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Chemistry

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Also known as: Isosorbide 5-mononitrate, 16051-77-7, Imdur, Corangin, Monosorbitrate, Monoket

Molecular Formula

C₆H₉NO₆

Molecular Weight

191.14 g/mol

InChI Key

YWXYYJSYQOXTPL-SLPGGIOYSA-N

FDA UNII

LX1OH63030

Isosorbide Mononitrate is the mononitrate salt form of isosorbide, an organic nitrate with vasodilator activity. Isosorbide mononitrate relaxes vascular smooth muscle by formation of the free radical nitric oxide (NO), which is identical to the endothelium-derived relaxing factor (EDRF). NO activates guanylyl cyclase, thereby increasing the synthesis of cGMP within smooth muscle, resulting in dephosphorylation of light chain myosin and relaxation of peripheral arteries and veins. In addition, isosorbide mononitrate relaxes coronary arteries, thereby increasing the blood circulation through the ischemic area. (NCI05)

Isosorbide mononitrate is a Nitrate Vasodilator. The physiologic effect of isosorbide mononitrate is by means of Vasodilation.

1 2D Structure

Isosorbide Mononitrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(3S,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate

2.1.2 InChI

InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1

2.1.3 InChI Key

YWXYYJSYQOXTPL-SLPGGIOYSA-N

2.1.4 Canonical SMILES

C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O

2.1.5 Isomeric SMILES

C1[C@@H]([C@@H]2[C@H](O1)[C@@H](CO2)O[N+](=O)[O-])O

2.2 Other Identifiers

2.2.1 UNII

LX1OH63030

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-ismn

2. 5-ismn Durules

3. Elantan

4. Imdur

5. Ismo

6. Isosorbide-5-mononitrate

7. Isosorbide-5-nitrate

8. Monizid

9. Mono Mac 50d

10. Monocinque

11. Monoket

12. Mononit

13. Olicard 40

14. Olicard-retard

2.3.2 Depositor-Supplied Synonyms

1. Isosorbide 5-mononitrate

2. 16051-77-7

3. Imdur

4. Corangin

5. Monosorbitrate

6. Monoket

7. Elantan

8. Mononit

9. Isosorbide-5-mononitrate

10. Isosorbide 5-nitrate

11. Ismn

12. Ismo

13. Monolong

14. Monopront

15. Monosordil

16. Nitramin

17. Orasorbil

18. Promocard

19. Sigacora

20. Sorbimon

21. Turimonit

22. Vasdilat

23. Duride

24. Imtrate

25. Ismexin

26. Medocor

27. Monicor

28. Olicard

29. Pertil

30. Uniket

31. Ismox

32. Monodur Durules

33. Mono Corax

34. Monisid

35. Monocord

36. Isosorbidi Mononitras [latin]

37. Isosorbidi Mononitras

38. Mononitrate D'isosorbide [french]

39. Is 5-mn

40. Mononitrate D'isosorbide

41. Mononitrato De Isosorbida [spanish]

42. 1,4:3,6-dianhydro-d-glucitol 5-nitrate

43. Mononitrato De Isosorbida

44. Iso-5-mononitrate

45. Ahr-4698

46. Is-5-mn

47. D-glucitol, 1,4:3,6-dianhydro-, 5-nitrate

48. Is-5mn

49. 1,4:3,6-dianhydro-5-o-nitro-d-erythro-hexitol

50. Monizid

51. Bm 22.145

52. Bm-22-145

53. Vasotrate

54. Epicordin

55. Monoclair

56. Monotrate

57. Olicardin

58. Percorina

59. Edistol

60. Etimonis

61. Isomonat

62. Isomonit

63. Multitab

64. Titarane

65. Conpin

66. Imazin

67. Imodur

68. Isomon

69. Iturol

70. Monis

71. Nitex

72. Plodin

73. Ihd

74. Monosigma

75. Elantan Retard

76. Mono-sanorania

77. Monoket Retard

78. Nsc-758619

79. Elantan Long

80. Imdur Durules

81. Corangin Sr

82. Mono Mack

83. Mono-mack

84. Conpin Retardkaps

85. Diluted Isosorbide Mononitrate

86. Fem-mono

87. Ismn Lannacher

88. Monoket Od

89. Ismn Apogepha

90. Ismn Heumann

91. Ismn Basics

92. Pentacard 20

93. [(3s,3ar,6r,6as)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] Nitrate

94. 1,4:3,6-dianhydro-5-o-nitro-d-glucitol

95. Mono Corax Retard

96. Chebi:6062

97. Ismn Hexal

98. Ismn Stada

99. Monocord 20

100. Monocord 40

101. Monolong 40

102. Monolong 60

103. Ismn Atid

104. Mononit 20

105. Mononit 40

106. Isopen-20

107. Monocord 50 Sr

108. Mononit Retard 50

109. 5-ismn

110. (3r,3as,6s,6ar)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl Nitrate

