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Nalidixic Acid

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Chemistry

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Also known as: 389-08-2, Nalidixate, Nalidixin, Nevigramon, Uronidix, Neggram

Molecular Formula

C₁₂H₁₂N₂O₃

Molecular Weight

232.23 g/mol

InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

FDA UNII

3B91HWA56M

A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA GYRASE.

1 2D Structure

Nalidixic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

2.1.2 InChI

InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

2.1.3 InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

3B91HWA56M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Nalidixic

2. Anhydrous, Nalidixate Sodium

3. Nalidixate Sodium

4. Nalidixate Sodium Anhydrous

5. Nalidixin

6. Nevigramon

7. Sodium Anhydrous, Nalidixate

8. Sodium Nalidixic Acid, Anhydrous

9. Sodium Nalidixic Acid, Monohydrate

10. Sodium, Nalidixate

2.3.2 Depositor-Supplied Synonyms

1. 389-08-2

2. Nalidixate

3. Nalidixin

4. Nevigramon

5. Uronidix

6. Neggram

7. Innoxalon

8. Nalidixan

9. Nalitucsan

10. Sicmylon

11. Unaserus

12. Nalidic Acid

13. Nalidixinic Acid

14. 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

15. Wintomylon

16. Dixiben

17. Dixinal

18. Jicsron

19. Nalurin

20. Naxuril

21. Nogram

22. Urisal

23. Cybis

24. Nalix

25. Uroman

26. Nalidicron

27. Betaxina

28. Kusnarin

29. Narigix

30. Nicelate

31. Specifen

32. Specifin

33. Uralgin

34. Uriclar

35. Urodixin

36. Negram

37. Poleon

38. Uriben

39. Uroneg

40. Uropan

41. Acide Nalidixique

42. Eucistin

43. Acide Nalidixico

44. Acido Nalidixico

45. Nsc-82174

46. Acidum Nalidixicum

47. 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid

48. Win 18,320

49. Nalidixane

50. 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid

51. 3-carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one

52. Nci-c56199

53. 1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid

54. 1,8-naphthyridine-3-carboxylic Acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-

55. 3-carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one

56. Mfcd00006884

57. 1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic Acid

58. 1-aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure

59. Nalidixic Acid (neggram)

60. Win-18320

61. Mls000028504

62. 3b91hwa56m

63. Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico

64. Win 18320

65. Chebi:100147

66. 1-ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic Acid

67. Nsc82174

68. Ncgc00018181-08

69. Smr000058264

70. Wintron

71. Dsstox_cid_912

72. Acido Nalidissico

73. Nalidixic Acid 100 Microg/ml In Acetonitrile

74. Dsstox_rid_75859

75. Dsstox_gsid_20912

76. Acido Nalidissico [dcit]

77. Acide Nalidixico [italian]

78. Acide Nalidixique [french]

79. Nalidixic

80. Acide Nalidixique [inn-french]

81. Acido Nalidixico [inn-spanish]

82. Acidum Nalidixicum [inn-latin]

83. Cas-389-08-2

84. Neggram (tn)

85. Ccris 2365

86. Hsdb 3241

87. Einecs 206-864-7

88. Brn 0750515

89. Unii-3b91hwa56m

90. Innoxalomn

91. Eucisten

92. Nalidixic-acid

93. Sr-01000003086

94. 1-aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [german]

95. Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [italian]

96. Nalidixicacid

97. Win 183203

98. Chembl5

99. Spectrum_000918

100. Nalidixic Acid [usan:usp:inn:ban:jan]

101. Maybridge1_007101

102. Opera_id_1064

103. Prestwick0_000187

104. Prestwick1_000187

105. Prestwick2_000187

106. Prestwick3_000187

107. Spectrum2_001360

108. Spectrum3_000075

109. Spectrum4_000817

110. Spectrum5_001540

111. 1,4-dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic Acid

112. Nalidixic Acid, >=98%

113. Upcmld-dp129

114. N-1200

115. Nalidixic Acid [mi]

116. Nciopen2_004342

117. Lopac0_000837

118. Oprea1_010545

119. Schembl21736

120. Bspbio_000113

121. Bspbio_001889

122. Kbiogr_001333

123. Kbioss_001398

124. Nalidixic Acid [inn]

125. Nalidixic Acid [jan]

126. 5-25-07-00384 (beilstein Handbook Reference)

