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Nitrofurantoin, Monohydrate

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ACTIVE PHARMA INGREDIENTS

54 API Suppliers, 34 USDMF, 16 CEP/COS, 7 EU WC, 28 NDC API, 20 Listed Suppliers, $ API Reference Price

54 API Suppliers
34 USDMF
16 CEP/COS
7 EU WC
28 NDC API
20 Listed Suppliers
$ API Reference Price

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2 Drugs in Development

2 Drugs in Development

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3 Intermediates Suppliers

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130 FDF Dossiers, 71 FDA Orange Book, 22 Europe, 6 Canada, 4 Australia, 8 South Africa, 19 Listed Dossiers

130 FDF Dossiers
71 FDA Orange Book
22 Europe
6 Canada
4 Australia
8 South Africa
19 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

CAPSULE;ORAL - 100MG, CAPSULE;ORAL - 25MG, CAPSULE;ORAL - 50MG, CAPSULE;ORAL - 75MG;25MG, SUSPENSION;ORAL - 25MG/5ML, SUSPENSION;ORAL - 50MG/5ML

drugProductComposition
CAPSULE;ORAL - 100MG
CAPSULE;ORAL - 25MG
CAPSULE;ORAL - 50MG
CAPSULE;ORAL - 75MG;25MG
SUSPENSION;ORAL - 25MG/5ML
SUSPENSION;ORAL - 50MG/5ML

RELATED EXCIPIENT COMPANIES

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relatedExcipients
5 Rochem International Inc
7 SPI Pharma
10 DKSH
1 Pharm-RX Chemical
1 Boai NKY Pharmaceuticals Ltd
13 Gangwal Healthcare
3 Nanjing Well Pharmaceutical
1 Pfanstiehl
4 ACG Worldwide
5 Actylis
2 Aeon Procare
6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd
15 BASF
1 Bioplus Life Sciences
15 Corel Pharma Chem
5 DFE Pharma
1 Finar
9 Gangwal Chemicals
6 Ideal Cures Pvt Ltd
2 Ingredion Pharma Solutions
36 Kerry
4 Kima Chemical
6 Lonza Capsugel
5 Lubrizol Life Science Health
15 Microlex e.U
2 Novo Excipients
2 Pharmatrans-Sanaq
8 Pluviaendo
2 Prachin Chemical
1 Qianhao Chemical (Hebei) Co., Ltd
2 Qualicaps
29 Roquette
8 Seppic
4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd
1 Shijiazhuang Huaxu Pharmaceutical
10 Sigachi Industries
3 The Dow Chemical Company
1 Ulanqab Kema New Material
1 Valens Pharmachem
2 Vasa Pharmachem
1 Zhejiang Huakang Pharmaceutical

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DIGITAL CONTENT

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GLOBAL SALES INFORMATION

4 US Medicaid Prescriptions, 17 Finished Drug Prices

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17 Finished Drug Prices

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27 APIs, 10 FDF Dossiers

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27 APIs
10 FDF Dossiers

REF. STANDARDS & IMPURITIES

2 USP , 3 Others

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2 USP
3 Others

ANALYTICAL

2 BioAnalytical Methods

otherMethods
2 BioAnalytical Methods

ASolution Nitrofurantoin

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 341

MARKET PLACE

API

FDF

3INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

130

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

2DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

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Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

34,732,765

Annual Reports (USD Million)

Finished Drug Prices

255 RELATED EXCIPIENT COMPANIES

431EXCIPIENTS BY APPLICATIONS

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

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 Formula	C₈H₆N₄O₅
Molecular Weight	238.16 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	238.03381930 g/mol
Monoisotopic Mass	238.03381930 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	390
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 8
Drug Name	Furadantin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Furadantin (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 Ingredient	Nitrofurantoin
Dosage Form	Suspension
Route	Oral
Strength	25mg/5ml
Market Status	Prescription
Company	Shionogi

2 of 8
Drug Name	Macrobid
PubMed Health	Nitrofurantoin Combination (By mouth)
Drug Classes	Antibiotic
Active Ingredient	nitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage Form	Capsule
Route	Oral
Strength	25mg; 75mg
Market Status	Prescription
Company	Alvogen

3 of 8
Drug Name	Macrodantin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Macrodantin (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 Ingredient	Nitrofurantoin, macrocrystalline
Dosage Form	Capsule
Route	Oral
Strength	25mg; 100mg; 50mg
Market Status	Prescription
Company	Alvogen

