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95058-81-4

Basic Information
CAS No.: 95058-81-4
Name: Gemcitabine
Article Data: 50
Cas Database
Molecular Structure:
Molecular Structure of 95058-81-4 (Gemcitabine)
Formula: C9H11F2N3O4
Molecular Weight: 263.201
Synonyms: 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;Cytidine, 2-deoxy-2,2-difluoro-2-Deoxy-.beta.-D-2,2-difluorocytidine;Gemcitabine [USAN:BAN:INN];DDFC;LY 188011;LY188011 hydrochloride;Cytosine, 1-(2-deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)-;Gemcitabine hydrochloride [USAN];LY188011;2-Deoxy-2,2-difluorocytidine monohydrochloride;Gemzar;2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl)-;2'-Deoxy-2',2'-Difluorocytidine;2',2'-Difluorodeoxycytidine(Gemcitabine base);Cytidine, 2'-deoxy-2',2'-difluoro-;
EINECS: 619-100-6
Density: 1.84 g/cm3
Melting Point: 168.64 °C
Boiling Point: 482.7 °C at 760 mmHg
Flash Point: 245.7 °C
Solubility: N/A
Appearance: white powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 21-36/38-46-62-63
Safety: 25-26-36/37-53
Transport Information: N/A
PSA: 110.60000
LogP: -0.70740
Synthetic route
942288-40-6

(2R,3R,5R)-5-(4-amino-2-oxopyrimidine-1(2H)-yl)-4,4-difluoro-2-((3-fluorobenzoyloxy)methyl)tetrahydrofuran-3-yl 3-fluorobenzoate

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonia; water at 20℃; for 3h;100%
With methanol; ammonia; water at 20℃; for 3h;100%
134790-39-9

(2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 20℃; for 3h;82.7%
With sodium t-butanolate In methanol at 20℃; for 2h;
896109-84-5

1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 12h; Product distribution / selectivity;76.9%

1-(5'-O-benzoyl-2'-deoxy-2',2'-difluoro-3-O-(p-phenylbenzoyl)-D-ribofuranosyl)-4-aminopyrimidin-2-one

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonia In methanol at 20℃; Product distribution / selectivity;72.6%
With ammonia In methanol at 20℃; Product distribution / selectivity;72.6%
With ammonia; water In methanol at 20℃; for 12h;71%
With ammonia In methanol at 20℃; Product distribution / selectivity;

(2R,3R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate

95058-81-4

gemcitabine

Conditions
ConditionsYield
With Amberlite IRA 400, OH-form In methanol at 40 - 45℃; for 36h; Product distribution / selectivity;71%
With ammonia In methanol; water at 20℃; for 24h; Product distribution / selectivity;

C31H25F2N3O7

95058-81-4

gemcitabine

Conditions
ConditionsYield
With ammonia In methanol Product distribution / selectivity;63%
With ammonia In methanol for 8h; Product distribution / selectivity;63%
With ammonia In methanol
1018907-93-1

2-amino-N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide trifluoroacetic acid

A

1018908-06-9

C11H14F2N4O5

B

95058-81-4

gemcitabine

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanolA 51%
B n/a
1260238-57-0

2'-deoxy-2',2'-difluoro-3',5'-di-O-(triisopropylsilyl)cytidine

A

95058-85-8

α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B

95058-81-4

gemcitabine

Conditions
ConditionsYield
With tetramethylammonium fluoride; acetic acid In N,N-dimethyl-formamide at 20℃; stereoselective reaction;A 42%
B 36%
With tetramethylammonium fluoride; acetic acid In N,N-dimethyl-formamide at 20℃;
1018908-14-9

C2HF3O2*C14H18F2N4O5

A

1018908-15-0

C14H18F2N4O5

B

95058-81-4

gemcitabine

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanolA 38%
B n/a
18027-23-1

bis(trimethylsilyl)-N-acetylcytosine

103882-89-9

3,5-bis-O-(tert-butyldimethylsilyl)-1-O-(methanesulfonyl)-2-deoxy-2,2-difluororibose

A

95058-85-8

α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

B

95058-81-4

gemcitabine

Conditions
ConditionsYield
Multistep reaction;
Downstream Products
122111-03-9
116371-67-6
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    Product name Gemcitabine CAS 95058-81-4 MF C9H11F2N3O4 MW 263.2 Melting point 168,64 C Boiling point 482.7±55.0 °C(Predicted) Density 1.84±0.1 g/cm3

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Specification

1. Introduction of Gemcitabine
Gemcitabine is one kind of white to light yellow powder. The IUPAC name of this chemical is 4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one. It belongs to API;Antineoplastic drug, difluorine nucleoside analog. In addition, the Classification Code of it is Anti-Infective Agents; Antimetabolites; Antimetabolites, Antineoplastic; Antineoplastic; Antineoplastic Agents; Antiviral Agents; Enzyme Inhibitors; Immunologic Factors; Immunosuppressive Agents; Noxae; Radiation-Sensitizing Agents. Gemcitabine can soluble in water.

2. Properties of Gemcitabine
Physical properties about Gemcitabine are:
(1)Melting Point: 168.64 °C; (2)Boiling Point: 482.7 °C at 760 mmHg; (3)Flash Point: 245.7 °C; (4)Index of Refraction: 1.652; (5)Molar Refractivity: 52.06 cm3; (6)Molar Volume: 142.3 cm3; (7)Surface Tension: 65.3 dyne/cm; (8)Enthalpy of Vaporization: 86.16 kJ/mol; (9)Vapour Pressure: 2.41E-11 mmHg at 25 °C; (10)XLogP3: -1.5; (11)H-Bond Donor: 3; (12)H-Bond Acceptor: 7; (13)Rotatable Bond Count: 2; (14)Tautomer Count: 3; (15)Exact Mass: 263.071762; (16)MonoIsotopic Mass: 263.071762; (17)Topological Polar Surface Area: 108; (18)Heavy Atom Count: 18.

3. Structure Descriptors of Gemcitabine 
(1)Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F
(2)Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
(3)InChI: InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
(4)InChIKey: SDUQYLNIPVEERB-QPPQHZFASA-N

4. Toxicity of Gemcitabine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 27mg/kg (27mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION
Journal of Cancer Research and Clinical Oncology. Vol. 125, Pg. 637, 1999.

5. Safety information of Gemcitabine
Hazard Codes: HarmfulXn, IrritantXi
Risk Statements: 21-36/38-46-62-63 
R21:Harmful in contact with skin. 
R36/38:Irritating to eyes and skin. 
R46:May cause heritable genetic damage. 
R62:Risk of impaired fertility. 
R63:Possible risk of harm to the unborn child.
Safety Statements: 25-26-36/37-53 
S25:Avoid contact with eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S53:Avoid exposure - obtain special instructions before use.
Human systemic effects When heated to decomposition it emits toxic vapors of NOx and F.

6. Uses of Gemcitabine
Gemcitabine (CAS NO.95058-81-4) is a nucleoside analog used as chemotherapy. It can be used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. Gemcitabine is a nucleoside analog used as chemotherapy. Gemcitabine is used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It is being investigated for use in oesophageal cancer, and is used experimentally in lymphomas and various other tumor types.