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Chemistry

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Also known as: 67-20-9, Macrodantin, Furadantin, 5-nitrofurantoin, Furadonine, Furadantine
Molecular Formula
C8H6N4O5
Molecular Weight
238.16  g/mol
InChI Key
NXFQHRVNIOXGAQ-YCRREMRBSA-N
FDA UNII
927AH8112L

Nitrofurantoin
A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.
Nitrofurantoin is a Nitrofuran Antibacterial.
1 2D Structure

Nitrofurantoin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
2.1.2 InChI
InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
2.1.3 InChI Key
NXFQHRVNIOXGAQ-YCRREMRBSA-N
2.1.4 Canonical SMILES
C1C(=O)NC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
2.1.5 Isomeric SMILES
C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
927AH8112L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Furadantin

2. Furadantine

3. Furadoine

4. Furadonine

5. Furantoin

6. Macrodantin

7. Nitrofurantoin Sodium Salt

8. Nitrofurantoin, Monohydrate

2.3.2 Depositor-Supplied Synonyms

1. 67-20-9

2. Macrodantin

3. Furadantin

4. 5-nitrofurantoin

5. Furadonine

6. Furadantine

7. Furadantoin

8. Furadoine

9. Furadontin

10. Furantoin

11. Nifurantin

12. Furalan

13. Nitrofuradantin

14. Nitrofurantoine

15. Berkfurin

16. Chemiofuran

17. Furachel

18. Furadonin

19. Furatoin

20. Furobactina

21. Macrobid

22. Novofuran

23. Orafuran

24. Parfuran

25. Trantoin

26. Urantoin

27. Urofurin

28. Welfurin

29. Zoofurin

30. Cyantin

31. Cystit

32. Furina

33. Ituran

34. Nitoin

35. Urizept

36. Urodin

37. Urolong

38. Furadantine Mc

39. Uro-tablinen

40. Fur-ren

41. Macrofuran

42. Nitrofurantoina

43. Benkfuran

44. Dantafur

45. Furaloid

46. Nierofu

47. Macpac

48. Nitrex

49. Nitrofurantoinum

50. Fua Med

51. N-toin

52. Usaf Ea-2

53. 1-(5-nitro-2-furfurylideneamino)hydantoin

54. 1-((5-nitrofurfurylidene)amino)hydantoin

55. N-(5-nitrofurfurylidene)-1-aminohydantoin

56. Nitrofurantoin, Macrocrystalline

57. 1-[(5-nitrofurfurylidene)amino]hydantoin

58. 1-(5-nitro-2-furfurylidenamino)hydantoin

59. N-(5-nitro-2-furfurylidene)-1-aminohydantoin

60. Nitrofurantoin Anhydrous

61. Nci-c55196

62. Nsc 2107

63. Nitrofurantoin Macrocrystalline

64. Nsc 44150

65. N-(5-nitro-2-furfurylideno)-1-aminohydantoina

66. Nsc-2107

67. Furadoninum

68. Nitrofurantoin Macrocrystal

69. 1-(((5-nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione

70. 2,4-imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene]amino]-

71. 1-[(e)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione

72. Nitrofurantoin, Macrocrystals

73. Mls000028500

74. Cistofuran

75. Macrodantina

76. Macrofurin

77. Nifuretten

78. Alfuran

79. Berkfuran

80. Ceduran

81. Furabid

82. Furedan

83. Gerofuran

84. Phenurin

85. Siraliden

86. Uerineks

87. Urofuran

88. Urolisa

89. Chebi:71415

90. Hydantoin, 1-((5-nitrofurfurylidene)amino)-

91. Piyeloseptyl

92. 1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione

93. Furadantina Mc

94. Furadantine-mc

95. 2,4-imidazolidinedione, 1-(((5-nitro-2-furanyl)methylene)amino)-

96. Furophen T

97. Nitrofur-c

98. Ro-antoin

99. Furadantin Retard

100. Uro-selz

101. Ivadantin

102. 927ah8112l

103. Smr000058271

104. 1-(((5-nitrofuran-2-yl)methylene)-amino)imidazolidine-2,4-dione

105. 1-{[(1e)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione

106. Nitrofurantoina [dcit]

107. Nitrofurantoine [inn-french]

108. Nitrofurantoinum [inn-latin]

