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    Chemistry

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    Also known as: 5-fluorocytosine, 2022-85-7, Ancobon, Ancotil, Fluorocytosine, 5-fluorocystosine
    Molecular Formula
    C4H4FN3O
    Molecular Weight
    129.09  g/mol
    InChI Key
    XRECTZIEBJDKEO-UHFFFAOYSA-N
    FDA UNII
    D83282DT06
    Fluocytosine
    A fluorinated cytosine analog that is used as an antifungal agent.
    Flucytosine is a Nucleoside Analog Antifungal.
    1 2D Structure

    Fluocytosine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-amino-5-fluoro-1H-pyrimidin-2-one
    2.1.2 InChI
    InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
    2.1.3 InChI Key
    XRECTZIEBJDKEO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=NC(=O)NC(=C1F)N
    2.2 Other Identifiers
    2.2.1 UNII
    D83282DT06
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-fluorocytosine

    2. Alcobon

    3. Ancobon

    4. Ancotil

    2.3.2 Depositor-Supplied Synonyms

    1. 5-fluorocytosine

    2. 2022-85-7

    3. Ancobon

    4. Ancotil

    5. Fluorocytosine

    6. 5-fluorocystosine

    7. 5-fc

    8. Flucytosin

    9. Fluocytosine

    10. 5-fluorocytosin

    11. Fluorcytosine

    12. Alcobon

    13. 4-amino-5-fluoropyrimidin-2(1h)-one

    14. Ro 2-9915

    15. Flucytosinum

    16. Cytosine, 5-fluoro-

    17. 5-fluoro Cytosine

    18. 4-amino-5-fluoro-2(1h)-pyrimidinone

    19. 4-amino-5-fluoropyrimidin-2-ol

    20. 2(1h)-pyrimidinone, 4-amino-5-fluoro-

    21. 117969-88-7

    22. 5-flurocytosine

    23. 5-flucytosine

    24. 2-hydroxy-4-amino-5-fluoropyrimidine

    25. Ancobon (tn)

    26. Ro 29915 E/265601

    27. Nsc 103805

    28. 6-amino-5-fluoro-1h-pyrimidin-2-one

    29. Flucytosine (ancobon)

    30. 4-amino-5-fluoro-2-hydroxypyrimidine

    31. 130256-61-0

    32. 2-pyrimidinol, 4-amino-5-fluoro- (9ci)

    33. Ro-2-9915

    34. Chebi:5100

    35. Mfcd00006035

    36. Ro-29915

    37. Nsc-103805

    38. Mls000069463

    39. Flucitosina

    40. 4-amino-2-hydroxy-5-fluoropyrimidine

    41. 5-fluoro-4-imino-1,2,3,4-tetrahydropyrimidin-2-one

    42. Nsc103805

    43. Flucytosine [usan)

    44. D83282dt06

    45. 4-amino-5-fluoro-1h-pyrimidin-2-one

    46. Ncgc00016599-01

    47. Flucitosina [dcit]

    48. Smr000059047

    49. Cas-2022-85-7

    50. 4-amino-5-fluoro-2(1h)-pyrimidine

    51. Dsstox_cid_3059

    52. Flucytosine [usan]

    53. Dsstox_rid_76856

    54. Dsstox_gsid_23059

    55. Flucytosinum [inn-latin]

    56. Flucytosone

    57. Ancotyl

    58. Hsdb 3082

    59. 6-amino-2-oxo-5-fluoropyrimidine

    60. Einecs 217-968-7

    61. Flucytosina

    62. Flourocytosine

    63. Ancoban

    64. 2(1h)-pyrimidinone, 4-amino-5-fluoro-)

