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122111-03-9

Basic Information
CAS No.: 122111-03-9
Name: Gemcitabine hydrochloride
Molecular Structure:
Molecular Structure of 122111-03-9 (Gemcitabine hydrochloride)
Formula: C9H11F2N3O4.HCl
Molecular Weight: 299.69
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
Solubility:
Appearance: White crystalline granular, odorless
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 21-36/38-46-62-63
Safety: 25-26-36/37-53
Transport Information:
PSA: 110.60000
LogP: 0.09460
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%
951314-37-7

α/β-1-(2-oxo-4-amino-1H-pyrimidin-1-yl)-2-desoxy-2,2'-difluororibose hydrochloride

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
In water; isopropyl alcohol at 25℃; for 2h; Purification / work up; Resolution of anomeric mixture;
103882-84-4

2’-deoxy-2’,2’-difluoro-cytidine

A

122111-05-1

2'-deoxy-2',2'-difluorocytidine hydrochloride

B

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at -4 - 60℃; for 6.5h;

C26H24F2N4O8

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: C26H24F2N4O8 With ammonia; water In methanol at 20℃; for 24h;
Stage #2: With hydrogenchloride In water at 0 - 5℃; for 4h; Product distribution / selectivity;
n/a

C26H24F2N4O8

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: C26H24F2N4O8 With ammonia; water In methanol at 20℃; for 24h;
Stage #2: With hydrogenchloride In water at 0 - 5℃; for 4h; Product distribution / selectivity;
n/a
103882-84-4

2’-deoxy-2’,2’-difluoro-cytidine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 10 - 68℃; for 1.5h; Product distribution / selectivity;
With hydrogenchloride In 1,2-dimethoxyethane; water at 10 - 68℃; for 1.5h; Product distribution / selectivity;

3',5'-dicinnamoyl-2'-deoxy-2',2'-difluorocytidine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: 3',5'-dicinnamoyl-2'-deoxy-2',2'-difluorocytidine With methanol; ammonia at 20℃; for 4 - 6h;
Stage #2: With hydrogenchloride In dichloromethane; water Product distribution / selectivity;
14631-20-0

4-N-Acetylcytosine

134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

A

122111-05-1

2'-deoxy-2',2'-difluorocytidine hydrochloride

B

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Stage #1: 4-N-Acetylcytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In 1,2-dichloro-ethane for 3h; Heating / reflux;
Stage #2: 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20 - 75℃; for 14 - 16h; Heating / reflux;
Stage #3: With hydrogenchloride In water; 1,2-dichloro-ethane

gemcitabine

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water; ethyl acetate at 20℃; Product distribution / selectivity;

C23H19F2N3O8*ClH

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / methanol / 3 h / 20 °C / pH Ca. 7 / Reflux
2.1: ammonium hydroxide; water / methanol / 6 h / Reflux
2.2: 12 h / 20 °C / pH 3
View Scheme

C26H27F2N3O8Si

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / toluene; water / 3 h / 20 - 70 °C
2.1: triethylamine / methanol / 3 h / 20 °C / pH Ca. 7 / Reflux
3.1: ammonium hydroxide; water / methanol / 6 h / Reflux
3.2: 12 h / 20 °C / pH 3
View Scheme
1173824-58-2

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

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 2 h / 5 - 20 °C
2: 3 h / 120 °C / Heating
3: sodium t-butanolate / methanol / 2 h / 20 °C
4: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C
View Scheme
134877-42-2

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3 h / 120 °C / Heating
2: sodium t-butanolate / methanol / 2 h / 20 °C
3: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C
View Scheme
134877-42-2, 134877-43-3, 122111-11-9

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 50 - 60 °C
2: 3 h / 120 °C / Heating
3: sodium t-butanolate / methanol / 2 h / 20 °C
4: hydrogenchloride / isopropyl alcohol; water / 20 - 70 °C
View Scheme
95058-92-7

(erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere; Industrial scale
2: diisobutylaluminium hydride / toluene; methanol / -50 - -20 °C / Inert atmosphere; Industrial scale
3: binaphthol phosphonate / N,N-dimethyl-formamide / 10 h / 20 °C / Industrial scale
4: hydrogenchloride / water; acetone; ethanol / 0 - 5 °C / Green chemistry; Industrial scale
View Scheme