111. Imdur 60

112. Ismn Abz

113. Lx1oh63030

114. Monit 20

115. Ismn Al

116. Ismo-20

117. Isosorbide-5-nitrate

118. Monocedocard

119. Bm-22145

120. Is 5mn

121. Monosorb

122. Bm-22.145

123. (3r,3as,6s,6ar)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl Nitrate

124. Bm 22.145is 5-mnahr-4698

125. Glucitol, 1,4:3,6-dianhydro-, 5-nitrate, D-

126. Monomax

127. Ahr 4698

128. Monosorb Xl 60

129. Ccris 1911

130. Imdur (tn)

131. Isosorbide Mononitrate (isosorbide 5-nitrate)

132. Ismo (tn)

133. Bm 22-145

134. Sr-05000001872

135. Einecs 240-197-2

136. Un3251

137. Brn 5851319

138. Leicester

139. Unii-lx1oh63030

140. Ncgc00159334-02

141. Isorbide Mononitrate

142. Mfcd00143462

143. Isosorbide-mononitrate

144. Isosobide-5-mononitrate

145. 5-isosorbide Mononitrate

146. Dsstox_cid_3176

147. Isosorbide Mononitrate,(s)

148. Chembl1311

149. Dsstox_rid_76905

150. Dsstox_gsid_23176

151. Isosorbide Mononitrate [usan:usp:inn:ban:jan]

152. Schembl26781

153. Gtpl7052

154. Dtxsid9023176

155. Niosh/lz4385560

156. Hms2093k07

157. Hms3715i08

158. Pharmakon1600-01503807

159. Hy-b0642

160. Zinc1849548

161. Isosorbide Mononitrate [inn]

162. Isosorbide Mononitrate [jan]

163. Tox21_111581

164. Isosorbide Mononitrate [usan]

165. Nsc758619

166. S4633

167. Isosorbide Mononitrate [vandf]

168. Akos005110986

169. Isosorbide Mononitrate [mart.]

170. Ac-8830

171. Ccg-213200

172. Cs-3495

173. Db01020

174. Isosorbide Mononitrate [who-dd]

175. Nsc 758619

176. Isosorbide Mononitrate (jp17/usp/inn)

177. Ncgc00167981-01

178. Ncgc00167981-03

179. D-1,4:3,6-dianhydroglucitol 5-nitrate

180. 1,4:3,6-dianhydrosorbitol 5-mononitrate

181. Sbi-0206724.p001

182. Cas-16051-77-7

183. Isosorbide Mononitrate [orange Book]

184. Bb 0261072

185. I0403

186. Isosorbide Dinitrate Isosorbide-5-mononitrate

187. Isosorbide Mononitrate [usp Impurity]

188. Lz43855600

189. C07714

190. D00630

191. Diluted Isosorbide Mononitrate [usp-rs]

192. W15583

193. Ab01563284_01

194. Q423401

195. Sr-05000001872-1

196. Sr-05000001872-2

197. W-107977

198. Brd-k82225283-001-01-5

199. Diluted Isosorbide Mononitrate [usp Monograph]

200. Isosobide-5-mononitrate [un3251] [flammable Solid]

201. Isosorbide Mononitrate 1.0 Mg/ml In Dimethyl Sulfoxide

202. Isosorbide Dinitrate Isosorbide-5-mononitrate [mi]

203. Isosorbide Dinitrate, Diluted Impurity C [ep Impurity]

204. [(3r,3as,6s,6ar)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] Nitrate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₆H₉NO₆
Molecular Weight	191.14 g/mol
XLogP3	-0.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	191.04298701 g/mol
Monoisotopic Mass	191.04298701 g/mol
Topological Polar Surface Area	93.7 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	216
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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 4
Drug Name	Isosorbide mononitrate
PubMed Health	Isosorbide Mononitrate (By mouth)
Drug Classes	Antianginal, Coronary Vasodilator
Drug Label	Isosorbide mononitrate (ISMN), an organic nitrate and the major biologically active metabolite of isosorbide dinitrate (ISDN), is a vasodilator with effects on both arteries and veins.Each tablet, for oral administration, contains either 30 mg, 60 mg...
Active Ingredient	Isosorbide mononitrate
Dosage Form	Tablet, extended release; Tablet
Route	Oral
Strength	30mg; 120mg; 60mg; 10mg; 20mg
Market Status	Prescription
Company	Vintage Pharms; Ani Pharms; Torrent Pharms; Hikma Pharms; Dexcel; Nesher Pharms; Kremers Urban Pharms; Actavis Elizabeth