    65. 5-fluorocytocine

    66. Unii-d83282dt06

    67. Flucytosine,(s)

    68. 5-fluoro-cytosine

    69. 5 Fluoro Cytosine

    70. 4-amino-5-fluoro-2-hyroxypyrimidine

    71. 6-amino-5-fluoropyrimidin-2(1h)-one

    72. Flucytosine (5-fc)

    73. Flucytosine [usan:usp:inn:ban:jan]

    74. Cpd000059047

    75. St028644

    76. 6-amino-5-fluoro-3-hydropyrimidin-2-one

    77. Opera_id_178

    78. 5-fluorocytosine Form I

    79. Flucytosine [mi]

    80. Prestwick0_000934

    81. Prestwick1_000934

    82. Prestwick2_000934

    83. Prestwick3_000934

    84. Flucytosine [inn]

    85. Flucytosine [jan]

    86. 5-fluorocytosine Form Ii

    87. F0321

    88. Flucytosine [hsdb]

    89. Ec 217-968-7

    90. Wln: T6mvnj Dz Ef

    91. Chembl1463

    92. Flucytosine [mart.]

    93. Schembl24063

    94. Bspbio_000868

    95. Flucytosine [usp-rs]

    96. Flucytosine [who-dd]

    97. Flucytosine [who-ip]

    98. Mls000759519

    99. Mls001076503

    100. Mls001424013

    101. Flucytosine, 5-fluorocytosine

    102. Spbio_003037

    103. Bpbio1_000956

    104. Flucytosine (jp17/usp/inn)

    105. Dtxsid3023059

    106. Schembl14696800

    107. 4-amino-5-fluoro-2-pyrimidinol

    108. Ala-ala-phep-nitroanilide

    109. Flucytosine [orange Book]

    110. Flucytosine For System Suitability

    111. 2-pyrimidinol,4-amino-5-fluoro-

    112. 4-amino-5-fluoro-pyrimidin-2-ol

    113. Flucytosine [ep Monograph]

    114. Flucytosine [usp Impurity]

    115. Hms1570l10

    116. Hms2051m04

    117. Hms2093j05

    118. Hms2097l10

    119. Hms2233i14

    120. Hms3373l05

    121. Hms3393m04

    122. Hms3655g17

    123. Hms3714l10

    124. Pharmakon1600-01505429

    125. Zinc896546

    126. 5-fluorocytosine [who-ip]

    127. Flucytosine [usp Monograph]

    128. 5-fluorocytosine, Nucleoside Analog

    129. Bcp02877

    130. Flucytosine 2.0 Mg/ml In Methanol

    131. Flucytosinum [who-ip Latin]

    132. Hy-b0139

    133. Tox21_110515

    134. Bdbm50248003

    135. Mfcd00179326

    136. Mfcd03547958

    137. Nsc759130

    138. S1666

    139. Stk292386

    140. Akos004912683

    141. Akos005063821

    142. Akos015896898

    143. Akos030241326

    144. Tox21_110515_1

    145. Bcp9000692

    146. Ccg-100837

    147. Ccg-213434

    148. Cs-1935

    149. Db01099

    150. Gs-5578

    151. Ks-1060

    152. Nc00087

    153. Nsc-759130

    154. Sb57097

    155. Cytosine, 5-fluoro- (6ci,7ci,8ci)

    156. Ncgc00016599-02

    157. Ncgc00016599-04

    158. Ncgc00016599-05

    159. Ac-11748

    160. Bp-30254

    161. Emtricitabine Impurity E [who-ip]

    162. Nci60_000093

    163. Sy004438

    164. Bcp0726000281

    165. Db-005380

    166. Ab00513969

    167. Am20090149

    168. Ft-0601273

    169. Ft-0695664

    170. Sw197278-3

    171. 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one

    172. 22p857

    173. D00323

    174. F-3010

    175. H10295

    176. Ab00444223-16

    177. Ab00513969-02

    178. Ab00513969_03

    179. Ab00513969_04

    180. Flucytosine 100 Microg/ml In Acetonitrile:water

    181. 5-fluorocytosine, Vetec(tm) Reagent Grade, 99%

    182. A814346

    183. Q238490

    184. Sr-01000721885

    185. Sr-01000721885-5

    186. Brd-k82143716-001-15-7

    187. 4-amino-5-fluoropyrimidin-2(1h)-one [who-ip]