109. Furodantin

110. 1-((5-nitro-2-furanyl)methylene)amino-2,4-imidazolidenedione

111. Fuamed

112. 1-{[(e)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione

113. Nsc-44150

114. Furadantin (tn)

115. Macrobid (tn)

116. 178170-37-1

117. Ccris 1192

118. Hydantoin, 1-[(5-nitrofurfurylidene)amino]-

119. Hsdb 3135

120. Sr-05000001681

121. Einecs 200-646-5

122. Nsc2107

123. Furantoina

124. Furadoin

125. Uvamin

126. N-(5-nitro-2-furfurylideno)-1-aminohydantoina [polish]

127. Nsc44150

128. Ai3-26388

129. (e)-1-(((5-nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione

130. Nitrofurantoin (jan/usp/inn)

131. Unii-927ah8112l

132. Furophen T-caps

133. Ncgc00091505-01

134. Ncgc00091505-07

135. Prestwick_358

136. Nitrofurantoin Macro

137. 5-nitrofurantoindorn

138. J01xe01

139. Nitrofurantoin [usp:inn:ban:jan]

140. Mfcd00003224

141. Nd-3320

142. Nd-7248

143. Nitrofurantoin, 97%

144. Nitrofurantoinum Anhydrous

145. Prestwick2_000168

146. Prestwick3_000168

147. Spectrum5_001367

148. Nitrofurantoin, Crystalline

149. Chembl572

150. Nitrofurantoin [mi]

151. Nitrofurantoin Macrocrystals

152. Cid_4509

153. Nitrofurantoin [inn]

154. Nitrofurantoin [jan]

155. Schembl29470

156. Schembl29472

157. Bspbio_000035

158. Bspbio_002073

159. Nitrofurantoin [hsdb]

160. Nitrofurantoin [iarc]

161. Bidd:gt0181

162. Nitrofurantoin [vandf]

163. Spectrum1500433

164. Nitrofurantoin [mart.]

165. Bpbio1_000039

166. Nitrofurantoin [usp-rs]

167. Nitrofurantoin [who-dd]

168. Bdbm57045

169. Chebi:95222

170. Hms500l06

171. Hms1568b17

172. Hms1920p21

173. Hms2091h16

174. Hms2095b17

175. Hms3712b17

176. Pharmakon1600-01500433

177. Nitrofurantoin [green Book]

178. 1-[(e)-(5-nitro-2-furyl)methyleneamino]imidazolidine-2,4-dione

179. Hy-a0090

180. Zinc7997568

181. Nitrofurantoin [orange Book]

182. 2,4-imidazolidenedione, 1-(((5-nitro-2-furanyl)methylene)amino)-

183. Ccg-40108

184. Nitrofurantoin [ep Monograph]

185. Nsc757243

186. S4536

187. Stk009471

188. Stl454163

189. Nitrofurantoin [usp Monograph]

190. Akos001678301

191. Db00698

192. Nsc-757243

193. Idi1_000224

194. Macrobid Component Nitrofurantoin

195. Ncgc00091505-03

196. Ncgc00091505-04

197. Ncgc00091505-05

198. Ncgc00091505-06

199. Ncgc00091505-08

200. Ncgc00091505-09

201. Ncgc00091505-10

202. Nitrofurantoin Anhydrous [who-ip]

203. Ls-13402

204. 1-((5-nitrofurfurylidene)amino)-hydantoin

205. Nitrofurantoin Component Of Macrobid

206. Sbi-0051457.p003

207. Ab00513815

208. Bb 0310231

209. N0883

210. Nitrofurantoin Macrocrystalline [vandf]

211. A16008

212. C07268

213. D00439

214. Ab00052052_03

215. Nitrofurantoinum Anhydrous [who-ip Latin]

216. A835659

217. Hydantoin, N-(5-nitro-2-furfurylidene)-1-amino-

218. Nitrofurantoin, Vetranal(tm), Analytical Standard

219. Q-201479

220. Sr-05000001681-1

221. Sr-05000001681-2

222. Sr-05000001681-3

223. Sr-05000001681-4

224. Brd-k76927775-001-05-0

225. Nitrofurantoin, Antibiotic For Culture Media Use Only

226. Hydantoin, 1-[(5-nitrofurfurylidene)amino]- (7ci,8ci)

227. Macrobid Component Nitrofurantoin, Macrocrystalline

228. 1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione

229. Nitrofurantoin, Macrocrystalline Component Of Macrobid

230. (e)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione

231. 1-([(5-nitro-2-furyl)methylidene]amino)-2,4-imidazolidinedione #

232. 1-[(e)-(5-nitro-2-furanyl)methylideneamino]imidazolidine-2,4-dione