127. Mls001148578

128. Mls002303041

129. Mls004820190

130. Mls006011875

131. 1-ethyl-7-methyl-4-oxo-1

132. Bidd:gt0529

133. Divk1c_000058

134. Nalidixic Acid [hsdb]

135. Nalidixic Acid [usan]

136. Spectrum1500756

137. Spbio_001579

138. Spbio_002034

139. Nalidixic Acid [vandf]

140. Bpbio1_000125

141. Nalidixic Acid [mart.]

142. Dtxsid3020912

143. Nalidixic Acid [who-dd]

144. Upcmld-dp129:001

145. Bdbm21691

146. Hms500c20

147. Hms561k17

148. Kbio1_000058

149. Kbio2_001398

150. Kbio2_003966

151. Kbio2_006534

152. Kbio3_001109

153. Zinc57421

154. Ninds_000058

155. Hms1921g10

156. Hms2092k04

157. Hms2232h24

158. Hms3259o13

159. Hms3374g11

160. Hms3656k05

161. Pharmakon1600-01500756

162. Nalidixic Acid (jp17/usp/inn)

163. Nalidixic Acid, Analytical Standard

164. Albb-021275

165. Hy-b0398

166. Tox21_110835

167. Tox21_201477

168. Tox21_302754

169. Bbl012279

170. Ccg-39298

171. Nalidixic Acid [ep Impurity]

172. Nalidixic Acid [orange Book]

173. Nsc757432

174. Stk735579

175. Nalidixic Acid [usp Impurity]

176. 1,8-naphthyridine-3-carboxylicacid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-

177. 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxilic Acid

178. Akos000120074

179. Tox21_110835_1

180. Db00779

181. Nc00494

182. Nsc-757432

183. Sdccgsbi-0050814.p004

184. Idi1_000058

185. Ncgc00018181-01

186. Ncgc00018181-02

187. Ncgc00018181-03

188. Ncgc00018181-04

189. Ncgc00018181-05

190. Ncgc00018181-06

191. Ncgc00018181-07

192. Ncgc00018181-09

193. Ncgc00018181-10

194. Ncgc00018181-12

195. Ncgc00018181-13

196. Ncgc00021730-03

197. Ncgc00021730-04

198. Ncgc00021730-05

199. Ncgc00021730-06

200. Ncgc00021730-07

201. Ncgc00256581-01

202. Ncgc00259028-01

203. As-13289

204. Nci60_041807

205. Smr004703506

206. Wln: T66 Bn Ev Jnj B2 Dvq I1

207. Sbi-0050814.p003

208. Db-049349

209. Nalidixic Acid 1000 Microg/ml In Methanol

210. 1, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-

211. Bb 0242389

212. Ft-0603390

213. N0490

214. S2328

215. Sw219624-1

216. 1-ethyl-1,8-naphthyridine-3-carboxilic Acid

217. 1-ethyl-1,8-naphthyridine-3-carboxylic Acid

218. Vu0239598-6

219. C05079

220. D00183

221. D91720

222. Nalidixic Acid 1000 Microg/ml In Acetonitrile

223. Nalidixic Acid, Meets Usp Testing Specifications

224. 389n082

225. Q281082

226. Sr-01000003086-4

227. Sr-01000003086-6

228. Brd-k47886988-323-03-0

229. Nalidixic Acid, Antibiotic For Culture Media Use Only

230. Sr-01000003086-10

231. F0850-6751

232. Z256708444

233. 1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic Acid

234. 1-ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic Acid

235. Nalidixic Acid, European Pharmacopoeia (ep) Reference Standard

236. Nalidixic Acid, United States Pharmacopeia (usp) Reference Standard

237. 1,8-naphthyridine-3-carboxylic Acid,1-ethyl-1,4-dihydro-7-methyl-4-oxo-

238. 1-ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naph Thyridine-3-carboxylic Acid