    188. 5-fluorocytosine, Antibiotic For Culture Media Use Only

    189. 6-amino-5-fluoro-2(1h)-pyrimidinone;5-fluorocytosine

    190. Flucytosine, European Pharmacopoeia (ep) Reference Standard

    191. Flucytosine, United States Pharmacopeia (usp) Reference Standard

    192. Flucytosine, Pharmaceutical Secondary Standard; Certified Reference Material

    193. Flucytosine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    194. 1ld

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 129.09 g/mol
    Molecular Formula C4H4FN3O
    XLogP3-0.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass129.03383992 g/mol
    Monoisotopic Mass129.03383992 g/mol
    Topological Polar Surface Area67.5 Ų
    Heavy Atom Count9
    Formal Charge0
    Complexity208
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAncobon
    PubMed HealthFlucytosine (By mouth)
    Drug ClassesAntifungal
    Drug LabelAncobon (flucytosine), an antifungal agent, is available as 250 mg and 500 mg capsules for oral administration. Each capsule also contains corn starch, lactose and talc. Gelatin capsule shells contain parabens (butyl, methyl, propyl) and sodium propi...
    Active IngredientFlucytosine
    Dosage FormCapsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanyValeant

    2 of 4  
    Drug NameFlucytosine
    PubMed HealthFlucytosine (By mouth)
    Drug ClassesAntifungal
    Drug LabelFlucytosine Capsules, USP are an antifungal agent available as 250 mg and 500 mg capsules for oral administration. Each capsule also contains corn starch, lactose monohydrate and talc. The 250 mg capsule shell contains FD and C Yellow No.6, FD and C...
    Active IngredientFlucytosine
    Dosage FormCapsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanySigmapharm Labs

    3 of 4  
    Drug NameAncobon
    PubMed HealthFlucytosine (By mouth)
    Drug ClassesAntifungal
    Drug LabelAncobon (flucytosine), an antifungal agent, is available as 250 mg and 500 mg capsules for oral administration. Each capsule also contains corn starch, lactose and talc. Gelatin capsule shells contain parabens (butyl, methyl, propyl) and sodium propi...
    Active IngredientFlucytosine
    Dosage FormCapsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanyValeant

    4 of 4  
    Drug NameFlucytosine
    PubMed HealthFlucytosine (By mouth)
    Drug ClassesAntifungal
    Drug LabelFlucytosine Capsules, USP are an antifungal agent available as 250 mg and 500 mg capsules for oral administration. Each capsule also contains corn starch, lactose monohydrate and talc. The 250 mg capsule shell contains FD and C Yellow No.6, FD and C...
    Active IngredientFlucytosine
    Dosage FormCapsule
    RouteOral
    Strength250mg; 500mg
    Market StatusPrescription
    CompanySigmapharm Labs

    4.2 Therapeutic Uses

    Antifungal Agents; Antimetabolites

    National Library of Medicine's Medical Subject Headings. Citalopram. Online file (MeSH, 2018). Available from, as of February 2, 2018: https://meshb.nlm.nih.gov/search

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Flucytosine is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of February 2, 2018: https://clinicaltrials.gov/

    Flucytosine Capsules are indicated only in the treatment of serious infections caused by susceptible strains of Candida and/or Cryptococcus. Candida: Septicemia, endocarditis and urinary system infections have been effectively treated with flucytosine. Limited trials in pulmonary infections justify the use of flucytosine. Cryptococcus: Meningitis and pulmonary infections have been treated effectively. Studies in septicemias and urinary tract infections are limited, but good responses have been reported. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Flucytosine Capsule (Updated: January 8, 2018). Available from, as of February 8, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58189ec7-118b-458a-8e4f-7867a97cfcbd

    Flucytosine Capsules should be used in combination with amphotericin B for the treatment of systemic candidiasis and cryptococcosis because of the emergence of resistance to Flucytosine Capsules. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Flucytosine Capsule (Updated: January 8, 2018). Available from, as of February 8, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58189ec7-118b-458a-8e4f-7867a97cfcbd

    For more Therapeutic Uses (Complete) data for Flucytosine (10 total), please visit the HSDB record page.

    4.3 Drug Warning

    /BOXED WARNING/ Use with extreme caution in patients with impaired renal function. Close monitoring of hematologic, renal and hepatic status of all patients is essential. These instructions should be thoroughly reviewed before administration of Flucytosine Capsules, USP.

