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Chemistry

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Also known as: 2-hydroxybenzamide, 65-45-2, O-hydroxybenzamide, Benzamide, 2-hydroxy-, Salicylic acid amide, 2-carbamoylphenol
Molecular Formula
C7H7NO2
Molecular Weight
137.14  g/mol
InChI Key
SKZKKFZAGNVIMN-UHFFFAOYSA-N
FDA UNII
EM8BM710ZC

Salicylamide
salicylamide is a natural product found in Streptomyces rimosus and Streptomyces spectabilis with data available.
1 2D Structure

Salicylamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-hydroxybenzamide
2.1.2 InChI
InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)
2.1.3 InChI Key
SKZKKFZAGNVIMN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C(=C1)C(=O)N)O
2.2 Other Identifiers
2.2.1 UNII
EM8BM710ZC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Salicylamide Sodium

2. Salicylamide Sulfate

3. Salicylamide, 3h-labeled

4. Salicylamide, Calcium (2:1) Salt

5. Salicylamide, Monosodium Salt

2.3.2 Depositor-Supplied Synonyms

1. 2-hydroxybenzamide

2. 65-45-2

3. O-hydroxybenzamide

4. Benzamide, 2-hydroxy-

5. Salicylic Acid Amide

6. 2-carbamoylphenol

7. Salamide

8. Urtosal

9. 2-carboxamidophenol

10. Flarpirina

11. Morsarinas

12. Algamon

13. Algiamida

14. Allevin

15. Amidosal

16. Andasol

17. Cetamide

18. Dolomide

19. Dropsprin

20. Eggosalil

21. Liquiprin

22. Novecyl

23. Panithal

24. Raspberin

25. Saliamid

26. Saliamin

27. Salicim

28. Salipur

29. Salizell

30. Salymid

31. Serramida

32. Acket

33. Anamid

34. Oramid

35. Salrin

36. Afko-sal

37. Amid-sal

38. Benzamide, O-hydroxy-

39. Salicilamida

40. Salicilamide

41. Salicylamidum

42. Amid Kyseliny Salicylove

43. Ohb

44. Nsc 3115

45. Mfcd00007978

46. 2-hydroxy-benzamide

47. H.p. 34

48. Sr 4326

49. Nsc-3115

50. Em8bm710zc

51. Chembl27577

52. Mls000069486

53. Chebi:32114

54. Ncgc00091414-02

55. Smr000046394

56. Salicylamide 100 Microg/ml In Acetonitrile

57. Dsstox_cid_1726

58. Dsstox_rid_76295

59. Dsstox_gsid_21726

60. Salizell (van)

61. Benesal (van)

62. Salicilamide [dcit]

63. Salicilamide [italian]

64. Salicylamidum [inn-latin]

65. Cas-65-45-2

66. Salicilamida [inn-spanish]

67. Ccris 6045

68. Hsdb 227

69. Amid Kyseliny Salicylove [czech]

70. Benzoic Acid, 2-hydroxy-, Amide

71. Einecs 200-609-3

72. Unii-em8bm710zc

73. Brn 0742439

74. Salicylamid

75. Samid

76. Ai3-03454

77. Hydroxy Benzamide

78. Saliclamide,(s)

79. Dihydroxybenzalamine

80. 2-oxidanylbenzamide

81. Salicylamide [usp:inn:ban:jan]

82. Salicylamide (tn)

83. Salicylamide, 99%

84. Spectrum_000946

85. Opera_id_1684

86. Spectrum2_001312

87. Spectrum3_000564

88. Spectrum4_000499

89. Spectrum5_001032

90. Salicylamide [mi]

91. Wln: Zvr Bq

92. Salicylamide [inn]

93. Salicylamide [jan]

94. Ec 200-609-3

95. Salicylamide [hsdb]

96. Salicylamide [inci]

97. Nciopen2_001127

98. Salicylamide [vandf]

99. Oprea1_069894

100. Schembl21646

101. Bspbio_001948

102. Kbiogr_001017

103. Kbioss_001426

104. Salicylamide [mart.]

105. 4-10-00-00169 (beilstein Handbook Reference)