C16H30F2O5Si

122111-03-9

gemcitabine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisobutylaluminium hydride / toluene; methanol / -50 - -20 °C / Inert atmosphere; Industrial scale
2: binaphthol phosphonate / N,N-dimethyl-formamide / 10 h / 20 °C / Industrial scale
3: hydrogenchloride / water; acetone; ethanol / 0 - 5 °C / Green chemistry; Industrial scale
View Scheme
122111-03-9

gemcitabine hydrochloride

2937-50-0

Allyl chloroformate

688008-78-8

4-allyloxycarbonylamino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

Conditions
ConditionsYield
Stage #1: gemcitabine hydrochloride With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In 1,4-dioxane for 2h; Heating;
Stage #2: Allyl chloroformate With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 4h;
Stage #3: With triethylamine In methanol at 20℃; Further stages.;
99%
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 0℃; for 2h;
Stage #2: Allyl chloroformate at 0 - 45℃;
70%
18162-48-6

tert-butyldimethylsilyl chloride

122111-03-9

gemcitabine hydrochloride

688009-09-8

4-amino-1-((2R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Conditions
ConditionsYield
at 20℃;98.5%
With 1H-imidazole; triethylamine In N,N-dimethyl-formamide at 25℃; for 24h;95%
With 1H-imidazole; triethylamine at 20℃; for 24h; Inert atmosphere;91%
With 1-methyl-1H-imidazole; iodine In tetrahydrofuran; pyridine at 20℃;64%
With 1H-imidazole In dichloromethane at 20℃;
18162-48-6

tert-butyldimethylsilyl chloride

122111-03-9

gemcitabine hydrochloride

1151528-36-7

4-amino-1-((2R,4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-3,3-difluoro-4-hydroxytetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 15h;98%
With 1H-imidazole In N,N-dimethyl-formamide at 20 - 25℃; for 2h;93%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;92%
122111-03-9

gemcitabine hydrochloride

98-59-9

p-toluenesulfonyl chloride

1519060-68-4

N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride at 20 - 60℃; for 20h; Inert atmosphere;
96%
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane
Stage #2: p-toluenesulfonyl chloride
Stage #3: With ammonia In methanol
24424-99-5

di-tert-butyl dicarbonate

122111-03-9

gemcitabine hydrochloride

250698-51-2

(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl tert-butyl carbonate

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 50h;95%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 48h;87%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 48h;87%
122111-03-9

gemcitabine hydrochloride

114248-23-6

Deoxydifluorouridine

Conditions
ConditionsYield
With acetic acid; sodium nitrite In water at 20℃; for 48h;95%
Multi-step reaction with 3 steps
1: pyridine / 15 h / 25 °C
2: acetic acid / water / 14 h / Reflux
3: ammonia / methanol / 15 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: pyridine / 15 h / 25 °C
2: acetic acid / water / 14 h / Reflux
3: ammonia / methanol / 15 h / 20 °C
View Scheme
98-88-4

benzoyl chloride

122111-03-9

gemcitabine hydrochloride

1445381-44-1

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

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 12h; Temperature; Inert atmosphere;93.5%
With pyridine at 0 - 20℃; Inert atmosphere;93.5%
With pyridine at 0 - 20℃; Inert atmosphere;93.5%
76-83-5

trityl chloride

122111-03-9

gemcitabine hydrochloride

5'-Tr-gemcytabine

Conditions
ConditionsYield
With pyridine In water at 30℃; for 22h; Inert atmosphere;91.2%
24424-99-5

di-tert-butyl dicarbonate

122111-03-9

gemcitabine hydrochloride

250698-52-3

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

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane at 24℃; Substitution;90%
With potassium hydroxide In 1,4-dioxane at 22℃; for 2h; Inert atmosphere;71%
With potassium hydroxide In 1,4-dioxane; water at 4 - 22℃; for 1h; Inert atmosphere;71%
98-88-4

benzoyl chloride

122111-03-9

gemcitabine hydrochloride

142816-70-4

N4-benzoyl-2'-deoxy-2',2'-difluorocytidine

Conditions
ConditionsYield
Stage #1: gemcitabine hydrochloride With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 2.5h; Reflux;
Stage #2: benzoyl chloride With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 3h;
Stage #3: With triethylamine In methanol; dichloromethane at 20℃; for 1.5h;
83%
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane at 0 - 20℃; for 0.5h;
Stage #2: benzoyl chloride at 0 - 20℃;
76%