2 of 4
Drug Name	Monoket
PubMed Health	Isosorbide Mononitrate (By mouth)
Drug Classes	Antianginal, Coronary Vasodilator
Drug Label	monoket, an organic nitrate, is a vasodilator with effects on both arteries and veins. The empirical formula is C6H9NO6 and the molecular weight is 191.14. The chemical name for monoket is 1,4:3,6-Dianhydro-D-glucitol 5-nitrate and the compound h...
Active Ingredient	Isosorbide mononitrate
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Kremers Urban Pharms

3 of 4
Drug Name	Isosorbide mononitrate
PubMed Health	Isosorbide Mononitrate (By mouth)
Drug Classes	Antianginal, Coronary Vasodilator
Drug Label	Isosorbide mononitrate (ISMN), an organic nitrate and the major biologically active metabolite of isosorbide dinitrate (ISDN), is a vasodilator with effects on both arteries and veins.Each tablet, for oral administration, contains either 30 mg, 60 mg...
Active Ingredient	Isosorbide mononitrate
Dosage Form	Tablet, extended release; Tablet
Route	Oral
Strength	30mg; 120mg; 60mg; 10mg; 20mg
Market Status	Prescription
Company	Vintage Pharms; Ani Pharms; Torrent Pharms; Hikma Pharms; Dexcel; Nesher Pharms; Kremers Urban Pharms; Actavis Elizabeth

4 of 4
Drug Name	Monoket
PubMed Health	Isosorbide Mononitrate (By mouth)
Drug Classes	Antianginal, Coronary Vasodilator
Drug Label	monoket, an organic nitrate, is a vasodilator with effects on both arteries and veins. The empirical formula is C6H9NO6 and the molecular weight is 191.14. The chemical name for monoket is 1,4:3,6-Dianhydro-D-glucitol 5-nitrate and the compound h...
Active Ingredient	Isosorbide mononitrate
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Kremers Urban Pharms

4.2 Drug Indication

Isosorbide mononitrate is indicated for the prevention and management of angina pectoris due to coronary artery disease. The onset of action of oral isosorbide mononitrate is not sufficiently rapid to be useful in aborting an acute anginal episode.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Isosorbide mononitrate is an anti-anginal agent and vasodilator that relaxes vascular smooth muscle to prevent and manage angina pectoris. The pharmacological action is mediated by the active metabolite, [nitric oxide], which is released when isosorbide mononitrate is metabolized. Nitric oxide works on both arteries and veins, but predominantly veins: by relaxing veins and reducing the central venous pressure, nitric oxide causes venous pooling and a decrease in the venous return to the heart, thus decreasing cardiac preload. In healthy subjects, the stroke volume is decreased and venous pooling can occur in the standing posture, leading to postural hypotension and dizziness. At therapeutic doses of isosorbide mononitrate, nitric oxide has a bigger effect on larger muscular arteries over small resistance arteries. Arterial relaxation leads to reduced systemic vascular resistance and systolic blood (aortic) pressure, decreasing to decreased cardiac afterload. The direct dilator effect on coronary arteries opposes the coronary artery spasm in variant angina or angina pectoris. At larger doses, nitric oxide causes the resistance arteries and arterioles to dilate, reducing arterial pressure via coronary vasodilatation. This leads to increased coronary blood flow. Reduced cardiac preload and afterload caused by nitric oxide causes a reduction in myocardial oxygen consumption; decreased myocardial oxygen demand, along with increased coronary blood flow, leads to an increased in the oxygen content of coronary sinus blood and the relief from ischemia. The end effect of isosorbide mononitrate include decreased cardiac oxygen consumption, redistribution coronary flow toward ischemic areas via collaterals, and the relief of coronary spasms. Nitric oxide can also increase the rate of relaxation of cardiac muscles, which is an effect outside of vascular smooth muscles. Organic nitrates can also relax other types of smooth muscles, including esophageal and biliary smooth muscle. The anti-anginal activity of isosorbide mononitrate was observed about 1 hour after dosing, and the peak effect was achieved from 1-4 hours after dosing. The duration of anti-anginal action of at least 12 hours was observed with an asymmetrical dosing regimen.

5.2 MeSH Pharmacological Classification

Nitric Oxide Donors

A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81) (See all compounds classified as Nitric Oxide Donors.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ISOSORBIDE MONONITRATE

5.3.2 FDA UNII

LX1OH63030

5.3.3 Pharmacological Classes

Nitrates [CS]; Vasodilation [PE]; Nitrate Vasodilator [EPC]

5.4 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01D - Vasodilators used in cardiac diseases

C01DA - Organic nitrates

C01DA14 - Isosorbide mononitrate

5.5 Absorption, Distribution and Excretion

Absorption

Upon oral administration, isosorbide mononitrate is rapidly and completely absorbed from the gastrointestinal tract. Isosorbide mononitrate has a dose-linear kinetics and the absolute bioavailability is nearly 100%. The Cmax is reached within 30 to 60 minutes following administration.