106. Divk1c_000858

107. Salicylamide [usp-rs]

108. Salicylamide [who-dd]

109. Spectrum1500532

110. Salicylamide (jan/usp/inn)

111. Spbio_001403

112. Zinc2055

113. Dtxsid3021726

114. Hms502k20

115. Kbio1_000858

116. Kbio2_001426

117. Kbio2_003994

118. Kbio2_006562

119. Kbio3_001448

120. Nsc3115

121. Ninds_000858

122. Hms1920p14

123. Hms2092g15

124. Hms2232e07

125. Pharmakon1600-01500532

126. Component Of Tolagesic (salt/mix)

127. Hy-b0811

128. Salicylamide [usp Monograph]

129. Tox21_111129

130. Tox21_201944

131. Tox21_302801

132. Bbl016007

133. Bdbm50056900

134. Ccg-39250

135. Nsc757318

136. S6404

137. Stk301812

138. Akos000120983

139. Tox21_111129_1

140. Cs-7630

141. Db08797

142. Nsc-757318

143. Idi1_000858

144. Ncgc00091414-01

145. Ncgc00091414-03

146. Ncgc00091414-04

147. Ncgc00091414-05

148. Ncgc00091414-07

149. Ncgc00256376-01

150. Ncgc00259493-01

151. Ds-16216

152. Salicylamide, Puriss., >=99.0% (t)

153. Sbi-0051509.p003

154. Eu-0000058

155. Ft-0659360

156. S0006

157. D01811

158. Ab00052089_12

159. A835120

160. Ah-034/32461056

161. Sr-01000721923

162. Benzoic Acid,2-hydroxy,amide Salicylamide

163. J-509663

164. Q2496906

165. Sr-01000721923-2

166. Brd-k81130846-001-02-6

167. Brd-k81130846-001-12-5

168. Z68590124

169. Salicylamide, United States Pharmacopeia (usp) Reference Standard

170. Salicylamide, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 137.14 g/mol
Molecular Formula C7H7NO2
XLogP31.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass137.047678466 g/mol
Monoisotopic Mass137.047678466 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count10
Formal Charge0
Complexity136
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

Salicylamide, which is not metabolized to salicylate in vivo, has antipyretic, analgesic, and antiinflammatory effects similar to those of salicylate.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 650


SALICYLAMIDE, THE AMIDE OF SALICYLIC ACID, IS NO LONGER AN OFFICIAL DRUG. ITS EFFECTS IN MAN ARE NOT RELIABLE, & ITS USE IS NOT RECOMMENDED. THE SMALL DOSES INCLUDED IN "OVER-THE-COUNTER" ANALGESIC AND SEDATIVE MIXTURES ARE PROBABLY INEFFECTIVE.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 695


THIRD MOST COMMON COMPONENT OF NONPRESCRIPTION HYPNOTIC MIXT IS SODIUM SALICYLAMIDE. DOSE OF 1.3 G HAS SLIGHT SEDATIVE EFFECT; DOSE INCL IN NONPRESCRIPTION PRODUCTS IS 200-380 MG. /SODIUM SALICYLAMIDE/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 369


MEDICATION (VET): DEPRESSES INTESTINAL SMOOTH MUSCLE FUNCTION IN RABBIT & DOG TRIALS. MOST PROMISING INDICATION IN VET MEDICINE MAY BE FOR DOGS WITH CALCIUM PHOSPHATE CONTAINING URINARY CALCULI WHICH ITS COMPLEX GLUCURONIDE METABOLITES MAY HELP SOLUBILIZE.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 518


For more Therapeutic Uses (Complete) data for SALICYLAMIDE (10 total), please visit the HSDB record page.


4.2 Drug Warning

RESULTS OF THE FEW ACCEPTABLE CONTROLLED STUDIES ON SALICYLAMIDE INDICATE THAT THIS AGENT IS MUCH LESS EFFECTIVE THAN ASPIRIN AS ANALGESIC OR ANTIPYRETIC WHEN GIVEN IN SAME DOSE & THEREFORE IS TOO WEAK & UNRELIABLE TO BE USEFUL.