    NIH; DailyMed. Current Medication Information for Flucytosine Capsule (Updated: January 8, 2018). Available from, as of February 8, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58189ec7-118b-458a-8e4f-7867a97cfcbd

    Flucytosine capsules must be given with extreme caution to patients with bone marrow depression. Patients may be more prone to depression of bone marrow function if they: 1) have a hematologic disease, 2) are being treated with radiation or drugs which depress bone marrow, or 3) have a history of treatment with such drugs or radiation. Bone marrow toxicity can be irreversible and may lead to death in immunosuppressed patients. Frequent monitoring of hepatic function and of the hematopoietic system is indicated during therapy.

    NIH; DailyMed. Current Medication Information for Flucytosine Capsule (Updated: January 8, 2018). Available from, as of February 8, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58189ec7-118b-458a-8e4f-7867a97cfcbd

    In addition to antiproliferative effects on the GI lining, adverse GI effects reported with flucytosine, which are sometimes severe, include anorexia, abdominal bloating, abdominal pain, diarrhea, dry mouth, duodenal ulcer, GI hemorrhage, nausea, vomiting, and ulcerative colitis.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 558

    There are no adequate or controlled studies to date using flucytosine in pregnant women, and the drug should be used during pregnancy only when the potential benefits justify the possible risks to the fetus.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

    For more Drug Warnings (Complete) data for Flucytosine (17 total), please visit the HSDB record page.

    4.4 Drug Indication

    For the treatment (in combination with amphotericin B) of serious infections caused by susceptible strains of Candida (septicemia, endocarditis and urinary system infections) and/or Cryptococcus (meningitis and pulmonary infections).

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Flucytosine is an antimetabolite that acts as an antifungal agent with in vitro and in vivo activity against Candida and Cryptococcus. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. Antifungal synergism between Ancobon and polyene antibiotics, particularly amphotericin B, has been reported.

    5.2 MeSH Pharmacological Classification

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    Antimetabolites

    Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    FLUCYTOSINE
    5.3.2 FDA UNII
    D83282DT06
    5.3.3 Pharmacological Classes
    Nucleoside Analog [EXT]; Nucleoside Analog Antifungal [EPC]
    5.4 ATC Code

    D - Dermatologicals

    D01 - Antifungals for dermatological use

    D01A - Antifungals for topical use

    D01AE - Other antifungals for topical use

    D01AE21 - Flucytosine

    J - Antiinfectives for systemic use

    J02 - Antimycotics for systemic use

    J02A - Antimycotics for systemic use

    J02AX - Other antimycotics for systemic use

    J02AX01 - Flucytosine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly and virtually completely absorbed following oral administration. Bioavailability 78% to 89%.

    Route of Elimination

    Flucytosine is excreted via the kidneys by means of glomerular filtration without significant tubular reabsorption. A small portion of the dose is excreted in the feces.

    Flucytosine is rapidly and well absorbed from the GI tract, with plasma levels peaking in 1-2 hr in animals that have received the drug for several days. The drug is widely distributed in the body, with a volume of distribution approximating the total body water. Flucytosine is minimally bound to plasma proteins. There is excellent penetration into body fluids such as the CSF, synovial fluids, and aqueous humor.

    Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 2310

    Flucytosine is rapidly and almost completed absorbed from the GI tract. Bioavailability is 78-89% following oral administration. Food decreases the rate, but not the extent, of absorption.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

    In a limited number of neonates receiving oral flucytosine in a dosage of 25, 50, or 100 mg/kg daily for the treatment of systemic candidiasis, median peak serum concentrations after 5 days of treatment were 19.6, 27.7, and 83.9 ug/mL, respectively, and the mean time to peak concentrations was 2.5 hours. There was considerable interindividual variation in serum concentrations, which did not correlate with gestational age, and some neonates had serum flucytosine concentrations greater than 100 ug/mL.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

    In patients with normal renal function, peak serum flucytosine concentrations of 30-40 mcg/mL are reached within 2 hours following a single 2-g oral dose. In other studies in patients with normal renal function receiving a 6-week regimen of oral flucytosine (150 mg/kg daily given in divided doses every 6 hours) and concomitant IV amphotericin B, mean serum concentrations of flucytosine 1-2 hours after a dose were approximately 70-80 ug/mL.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

    For more Absorption, Distribution and Excretion (Complete) data for Flucytosine (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite.