3-(N-methacryloylglycyl-DL-phenylalanylleucylglycyl)thiazolidine-2-thione

122111-03-9

gemcitabine hydrochloride

C32H41F2N7O9

Conditions
ConditionsYield
With pyridine at 50℃; for 20h; Inert atmosphere;80.1%
122111-03-9

gemcitabine hydrochloride

4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-yl)-5-hydroxypyrimidine-2(1H)-one

Conditions
ConditionsYield
Stage #1: gemcitabine hydrochloride With water; bromine at 0 - 5℃; for 1h;
Stage #2: With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine In hexane at 0 - 60℃; for 1h; Reagent/catalyst; Temperature;
70.8%
122111-03-9

gemcitabine hydrochloride

118162-45-1

11-azidoundecanoic acid

4-N-(11-azidoundecanoyl)-2'-deoxy-2',2'-difluorocytidine

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 65℃; Inert atmosphere;70%

C47H55N3O15

122111-03-9

gemcitabine hydrochloride

C53H62F2N4O19

Conditions
ConditionsYield
With pyridine In dimethyl sulfoxide at 20℃; for 24h;68.6%
831242-05-8

(N-(methacryloyl)glycylphenylalanylleucylglycyl)thiazolidine-2-thione

122111-03-9

gemcitabine hydrochloride

1334238-76-4

N-methacyloylglycylphenylalanylleucylglycyl-gemcitabine

Conditions
ConditionsYield
With pyridine at 50℃; for 12h; Inert atmosphere;66.1%
With pyridine at 50℃; for 12h; Inert atmosphere;66.1%
112-38-9

10-undecenoic acid

122111-03-9

gemcitabine hydrochloride

1519060-51-5

4-N-(10-undecenoyl)-2'-deoxy-2',2'-difluorocytidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 65℃; Inert atmosphere;66%
122111-03-9

gemcitabine hydrochloride

59-05-2

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid

C29H31F2N11O8

Conditions
ConditionsYield
Stage #1: N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: gemcitabine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h;
65%
3303-84-2

3-(tert-butyloxycarbonylamino)propionic acid

122111-03-9

gemcitabine hydrochloride

4-N-[3-N-(tert-butoxycarbonyl)-3-aminopropanoyl]-2′-deoxy-2′,2′-difluorocytidine

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide; N,N-dimethyl-formamide Inert atmosphere; Heating;65%
505-95-3

12-hydroxydodecanoic acid

7693-46-1

4-Nitrophenyl chloroformate

122111-03-9

gemcitabine hydrochloride

C22H33F2N3O8

Conditions
ConditionsYield
Stage #1: 12-hydroxydodecanoic acid; 4-Nitrophenyl chloroformate With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 5h;
Stage #2: gemcitabine hydrochloride With triethylamine In N,N-dimethyl-formamide for 24h;
64.3%
27144-18-9

3-(tritylthio) propanoic acid

122111-03-9

gemcitabine hydrochloride

C31H29F2N3O5S

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 25℃; for 18h; Inert atmosphere;63%
Stage #1: 3-(tritylthio) propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: gemcitabine hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 0.408333h;
45%
53293-00-8

hex-5-ynoic acid

122111-03-9

gemcitabine hydrochloride

4-N-(hexynoyl)gemcitabine

Conditions
ConditionsYield
Stage #1: gemcitabine hydrochloride With pyridine; chloro-trimethyl-silane In acetonitrile at 0 - 20℃; for 4h;
Stage #2: hex-5-ynoic acid With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 60℃; for 18h;
Stage #3: With ethanol at 45℃; for 4h;
63%
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    122111-03-9

    Gemcitabine hydrochloride

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  • Gemcitabine hydrochloride ( GMP)

  • Casno:

    122111-03-9

    Gemcitabine hydrochloride ( GMP)

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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.