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Acetohexamide
Also known as: 968-81-0, Dymelor, Acetohexamid, Gamadiabet, Dimelor, Hypoglicil
Molecular Formula
C15H20N2O4S
Molecular Weight
324.4  g/mol
InChI Key
VGZSUPCWNCWDAN-UHFFFAOYSA-N
FDA UNII
QGC8W08I6I

A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide.
1 2D Structure

Acetohexamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(4-acetylphenyl)sulfonyl-3-cyclohexylurea
2.1.2 InChI
InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
2.1.3 InChI Key
VGZSUPCWNCWDAN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2CCCCC2
2.2 Other Identifiers
2.2.1 UNII
QGC8W08I6I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimelor

2. Dymelor

3. Gamadiabet

2.3.2 Depositor-Supplied Synonyms

1. 968-81-0

2. Dymelor

3. Acetohexamid

4. Gamadiabet

5. Dimelor

6. Hypoglicil

7. Metaglucina

8. Tsiklamid

9. Minoral

10. Ordimel

11. Acetohexamida

12. Acetohexamidum

13. 1-(4-acetylphenyl)sulfonyl-3-cyclohexylurea

14. N-(p-acetylphenylsulfonyl)-n'-cyclohexylurea

15. 1-((p-acetylphenyl)sulfonyl)-3-cyclohexylurea

16. 4-acetyl-n-[(cyclohexylamino)carbonyl]benzenesulfonamide

17. Nci-c03247

18. 1-(p-acetylbenzenesulfonyl)-3-cyclohexylurea

19. U-14812

20. 4-acetyl-n-((cyclohexylamino)carbonyl)benzenesulfonamide

21. Benzenesulfonamide, 4-acetyl-n-[(cyclohexylamino)carbonyl]-

22. Nsc-759128

23. Qgc8w08i6i

24. Benzenesulfonamide, 4-acetyl-n-((cyclohexylamino)carbonyl)-

25. 3-(4-acetylbenzenesulfonyl)-1-cyclohexylurea

26. Chebi:28052

27. 4-acetyl-n-(cyclohexylcarbamoyl)benzenesulfonamide

28. Acetohexamide [usan)

29. Dsstox_cid_7

30. Ncgc00015014-05

31. Cas-968-81-0

32. 1-(4-acetylphenyl)sulfonyl-3-cyclohexyl-urea

33. 1-[(p-acetylphenyl)sulfonyl]-3-cyclohexylurea

34. Acetohexamide [usan]

35. Dsstox_rid_75319

36. Dsstox_gsid_20007

37. Urea, 1-((p-acetylphenyl)sulfonyl)-3-cyclohexyl-

38. Urea, 1-[(p-acetylphenyl)sulfonyl]-3-cyclohexyl-

39. Acetohexamidum [inn-latin]

40. Acetohexamida [inn-spanish]

41. Ccris 4

42. Dymelor (tn)

43. Hsdb 3280

44. Sr-01000075539

45. Einecs 213-530-4

46. U 14812

47. Unii-qgc8w08i6i

48. Brn 2225115

49. N-(p-acetylbenzenesulfonyl)-n'-cyclohexylurea

50. Prestwick_3

51. 3-aminomethylbenzamide

52. 4-acetyl-n-[(cyclohexylamino)-carbonyl]benzenesulfonamide

53. Acetohexamide [usan:usp:inn:ban:jan]

54. Lopac-a-178

55. Prestwick0_000055

56. Prestwick1_000055

57. Prestwick2_000055

58. Prestwick3_000055

59. A-178

60. Acetohexamide [mi]

61. Acetohexamide [inn]

62. Acetohexamide [jan]

63. Acetohexamide [hsdb]

64. Chembl1589

65. Lopac0_000088

66. Schembl37620

67. Acetohexamide [vandf]

68. Bspbio_000209

69. Mls002154186

70. Acetohexamide [mart.]

71. Spbio_002130

72. Acetohexamide [who-dd]

73. 4-acetyl-n-(cyclohexylcarbamoyl)benzene-1-sulfonamide

74. Bpbio1_000231

75. Gtpl6793

76. Dtxsid7020007

77. Acetohexamide (jp17/usp/inn)

78. Acetohexamide, Analytical Standard

79. Hms1568k11

80. Hms2093h21

81. Hms2095k11

82. Hms2236m07

83. Hms3260a18

84. Hms3372b02

85. Hms3712k11

86. Pharmakon1600-01505425

87. Acetohexamide [orange Book]

88. Bcp34666

89. Hy-b0881

90. Acetohexamide [usp Impurity]

91. Tox21_110067

92. Tox21_202022

93. Tox21_302735

94. Tox21_500088

95. Nsc759128

96. S5717

97. Zinc18067894

98. Akos015916290

99. Tox21_110067_1

100. Ccg-204183

101. Db00414

102. Lp00088

103. Nsc 759128

104. Sdccgsbi-0050076.p003

105. Ncgc00015014-01

106. Ncgc00015014-02

107. Ncgc00015014-03

108. Ncgc00015014-04

109. Ncgc00015014-06

110. Ncgc00015014-07

111. Ncgc00015014-08

112. Ncgc00015014-11

113. Ncgc00015014-15

114. Ncgc00016555-01

115. Ncgc00091230-01

116. Ncgc00091230-02

117. Ncgc00091230-03

118. Ncgc00091230-04

119. Ncgc00256467-01

120. Ncgc00259571-01

121. Ncgc00260773-01

122. Smr001233477

123. Sbi-0050076.p002

124. Db-057652

125. Eu-0100088

126. Ft-0661053

127. C06806

128. D00219