    Flucytosine may be fungistatic or fungicidal in action depending on the concentration of the drug. Two possible mechanisms of action have been identified for flucytosine. Flucytosine appears to enter fungal cells via the action of fungal-specific cytosine permease. Inside the cell, flucytosine is converted into fluorouracil (5-FU) by cytosine deaminase and then after several intermediate steps is converted into 5-fluorouridine triphosphate (FUTP). FUTP is incorporated into fungal RNA and interferes with protein synthesis. Flucytosine also appears to be converted to 5-fluorodeoxyuridine monophosphate, which noncompetitively inhibits thymidylate synthetase and interferes with DNA synthesis. Flucytosine does not appear to have antineoplastic activity.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

    The aim of this study is to investigate whether fluorouracil (5-FU) could be responsible for bone-marrow depression occurring in fluorocytosine (5-FC) treated patients. Six 5-FC treated patients were included in this pilot study. Toxicity was monitored by means of thrombocyte and leucocyte counts. 5-FC and 5-FU serum levels were measured using a high-performance liquid chromatography (HPLC) assay that allows simultaneous determination of both compounds. The amounts of 5-FU in the 34 available serum samples remained below the limit of quantitation (< 0.05 mg/L), whereas 5-FC levels could be detected in all samples. Instead, low levels of the 5-FU catabolite alpha-fluoro-beta-alanine (FBAL) were detected in several of the investigated serum samples. In case of three patients thrombocyte counts remained within the normal range during 5-FC treatment, whereas one patient developed thrombocytopenia (50 x 10(9) thrombocytes/L) during therapy. Furthermore, one patient developed leucocytopenia (2.6 x 10(9) leucocytes/L) during 5-FC therapy, whereas the remaining five patients were suffering from leucocytosis prior to 5-FC therapy. In conclusion, we found nondetectable 5-FU serum concentrations (< 0.05 mg/L) in ICU patients treated with intravenous 5-FC, making it unlikely that 5-FC-associated toxicity results from 5-FU exposure in patients receiving intravenous 5-FC therapy. These findings may be explained by the fact that our patients received 5-FC intravenously instead of orally, therefore not allowing active conversion of 5-FC to 5-FU by the human intestinal microflora. /5-Fluorouracil/

    PMID:11903511 Vermes A et al; Fundam Clin Pharmacol 16 (1): 39-47 (2002)

    A gas chromatographic-mass spectrometric method for detecting 5-fluorouracil (5-FU) in serum at concentrations as low as 10 ng/mL was used to determine to what extent 5-FU was present in the serum of patients taking oral 5-fluorocytosine (5-FC). Preliminary studies in two patients and two healthy volunteers given an initial 2-g oral dose of 5-FC demonstrated sustained serum 5-FU levels (>100 ng/mL) during the 5 hr after ingestion of drug. Pharmaceutical preparations of 5-FC used in these studies were shown to be insignificantly contaminated with 5-FU (<0.03%), suggesting in vivo conversion of 5-FC to 5-FU had occurred. Serum samples from seven patients with cryptococcal meningitis treated with amphotericin B and 5-FC were examined for 5-FU. Five of these patients had experienced hematological or other toxicity attributed to 5-FC at some time during the course of therapy. Of 41 serum samples, 20 were observed to have 5-FU levels greater than 1,000 ng/mL in the range observed with cancer chemotherapeutic doses of 5-FU known to be associated with hematological toxicity. It is concluded that conversion of 5-FC to 5-FU occurs in humans and furthermore that 5-FU may account for some of the toxicity observed with 5-FC. /5-Fluorouracil/

    PMID:742878 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC352577 Diasio RB et al; Antimicrob Agents Chemother 14 (6): 903-8 (1978)

