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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)

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

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    (USD/KGS)    		 Number of Transactions

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    DOSAGE - CAPSULE;ORAL - 100MG

    USFDA APPLICATION NUMBER - 16620

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    USFDA APPLICATION NUMBER - 16620

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    USFDA APPLICATION NUMBER - 16620

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    USFDA APPLICATION NUMBER - 20064

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    USFDA APPLICATION NUMBER - 9175

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    USFDA APPLICATION NUMBER - 9175

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