalmic
Strength0.2%; 10%
Market StatusPrescription
CompanyAllergan

2 of 10  
Drug NameFlo-pred
PubMed HealthPrednisolone
Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
Drug LabelOMNIPRED (prednisolone acetate ophthalmic suspension) is an adrenocortical steroid product prepared as sterile ophthalmic suspension. The active ingredient is represented by the chemical structure:Established name: Prednisolone AcetateChemical name...
Active IngredientPrednisolone acetate
Dosage FormSuspension
RouteOral
Strengtheq 15mg base/5ml
Market StatusPrescription
CompanyTaro

3 of 10  
Drug NameOmnipred
PubMed HealthPrednisolone (Into the eye)
Drug ClassesOphthalmologic Agent
Drug LabelPRED FORTE (prednisolone acetate ophthalmic suspension, USP) 1% is a topical anti-inflammatory agent for ophthalmic use....
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyAlcon

4 of 10  
Drug NamePred forte
Drug LabelPRED MILD (prednisolone acetate ophthalmic suspension, USP) 0.12% is a topical anti-inflammatory agent for ophthalmic use. Structural Formula:...
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyAllergan

5 of 10  
Drug NamePred mild
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.12%
Market StatusPrescription
CompanyAllergan

6 of 10  
Drug NameBlephamide s.o.p.
PubMed HealthPrednisolone
Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
Drug LabelFlo-Pred (prednisolone acetate oral suspension) contains prednisolone which is the acetate ester of the glucocorticoid prednisolone. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from...
Active Ingredientsulfacetamide sodium; Prednisolone acetate
Dosage FormOintment
RouteOphthalmic
Strength0.2%; 10%
Market StatusPrescription
CompanyAllergan

7 of 10  
Drug NameFlo-pred
PubMed HealthPrednisolone
Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
Drug LabelOMNIPRED (prednisolone acetate ophthalmic suspension) is an adrenocortical steroid product prepared as sterile ophthalmic suspension. The active ingredient is represented by the chemical structure:Established name: Prednisolone AcetateChemical name...
Active IngredientPrednisolone acetate
Dosage FormSuspension
RouteOral
Strengtheq 15mg base/5ml
Market StatusPrescription
CompanyTaro

8 of 10  
Drug NameOmnipred
PubMed HealthPrednisolone (Into the eye)
Drug ClassesOphthalmologic Agent
Drug LabelPRED FORTE (prednisolone acetate ophthalmic suspension, USP) 1% is a topical anti-inflammatory agent for ophthalmic use....
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyAlcon

9 of 10  
Drug NamePred forte
Drug LabelPRED MILD (prednisolone acetate ophthalmic suspension, USP) 0.12% is a topical anti-inflammatory agent for ophthalmic use. Structural Formula:...
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyAllergan

10 of 10  
Drug NamePred mild
Active IngredientPrednisolone acetate
Dosage FormSuspension/drops
RouteOphthalmic
Strength0.12%
Market StatusPrescription
CompanyAllergan

4.2 Drug Indication

Prednisolone acetate is indicated as an anti-inflammatory or immunosuppressive agent for allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, or infectious conditions. Prednisolone acetate is also indicated in organ transplant patients, as well as endocrine or neoplastic conditions.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Prednisolone acetate has a short duration of action as the half life is 2-3 hours. Corticosteroids have a wide therapeutic window as patients make require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

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

Prednisolone acetate oral suspension given at a dose equivalent to 15mg prednisolone has a Cmax of 321.1ng/hr, a Tmaxof 1-2 hours, and an AUC of 1999.4ng\*hr/mL. The absorption pharmacokinetics of prednisolone acetate are not significantly different from a comparable dose of prednisolone.


Route of Elimination

Prednisolone acetate is predominantly excreted in the urine.


Volume of Distribution

The volume of distribution of the active metabolite, prednisolone, is 0.22/0.7L/kg.


Clearance

Data regarding the clearance of prednisolone acetate is not readily available.