233. 1-{[(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione

234. Nitrofurantoin, United States Pharmacopeia (usp) Reference Standard

235. 1-{[(e)-1-(5-nitro-2-furyl)methylidene]amino}-1h-imidazole-2,4(3h,5h)-dione

236. 4-hydroxy-1-{[(e)-(5-nitrofuran-2-yl)methylidene]amino}-1,5-dihydro-2h-imidazol-2-one

237. N-(5-nitro-2-furfurylidine)-1-aminohydantoin; N-(5-nitrofurfurylidene)-1aminohydantoin

238. Nitrofurantoin, Pharmaceutical Secondary Standard; Certified Reference Material

2.3.3 Other Synonyms

1. Nitrofurantoin [monohydrate]

2. 1-((5-nitrofurfurylidene)amino)hydantoin Monohydrate

3. Anw-71970

4. Nifurantin Monohydrate

2.4 Create Date
2006-05-30
3 Chemical and Physical Properties
Molecular Weight 238.16 g/mol
Molecular Formula C8H6N4O5
XLogP3-0.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass238.03381930 g/mol
Monoisotopic Mass238.03381930 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count17
Formal Charge0
Complexity390
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameFuradantin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelFuradantin (nitrofurantoin), a synthetic chemical, is a stable, yellow, crystalline compound. Furadantin is an antibacterial agent for specific urinary tract infections. Furadantin is available in 25mg/5mL liquid suspension for oral administration.1-...
Active IngredientNitrofurantoin
Dosage FormSuspension
RouteOral
Strength25mg/5ml
Market StatusPrescription
CompanyShionogi

2 of 8  
Drug NameMacrobid
PubMed HealthNitrofurantoin Combination (By mouth)
Drug ClassesAntibiotic
Active Ingredientnitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage FormCapsule
RouteOral
Strength25mg; 75mg
Market StatusPrescription
CompanyAlvogen

3 of 8  
Drug NameMacrodantin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelMacrodantin (nitrofurantoin macrocrystals) is a synthetic chemical of controlled crystal size. It is a stable, yellow, crystalline compound. Macrodantin is an antibacterial agent for specific urinary tract infections. It is available in 25 mg, 50 mg,...
Active IngredientNitrofurantoin, macrocrystalline
Dosage FormCapsule
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAlvogen

4 of 8  
Drug NameNitrofurantoin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelNitrofurantoin oral suspension, USP, a synthetic chemical, is a stable, yellow, crystalline compound. Nitrofurantoin oral suspension, USP is an antibacterial agent for specific urinary tract infections. Nitrofurantoinoral suspension, USP is available...
Active IngredientNitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage FormCapsule; Suspension
RouteOral
Strength25mg/5ml; 100mg; 50mg
Market StatusPrescription
CompanyAmneal Pharms; Novel Labs; Ivax Sub Teva Pharms; Caraco; Mylan

5 of 8  
Drug NameFuradantin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelFuradantin (nitrofurantoin), a synthetic chemical, is a stable, yellow, crystalline compound. Furadantin is an antibacterial agent for specific urinary tract infections. Furadantin is available in 25mg/5mL liquid suspension for oral administration.1-...
Active IngredientNitrofurantoin
Dosage FormSuspension
RouteOral
Strength25mg/5ml
Market StatusPrescription
CompanyShionogi

6 of 8  
Drug NameMacrobid
PubMed HealthNitrofurantoin Combination (By mouth)
Drug ClassesAntibiotic
Active Ingredientnitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage FormCapsule
RouteOral
Strength25mg; 75mg
Market StatusPrescription
CompanyAlvogen