    Metabolism of 5-fluorocytosine-6-14C (5-FC) was studied in mice, rats, rabbits and dogs after oral and subcutaneous, single and repeated administration. In the urines of all species, intact 5-FC accounted for more than 90% of the total radioactivity at any time of the various treatment schedules. The average proportion of the urinary metabolites was around 5% in dogs, 3% in rabbits, 2.5% in rats, and 2% in mice of the total radioactivity. At repeated dosage, there was an increase of metabolites in mice but a decrease in rats treated subcutaneously. Neither increase nor decrease was observed in rabbits (treated orally) and dogs. Two metabolites were identified, alpha-fluoro-beta-ureido-propionic acid (FUPA) and alpha-fluoro-beta-alanine, the latter occurring mainly after oral treatment. These compounds represent probably that part of 5-FC which was deaminated to 5-fluorouracil (5-FU) or directly to 5-fluorodihydrouracil. FUPA was the only metabolite found in the urines collected from 4 out of 5 human volunteers during the first 12 h after single oral administration of 3.5 g of the radiolabelled drug. Its maximum proportion was 1.1% of the total radioactivity. No metabolites were detected in the urine neither of the 5th volunteer nor in those of 3 mycosis patients who were given the radioactive dose after they had received regular chemotherapy with unlabelled 5-FC (150 mg/kg/day) for at least 2 weeks. The sensitivity threshold of the method was 0.1-0.4% of the total radioactivity. One of the patients had developed thrombocytopenia which was probably due to 5-FC chemotherapy. The symptoms of 5-FC intolerance were in most of the examined species similar to those observed with 5-FU [9]. However, no quantitative correlation between proportion of metabolites and 5-FC toxicity is apparent except that man is the species in which both metabolism and toxicity are the lowest. It has not been proved yet that 5-FC intolerance occurring in a small percentage of patients receiving 5-FC chemotherapy (mainly leukopenia, thrombocytopenia) results in fact from conversion to 5-FU.

    PMID:773604 Polak A et al; Chemotherapy 22 (3-4): 137-53 (1976)

    For more Metabolism/Metabolites (Complete) data for Flucytosine (6 total), please visit the HSDB record page.

    5.7 Biological Half-Life

    2.4 to 4.8 hours.

    In a limited number of infants, the median half-life of flucytosine was 7.4 hours.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 560

    The half-life of flucytosine is prolonged in patients with renal insufficiency; the average half-life in nephrectomized or anuric patients was 85 hours (range: 29.9 to 250 hours). A linear correlation was found between the elimination rate constant of flucytosine and creatinine clearance.

    NIH; DailyMed. Current Medication Information for Flucytosine Capsule (Updated: January 8, 2018). Available from, as of February 8, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=58189ec7-118b-458a-8e4f-7867a97cfcbd

    The elimination half-life of flucytosine has been variously reported to be 2.4-6 hours in patients with normal renal function, 6-14 hours in patients with creatinine clearances of 40 mL/minute, 12-15 hours in patients with creatinine clearances of 20 mL/minute, 21-27 hours in patients with creatinine clearances of 10 mL/minute, and 30-250 hours in patients with creatinine clearances less than 10 mL/minute. Half-lives up to 1160 hours have been reported in a few patients with creatinine clearances less than 2 mL/minute. Some clinicians have suggested that the half-life of flucytosine in hours is approximately 5 or 6 times the serum creatinine concentration in mg/dL.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 560

    5.8 Mechanism of Action

    Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase.

    Flucytosine may be fungistatic or fungicidal in action depending on the concentration of the drug. Two possible mechanisms of action have been identified for flucytosine. Flucytosine appears to enter fungal cells via the action of fungal-specific cytosine permease. Inside the cell, flucytosine is converted into fluorouracil (5-FU) by cytosine deaminase and then after several intermediate steps is converted into 5-fluorouridine triphosphate (FUTP). FUTP is incorporated into fungal RNA and interferes with protein synthesis. Flucytosine also appears to be converted to 5-fluorodeoxyuridine monophosphate, which noncompetitively inhibits thymidylate synthetase and interferes with DNA synthesis. Flucytosine does not appear to have antineoplastic activity.

