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| CAS No.: | 122111-03-9 |
|---|---|
| Name: | Gemcitabine hydrochloride |
| Molecular Structure: | |
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|
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| Formula: | C9H11F2N3O4.HCl |
| Molecular Weight: | 299.662 |
| Synonyms: | Gemcitabine HCl;2',2'-Difluorodeoxycytidine monohydrochloride;2'-Deoxy-2',2'-difluorocytidine monohydrochloride;2'-Deoxy-2',2'-difluorocytidine monohydrochloride (beta-isomer); |
| EINECS: | 601-823-3 |
| Density: | == |
| Melting Point: | >250 °C dec |
| Boiling Point: | 482.7 °C at 760 mmHg |
| Flash Point: | 245.7 °C |
| Appearance: | White crystalline granular, odorless |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 21-36/38-46-62-63 |
| Safety: | 25-26-36/37-53 |
| PSA: | 110.60000 |
| LogP: | 0.09460 |
gemcitabine
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; isopropyl alcohol at 20 - 70℃; | 93.4% |
| With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
| With hydrogenchloride In isopropyl alcohol at 0 - 5℃; for 2h; pH=2; | 90% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.9% |
| With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.9% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
| With hydrogenchloride In water; acetone at 20℃; for 2h; Product distribution / selectivity; | 91.5% |
(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate With ammonia In methanol at 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; pH=2; Heating; | 90% |
| With sodium methylate In methanol at 20℃; for 4h; Reagent/catalyst; | 90% |
| Stage #1: (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate With ammonium hydroxide In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; | 78% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water; acetone at 0 - 5℃; Green chemistry; Industrial scale; | 88% |
3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine
A
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| With sodium carbonate In methanol at 24℃; for 4h; Hydrolysis; | A 10% B 85% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: 3',5'-di-O-benzoyl-β-2'-deoxy-2',2'-difluorocytidine With ammonium hydroxide; water In methanol for 6h; Reflux; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 12h; pH=3; | 85% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: N-1-acetyl-2-deoxy-2,2-difluorocytidine 3,5-dicinnamonate With ammonia In methanol Stage #2: With hydrogenchloride In water | 80% |
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: C30H21Cl2F2N3O7 With ammonium hydroxide In methanol at 20℃; for 16h; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; | 79% |
(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine
gemcitabine hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate With triethylamine In tetrahydrofuran at 0 - 5℃; Stage #2: 4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 5℃; Stage #3: In methanol at 40℃; | 50.5% |
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The Gemcitabine hydrochloride, with the CAS registry number 122111-03-9, is also known as 4-Amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidin-2-one hydrochloride. It belongs to the product categories of Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals.This chemical's molecular formula is C20H24O2 and molecular weight is 296.40. What's more,Its systematic name is Cytidine,2'-deoxy-2',2'-difluor-,monohydrochloride. Ii is a White crystalline granular, odorless. Gemcitabine hydrochloride is approved by the Food and Drug Administration (FDA) to be used by itself to treat pancreatic cancer that is advanced or has metastasized (spread to other parts of the body). It is used in patients who cannot be treated with surgery and have already been treated with other chemotherapy.[National Cancer Institute].
Physical properties about Gemcitabine hydrochloride are:
(1)#H bond acceptors: 7; (2)#H bond donors: 4 ; (3)#Freely Rotating Bonds: 4; (4)Polar Surface Area: 108.38 Å2; (5)Flash Point: 255.1 °C; (6)Enthalpy of Vaporization: 88.26 kJ/mol ; (7)Boiling Point: 498.2 °C at 760 mmHg; (8)Vapour Pressure: 5.15E-12 mmHg at 25°C.(9)Melting Point: >250°C dec; (10)Appearance: White crystalline granular, odorless.
Safety Information of Gemcitabine hydrochloride:
The Gemcitabine hydrochloride is harmful in contact with skin,may cause heritable genetic damage,possible risk of impaired fertility, and possible risk of harm to the unborn child.It is irritating to eyes and skin.Avoid contact with eyes.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it wear suitable protective clothing and gloves.Avoid exposure - obtain special instruction before use.
Uses of Gemcitabine hydrochloride:
Gemcitabine hydrochloride can be used as an antineoplastic. It is a chemotherapy drug that is given as a treatment for some types of cancer. Gemcitabine hydrochloride is most commonly used to treat non small cell lung cancer, pancreatic,bladder cancer and breast cancer.
You can still convert the following datas into molecular structure:
(1)SMILES:Cl.N/C1=N/C(=O)N(/C=C1)C2O[C@H](CO)[C@@H](O)C2(F)F;
(2)Std. InChI:InChI=1S/C9H11F2N3O4.ClH/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);1H/t4-,6-,7?;/m1./s1;
(3)Std. InChIKey:OKKDEIYWILRZIA-UNPZIQMISA-N.
The toxicity data of Gemcitabine hydrochloride as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 500mg/kg (500mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000. | |
| rat | LD50 | intravenous | 236mg/kg (236mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000. | |
| women | TDLo | parenteral | 300mg/kg/12W- (300mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" LUNGS, THORAX, OR RESPIRATION: CONSOLIDATION LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Cancer Vol. 80, Pg. 286, 1997. |
