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Floxuridine

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Name

Floxuridine

EINECS 200-072-5
CAS No. 50-91-9 Density 1.64 g/cm3
PSA 104.55000 LogP -1.68360
Solubility soluble in water Melting Point 148 °C(lit.)
Formula C9H11FN2O5 Boiling Point 150 °C
Molecular Weight 246.195 Flash Point N/A
Transport Information UN 2811 6.1/PG 3 Appearance white solid
Safety 22-36/37/39-26 Risk Codes 68-36/37/38-40-20/21/22
Molecular Structure Molecular Structure of 50-91-9 (Floxuridine) Hazard Symbols HarmfulXn,ToxicT,IrritantXi
Synonyms

1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil;5-Fluoro-2'-deoxy-b-uridine;5-Fluoro-2'-deoxyuridine;5-Fluorodeoxyuridine;5-Fluorouracil 2'-deoxyriboside;5-Fluorouracil deoxyriboside;Floxuridin;NSC 26740;NSC 27640;2'-Deoxy-5-fluorouridine;

Article Data 50

Floxuridine Synthetic route

1384553-43-8

5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 3h;98%
1582-79-2

3',5'-di-O-(p-chlorobenzoyl)-5-fluoro-2'-deoxy-β-uridine

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With methanol; ammonia at 10 - 25℃;86.2%
With ammonia In methanol at 30℃; for 16h;
With methanol; barium methoxide
51-21-8

5-fluorouracil

7-methyl-2′-deoxyguanosine hydroiodide

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With potassium dihydrogenphosphate; Escherichia coli thymidine phosphorylase; Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 20h; pH=7.5; Enzymatic reaction;81%
51-21-8

5-fluorouracil

951-78-0

2'-deoxyuridine

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
at 37℃; for 16h; alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli, ammonium acetate buffer pH 5.8;62%
With purine nucleoside phosphorylase; uridine phosphorylase In aq. phosphate buffer; dimethyl sulfoxide at 80℃; for 3h; Enzymatic reaction;
51-21-8

5-fluorouracil

50-89-5

thymidine

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose In aq. buffer at 30℃; pH=7; Concentration; Reagent/catalyst; Green chemistry; Enzymatic reaction;35%
With thymidine phosphorylase In aq. phosphate buffer at 37℃; for 0.2h; pH=6.8; Enzymatic reaction;
With ammonium dihydrogen phosphate; ammonia In water at 45 - 55℃; for 45h; pH=6.6; Large scale; Enzymatic reaction;
With recobinant purine nucleoside phosphorylase from Escherichia coli In aq. phosphate buffer pH=6.8; Heating; Enzymatic reaction;
51-21-8

5-fluorouracil

1463-10-1

5-Methyluridine

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With lactobacillus animalis ATCC 35046 at 30℃; for 0.5h; pH=7; aq. buffer; Enzymatic reaction;22%
7585-89-9

5-fluoro-O3',O5'-bis-(4-methyl-benzoyl)-2'-deoxy-uridine

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With methanol; barium methoxide
With methanol; barium methoxide
951-78-0

2'-deoxyuridine

78948-09-1

acetyl hypofluorite

A

3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1

(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B

3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1

(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

C

119003-28-0, 119068-00-7

Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D

119003-28-0, 119068-00-7

Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

E

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
In acetic acid Product distribution; different solvents (AcOH,H2O), various nucleosides;A n/a
B n/a
C n/a
D n/a
E 5 % Chromat.
951-78-0

2'-deoxyuridine

78948-09-1

acetyl hypofluorite

A

3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1

(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B

119003-28-0, 119068-00-7

Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

C

119003-28-0, 119068-00-7

Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
In acetic acid Yield given. Further byproducts given. Yields of byproduct given;
951-78-0

2'-deoxyuridine

A

3180-64-1, 13964-07-3, 119180-46-0, 119180-47-1

(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione

B

119003-28-0, 119068-00-7

Acetic acid (4R,5S)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

C

119003-28-0, 119068-00-7

Acetic acid (4S,5R)-5-fluoro-3-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-hexahydro-pyrimidin-4-yl ester

D

50-91-9

5-Fluoro-2'-deoxyuridine

Conditions
ConditionsYield
With acetyl hypofluorite In water Yield given. Further byproducts given;A n/a
B n/a
C n/a
D 5 % Chromat.