7 of 8  
Drug NameMacrodantin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelMacrodantin (nitrofurantoin macrocrystals) is a synthetic chemical of controlled crystal size. It is a stable, yellow, crystalline compound. Macrodantin is an antibacterial agent for specific urinary tract infections. It is available in 25 mg, 50 mg,...
Active IngredientNitrofurantoin, macrocrystalline
Dosage FormCapsule
RouteOral
Strength25mg; 100mg; 50mg
Market StatusPrescription
CompanyAlvogen

8 of 8  
Drug NameNitrofurantoin
PubMed HealthNitrofurantoin
Drug ClassesAntibiotic
Drug LabelNitrofurantoin oral suspension, USP, a synthetic chemical, is a stable, yellow, crystalline compound. Nitrofurantoin oral suspension, USP is an antibacterial agent for specific urinary tract infections. Nitrofurantoinoral suspension, USP is available...
Active IngredientNitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage FormCapsule; Suspension
RouteOral
Strength25mg/5ml; 100mg; 50mg
Market StatusPrescription
CompanyAmneal Pharms; Novel Labs; Ivax Sub Teva Pharms; Caraco; Mylan

4.2 Therapeutic Uses

Anti-Infective Agents, Urinary /SRP: Antibacterial/

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


NITROFURANTOIN IS BACTERIOSTATIC AT CONCN OF 5-10 UG/ML & BACTERICIDAL AT 100 UG/ML, BUT IT IS NOT KNOWN WHETHER BACTERICIDAL ACTION OCCURS IN VIVO. ANTIBACTERIAL ACTIVITY IS HIGHER IN ACIDIC URINE. ...SUPERSATURATED SOLN OF NITROFURANTOIN DO NOT CAUSE CRYSTALLURIA.

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


NITROFURANTOIN IS ACTIVE AGAINST MANY STRAINS OF COMMON URINARY TRACT PATHOGENS E COLI, PROTEUS SPECIES, PSEUDOMONAS...ENTEROBACTER, AND STAPHYLOCOCCI, AS WELL AS ENTEROCOCCI, STREPTOCOCCI, CLOSTRIDIA, & BACILLUS SUBTILIS.

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


...APPROVED ONLY FOR TREATMENT OF URINARY TRACT INFECTIONS CAUSED BY MICROORGANISMS THAT ARE KNOWN TO BE SENSITIVE TO DRUG. ... IT HAS BEEN USED EFFECTIVELY TO PREVENT RECURRENT INFECTIONS & FOR PREVENTION OF BACTERIURIA AFTER PROSTATECTOMY.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1070


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


4.3 Drug Warning

A COURSE OF THERAPY SHOULD NOT EXCEED 14 DAYS, & REPEATED COURSES SHOULD BE SEPARATED BY REST PERIODS. ... PREGNANT WOMEN AT TERM, INDIVIDUALS WITH IMPAIRED RENAL FUNCTION (CREATININE CLEARANCE LESS THAN 40 ML/MIN), & CHILDREN BELOW 1 MONTH OF AGE SHOULD NOT RECEIVE NITROFURANTOIN.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1070


Maternal Medication Usually Compatible with Breast-Feeding: Nitrofurantoin: Hemolysis in infant with glucose-6-phosphate dehydrogenase (G-6-PD) deficiency. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 141 (1994)


...MOST SPECIES OF PROTEUS & PSEUDOMONAS & MANY OF ENTEROBACTER & KLEBSIELLA ARE RESISTANT. ANTIBACTERIAL CONCN ARE NOT ACHIEVED IN PLASMA FOLLOWING INGESTION OF RECOMMENDED DOSES, BECAUSE DRUG IS RAPIDLY ELIMINATED. ...IN PT WITH IMPAIRED GLOMERULAR FUNCTION EFFICACY OF DRUG MAY BE DECR & SYSTEMIC TOXICITY INCR.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1069


INJECTION OF NITROFURANTOIN SODIUM IS INDICATED ONLY FOR USE IN ACUTELY ILL PT WHO CANNOT TOLERATE ORAL NITROFURANTOIN. /SODIUM NITROFURANTOIN/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1009


For more Drug Warnings (Complete) data for NITROFURANTOIN (31 total), please visit the HSDB record page.