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 265


VET: WARNING: CATS MAY BE VERY SENSITIVE TO TOXIC EFFECT OF THIS DRUG.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 518


Dose related GI and CNS disturbances are the most common adverse effects of salicylamide. GI disturbances may include nausea, vomiting, heartburn, anorexia, or diarrhea. CNS disturbances may include dizziness, drowsiness, lightheadedness, faintness, or headache. Flushing, hyperventilation, sweating, dry mouth, rash, and thrombocytopenic purpura have also been reported. Adverse Gi and CNS effects occur infrequently with salicylamide doses occur infrequently with salicylamide doses of 325-650 mg but occur often with higher doses. Tinnitus, ecchymoses, hemorrhagic lesions, leukopenia, or thrombocytopenia may also occur with high doses.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 1417


4.3 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE AND 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-138


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


5.2 ATC Code

N - Nervous system

N02 - Analgesics

N02B - Other analgesics and antipyretics

N02BA - Salicylic acid and derivatives

N02BA05 - Salicylamide


5.3 Absorption, Distribution and Excretion

WHEN...GIVEN ORALLY...IT IS ABSORBED AND EXCRETED SO RAPIDLY THAT HIGH PLASMA LEVELS ARE NOT OBTAINED. IT DIFFUSES QUICKLY INTO THE VARIOUS BODY TISSUES AND INTO A MUCH GREATER APPARENT VOLUME OF BODY WATER... ANIMAL STUDIES SHOW...DIFFUSION RAPIDLY INTO THE BRAIN.

Di Palma, J. (ed.). Drill's Pharmacology in Medicine. 4th ed. New York: McGraw Hill Book Co., 1971., p. 401


/IN THE RABBIT/ RATE OF TRANSPORT OF FREE DRUG ACROSS BASAL BARRIER WAS BLOOD-FLOW-LIMITED, WHILE TRANSPORT OF THE GLUCURONIDE WAS LIMITED BY TRANSPORT STEP OUT OF EPITHELIAL CELL RATHER THAN BY RATE OF SYNTHESIS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 424


...WHEN DOSE OF SALICYLAMIDE EXCEEDS ABOUT 1 G...SIGNIFICANT LEVELS OF UNCHANGED DRUG APPEAR IN PLASMA.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 28:08


BIOAVAILABILITY STUDIES IN HUMAN/S/...INDICATED THAT SODIUM SALICYLAMIDE IN SOLN IS ABSORBED FASTER AFTER ORAL DOSES THAN SALICYLAMIDE IN TABLETS. SEDATIVE EFFECT OCCURRED EARLIER WITH NA SALT THAN WITH SALICYLAMIDE & EXTENT OF SEDATION INCR WITH INCR DOSES OF BOTH COMPD.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 25


For more Absorption, Distribution and Excretion (Complete) data for SALICYLAMIDE (9 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

SALICYLAMIDE IS CONJUGATED BY INTESTINAL MUCOSA AFTER ORAL ADMINISTRATION...

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 265


AFTER ADMIN OF SALICYLAMIDE TO CATS NO GLUCURONIDE CONJUGATE COULD BE DETECTED IN URINE. INCR AMT OF SULFURIC ACID ESTER CONJUGATE & SUBSTANTIALLY GREATER AMT OF 2,3-DIHYDROXYBENZAMIDE WERE PRODUCED BY CAT COMPARED WITH RABBIT.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 367


SALICYLAMIDE GIVES SALICYLAMIDE-2-BETA-D-GLUCURONIDE & SALICYLAMIDE-2-SULFATE IN MAN. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. S-3


AFTER ADMIN OF 5 MG/KG SALICYLAMIDE IN 5 MG/KG TYLENOL SUSPENSION, CHILDREN EXCRETED 78% OF DOSE AS SALICYLAMIDE SULFATE; ADULTS 36%. IN ADULTS, GLUCURONIDE WAS MAJOR PRODUCT. GLUCURONIDE CONJUGATION DEFICIENCY IN CHILDREN IS ACCOMPANIED BY A HIGHER RATE OF SULFATE FORMATION.

PMID:830879 ROBERTS ET AL; J PEDIATR 90 (JAN): 130 (1977)


For more Metabolism/Metabolites (Complete) data for SALICYLAMIDE (10 total), please visit the HSDB record page.


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28-Jan-2021
27-Jul-2024
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