239. N-benzyl-4-[(5-cyclobutyl-1,2,4-oxadiazol-3-yl)methyl]-n-ethyl-3-oxo-3,4-dihydro-2h-1,4-benzoxazine-6-sulfonamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₂N₂O₃
Molecular Weight	232.23 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	232.08479225 g/mol
Monoisotopic Mass	232.08479225 g/mol
Topological Polar Surface Area	70.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	378
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

Anti-Infective Agents, Quinolone /SRP: Antibacterial/

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

IN US, NALIDIXIC ACID IS APPROVED ONLY FOR TREATMENT OF URINARY TRACT INFECTIONS CAUSED BY SUSCEPTIBLE MICROORGANISMS. EFFECTIVENESS AGAINST INDOLE-POSITIVE PROTEUS IS ESP IMPORTANT. APPARENT CURES...IN 30-50% OF UNCOMPLICATED URINARY TRACT INFECTIONS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1007

...BRUCELLOSIS HAS BEEN SUCCESSFULLY MANAGED WITH ORAL NALIDIXIC ACID. DRUG HAS BEEN GIVEN IV TO TREAT GRAM-NEGATIVE SEPTICEMIAS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1008

...BACTERICIDAL TO MOST OF COMMON GRAM-NEGATIVE BACTERIA THAT CAUSE URINARY TRACT INFECTIONS. ...99% OF STRAINS OF E COLI, 98% OF PROTEUS MIRABILIS & 75-97% OF OTHER PROTEUS SPECIES, 92% OF KLEBSIELLA-ENTEROBACTER, & 80% OF OTHER COLIFORM BACTERIA ARE SENSITIVE TO DRUG. ... SOME STRAINS OF SALMONELLA & SHIGELLA...SENSITIVE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1007

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

4.2 Drug Warning

BECAUSE...MAY ACCUMULATE IN PT WITH RENAL OR HEPATIC INSUFFICIENCY, IT SHOULD BE USED VERY CAUTIOUSLY IN THESE PT, ESP IF NEUROLOGIC DAMAGE IS PRESENT. ... CAUTION IS INDICATED IF THIS DRUG IS USED DURING PREGNANCY, ALTHOUGH SOME... HAVE TAKEN IT DURING 2ND & 3RD TRIMESTERS WITHOUT ADVERSELY AFFECTING MOTHER OR FETUS.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 793

BY ORAL ROUTE IT IS DIFFICULT TO ACHIEVE EFFECTIVE PLASMA LEVELS. FUTHERMORE, BINDING TO PLASMA PROTEIN INHIBITS ACTIVITY. ... 4% THAT PASSES INTO BOWEL IS INSUFFICIENT TO BE EFFICACIOUS IN TREATMENT OF INTESTINAL SHIGELLOSIS...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1152

PSEUDOMONAS SPECIES ARE RESISTANT. ... ACQUIRED RESISTANCE TO DRUG OCCURS, BUT IT DOES NOT SEEM TO BE TRANSFERABLE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1007

DETERMINATION OF URINARY LEVELS OF 17-KETOSTEROIDS & 17-KETOGENIC STEROIDS MAY BE FALSELY ELEVATED WHEN NALIDIXIC ACID HAS BEEN PRESCRIBED.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 182

For more Drug Warnings (Complete) data for NALIDIXIC ACID (19 total), please visit the HSDB record page.

4.3 Drug Indication

For the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of E. Coli, Enterobacter species, Klebsiella species, and Proteus species.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nalidixic acid is a quinolone antibacterial agent for oral administration. Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri. Pseudomonas species are generally resistant to the drug. Nalidixic acid is bactericidal and is effective over the entire urinary pH range. Conventional chromosomal resistance to nalidixic acid taken in full dosage has been reported to emerge in approximately 2 to 14 percent of patients during treatment; however, bacterial resistance to nalidixic acid has not been shown to be transferable via R factor.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01M - Quinolone antibacterials

J01MB - Other quinolones

J01MB02 - Nalidixic acid

5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration, nalidixic acid is rapidly absorbed from the gastrointestinal tract. Bioavailability is approximately 96%. Absorption may be delayed if taken with antacids.

