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Isosorbide
Also known as: 652-67-5, Isobide, Devicoran, Hydronol, Ismotic, 1,4:3,6-dianhydro-d-glucitol
Molecular Formula
C6H10O4
Molecular Weight
146.14  g/mol
InChI Key
KLDXJTOLSGUMSJ-JGWLITMVSA-N
FDA UNII
WXR179L51S

1,4:3,6-Dianhydro D-glucitol. Chemically inert osmotic diuretic used mainly to treat hydrocephalus; also used in glaucoma.
1 2D Structure

Isosorbide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
2.1.2 InChI
InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
2.1.3 InChI Key
KLDXJTOLSGUMSJ-JGWLITMVSA-N
2.1.4 Canonical SMILES
C1C(C2C(O1)C(CO2)O)O
2.1.5 Isomeric SMILES
C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O)O
2.2 Other Identifiers
2.2.1 UNII
WXR179L51S
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dianhydrosorbitol

2.3.2 Depositor-Supplied Synonyms

1. 652-67-5

2. Isobide

3. Devicoran

4. Hydronol

5. Ismotic

6. 1,4:3,6-dianhydro-d-glucitol

7. Sorbid

8. (3r,3ar,6s,6ar)-hexahydrofuro[3,2-b]furan-3,6-diol

9. (+)-d-isosorbide

10. Vascardin Dinitrate

11. Dianhydro-d-glucitol

12. D-glucitol, 1,4:3,6-dianhydro-

13. 1,4-dianhydrosorbitol

14. At-101

15. 1,4:3,6-dianhydro-d-sorbitol

16. 1,4:3,6-dianhydrosorbitol

17. D-isosorbide

18. (3s,3ar,6r,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol

19. Nsc-40725

20. Wxr179l51s

21. Sorbitol, 1,4:3,6-dianhydro-

22. Nsc40725

23. D-1,4:3,6-dianhydroglucitol

24. Ncgc00160508-01

25. Isosorbide 100 Microg/ml In Acetonitrile

26. Glucitol, 1,4:3,6-dianhydro-, D-

27. Dsstox_cid_26196

28. Dsstox_rid_81427

29. Dsstox_gsid_46196

30. Hydronol (van)

31. Isosorbida

32. Isosorbidum

33. Isosorbidum [inn-latin]

34. Polysorb P

35. Polysorb Ps

36. Isosorbida [inn-spanish]

37. Cas-652-67-5

38. Hsdb 3105

39. Einecs 211-492-3

40. Nsc 40725

41. Brn 0080510

42. Unii-wxr179l51s

43. Ismotic (tn)

44. Isobide (tn)

45. Mfcd00064827

46. Isosorbide [usan:usp:inn:ban:jan]

47. 1,6-dianhydrosorbitol

48. Isosorbide [mi]

49. Isosorbide [inn]

50. Isosorbide [jan]

51. Isosorbide [hsdb]

52. Isosorbide [inci]

53. Isosorbide [usan]

54. Isosorbide [vandf]

55. 1,6-dianhydro-d-glucitol

56. 1,6-dianhydro-d-sorbitol

57. Ec 211-492-3

58. Isosorbide [mart.]

59. Isosorbide [usp-rs]

60. Isosorbide [who-dd]

61. Dianhydro-d-glucitol, 98%

62. Schembl15495

63. 1,4:3,6-dianhydroglucitol

64. 5-19-03-00201 (beilstein Handbook Reference)

65. Bidd:gt0695

66. 1,4; 3,6-dianhydrosorbitol

67. Chebi:6060

68. Isosorbide (jp17/usp/inn)

69. D-glucitol,4:3,6-dianhydro-

70. Chembl1200660

71. Dtxsid5046196

72. Isosorbide [orange Book]

73. 1.4:3.6-dianhydro-d-glucitol

74. 1.4;3.6-dianhydro-d-glucitol

75. Isosorbide [usp Impurity]

76. Glucitol,4:3,6-dianhydro-, D-

77. Hy-b1469

78. Tox21_111861

79. Bbl029591

80. S4204

81. Stk801813

82. Zinc18284778

83. Akos005622709

84. Tox21_111861_1

85. Ccg-266173

86. Cs-5157

87. Db09401

88. Smp1_000177

89. Ncgc00160508-02

90. Ncgc00160508-03

91. As-14140

92. I0407

93. D00347

94. Ab01566931_01

95. Q1243800

96. Z2785909604

97. A912284d-27e1-4fb0-91b8-86c8ab905297

98. Wurcs=2.0/1,1,0/[h2122h_1-4_3-6]/1/

99. D-sorbitol, {1,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol,} Hexahydro-)

100. D-sorbitol,4:3,6-dianhydro(furo[3,2-b]furan-3,6-diol, Hexahydro-)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 146.14 g/mol
Molecular Formula C6H10O4
XLogP3-1.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass146.05790880 g/mol
Monoisotopic Mass146.05790880 g/mol
Topological Polar Surface Area58.9 Ų
Heavy Atom Count10
Formal Charge0
Complexity122
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Diuretics, Osmotic