    American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 559

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Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1728325800,"product":"5-FLUOROCYTOSINE","address":"H NO 31-15-8 PLAT NO 302,3RD FLOOR","city":"KURMANAPALEM VILLAGE VADLAPUDI,ANDH","supplier":"SHANGHAI ACEBRIGHT PHARMACEUTICALS","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"STYRAX LIFE SCIENCES ","customerCountry":"INDIA","quantity":"3850.00","actualQuantity":"3850","unit":"KGS","unitRateFc":"30.3","totalValueFC":"117257.3","currency":"USD","unitRateINR":"2559.2","date":"08-Oct-2024","totalValueINR":"9852727.5","totalValueInUsd":"117257.3","indian_port":"Vizag Sea","hs_no":"29335990","bill_no":"6017405","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"GROUP CO LTD BUILDING NO 5 1999 ZHANGHENG ROAD ZHANGJIANG HI-TECH PARK SHANGHAI CHINA","customerAddress":"H NO 31-15-8 PLAT NO 302,3RD FLOOR"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729103400,"product":"5-FLUOROCYTOSINE","address":"8-3-166\/7\/1, HETERO HOUSE,","city":"HYDERABAD, AP.","supplier":"BEIJING TOACHEM CHEMICAL CO LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"HONOUR LAB LTD","customerCountry":"INDIA","quantity":"2500.00","actualQuantity":"2500","unit":"KGS","unitRateFc":"29.8","totalValueFC":"75230.1","currency":"USD","unitRateINR":"2528.5","date":"17-Oct-2024","totalValueINR":"6321325","totalValueInUsd":"75230.1","indian_port":"Madras Sea","hs_no":"29335990","bill_no":"6172220","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"ROOM 1626 16TH FLOOR 25 SOUTH ROAD OF THE 3RD RING EAST CHAOYANG DISTRICT BEIJING CHINA","customerAddress":"8-3-166\/7\/1, HETERO HOUSE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729535400,"product":"5-FLUOROCYTOSINE","address":"2ND FLOOR, SERENE CHAMBERS,","city":"","supplier":"ZHEJIANG MEDICINE CO LTD","supplierCountry":"CHINA","foreign_port":"NINGBO","customer":"LAURUS LABS","customerCountry":"INDIA","quantity":"5000.00","actualQuantity":"5000","unit":"KGS","unitRateFc":"40","totalValueFC":"201364.9","currency":"USD","unitRateINR":"3384","date":"22-Oct-2024","totalValueINR":"16920000","totalValueInUsd":"201364.9","indian_port":"Vizag Sea","hs_no":"29335990","bill_no":"6255721","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NINGBO","supplierAddress":"S IMPORT & EXPORT CO LTD 6-7\/F 310 NORTH ZHONGSHAN ROAD HANGZHOU CHINA","customerAddress":"2ND FLOOR, SERENE CHAMBERS,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1730399400,"product":"5-FLUOROCYTOSINE","address":"8-3-166\/7\/1, HETERO HOUSE,","city":"HYDERABAD, AP.","supplier":"HENAN DINGXIN PHARMACEUTICAL TECHNOLOGY CO LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"HONOUR LAB LTD","customerCountry":"INDIA","quantity":"10000.00","actualQuantity":"10000","unit":"KGS","unitRateFc":"32.5","totalValueFC":"327163.7","currency":"USD","unitRateINR":"2760.9","date":"01-Nov-2024","totalValueINR":"27608750","totalValueInUsd":"327163.7","indian_port":"Madras Sea","hs_no":"29335990","bill_no":"6448775","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"NO 2369 MUYE ROAD (SOUTH) ADVANCE TECHNOLOGY DISTRICT XINXIANG CITY HENAN CHINA","customerAddress":"8-3-166\/7\/1, HETERO HOUSE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1732818600,"product":"5-FLUOROCYTOSINE","address":"8-3-166\/7\/1, HETERO HOUSE,","city":"HYDERABAD, AP.","supplier":"HENAN DINGXIN PHARMACEUTICAL TECHNOLOGY CO.,LTD","supplierCountry":"CHINA","foreign_port":"QINGDAO","customer":"HONOUR LAB LTD","customerCountry":"INDIA","quantity":"6000.00","actualQuantity":"6000","unit":"KGS","unitRateFc":"39.5","totalValueFC":"249205.5","currency":"USD","unitRateINR":"3505","date":"29-Nov-2024","totalValueINR":"21030000","totalValueInUsd":"249205.5","indian_port":"Madras Sea","hs_no":"29335990","bill_no":"6949846","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"QINGDAO","supplierAddress":"NO.2369 MUYE ROAD(SOUTH) ADVANCED TECHNOLOGY DISTRICT XINXIANG CITY HENAN CN","customerAddress":"8-3-166\/7\/1, HETERO HOUSE,"}]
    07-May-2021
    29-Nov-2024
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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - CAPSULE;ORAL - 250MG