Route of Elimination

Following oral administration, NegGram is rapidly absorbed from the gastrointestinal tract, partially metabolized in the liver, and rapidly excreted through the kidneys. Approximately four percent of NegGram is excreted in the feces.

ABSORPTION & ELIMINATION RATES OF NALIDIXIC ACID WERE SHOWN TO BE LOW IN NEWBORN CHILDREN COMPARED WITH ADULTS, & ADULT VALUES WERE NOT OBTAINED UNTIL ABOUT THIRD YR OF LIFE. RELATIVE DISTRIBUTION VOL, HOWEVER, WERE SIMILAR IN BOTH AGE GROUPS.

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. 437

IN RATS & MICE ORAL DOSES ARE RAPIDLY ABSORBED WITH PEAK BLOOD CONCN ABOUT 1 HR LATER. ...ELIMINATION IS VIA KIDNEYS, PEAKING @ ABOUT 6TH HR. 80% OF ADMIN DOSE IS ELIMINATED IN 1ST 8 HR. IN DOGS HIGHLY EFFECTIVE CONCN APPEAR IN URINE WITHIN 2-3 HR AFTER ORAL ADMIN.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 375

ABSORPTION EFFICIENCY & RATE OF ELIMINATION OF...NALIDIXIC ACID...DECR IN PT WITH SHIGELLOSIS. POOR ABSORPTION WAS GENERALLY OBSERVED IN YOUNGER PT WITH MARKED DIARRHEA BUT THERE WAS NO READY EXPLANATION FOR DELAYED EXCRETION.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 169

Rapidly and almost completely absorbed from the gastrointestinal tract; bioavailability is approximately 96%. Absorption may be delayed if taken with antacids.

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 2092

For more Absorption, Distribution and Excretion (Complete) data for NALIDIXIC ACID (7 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Hepatic. 30% of administered dose is metabolized to the active metabolite, hydroxynalidixic acid. Rapid conjugation of parent drug and active metabolite to inactive metabolites. Metabolism may vary widely among individuals. In the urine, hydroxynalidixic acid represents 80 to 85% of the antibacterial activity.

WHEN NALIDIXIC ACID...IS INGESTED BY MAN, IT IS PARTLY EXCRETED AS FREE... /ACID/ BUT MUCH BIGGER PROPORTION IS EXCRETED AS MONOGLUCURONIDE...& CONSIDERABLE FRACTION AS 7-HYDROXYMETHYL METABOLITE...TOGETHER WITH SMALLER AMT OF LATTER IN CONJUGATED FORM. 3,7-DICARBOXYLIC ACID...IS MINOR METABOLITE.

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. 205

Nalidixic acid is partially metabolized in the liver to hydroxynalidixic acid and the glucuronic acid conjugates of nalidixic acid and hydroxynalidixic acid. The drug is also partially metabolized to the dicarboxylic acid derivative; there is some evidence suggesting that this metabolite is formed in the kidney.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 593

5.6 Biological Half-Life

1.1 to 2.5 hours in healthy adult patients, and up to 21 hours in patients with impaired renal function.

APPROX 96% OF ORALLY ADMIN...IS ABSORBED. PLASMA CONCN OF 20-50 UG/ML MAY BE ACHIEVED, BUT ACID IS 93-97% BOUND TO PLASMA PROTEINS. IN BODY SOME... CONVERTED TO ACTIVE HYDROXYNALIDIXIC ACID, & BOTH ARE EXCRETED INTO URINE. MOST...IS CONJUGATED IN LIVER. PLASMA T/2 IS...8 HR...MAY BE...21 HR IN...RENAL FAILURE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1007

5.7 Mechanism of Action

Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.

IT APPEARS TO ACT BY INHIBITING DNA SYNTH.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1007

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API Reference Price

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