Product Name

  • Name

    Irinotecan hydrochloride

  • EINECS 600-054-0
  • CAS No. 100286-90-6
  • Article Data24
  • CAS DataBase
  • Density
  • Solubility Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming
  • Melting Point 250-256 ºC (dec.)
  • Formula C33H38N4O6.HCl
  • Boiling Point 873.4 ºC at 760 mmHg
  • Molecular Weight 623.149
  • Flash Point 482 ºC
  • Transport Information
  • Appearance Yellow crystalline powder
  • Safety
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 100286-90-6 (Irinotecan hydrochloride)
  • Hazard Symbols Xn
  • Synonyms [1,4'-Bipiperidine]-1'-carboxylicacid,(4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, monohydrochloride(9CI);[1,4'-Bipiperidine]-1'-carboxylic acid,4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester, monohydrochloride,(S)-;1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline, [1,4'-bipiperidine]-1'-carboxylic acid deriv.;7-Ethyl-10-[[4-(1-piperidyl)-1-piperidyl]carbonyloxy]camptothecin hydrochloride;CPT 11;Campto;Camptosar;Camptothecin 11;Camptothecin 11 hydrochloride;Topotecin;U 101440E;
  • PSA 114.20000
  • LogP 4.76890

Synthetic route

irinotecan
97682-44-5, 130144-33-1

irinotecan

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 0℃; for 2 - 3h; Product distribution / selectivity;100%
With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity;100%
With hydrogenchloride In water Product distribution / selectivity;95%
4-piperidinopiperidin
4897-50-1

4-piperidinopiperidin

7-ethyl-10-hydroxycamptothecin
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With triethylamine In pyridine; dichloromethane at 30 - 40℃; for 1.5h;
Stage #2: 4-piperidinopiperidin In pyridine; dichloromethane for 0.5h;		90%
1-chloroformyl-4-piperidinylpiperidine monohydrochloride

1-chloroformyl-4-piperidinylpiperidine monohydrochloride

7-ethyl-10-hydroxycamptothecin
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With pyridine; triethylamine In dichloromethane at 30 - 40℃; for 1.5h;
Stage #2: With 4-piperidinopiperidin In dichloromethane at 0 - 80℃; for 0.5h; pH=4.0;
Stage #3: With hydrogenchloride In water; acetonitrile at 20℃; for 20h; Product distribution / selectivity;		90%
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin With pyridine; triethylamine In dichloromethane at 20℃; for 2h;
Stage #2: With hydrogenchloride In water at 0 - 80℃; for 20h; pH=4.0; Product distribution / selectivity;		80%
With triethylamine In pyridine; dichloromethane; water at 20℃; for 2h;80%
irinotecan carboxylate

irinotecan carboxylate

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
With Britton-Robinson's buffer pH 6.0; water at 37℃; Equilibrium constant; Kinetics; Thermodynamic data; Ea, A, var. pH, var. temp., var. time;
7-ethyl-10-[4-(1-piperidino)-1-piperidino]carboxyoxycamptothecin acetic acid salt

7-ethyl-10-[4-(1-piperidino)-1-piperidino]carboxyoxycamptothecin acetic acid salt

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
With hydrogenchloride In ethanol; n-heptane; water at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In ethanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In ethanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In methanol; water; ethyl acetate at 0 - 10℃; for 1h; pH=< 4;
With hydrogenchloride In methanol at 50℃;
(S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinolin-9-yl [1,4'bipiperidine]-1'-carboxylate acetate

(S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinolin-9-yl [1,4'bipiperidine]-1'-carboxylate acetate

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 50℃;
4-piperidinopiperidin
4897-50-1

4-piperidinopiperidin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane; acetonitrile / 20 - 70 °C
1.2: 20 °C
2.1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere
3.1: hydrogenchloride / water
View Scheme
Multi-step reaction with 3 steps
1.1: dichloromethane; hexane; acetonitrile / 20 - 25 °C
1.2: 20 °C
2.1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere
3.1: hydrogenchloride / water / 20 h / 2 - 70 °C
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 0 - 20 °C
2: 1-Methylpyrrolidine / dichloromethane / 20 - 45 °C
3: hydrogenchloride / water / 3 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 3 h / 60 - 65 °C
2: dichloromethane / 6 h / 45 - 50 °C
3: hydrogenchloride / water / 12 h / 20 °C
View Scheme
7-ethyl-10-hydroxycamptothecin
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere
2: hydrogenchloride / water
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere
2: hydrogenchloride / water / 20 h / 2 - 70 °C
View Scheme
4-piperidinopiperidine-1-carbonyl chloride
103816-19-9

4-piperidinopiperidine-1-carbonyl chloride

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; pyridine; acetamide / dichloromethane / 2 h / 30 - 40 °C / Inert atmosphere
2: hydrogenchloride / water
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane; acetamide / 2 h / 30 - 40 °C / Inert atmosphere
2: hydrogenchloride / water / 20 h / 2 - 70 °C
View Scheme
(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
110351-94-5

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / toluene / 20 h / 85 - 90 °C / Industry scale
2: 1-Methylpyrrolidine / dichloromethane / 20 - 45 °C
3: hydrogenchloride / water / 3 h / 70 °C
View Scheme
2'-amino-5'-hydroxypropiophenone
35364-15-9

