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Chemistry

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Also known as: N-phenylacetamide, 103-84-4, Antifebrin, Acetamidobenzene, Acetanilid, Acetanil

Molecular Formula

C₈H₉NO

Molecular Weight

135.16 g/mol

InChI Key

FZERHIULMFGESH-UHFFFAOYSA-N

FDA UNII

SP86R356CC

acetanilide is a natural product found in Dendrobium moniliforme, Dendrobium officinale, and other organisms with data available.

1 2D Structure

Acetanilide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-phenylacetamide

2.1.2 InChI

InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

2.1.3 InChI Key

FZERHIULMFGESH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)NC1=CC=CC=C1

2.2 Other Identifiers

2.2.1 UNII

SP86R356CC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetanilid

2.3.2 Depositor-Supplied Synonyms

1. N-phenylacetamide

2. 103-84-4

3. Antifebrin

4. Acetamidobenzene

5. Acetanilid

6. Acetanil

7. Acetylaniline

8. Acetamide, N-phenyl-

9. N-acetylaniline

10. Phenalgene

11. Acetic Acid Anilide

12. Acetylaminobenzene

13. Acetoanilide

14. Phenalgin

15. Aniline, N-acetyl-

16. N-acetylarylamine

17. Benzenamine, N-acetyl-

18. Usaf Ek-3

19. Nsc 7636

20. An [analgesic]

21. N-acetylaminobenzene

22. Acetanilidum

23. Antifebrinum

24. Ethananilide

25. Mfcd00008674

26. N-phenyl-acetamide

27. Acetanilide (antifebrin)

28. Nsc-7636

29. Sp86r356cc

30. Chebi:28884

31. Nsc7636

32. Acetamide, N-phenyl-, Homopolymer

33. N-phenylacetamide;n-phenylacetamide

34. Nsc-203231

35. Ncgc00091326-01

36. Dsstox_cid_2543

37. Dsstox_rid_76620

38. Dsstox_gsid_22543

39. N-phenylacetamide (acetanilide)

40. Caswell No. 003e

41. Acetanilide (ring-13c6)

42. N-phenylethanamide

43. Acetanilide [nf]

44. 137020-73-6

45. Cas-103-84-4

46. Smr001306799

47. Acetic Acid Amide, N-phenyl-

48. Ccris 4452

49. Hsdb 2665

50. Einecs 203-150-7

51. Unii-sp86r356cc

52. Ai3-01045

53. Phnhac

54. N-phenyl Acetamide

55. Acetanilide, 99%

56. Spectrum_000178

57. Acetanilide [mi]

58. Spectrum2_001434

59. Spectrum3_000935

60. Spectrum4_001034

61. Spectrum5_000989

62. Acetanilid [inci]

63. Acetanilide [hsdb]

64. Wln: 1vmr

65. Acetanilide (acetylaniline)

66. Acetanilide [vandf]

67. Acetanilidum [hpus]

68. Acetanilide-[ring-13c6]

69. Acetanilide [mart.]

70. Schembl24681

71. Acetanilide [usp-rs]

72. Acetanilide [who-dd]

73. Kbiogr_001587

74. Kbioss_000658

75. 55576-55-1

76. Mls002207284

77. Mls002415707

78. Divk1c_000073

79. Spectrum1501173

80. Spbio_001568

81. Chembl269644

82. Acetaminophen Related Compound D

83. Dtxsid2022543

84. Schembl14255226

85. Acetanilide, Lr, >=98.5%

86. Hms500d15

87. Kbio1_000073

88. Kbio2_000658

89. Kbio2_003226

90. Kbio2_005794

91. Kbio3_001970

92. Ninds_000073

93. Acetic Acid,amide,n-phenyl

94. Bcpp000440

95. Hms1921n07

96. Hms2092j11

97. Hms2234e18

98. Hms3374l04

99. Hms3651d07

100. Pharmakon1600-01501173

101. Zinc142824

102. Bcp02363

103. Tox21_111113

104. Tox21_200925

105. Ccg-38984

106. Nsc757879

107. S2538

108. Stk046402

109. Akos000121114

110. Tox21_111113_1

111. Bcp9000226

112. Nsc-757879

113. Acetanilide, Nist(r) Srm(r) 141d

114. Idi1_000073

115. Acetanilide Melting Point Standard

116. Ncgc00091326-02

117. Ncgc00091326-03

118. Ncgc00091326-04

119. Ncgc00091326-06

120. Ncgc00258479-01

121. As-13389

122. Sbi-0051673.p002

123. B2071

124. Cs-0010112

125. Ft-0621730

126. Ft-0621731

127. Ft-0661046

128. Ft-0661047

129. Ft-0661154

130. Paracetamol Impurity D [ep Impurity]

131. Sw220057-1

132. C07565

133. D72485

134. Ab00052235_07

135. Ab00052235_08

136. Acetanilide, Purified By Sublimation, >=99.9%

137. Acetanilide, Puriss. P.a., >=99.5% (chn)

138. Acetaminophen Related Compound D [usp-rs]

139. Ah-034/32461060

140. Q421761

141. Sr-05000001777

142. Q-200578

143. Sr-05000001777-1

144. Acetaminophen Related Compound D [usp Impurity]

145. Brd-k11094367-001-04-4

146. F0808-0907

147. Acetanilide, Zone-refined, Purified By Sublimation, >=99.95%

148. Acetaminophen Related Compound D, United States Pharmacopeia (usp) Reference Standard

149. Acetanilide Melting Point Standard, United States Pharmacopeia (usp) Reference Standard

150. Acetanilide (acetaminophen Related Compound D), Pharmaceutical Secondary Standard; Certified Reference Material

151. Acetanilide Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₈H₉NO
Molecular Weight	135.16 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	135.068413911 g/mol
Monoisotopic Mass	135.068413911 g/mol
Topological Polar Surface Area	29.1 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	116
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Therapeutic Uses