Floxuridine Chemical Properties

IUPAC Name: 5-Fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Synonyms of 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil ; 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil ; 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil ; 5-24-06-00291 (Beilstein Handbook Reference) ; 5-FUDR ; 5-FdUrd ; 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion ; 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion [Czech] ; 5-Fluoro-2-desoxyuridine ; 5-Fluorodeoxyuridine ; 5-Fluorouracil 2'-deoxyriboside ; 5-Fluorouracil deoxyriboside ; AI3-50691 ; BRN 0090221 ; Deoxyfluorouridine ; EINECS 200-072-5; Floxiridina ; Floxiridina [INN-Spanish] ; Floxuridin ; Floxuridine ; Floxuridinum ; Floxuridinum [INN-Latin] ; Fluorodeoxyuridine ; Fluoruridine deoxyribose ; HSDB 3227 ; NSC 27640 ; NSC-27640 ; Ro 5-0360 ; UNII-039LU44I5M ; Uridine, 2'-deoxy-5'-fluoro- ; beta-5-Fluoro-2'-deoxyuridine
CAS NO: 50-91-9
Classification Code: Antimetabolites ; Antimetabolites, antineoplastic ; Antineoplastic ; Antineoplastic Agents ; Antiviral ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Noxae ; Reproductive Effect
Molecular Formula: C9H11FN2O5
Molecular Weight: 246.1924
Molecular Structure:

Melting Point: 148 °C 
H bond acceptors: 7
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 68.31 Å2
Index of Refraction: 1.608
Molar Refractivity: 51.94 cm3
Molar Volume: 150 cm3
Surface Tension: 72.3 dyne/cm
Density: 1.64 g/cm3

Floxuridine Uses

 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9) can be used as antineoplastic agents.It is applicable in the treatment of liver cancer, gastrointestinal cancer, breast cancer and head and neck cancer. It may make bone marrow suppression. Local gastrointestinal reactions and skin reactions similar to side effects and fluorouracil. Also it can have the phenomenon which alkaline phosphatase, serum transaminases, serum bilirubin and lactate dehydrogenase increased .

Floxuridine Production

The production methods of 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9) is methyl -2 - deoxy-D-glucoside hydrolyzed by  P-Toluoyl chlorid and acetic acid - hydrochloric acid ,make a methoxy substituted by chlorine. Then the product is of condensation with 1 -acetyl-oxygen Mercury -5 - fluorouracil, and the condensation product removed benzoyl- A by hydrolyzed and derived the product.

Floxuridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 5mg/kg/14D-C (5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES
Cancer Vol. 34, Pg. 972, 1974.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Proceedings of the Society for Experimental Biology and Medicine. Vol. 97, Pg. 470, 1958.
mouse LD50 oral 147mg/kg (147mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
mouse LD50 unreported 550mg/kg (550mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
rat LD50 intraperitoneal 1600mg/kg (1600mg/kg)   Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.
rat LD50 oral 215mg/kg (215mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
women TDLo parenteral 173mg/kg/82W- (173mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Journal of the National Medical Association. Vol. 79, Pg. 669, 1987.

Floxuridine Consensus Reports

EPA Genetic Toxicology Program.

Floxuridine Safety Profile

Hazard Codes 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): HarmfulXn,ToxicT,IrritantXi
Risk Statements: 68-36/37/38-40-20/21/22 
R68: Possible risk of irreversible effects. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R40: Limited evidence of a carcinogenic effect. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-26 
S22: Do not breathe dust. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: YU7525000
F: 10-23
Hazard Note: Toxic
HazardClass: 6.1
PackingGroup: III
Poison by ingestion. Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects: hypermotility, diarrhea, nausea, vomiting and other gastrointestinal effects, allergic dermatitis, and bone marrow changes. Human mutation data reported. When heated to decomposition it emits very toxic fumes of F and NOx . 

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