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


...IS ORAL OSMOTIC AGENT USED FOR EMERGENCY TREATMENT OF ACUTE ANGLE-CLOSURE GLAUCOMA & OTHER CONDITIONS IN WHICH RAPID REDUCTION IN INTRAOCULAR PRESSURE & VITREOUS VOLUME IS INDICATED.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 366


ISOSORBIDE PRODUCES MORE SIGNIFICANT DIURESIS THAN GLYCERIN & CATHETERIZATION MAY BE NECESSARY.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 366


USE OF ISOSORBIDE STUDIED IN 23 CHILDREN WITH MYELODYSPLASIA & HYDROCEPHALUS. HEAD GROWTH RATE SIGNIFICANTLY DECR IN 18 PATIENTS. CEREBROSPINAL FLUID FLOW DECR BY 50% IN 12 ISOSORBIDE TRIALS. DRUG IS OF BENEFIT FOR TEMPORARY USE PRIOR TO INSERTION OF MECHANICAL SHUNT SYSTEM.

SHURTLEFF DB ET AL; J PEDIAT 83(OCT) 651 (1973)


For more Therapeutic Uses (Complete) data for ISOSORBIDE (8 total), please visit the HSDB record page.


4.2 Drug Indication

Isosorbide was previously indicated for temporary reduction of intraocular pressure and used to interrupt an acute glaucoma attack, however, this is not a currently approved indication. Refer to [isosorbide mononitrate] and [isosorbide dinitrate] drug entries for more isosorbide indications.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Isosorbide reduces intraocular pressure through its effects on ocular blood vessels. While in the blood, isosorbide promotes redistribution of water toward the circulation, promoting the excretion of urine.


5.2 MeSH Pharmacological Classification

Diuretics, Osmotic

Compounds that increase urine volume by increasing the amount of osmotically active solute in the urine. Osmotic diuretics also increase the osmolarity of plasma. (See all compounds classified as Diuretics, Osmotic.)


5.3 Absorption, Distribution and Excretion

Absorption

Isosorbide is rapidly absorbed after oral administration. Refer to [isosorbide mononitrate] for detailed absorption information.


IN DOGS, 5.5 MILLIMOLES/KG IV CAUSED LESS SOLUTE EXCRETION THAN AN EQUIMOLAR DOSE OF MANNITOL. THE DISTRIBUTION SPACE OF LABELED ISOSORBIDE WAS 54% OF BODY WT IN INTACT & NEPHRECTOMIZED DOGS. PROXIMAL TUBULAR REABSORPTION OF ISOSORBIDE WAS PROBABLY PASSIVE.

SHINABERGER JH ET AL; J PHARMACOL EXP THER 158(3) 460 (1967)


5.4 Biological Half-Life

TEN NORMAL MALES RECEIVED 0.25-1.5 G/KG ISOSORBIDE. DOSE RESPONSE EFFECTS ON WATER & OSMOLAR EXCRETION STATISTICALLY SIGNIFICANT. IN 9 VOLUNTEERS, ORALLY ADMIN ISOSORBIDE APPEARED RAPIDLY IN PLASMA & EXCRETED IN URINE WITH MEAN DISAPPEARANCE HALF-LIFE OF 8 HR.

NODINE JH ET AL; CLIN PHARMACOL THER 14(MAR-APR) 196 (1973)


ISOSORBIDE WAS RAPIDLY ABSORBED BY HUMANS FOLLOWING ORAL ADMIN & WAS EXCRETED UNCHANGED VIA KIDNEY WITH A MEAN DISAPPEARANCE T/2 OF APPROX 7 HR. IT INCREASED URINE VOLUME, CREATININE CLEARANCE, & SODIUM & CHLORIDE EXCRETION.

MODI KN ET AL; NEUROL INDIA 20(SUPPL 1) 122 (1972)


RABBITS GIVEN ORAL DOSES OF 2 G/KG FOR 1-7 DAYS HAD EST EXCRETION T/2 OF LESS THAN 6 HR IN ALL EYE TISSUE. PEAK LEVEL & EXCRETION T/2 WAS SIMILAR IN DAMAGED & UNDAMAGED EYE TISSUE, EXCEPT IN LENS OF DAMAGED EYES IN WHICH EXCRETION T/2 WAS SHORTER THAN OF NORMAL EYES.

HART LG ET AL; PROC SOC EXP BIOL MED 140(2) 715 (1972)


5.5 Mechanism of Action

Isosorbide causes vascular relaxation, reducing systolic ophthalmic artery pressure (SOAP), systolic ocular perfusion pressure (SOPP).


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