IT IS PARTICULARLY EFFECTIVE AS AN ANALGESIC IN PAIN OF THE NEURALGIC TYPE...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1053

MEDICATION (VET): ANALGESIC, ANTIPYRETIC AGENT

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 10

4.2 Drug Warning

.../ACETANILID IS/ ESPECIALLY DANGEROUS IN ANEMIA, AFTER HEMORRHAGE AND DURING MENSTRUATION.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 81

...ITS USE AS AN ANALGESIC /IS CONDEMNED/ BECAUSE SAFER & EQUALLY EFFECTIVE DRUGS ARE AVAILABLE.

American Medical Association, Council on Drugs. AMA Drug Evaluations. 2nd ed. Acton, Mass.: Publishing Sciences Group, Inc., 1973., p. 262

...NECROSIS OF RENAL PAPILLAE & TERMINAL TUBULES HAS BEEN ASSOCIATED WITH EXCESSIVE DOSES OF DRUG MIXTURES CONTAINING ACETOPHENETIDIN WITH...ACETANILID...

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 81

...ACETANILID.../PRODUCES/ HEMOLYTIC ANEMIA IN INDIVIDUALS WITH GENETIC DEFICIENCY OF ERYTHROCYTIC GLUCOSE-6-PHOSPHATE DEHYDROGENASE. DARK SKINNED RACES HAVE HIGHER INCIDENCE THAN LIGHT SKINNED BUT DISEASE HAS NOT BEEN NOTED IN NORTH AMERICAN INDIANS OR ESKIMOS.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 232

For more Drug Warnings (Complete) data for ACETANILIDE (6 total), please visit the HSDB record page.

4.3 Minimum/Potential Fatal Human Dose

/BETWEEN 4 & 5/: 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOONFUL & 1 OZ FOR A 70 KG PERSON (150 LB). 5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL 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-139

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

IT IS READILY EXCRETED IN THE URINE AS SULFATE OR GLUCURONATE CONJUGATE OF THE PHENOL /N-ACETYL-P-AMINOPHENOL/.

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1835

36% OF ACETANILIDE DISSOLVED IN 0.1 N HCL (PKA 0.3) WAS ABSORBED FROM RAT STOMACH IN ONE HOUR. /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 27

...GREATER THAN 99.9% OF ACETANILIDE REMAINS UN-IONIZED @ BODY PH, FACILITATING ABSORPTION FROM BLOOD TO CEREBROSPINAL FLUID. THE BLOOD-CEREBROSPINAL FLUID PERMEABILITY COEFFICIENT IS 0.039/MIN. /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 82

.../ACETANILID IS/ READILY ABSORBED FROM GASTROINTESTINAL TRACT.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 80

For more Absorption, Distribution and Excretion (Complete) data for ACETANILIDE (14 total), please visit the HSDB record page.

5.2 Metabolism/Metabolites

.../RESEARCHERS/ FOUND THAT STARVATION DECREASED RATE OF METABOLISM OF...ACETANILIDE. ...STARVATION REDUCED OXIDATIVE PATHWAYS OF MALE RATS...

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 529

STRAIN DIFFERENCES /WITHIN THE SAME SPECIES/ WERE...NOTED IN ACETANILIDE...METABOLISM.

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 530

HEPATIC MICROSOMES FROM RABBITS WITH OBSTRUCTIVE JAUNDICE SHOW IMPAIRED METABOLISM OF ACETANILIDE...

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 530

2 NEW URINARY METABOLITES OF ACETANILIDE IN RATS THAT HAVE BEEN IDENTIFIED AS N-ACETYL-S-(5-ACETAMIDO-2-HYDROXYPHENYL)CYSTEINE & N-ACETYL-S-(3-ACETAMIDOPHENYL)CYSTEINE MAY HAVE BEEN FORMED VIA AN INTERMEDIATE EPOXIDE.

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. 182

For more Metabolism/Metabolites (Complete) data for ACETANILIDE (20 total), please visit the HSDB record page.

Acetanilide has known human metabolites that include N-Hydroxy-N-phenylacetamide and acetaminophen.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.3 Biological Half-Life

T/2 OF ACETANILID MEASURED IN POPULATIONS OF YOUNG (AGED 20-35 YR) & ELDERLY (AGED OVER 65 YR) PEOPLE (TOTAL= 93). T/2 WERE SIGNIFICANTLY LONGER IN THE ELDERLY.

FARAH F ET AL; HEPATIC DRUG ACETYLATION AND OXIDATION: EFFECTS OF AGING IN MAN; BR MED J 2(JUL 16) 155 (1977)

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CORP","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"COLOURTEX INDUSTRIES PRIVATE ","customerCountry":"INDIA","quantity":"15538.00","actualQuantity":"15538","unit":"KGS","unitRateFc":"2.2","totalValueFC":"34245.1","currency":"USD","unitRateINR":"185.2","date":"29-Oct-2024","totalValueINR":"2877497.76","totalValueInUsd":"34245.1","indian_port":"JNPT","hs_no":"29242990","bill_no":"6398632","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"10F, BUILDING 4, TAIPING FINANCE TO WER,NO.199 SHIMIN STREET,SHANGCHENG DISTRICT,HANGZHOU,CHINA China","customerAddress":"SURVEY NO. 80., G.I.D.C.,,PANDESAR"}]

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