5.5 Metabolism/Metabolites

Prednisolone acetate undergoes ester hydrolysis to [prednisolone]. After this step, the drug undergoes the normal metabolism of prednisolone. Prednisolone can be reversibly metabolized to [prednisone] which is then metabolized to 17,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII), 20-dihydro-prednisone (M-V), 6hydroxy-prednisone (M-XII), 6-hydroxy-prednisone (M-XIII), or 20-dihydro-prednisone (M-IV). 20-dihydro-prednisone is metabolized to 17,20,21-trihydroxy-5-pregn-1-en-3,11-dione(M-XVIII). Prednisolone is metabolized to 6-prednisolone (M-XI), 20-dihydro-prednisolone (M-III), 20-dihydro-prednisolone (M-II), 6hydroxy-prednisolone (M-VII), or 6hydroxy-prednisolone(M-VI). 6hydroxy-prednisolone is metabolized to 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-X). 6hydroxy-prednisolone is metabolized to 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII), 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-IX), and 6,11,17,21-tetrahydroxy-5-pregn-1-en-3,20-dione (M-XIV). MVIII is metabolized to 6,11,17,20,21-pentahydroxy-5-pregn-1-en-3-one (M-XV) and then to MXIV, while MIX is metabolized to 6,11,17,20,21-pentahydroxy-5-pregn-1-en-3-one (M-XVI) and then to MXIV. These metabolites and their glucuronide conjugates are excreted predominantly in the urine.


5.6 Biological Half-Life

Oral prednisolone acetate has a plasma half life of 2-3 hours.


5.7 Mechanism of Action

The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.


API Reference Price

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NEW MARINE LINES CHURCHGATE MUMBAI CITY ,? MUMBAI , ?MUMBAI ,? MAHARASHTRA,? 400020","city":"","supplier":"HENAN LIHUA PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"B M CHEMIE PRIVATE LIMITED","customerCountry":"INDIA","quantity":"60.00","actualQuantity":"60","unit":"KGS","unitRateFc":"665","totalValueFC":"40624.2","currency":"USD","unitRateINR":"56225.8","date":"26-Jul-2024","totalValueINR":"3373545","totalValueInUsd":"40624.2","indian_port":"Bombay Air","hs_no":"29372100","bill_no":"4710434","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"MIDDLE OF HUANGHE STREET, ANYANG HI- TECH INDUSTRY DEVELOPMENT ZONE,HENAN CHINA","customerAddress":"502 FLOOR 5 PLOT 7 2 JOLLY BHAWAN ,? NEW MARINE LINES CHURCHGATE MUMBAI CITY ,? MUMBAI , ?MUMBAI ,? MAHARASHTRA,? 400020"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723401000,"product":"METHYLPREDNISOLONE ACETATE STERILE MICRO","address":"PLOT NO-51,MEENAKSHI BAMBOO,GACHIB","city":"HYDERABAD,TELANGANA","supplier":"AXPLORA","supplierCountry":"ITALY","foreign_port":"MILANO","customer":"CRONUS PHARMA SPECIALITIES ","customerCountry":"INDIA","quantity":"2.29","actualQuantity":"2291","unit":"GMS","unitRateFc":"7.5","totalValueFC":"17504.7","currency":"USD","unitRateINR":"634.5","date":"12-Aug-2024","totalValueINR":"1453639.5","totalValueInUsd":"17504.7","indian_port":"GMR HYDERABAD AVIATION-SEZ","hs_no":"29372900","bill_no":"5006186","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Sterile","supplierPort":"MILANO","supplierAddress":"VIA PAVIA 1 GROPELLO CAIROLI PV IT SDNF Italy","customerAddress":"PLOT NO-51,MEENAKSHI BAMBOO,GACHIB"}]
20-Jan-2021
24-Aug-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)
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - SUSPENSION;OPHTHALMIC - 0.2%;10%

USFDA APPLICATION NUMBER - 12813

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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 1%

USFDA APPLICATION NUMBER - 17011

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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 0.12%

USFDA APPLICATION NUMBER - 17100

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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 1%

USFDA APPLICATION NUMBER - 17469

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DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - EQ 0.3...DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - EQ 0.3% BASE;1%

USFDA APPLICATION NUMBER - 50586

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DOSAGE - OINTMENT;OPHTHALMIC - EQ 0.3% BASE;0...DOSAGE - OINTMENT;OPHTHALMIC - EQ 0.3% BASE;0.6%

USFDA APPLICATION NUMBER - 50612

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