4 of 8
Drug Name	Nitrofurantoin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Nitrofurantoin 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 Ingredient	Nitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage Form	Capsule; Suspension
Route	Oral
Strength	25mg/5ml; 100mg; 50mg
Market Status	Prescription
Company	Amneal Pharms; Novel Labs; Ivax Sub Teva Pharms; Caraco; Mylan

5 of 8
Drug Name	Furadantin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Furadantin (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 Ingredient	Nitrofurantoin
Dosage Form	Suspension
Route	Oral
Strength	25mg/5ml
Market Status	Prescription
Company	Shionogi

6 of 8
Drug Name	Macrobid
PubMed Health	Nitrofurantoin Combination (By mouth)
Drug Classes	Antibiotic
Active Ingredient	nitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage Form	Capsule
Route	Oral
Strength	25mg; 75mg
Market Status	Prescription
Company	Alvogen

7 of 8
Drug Name	Macrodantin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Macrodantin (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 Ingredient	Nitrofurantoin, macrocrystalline
Dosage Form	Capsule
Route	Oral
Strength	25mg; 100mg; 50mg
Market Status	Prescription
Company	Alvogen

8 of 8
Drug Name	Nitrofurantoin
PubMed Health	Nitrofurantoin
Drug Classes	Antibiotic
Drug Label	Nitrofurantoin 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 Ingredient	Nitrofurantoin, macrocrystalline; Nitrofurantoin
Dosage Form	Capsule; Suspension
Route	Oral
Strength	25mg/5ml; 100mg; 50mg
Market Status	Prescription
Company	Amneal 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 C_max 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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DOSAGE - CAPSULE;ORAL - 100MG

USFDA APPLICATION NUMBER - 16620

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DATA COMPILATION #PharmaFlow

GSK, Google form first bioelectronics firm; 11 generic companies benefit from the Teva Allergan deal

