5-Flucytosine

Modify Date: 2024-01-01 18:57:34

5-Flucytosine Structure
5-Flucytosine structure
 Common Name 5-Flucytosine
CAS Number 2022-85-7 Molecular Weight 129.092
Density 1.7±0.1 g/cm3 Boiling Point 298ºC
Molecular Formula C4H4FN3O Melting Point 298-300 °C (dec.)(lit.)
MSDS Chinese USA Flash Point N/A
Symbol GHS08
GHS08		 Signal Word Warning

 Use of 5-Flucytosine


Flucytosine (5-Fluorocytosine, 5-FC, Ancobon), a fluorinated pyrimidine analogue, is an antifungal drug.Target: antifungalFlucytosine, or 5-fluorocytosine, a fluorinated pyrimidine analogue, is a synthetic antimycotic drug. It is structurally related to the cytostatic fluorouracil and to floxuridine. It is available in oral and in some countries also in injectable form. A common brand name is Ancobon. Flucytosine was first synthesized in 1957 but its antifungal properties were discovered in 1964. The drug is dispensed in capsules of 250 mg and 500 mg strength. The injectable form is diluted in 250 mL saline solution to contain 2.5 g total (10 mg/mL). The solution is physically incompatible with other drugs including amphotericin B.Flucytosine is well absorbed (75 to 90%) from the gastrointestinal tract. Intake with meals slows the absorption, but does not decrease the amount absorbed. Following an oral dose of 2 grams peak serum levels are reached after approximately 6 hours. The time to peak level decreases with continued therapy. After 4 days peak levels are measured after 2 hours. The drug is eliminated renally. In normal patients flucytosine has reportedly a half-life of 2.5 to 6 hours. In patients with impaired renal function higher serum levels are seen and the drug tends to cumulate in these patients. The drug is mainly excreted unchanged in the urine (90% of an oral dose) and only traces are metabolized and excreted in the feces. Therapeutic serum levels range from 25 to 100 ?g/ml. Serum levels in excess of 100 ug are associated with a higher incidence of side effects. Periodic measurements of serum levels are recommended for all patients and are a must in patients with renal damage.

 Names

Name flucytosine
Synonym More Synonyms

 5-Flucytosine Biological Activity

Description Flucytosine (5-Fluorocytosine, 5-FC, Ancobon), a fluorinated pyrimidine analogue, is an antifungal drug.Target: antifungalFlucytosine, or 5-fluorocytosine, a fluorinated pyrimidine analogue, is a synthetic antimycotic drug. It is structurally related to the cytostatic fluorouracil and to floxuridine. It is available in oral and in some countries also in injectable form. A common brand name is Ancobon. Flucytosine was first synthesized in 1957 but its antifungal properties were discovered in 1964. The drug is dispensed in capsules of 250 mg and 500 mg strength. The injectable form is diluted in 250 mL saline solution to contain 2.5 g total (10 mg/mL). The solution is physically incompatible with other drugs including amphotericin B.Flucytosine is well absorbed (75 to 90%) from the gastrointestinal tract. Intake with meals slows the absorption, but does not decrease the amount absorbed. Following an oral dose of 2 grams peak serum levels are reached after approximately 6 hours. The time to peak level decreases with continued therapy. After 4 days peak levels are measured after 2 hours. The drug is eliminated renally. In normal patients flucytosine has reportedly a half-life of 2.5 to 6 hours. In patients with impaired renal function higher serum levels are seen and the drug tends to cumulate in these patients. The drug is mainly excreted unchanged in the urine (90% of an oral dose) and only traces are metabolized and excreted in the feces. Therapeutic serum levels range from 25 to 100 ?g/ml. Serum levels in excess of 100 ug are associated with a higher incidence of side effects. Periodic measurements of serum levels are recommended for all patients and are a must in patients with renal damage.
Related Catalog
References

[1]. Vermes A, et al. Flucytosine: a review of its pharmacology, clinical indications, pharmacokinetics, toxicity and drug interactions. J Antimicrob Chemother. 2000 Aug;46(2):171-9.