129. 1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea

130. A845651

131. A935756

132. Dymelor; Gamadiabet; Acetohexamid; Dimelin; Dimelor

133. Q4673274

134. Sr-01000075539-1

135. Sr-01000075539-3

136. Sr-01000075539-6

137. Brd-k52960356-001-03-1

138. Brd-k52960356-001-06-4

139. Z1558572527

140. 1-acetyl-4-(([(cyclohexylamino)carbonyl]amino)sulfonyl)benzene #

141. Acetohexamide, United States Pharmacopeia (usp) Reference Standard

142. Benzenesulfonamide, 4-acetyl-n-((cyclohexylamino)carbonyl)

143. 1-[(4-acetylbenzene)sulfonyl]-3-cyclohexylurea 4-acetyl-n-(cyclohexylcarbamoyl)benzenesulfonamide

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 324.4 g/mol
Molecular Formula C15H20N2O4S
XLogP32.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass324.11437830 g/mol
Monoisotopic Mass324.11437830 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count22
Formal Charge0
Complexity498
Isotope Atom Count0
Defined Atom Stereocenter Count0
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

Hypoglycemic Agents

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


...USED IN TREATMENT OF MILD TO MODERATELY SEVERE DIABETES MELLITUS OF MATURITY-ONSET, NONKETOTIC TYPE IN PT IN WHOM DIET ALONE CANNOT CONTROL GLYCOSURIA.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 904


...MAY BE USEFUL IN PT WHO ARE ALLERGIC TO INSULIN & ARE UNWILLING OR UNABLE TO UNDERGO DESENSITIZATION OR...TO INJECT INSULIN. ...ESP USEFUL IN ELDERLY DIABETIC WITH POOR VISION WHO LIVES ALONE & IS IN DANGER OF DEVELOPING HYPOGLYCEMIA FROM INCORRECT INSULIN DOSAGE. /ORAL HYPOGLYCEMIC AGENTS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 593


...IT IS ONLY ONE WITH URICOSURIC PROPERTIES, SOME CLINICIANS PREFER THIS AGENT FOR DIABETIC WITH GOUT.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 595


For more Therapeutic Uses (Complete) data for ACETOHEXAMIDE (6 total), please visit the HSDB record page.


4.2 Drug Warning

HEMATOLOGICAL (LEUKOPENIA, AGRANULOCYTOSIS, THROMBOCYTOPENIA, PANCYTOPENIA, & HEMOLYTIC ANEMIA), CUTANEOUS (RASHES, PHOTOSENSITIVITY), GI (NAUSEA, VOMITING, RARELY HEMORRHAGE), & HEPATIC (INCR SERUM ALKALINE PHOSPHATASE, CHOLESTATIC JAUNDICE) REACTIONS HAVE BEEN REPORTED.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1521


INCIDENCE OF UNTOWARD EFFECTS IS LOW & REACTIONS ARE REVERSIBLE WHEN...DISCONTINUED.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 595


IT IS INEFFECTIVE IN JUVENILE-ONSET, UNSTABLE, OR BRITTLE DIABETES & IS CONTRAINDICATED IN DIABETES COMPLICATED BY ACIDOSIS, KETOSIS, SEVERE INFECTIONS, COMA, SEVERE TRAUMA, OR MAJOR SURGERY.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 904


Caution in elderly and patients with renal disease. Significant uricosuric effects. /from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 48-37


For more Drug Warnings (Complete) data for ACETOHEXAMIDE (17 total), please visit the HSDB record page.


4.3 Drug Indication

Used in the management of diabetes mellitus type 2 (adult-onset).


5 Pharmacology and Biochemistry
5.1 Pharmacology

Acetohexamide is an intermediate-acting, first-generation oral sulfonylurea. It lowers blood sugar by stimulating the pancreatic beta cells to secrete insulin and by helping the body use insulin efficiently. Due to its primary action on the pancreatic beta cells, the drug is only effective when there are functional pancreatic beta cells that can produce insulin granules. Acetohexamide has one-third the potency of chlorpropamide, and twice the potency of tolbutamide; however, similar hypoglycemic efficacy occurs with equipotent dosage of sulfonylureas.


5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)


5.3 ATC Code

A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10B - Blood glucose lowering drugs, excl. insulins

A10BB - Sulfonylureas

A10BB31 - Acetohexamide


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed from the GI tract.