Route of Elimination

In a human radio-labelled drug study, about 93% of the total dose was excreted in the urine within 48 hours. Following oral administration of 20 mg, only 2% of isosorbide mononitrate was excreted unchanged in the urine within 24 hours. Among the excreted dose, nearly half of the dose was found de-nitrated in urine as isosorbide and sorbitol: approximately 30% is excreted as isosorbide and about 17% is the 2-glucuronide of mononitrate. These metabolites were not vasoactive or pharmacologically active. Renal excretion was complete after 5 days, and fecal excretion accounted for only 1% of drug elimination.

Volume of Distribution

The volume of distribution is approximately 0.6 L/kg, which is approximately the volume of total body water.

Clearance

The total body clearance is 115-120 mL/min.

5.6 Metabolism/Metabolites

Isosorbide mononitrate is not subject to first pass metabolism in human liver. Detectable metabolites include isosorbide, sorbitol, and 2-glucuronide of mononitrate, which are pharmacologically inactive.

5.7 Biological Half-Life

The elimination half-life of isosorbide mononitrate is about 5 hours. The elimination half-life of its metabolites, isosorbide and 2-glucuronide of mononitrate, are 8 hours and 6 hours, respectively.

5.8 Mechanism of Action

Isosorbide mononitrate acts as a prodrug for nitric oxide (NO), which is a potent vasodilator gas that is released when the drug is metabolized. NO activates soluble guanylyl cyclase in vascular endothelial cells, which increases the intracellular concentrations of cyclic GMP (cGMP). cGMP activates cGMP-dependent protein kinases, such as protein kinase G and I, which activates the downstream intracellular cascades. The downstream cascade results in reduced intracellular concentrations of calcium, caused by processes including inhibition of IP₃-mediated pathway, phosphorylation of big calcium-activated potassium channel leading to cell hyperpolarization and reduced calcium influx, and increased calcium efflux via the Ca2+-ATPase-pump. Reduced intracellular calcium concentrations lead to the dephosphorylation of myosin light chains and the relaxation of smooth muscle cells.

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API Reference Price

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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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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 20215

DOSAGE - TABLET;ORAL - 20MG

USFDA APPLICATION NUMBER - 20215

Related Excipient Companies

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Excipients by Applications

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Fillers, Diluents & Binders

Coating Systems & Additives

Direct Compression

Controlled & Modified Release

Thickeners and Stabilizers

Granulation

Solubilizers

Lubricants & Glidants

Disintegrants & Superdisintegrants

Co-Processed Excipients

Film Formers & Plasticizers

Parenteral

Taste Masking

Topical

Emulsifying Agents

Chewable & Orodispersible Aids

Empty Capsules

API Stability Enhancers

Vegetarian Capsules

Coloring Agents

Rheology Modifiers

Surfactant & Foaming Agents

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Global Sales Information

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US Medicaid Prescriptions

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APIs

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REF. STANDARDS & IMPURITIES

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EDQM

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USP

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Market Place

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

29 API Suppliers

12 USDMF

10 CEP/COS

4 JDMF

2 EU WC

5 KDMF

5 NDC API

11 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

1 Drugs in Development

FINISHED DOSAGE FORMULATIONS

218 FDF Dossiers

49 FDA Orange Book

114 Europe

5 Canada

12 Australia

7 South Africa

31 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

TABLET;ORAL - 10MG

TABLET;ORAL - 20MG

RELATED EXCIPIENT COMPANIES

4 SPI Pharma

2 Seqens

3 DKSH

4 Faran Shimi Pharmaceutical

1 Boai NKY Pharmaceuticals Ltd

12 Gangwal Healthcare

2 Nanjing Well Pharmaceutical

1 Pfanstiehl

1 ACG Worldwide

6 Actylis

1 Aeon Procare

1 Alcedo Pharmachem

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

19 BASF

12 Corel Pharma Chem

6 DFE Pharma

1 Finar

10 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

3 Ingredion Pharma Solutions

36 Kerry

4 Kima Chemical

6 Lonza Capsugel

14 Microlex e.U

1 Nanjing Bold Chemical

2 Nomisma Healthcare

2 Novo Excipients

3 Pharmatrans-Sanaq

4 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

17 Roquette

13 Seppic

5 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

11 Sigachi Industries

3 The Dow Chemical Company

4 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

68 Fillers, Diluents & Binders

46 Coating Systems & Additives

33 Direct Compression

32 Controlled & Modified Release

23 Thickeners and Stabilizers

22 Granulation

21 Solubilizers

21 Lubricants & Glidants

20 Disintegrants & Superdisintegrants

17 Co-Processed Excipients

13 Film Formers & Plasticizers

11 Parenteral