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CAS No.: | 50-91-9 |
---|---|
Name: | Floxuridine |
Article Data: | 50 |
Molecular Structure: | |
Formula: | C9H11FN2O5 |
Molecular Weight: | 246.195 |
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; |
EINECS: | 200-072-5 |
Density: | 1.64 g/cm3 |
Melting Point: | 148 °C(lit.) |
Boiling Point: | 150 °C |
Solubility: | soluble in water |
Appearance: | white solid |
Hazard Symbols: | Xn,T,Xi |
Risk Codes: | 68-36/37/38-40-20/21/22 |
Safety: | 22-36/37/39-26 |
Transport Information: | UN 2811 6.1/PG 3 |
PSA: | 104.55000 |
LogP: | -1.68360 |
5-fluoro-1-(3',5'-di-O-p-methoxybenzoyl-2'-deoxy-D-ribofuranosyl)uracil
5-Fluoro-2'-deoxyuridine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 3h; | 98% |
Conditions | Yield |
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With methanol; ammonia at 10 - 25℃; | 86.2% |
With ammonia In methanol at 30℃; for 16h; | |
With methanol; barium methoxide |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With lactobacillus animalis ATCC 35046 at 30℃; for 0.5h; pH=7; aq. buffer; Enzymatic reaction; | 22% |
Conditions | Yield |
---|---|
With methanol; barium methoxide | |
With methanol; barium methoxide |
2'-deoxyuridine
acetyl hypofluorite
A
(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione
B
(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione
C
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
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
5-Fluoro-2'-deoxyuridine
Conditions | Yield |
---|---|
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. |
2'-deoxyuridine
acetyl hypofluorite
A
(5R,6S)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione
B
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
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
5-Fluoro-2'-deoxyuridine
Conditions | Yield |
---|---|
In acetic acid Yield given. Further byproducts given. Yields of byproduct given; |
2'-deoxyuridine
A
(5S,6R)-5-Fluoro-6-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-dihydro-pyrimidine-2,4-dione
B
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
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
5-Fluoro-2'-deoxyuridine
Conditions | Yield |
---|---|
With acetyl hypofluorite In water Yield given. Further byproducts given; | A n/a B n/a C n/a D 5 % Chromat. |
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
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 .
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.
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. |
EPA Genetic Toxicology Program.
Hazard Codes 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): Xn,T,Xi
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 .