    USFDA APPLICATION NUMBER - 17001

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    DOSAGE - CAPSULE;ORAL - 500MG

    USFDA APPLICATION NUMBER - 17001

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    USP

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    ABOUT THIS PAGE

    Flucytosine Manufacturers

    A Flucytosine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Flucytosine, including repackagers and relabelers. The FDA regulates Flucytosine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Flucytosine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Flucytosine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Flucytosine Suppliers

    A Flucytosine supplier is an individual or a company that provides Flucytosine active pharmaceutical ingredient (API) or Flucytosine finished formulations upon request. The Flucytosine suppliers may include Flucytosine API manufacturers, exporters, distributors and traders.

    click here to find a list of Flucytosine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Flucytosine USDMF

    A Flucytosine DMF (Drug Master File) is a document detailing the whole manufacturing process of Flucytosine active pharmaceutical ingredient (API) in detail. Different forms of Flucytosine DMFs exist exist since differing nations have different regulations, such as Flucytosine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Flucytosine DMF submitted to regulatory agencies in the US is known as a USDMF. Flucytosine USDMF includes data on Flucytosine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Flucytosine USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Flucytosine suppliers with USDMF on PharmaCompass.

    Flucytosine JDMF

    The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

    The Flucytosine Drug Master File in Japan (Flucytosine JDMF) empowers Flucytosine API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

    PMDA reviews the Flucytosine JDMF during the approval evaluation for pharmaceutical products. At the time of Flucytosine JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

    click here to find a list of Flucytosine suppliers with JDMF on PharmaCompass.

    Flucytosine CEP

    A Flucytosine CEP of the European Pharmacopoeia monograph is often referred to as a Flucytosine Certificate of Suitability (COS). The purpose of a Flucytosine CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Flucytosine EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Flucytosine to their clients by showing that a Flucytosine CEP has been issued for it. The manufacturer submits a Flucytosine CEP (COS) as part of the market authorization procedure, and it takes on the role of a Flucytosine CEP holder for the record. Additionally, the data presented in the Flucytosine CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Flucytosine DMF.

    A Flucytosine CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Flucytosine CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of Flucytosine suppliers with CEP (COS) on PharmaCompass.

    Flucytosine WC

    A Flucytosine written confirmation (Flucytosine WC) is an official document issued by a regulatory agency to a Flucytosine manufacturer, verifying that the manufacturing facility of a Flucytosine active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Flucytosine APIs or Flucytosine finished pharmaceutical products to another nation, regulatory agencies frequently require a Flucytosine WC (written confirmation) as part of the regulatory process.

    click here to find a list of Flucytosine suppliers with Written Confirmation (WC) on PharmaCompass.

    Flucytosine NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Flucytosine as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Flucytosine API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Flucytosine as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Flucytosine and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Flucytosine NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Flucytosine suppliers with NDC on PharmaCompass.

    Flucytosine GMP

    Flucytosine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Flucytosine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Flucytosine GMP manufacturer or Flucytosine GMP API supplier for your needs.

    Flucytosine CoA

    A Flucytosine CoA (Certificate of Analysis) is a formal document that attests to Flucytosine's compliance with Flucytosine specifications and serves as a tool for batch-level quality control.

    Flucytosine CoA mostly includes findings from lab analyses of a specific batch. For each Flucytosine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Flucytosine may be tested according to a variety of international standards, such as European Pharmacopoeia (Flucytosine EP), Flucytosine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Flucytosine USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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