ACETOHEXAMIDE IS RAPIDLY ABSORBED, & MAX HYPOGLYCEMIC ACTIVITY IS OBSERVED ABOUT 3 HR AFTER INGESTION. TOTAL DURATION OF ACTION IS 12-24 HR. MUCH OF ACTIVITY IS ASCRIBABLE TO METABOLITE, HYDROXYHEXAMIDE, WHICH HAS PLASMA T/2 OF ABOUT 6 HR...ACETOHEXAMIDE, HAS PLASMA T/2 OF 1.3 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1521


IN PERSONS WITH NORMAL RENAL & HEPATIC FUNCTION, MORE THAN 80% IS EXCRETED, LARGELY AS METABOLITES, IN 24 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1521


TIME OF PEAK CONCN AFTER ORAL DOSE: 3 HR /FROM TABLE/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 688


...5 DAYS AFTER ORAL DOSE...TO RATS. 86% WAS EXCRETED IN 24-HR URINE & 9% IN 48-HR FECES. RESULTS INDICATED RAPID ABSORPTION & EXCRETION...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 64


For more Absorption, Distribution and Excretion (Complete) data for ACETOHEXAMIDE (8 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Extensively metabolized in the liver to the active metabolite hydroxyhexamide, which exhibits greater hypoglycemic potency than acetohexamide. Hydroxyhexamide is believed to be responsible for prolonged hypoglycemic effects.


HYDROXYHEXAMIDE...MAJOR METABOLITE OF ACETOHEXAMIDE...IN HUMANS, HAS L-CONFIGURATION. ...CONTRIBUTES SIGNIFICANTLY TO HYPOGLYCEMIC RESPONSE THAT FOLLOWS ADMIN...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 221


PRINCIPAL ROUTE OF METABOLIC DEGRADATION IN MAN...REDUCTION OF P-ACETYL GROUP TO /1-[(P-ALPHA-HYDROXYETHYLBENZENE)SULFONYL]-3-CYCLOHEXYLUREA WHICH/ EXHIBITS HYPOGLYCEMIA IN MAN & OTHER ANIMALS. &...MAY PROLONG HYPOGLYCEMIC ACTIVITY OF ACETOHEXAMIDE /ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1964


Sulfonylureas are rapidly absorbed from the gastrointestinal tract, transported in the blood in highly protein-bound complexes, and subjected to extensive hepatic metabolism (except for chlorpropamide). Wide variation exists among the sulfonylureas in hepatic metabolism and remnal clearance, factors that tend to alter the steady-state serum levels. Metabolites may be active, so there may be a variation between the plasma half-life of the parent drug and the degree of hypoglycemia encountered. /Sulfonylurea/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 722


Active metabolite greater than parent drug. Metabolite excreted, in part, by kidney. /from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 48-37


5.6 Biological Half-Life

Elimination half-life of the parent compound is 1.3 hours and the elimination half-life of the active metabolite is approximately 5-6 hours.


Half-life...3.5-11 /hours/ /from table/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 722


5.7 Mechanism of Action

Sulfonylureas such as acetohexamide bind to an ATP-dependent K+ channel on the cell membrane of pancreatic beta cells. This inhibits a tonic, hyperpolarizing outflux of potassium, which causes the electric potential over the membrane to become more positive. This depolarization opens voltage-gated Ca2+ channels. The rise in intracellular calcium leads to increased fusion of insulin granulae with the cell membrane, and therefore increased secretion of (pro)insulin.


SULFONYLUREAS STIMULATE ISLET TISSUE TO SECRETE INSULIN. ... ADMIN OF SULFONYLUREAS INCR CONCN OF INSULIN IN PANCREATIC REIN... /SULFONYLUREAS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1520


Sulfonylureas are now...thought to act by a number of different mechanisms. 1. ...produce a depolarization of the pancreatic islet beta cell membrane potassium ion permeability. This results in a release of preformed insulin into the circulation and occurs mostly in non-insulin dependent diabetics. 2. ...reduce basal glucose output from the liver... 3. increase insulin receptor binding... 4. ...increasing intracellular levels of AMP... 5. increase insulin secretion by suppressing the release of glucagon and somatostatin from alpha and delta pancreatic cells. /Sulfonylureas/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 723


Sulfonylureas lower blood glucose in NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor on the beta cell. Sulfonylureas inhibit the ATP potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin containing granules by exocytosis, an effect similar to that of glucose. Insulin is a hormone that lowers blood glucose and controls the storage and metabolism of carbohydrates, proteins, and fats. Therefore, sulfonylureas are effective only in patients whose pancreata are capable of producing insulin. /Sulfonylurea antidiabetic agents/

USP. Convention. USPDI - Drug Information for the Health Care Professional. 19th ed. Volume I.Micromedex, Inc. Englewood, CO., 1999. Content Prepared by the U.S. Pharmacopieal Convention, Inc., p. 284


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