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| CAS No.: | 95058-81-4 |
|---|---|
| Name: | Gemcitabine |
| Article Data: | 50 |
| Molecular Structure: | |
|
|
|
| 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 |
| Appearance: | white powder |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 21-36/38-46-62-63 |
| Safety: | 25-26-36/37-53 |
| PSA: | 110.60000 |
| LogP: | -0.70740 |
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
- 97730-31-9(S)-4'-(2-Methylbutyl)Biphenyl-4-Carbonitrile
- 95789-13-21,3,7-trimethylpurine-2,6-dione
- 956104-42-02-Bromo-5-nitro-3-(trifluoromethyl)pyridine
- 960294-15-95-BROMOISOQUINOLIN-1-AMINE
- 960294-12-6tert-Butyl 2-(2-chloro-ethyl)-2-cyanopyrrolidine-1-carboxylate
- 98020-47-46-Amino-5-nitro-2-thio-uracil
- 952652-79-8Valsartan n-Propyl
- 97271-97-12-AMINO-3-NITRO-BENZALDEHYDE
- 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With ammonia In methanol at 20℃; for 12h; Product distribution / selectivity; | 76.9% |
- 95058-81-4
gemcitabine
| Conditions | Yield |
|---|---|
| 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; |
- 95058-81-4
gemcitabine
| Conditions | Yield |
|---|---|
| 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; |
- 95058-81-4
gemcitabine
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium hydrogencarbonate In methanol | A 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 | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In methanol | A 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 | Yield |
|---|---|
| Multistep reaction; |
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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: 
Xn, 
Xi
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.