This week, Phispers brings to you the details of the bioelectronics firm formed by GSK and Google. There is also news on companies like Teva, Takeda, Jinan Jinda and Eli Lilly, besides two other news snippets pertaining to the FDA -- while the first one pertains to generic approvals, the other one relates to an additional black box warning on a few antibiotics. GSK and Google join hands to form first bioelectronics startupGlaxoSmithKline and Google’s parent company – Alphabet – have joined hands to create a new company that is focused on fighting diseases by targeting electrical signals in the human body. This way, GSK and Alphabet’s life sciences unit – known as Verily Life Sciences – will be jump-starting a new field of medicine known as bioelectronics.Verily Life Sciences and GSK will together contribute US $ 715.12 million over seven years to the startup Galvani Bioelectronics. The startup will develop miniature electronic implants for the treatment of asthma, diabetes and other chronic conditions. The implantable devices developed by Galvani, which is owned 55 percent by GSK and 45 percent by Verily, can modify electrical nerve signals. The aim is to modulate irregular or altered impulses that occur in many illnesses.The new company will be based at GSK’s Stevenage research center north of London, with a second research hub in South San Francisco.The announcement comes just weeks after GSK had said it was going to use Apple’s HealthKit to conduct clinical trials.Three years ago, GSK had first unveiled its ambitions in bioelectronics in the journal – Nature. Bioelectronic remedies attach battery-powered implants the size of a grain of rice (or even smaller) to individual nerves to correct faulty electrical signals between the nervous system and the body’s organs.GSK believes altering these nerve signals could open up the airways of asthma patients, reduce inflammation in the gut from Crohn’s disease and treat patients with a range of other chronic ailments such as arthritis. So far, the implants have only been tested on animals but the aim is to produce treatments that will supplement or replace drugs that often come with side-effects.GSK has been working on bioelectronic medicines since 2012 in a push to develop new patentable treatments, since its Advair respiratory treatment faces competition from generic versions. It has invested US $50 million in a venture capital fund for bioelectronics and provided funding to scientists working in the field. Teva divests 79 products to 11 generic players to close Allergan dealTeva Pharmaceutical Industries – the world’s largest generics drug company – won a US anti-trust approval to purchase Allergan's generics business, after agreeing to divest 79 generic drugs to rival firms. This was arrived at to settle Federal Trade Commission (FTC) charges that its proposed US $ 40.5 billion acquisition of Allergan’s generic pharmaceutical business would be anti-competitive. The remedy requires Teva to divest the drug portfolio to 11 firms, and marks the largest drug divestiture order in a FTC pharmaceutical merger case.The Teva-Allergan deal, which was announced in July 2015, solidifies Teva’s position as the world's largest maker of generics while freeing Allergan to focus on branded drugs.The companies that have acquired the divested products are Mayne Pharma Group, Impax Laboratories, Dr Reddy’s Laboratories, Sagent Pharmaceuticals, Cipla Limited, Zydus Worldwide DMCC, Mikah Pharma, Perrigo Pharma International, Aurobindo Pharma USA, Prasco and 3M Company. Eli Lilly CEO steps down; company under probe by US Justice Department Eli Lilly CEO John Lechleiter has stepped down after steering the pharma company through long R&D droughts. The company’s president David Ricks will move up to the top spot. And after a brief spell as executive chairman, Lechleiter will leave the company next spring.Lechleiter has been the company's CEO since April 1, 2008, and the chairman of its board of directors since January 1, 2009.The announcement has come at a time when Eli Lilly has been asked by the Justice Department to disclose information on relationships with pharmacy benefits managers (PBMs), the companies that negotiate prices and set reimbursement conditions.It has not been clear what exactly the department of justice is looking for. In the past, drug makers such as Novartis and AstraZeneca have agreed to pay fines and penalties to settle allegations pertaining to PBMs. FDA continues to race ahead with generic approvals The American regulator has reduced its pile of ANDA (abbreviated new drug applications) by about 500 applications in the first six months of 2016. The FDA has also approved 315 more ANDAs over the same time period and has sent 66 more complete response letters — or rejections — to drug makers.This news comes after Bloomberg reported last month that the FDA has become ‘something of a bogeyman’ for India’s stock markets by approving generic drug applications from India at a record place. Similarly, PharmaCompass had reported last week that Indian companies have been fixing compliance issues. China’s Jinan Jinda fails another EDQM inspection; compliance troubles in Denmark In regulatory news from across the world, Jinan Jinda, a Chinese API manufacturer that had failed an inspection by Italian regulators in June 2015, had more bad news awaiting it a year on. In a June 2016 re-inspection, this time by the Spanish Health Authority, the regulator maintained the ‘facilities non-compliance standing’ since two critical observations were made and the corrections from the previous inspection “were found as not having been implemented in a satisfactory way”. And critical deficiencies were found on raw data.In the June 2015 inspection, the critical observation was related to an unofficial and non-controlled storage area containing mainly raw materials and finished products which had been made inaccessible to inspectors as the door had been removed and replaced with a panel fixed with screws to the wall.Meanwhile, the FDA issued an untitled letter (dated July 15, 2016) to Danish allergy immunotherapy company ALK-Abelló (ALK) over manufacturing and quality control issues at its Horsholm, Denmark facility. The letter comes after a 12-day inspection of the facility in March 2016. During the inspection, the FDA had cited ALK for four “significant deviations” from cGMP requirements. Another black box warning added to antibiotics like Cipro and LevaquinThe FDA has upgraded warnings on certain antibiotics, such as Johnson & Johnson’s Levaquin, Bayer’s Cipro extended-release tablets and Merck’s Avelox. The FDA had added a black box warning in 2008 about the increased risk of tendinitis in which the tissue connecting muscle to bone becomes inflamed. In May this year, the FDA had advised restricting the use of fluoroquinolone antibiotic for certain uncomplicated infections and had warned about the disabling side-effects of the drug.The new warning talks about long-term risks to the drugs’ current black box warning. The agency also advised using the drugs only for serious infections. Manufacturers of fluoroquinolone have faced thousands of lawsuits from patients who claim that their injuries were caused by the drugs. J&J alone faced 3,400 lawsuits over Levaquin’s links to tendon problems and has also settled many of those cases. Takeda to overhaul R&D, downsize operations in the UKTakeda Pharmaceutical of Japan has said it plans to build a new pipeline of drugs. It plans to revamp its research operations at the cost of around US $ 727 million.. The company also plans to close some of its R&D operations in the UK. Takeda is beginning the first ‘consultation stage’ of the layoff process in the UK, which hosts a pre-clinical R&D operation in Cambridge as well as a development center headquarter with facilities in the UK, Switzerland and Denmark.Under the revamp, Takeda’s R&D activities will be concentrated in Japan and the US, the 235-year old drug company said in a statement. Takeda plans to now focus on the three therapeutic areas of oncology, gastroenterology and the central nervous system.“We need to first build new capabilities and embrace new ways of working,” Andy Plump, Takeda’s chief medical and scientific officer, said in the statement.