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Gemcitabine hydrochloride

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Name

Gemcitabine hydrochloride

EINECS 601-823-3
CAS No. 122111-03-9 Density ==
PSA 110.60000 LogP 0.09460
Solubility N/A Melting Point >250 °C dec
Formula C9H11F2N3O4.HCl Boiling Point 482.7 °C at 760 mmHg
Molecular Weight 299.662 Flash Point 245.7 °C
Transport Information N/A Appearance White crystalline granular, odorless
Safety 25-26-36/37-53 Risk Codes 21-36/38-46-62-63
Molecular Structure Molecular Structure of 122111-03-9 (Gemcitabine hydrochloride) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

Gemcitabine HCl;2',2'-Difluorodeoxycytidine monohydrochloride;2'-Deoxy-2',2'-difluorocytidine monohydrochloride;2'-Deoxy-2',2'-difluorocytidine monohydrochloride (beta-isomer);

Article Data 30

Gemcitabine hydrochloride Synthetic route

95058-81-4

gemcitabine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%

β-2'-deoxy-2',2'-difluorocytidine hemihydrate

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%

β-2'-deoxy-2',2'-difluorocytidine dihydrate

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%
1445381-44-1

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

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%

C18H33F2N3O4Si2

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water; acetone at 0 - 5℃; Green chemistry; Industrial scale;88%
250698-52-3

3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine

A

122111-03-9

gemcitabine hydrochloride

B

5'-O-(tert-butoxycarbonyl)gemcitabine

Conditions
ConditionsYield
With sodium carbonate In methanol at 24℃; for 4h; Hydrolysis;A 10%
B 85%

3',5'-di-O-benzoyl-β-2'-deoxy-2',2'-difluorocytidine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%

N-1-acetyl-2-deoxy-2,2-difluorocytidine 3,5-dicinnamonate

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: N-1-acetyl-2-deoxy-2,2-difluorocytidine 3,5-dicinnamonate With ammonia In methanol
Stage #2: With hydrogenchloride In water
80%

C30H21Cl2F2N3O7

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: C30H21Cl2F2N3O7 With ammonium hydroxide In methanol at 20℃; for 16h;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃;
79%
1173824-58-2

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

18027-23-1

4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
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%

Gemcitabine hydrochloride Specification

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.

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