4.4 Drug Indication

Nitrofurantoin is indicated to treat acute uncomplicated urinary tract infections.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nitrofurantoin interferes with vital processes in bacteria, which leads to their death. Nitrofurantoin rapidly reaches therapeutic concentrations in the urine and is also cleared rapidly.


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.)


Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NITROFURANTOIN
5.3.2 FDA UNII
927AH8112L
5.3.3 Pharmacological Classes
Nitrofurans [CS]; Nitrofuran Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XE - Nitrofuran derivatives

J01XE01 - Nitrofurantoin


5.5 Absorption, Distribution and Excretion

Absorption

Nitrofurantoin reaches a Cmax of 0.875-0.963mg/L with an AUC of 2.21-2.42mg\*h/L. It is 38.8-44.3% bioavailable. Taking nitrofurantoin with food increases the absorption and duration of therapeutic concentrations in the urine.


Route of Elimination

27-50% of an oral dose is excreted in the urine as unchanged nitrofurantoin. 90% of the total dose is eliminated in the urine.


Volume of Distribution

Data regarding the volume of distribution in humans is scarce but it has been reported as 0.46L/kg in dogs.


Clearance

The clearance of nitrofurantoin is 16.7-19.4L/h.


.../IT/ IS RAPIDLY & COMPLETELY ABSORBED FROM GI TRACT. ... PLASMA HALF-LIFE IS 0.3 TO 1 HR; ABOUT 40% IS EXCRETED UNCHANGED INTO URINE. AVG DOSE OF NITROFURANTOIN YIELDS URINE CONCN OF APPROX 200 UG/ML. ... RATE OF EXCRETION IS LINEARLY RELATED TO CREATININE CLEARANCE...

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1069


CLINICAL STUDIES...INDICATE THAT IN NORMAL FASTING INDIVIDUALS, LESS NITROFURANTOIN IS ABSORBED & AT SLOWER RATE FROM MACROCRYSTALLINE THAN MICROCRYSTALLINE FORM. PRESENCE OF FOOD IN INTESTINE DELAYS ABSORPTION OF BOTH FORMS APPRECIABLY, INCR PEAK LEVELS OF MACROCRYSTALLINE COMPD, BUT NOT MICROCRYSTALLINE COMPD, ENHANCES BIOAVAILABILITY OF BOTH FORMS, & PROLONGS DURATION OF THERAPEUTIC URINARY CONCN.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 1323


ENHANCEMENT OF...ABSORPTION BY FOOD RANGED FROM 20 TO 400%, WITH GREATEST EFFECT OCCURRING WITH LEAST SOLUBLE DOSAGE FORMS. .../IT/ IS INEFFICIENTLY ABSORBED FROM RECTAL SUPPOSITORIES...

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. 76


NITROFURANTOIN ABSORPTION IS SIGNIFICANTLY INCR IN MAN FROM A DRUG-DEOXYCHOLIC ACID CO-PRECIPITATE COMPARED WITH PHYS MIXT, & FASTER ABSORPTION...FROM CO-PRECIPITATE WAS ASSOCIATED WITH FASTER IN VITRO DISSOLUTION RATE. ... EXCRETED IN BILE OF DOGS & ABOUT 1/3 OF THAT EXCRETED IS REABSORBED FROM INTESTINE WITHIN 3 HR.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 187


For more Absorption, Distribution and Excretion (Complete) data for NITROFURANTOIN (13 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

0.8-1.8% of a dose is metabolized to aminofurantoin, and 0.9% of a dose is metabolized to other metabolites.


AFTER DOSE OF 0.200 MG/KG, 22% IS EXCRETED IN URINE AS N-(5-NITROFURFURYLIDENEAMINO)-2-IMIDAZOLINE-ONE. /FROM TABLE/

Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 356


READILY DEGRADED BY ALL /BODY/ TISSUES (EXCEPT BLOOD) INTO INACTIVE METABOLITES-HYDROXYLAMINO COMPD & AMINOFURALDEHYDENITROFURIC ACID. /HUMAN, ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1971


AFTER NITROFURANTOIN (50 MG) IV INFUSION, 47% OF THE DOSE WAS EXCRETED UNCHANGED IN THE URINE AND 1.2% WAS RECOVERED AS THE REDUCED METABOLITE AMINOFURANTOIN.