[2]. Te Dorsthorst DT, et al. In vitro interaction of flucytosine combined with amphotericin B or fluconazole against thirty-five yeast isolates determined by both the fractional inhibitory concentration index and the response surface approach. Antimicrob Agen

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 298ºC
Melting Point 298-300 °C (dec.)(lit.)
Molecular Formula C4H4FN3O
Molecular Weight 129.092
Exact Mass 129.033844
PSA 71.77000
LogP -2.36
Vapour Pressure 0.0492mmHg at 25°C
Index of Refraction 1.649
Storage condition 2-8°C
Stability Light Sensitive
Water Solubility 1.5g/100mL (25 ºC)

 MSDS

Name: 5-Fluorocytosine 98% Material Safety Data Sheet
Synonym:
CAS: 2022-85-7
Section 1 - Chemical Product MSDS Name:5-Fluorocytosine 98% Material Safety Data Sheet
Synonym:
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
2022-85-7 5-Fluorocytosine 217-968-7
Hazard Symbols: XN
Risk Phrases: 40
Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Limited evidence of a carcinogenic effect.Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
No hazard expected in normal industrial use.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
Prolonged or repeated exposure may cause adverse reproductive effects.
Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.
Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.
Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Store protected from light.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Keep refrigerated. (Store below 4C/39F.)
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2022-85-7: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 296 deg C dec
Autoignition Temperature: Not available.
Flash Point: 296 deg C ( 564.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 296 deg C
Solubility in water: IN WATER: 1.5 G/100 ML (25C)
Specific Gravity/Density:
Molecular Formula:
Molecular Weight: 129.09
Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, light, excess heat, exposure to flame.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported
Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2022-85-7: HA6040000 LD50/LC50:
CAS# 2022-85-7: Oral, rat: LD50 = >15 gm/kg.
Carcinogenicity:
5-Fluorocytosine - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.
Section 12 - ECOLOGICAL INFORMATION

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.
Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 40 Limited evidence of a carcinogenic effect.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 2022-85-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2022-85-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2022-85-7 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA6040000
CHEMICAL NAME :
Cytosine, 5-fluoro-
CAS REGISTRY NUMBER :
2022-85-7
LAST UPDATED :
199801
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C4-H4-F-N3-O
MOLECULAR WEIGHT :
129.11
WISWESSER LINE NOTATION :
T6MVNJ DZ EF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1080 mg/kg/10D-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Behavioral - changes in motor activity (specific assay) Behavioral - ataxia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>15 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3811 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3336 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>15 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Yeast - Saccharomyces cerevisiae
DOSE/DURATION :
8 mg/L
REFERENCE :
MGGEAE Molecular and General Genetics. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.99- 1967- Volume(issue)/page/year: 146,253,1976 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6122 No. of Facilities: 53 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1033 (estimated) No. of Female Employees: 480 (estimated)

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H361
Precautionary Statements P280
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn:Harmful
Risk Phrases R40
Safety Phrases S22-S24/25-S45-S36/37
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS HA6040000
HS Code 2933599090

 Customs

HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

4-amino-5-fluoro-1,2-dihydropyrimidin-2-one
4-Amino-5-fluoro-2(1H)-pyrimidinone
5-Fluorocytosine
Fluocytosine
6-amino-5-fluoro-1H-pyrimidin-2-one
Flucytosin
Ancotil
4-amino-5-fluoro-2(1H)-pyrimidinone,5-Fluorocytosine,Flucytosine
5-Fluorocytosin
4-amino-5-fluoro-2(1H)-pyrimidinone,Flucytosine
MFCD00006035
4-Amino-5-fluoro-2-hydroxypyrimidine
EINECS 217-968-7
Fluorcytosine
Flucytosine
Ancobon
5-Fluorocystosine
4-amino-5-fluoro-2-pyrimidone
Fluorocytosine
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