CAS No.50-91-9,Floxuridine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	50-91-9
Name:	Floxuridine
Article Data:	50

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

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

Conditions	Yield
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

Conditions	Yield
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

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%

: 51-21-8
5-fluorouracil

: 951-78-0
2'-deoxyuridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

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;

: 51-21-8
5-fluorouracil

: 50-89-5
thymidine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

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;

: 51-21-8
5-fluorouracil

: 1463-10-1
5-Methyluridine

: 50-91-9
5-Fluoro-2'-deoxyuridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

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.

...Expand

: 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

Conditions	Yield
In acetic acid Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 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

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

...Expand

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Chemistry

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

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 .

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.

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.

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes 2'-Deoxy-5-fluorouridine (CAS NO.50-91-9): Harmful Xn, Toxic T, Irritant 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 NO_x .