HOENER BA, PATTERSON SE; NITROFURANTOIN DISPOSITION; CLIN PHARMACOL THER 29(6) 808 (1981)


Nitrofurantoin is partially metabolized, mainly in the liver. A small fraction of the drug is reduced to form aminofurantoin.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 632


5.7 Biological Half-Life

The half life of nitrofurantoin is 0.72-0.78h.


PLASMA HALF-LIFE IS 0.3 TO 1 HR...

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1069


NITROFURANTOIN HALF-LIFE WAS 0.41 HOURS IN ADULTS AND 0.95 HOURS IN 2-WEEK-OLD RATS.

WIERZBA K ET AL; PAEDIATR PAEDOL 17 (2): 293 (1982)


5.8 Mechanism of Action

Nitrofurantoin is converted by bacterial nitroreductases to electrophilic intermediates which inhibit the citric acid cycle as well as synthesis of DNA, RNA, and protein.


MICROSOMAL AND SOLUBLE FRACTIONS FROM BOTH RAT LIVER AND LUNG MEDIATED THE COVALENT BINDING OF (14)C-LABELED NITROFURANTOIN (I) TO TISSUE MACROMOLECULES IN VITRO. OXYGEN STRONGLY INHIBITED THE BINDING IN BOTH FRACTIONS, AND CARBON MONOXIDE FAILED TO INHIBIT THE BINDING IN MICROSOMAL PREPARATIONS, INDICATING ACTIVATION OF I IN BOTH SYSTEMS BY NITROREDUCTION RATHER THAN OXIDATION OF THE FURAN RING. MICROSOMAL NITROREDUCTION AND COVALENT BINDING OF I WERE INHIBITED BY AN ANTIBODY AGAINST NADPH-CYTOCHROME C REDUCTASE AND COVALENT BINDING WAS ENHANCED BY THE ADDITION OF FAD. IN SOLUBLE FRACTIONS, MAXIMUM RATES OF COVALENT BINDING WERE OBTAINED IN THE PRESENCE OF NADH AND HYPOXANTHINE, AND IT WAS INHIBITED BY ALLOPURINOL, A XANTHINE OXIDASE INHIBITOR. REDUCED GLUTATHIONE DECREASED COVALENT BINDING OF I IN BOTH MICROSOMAL AND SOLUBLE FRACTIONS OF LIVER AND LUNG, BUT THE RATE OF NITROREDUCTION WAS UNAFFECTED.

PMID:36083 BOYD MR ET AL; BIOCHEM PHARMACOL 28 (5): 601 (1979)


THE HYPOTHESIS IS PRESENTED THAT THE TOXICITY OF NITROFURANS SUCH AS NITROFURANTOIN (I), WHICH ARE USED IN COMMERCIAL POULTRY PRODUCTION, IS DUE TO OXIDATIVE METABOLIC STRESS CAUSED BY THE O2- FREE RADICAL FORMED DURING METABOLISM OF THE COMPOUNDS.

COMBS GF JR; PROC-CORNELL NUTR CONF FEED MANUF: 9 (1979)


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07-Jan-2021
29-Aug-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CAPSULE;ORAL - 100MG

USFDA APPLICATION NUMBER - 16620

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DOSAGE - CAPSULE;ORAL - 25MG

USFDA APPLICATION NUMBER - 16620

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DOSAGE - CAPSULE;ORAL - 50MG

USFDA APPLICATION NUMBER - 16620

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DOSAGE - CAPSULE;ORAL - 75MG;25MG

USFDA APPLICATION NUMBER - 20064

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DOSAGE - SUSPENSION;ORAL - 25MG/5ML

USFDA APPLICATION NUMBER - 9175

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DOSAGE - SUSPENSION;ORAL - 50MG/5ML

USFDA APPLICATION NUMBER - 9175

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