2'-amino-5'-hydroxypropiophenone

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / toluene / 20 h / 85 - 90 °C / Industry scale
2: 1-Methylpyrrolidine / dichloromethane / 20 - 45 °C
3: hydrogenchloride / water / 3 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / toluene / 6 h / 80 °C
2: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
3: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / toluene / 5 h / Reflux
2.1: lithium hydroxide / methanol; water / 1 h / 25 - 30 °C
2.2: 18 - 22 °C
3.1: sulfuric acid / 2 h / 0 - 5 °C
4.1: triethylamine; pyridine / dichloromethane / 20 - 40 °C
4.2: pH 2-3
View Scheme
1-(5-fluoro-2-nitrophenyl)propan-1-one
924648-17-9

1-(5-fluoro-2-nitrophenyl)propan-1-one

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide / 2 h / 0 - 20 °C
2: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
3: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
4: trifluoroacetic acid / toluene / 6 h / 80 °C
5: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
6: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
1-(5-methoxy-2-nitrophenyl)propan-1-one

1-(5-methoxy-2-nitrophenyl)propan-1-one

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
2: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
3: trifluoroacetic acid / toluene / 6 h / 80 °C
4: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
5: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
1-(5-hydroxy-2-nitrophenyl)propan-1-one
453518-19-9

1-(5-hydroxy-2-nitrophenyl)propan-1-one

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
2: trifluoroacetic acid / toluene / 6 h / 80 °C
3: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
4: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide; water / ethanol / 4 h / 5 °C
2.1: acetic anhydride / 2 h / 110 °C
3.1: magnesium / tetrahydrofuran / 0.5 h / 40 °C
3.2: 1 h / 40 °C
4.1: nitric acid / dichloromethane / 12 h / 10 - 20 °C
5.1: sodium hydroxide / 2 h / 0 - 20 °C
6.1: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
7.1: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
8.1: trifluoroacetic acid / toluene / 6 h / 80 °C
9.1: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
10.1: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
3-fluorobenzaldehyde oxime
458-02-6

3-fluorobenzaldehyde oxime

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: acetic anhydride / 2 h / 110 °C
2.1: magnesium / tetrahydrofuran / 0.5 h / 40 °C
2.2: 1 h / 40 °C
3.1: nitric acid / dichloromethane / 12 h / 10 - 20 °C
4.1: sodium hydroxide / 2 h / 0 - 20 °C
5.1: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
6.1: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
7.1: trifluoroacetic acid / toluene / 6 h / 80 °C
8.1: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
9.1: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
m-Fluorobenzonitrile
403-54-3

m-Fluorobenzonitrile

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: magnesium / tetrahydrofuran / 0.5 h / 40 °C
1.2: 1 h / 40 °C
2.1: nitric acid / dichloromethane / 12 h / 10 - 20 °C
3.1: sodium hydroxide / 2 h / 0 - 20 °C
4.1: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
5.1: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
6.1: trifluoroacetic acid / toluene / 6 h / 80 °C
7.1: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
8.1: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
1-(3-fluorophenyl)propan-1-one
455-67-4

1-(3-fluorophenyl)propan-1-one

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: nitric acid / dichloromethane / 12 h / 10 - 20 °C
2: sodium hydroxide / 2 h / 0 - 20 °C
3: lithium chloride / N,N-dimethyl-formamide / 6 h / Reflux
4: sodium carbonate; sodium dithionite; water / 1 h / 20 °C
5: trifluoroacetic acid / toluene / 6 h / 80 °C
6: triethylamine; pyridine / 2 h / 20 °C / Inert atmosphere
7: hydrogenchloride; water / 3 h / 20 - 70 °C
View Scheme
4-piperidinopiperidine-1-carbonyl chloride
103816-19-9

4-piperidinopiperidine-1-carbonyl chloride

7-ethyl-10-hydroxycamptothecin
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Stage #1: 4-piperidinopiperidine-1-carbonyl chloride; 7-ethyl-10-hydroxycamptothecin With dmap; triethylamine In dichloromethane at 20℃;
Stage #2: With hydrogenchloride In methanol pH=1 - 2; Reagent/catalyst;		14.1 g
4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
102978-40-5

4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / toluene / 5 h / Reflux
2.1: lithium hydroxide / methanol; water / 1 h / 25 - 30 °C
2.2: 18 - 22 °C
3.1: sulfuric acid / 2 h / 0 - 5 °C
4.1: triethylamine; pyridine / dichloromethane / 20 - 40 °C
4.2: pH 2-3
View Scheme
4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione
130144-34-2

4,11-diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium hydroxide / methanol; water / 1 h / 25 - 30 °C
1.2: 18 - 22 °C
2.1: sulfuric acid / 2 h / 0 - 5 °C
3.1: triethylamine; pyridine / dichloromethane / 20 - 40 °C
3.2: pH 2-3
View Scheme
camptothecin
7689-03-4

camptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ferrous(II) sulfate heptahydrate; sulfuric acid; acetic acid / water / 5 °C
1.2: 0.25 h / 5 °C
2.1: acetic acid; dihydrogen peroxide / 8 h / 80 °C
3.1: sulfuric acid; water / 1,4-dioxane; acetonitrile / Inert atmosphere; Irradiation
4.1: dichloromethane / 6 h / 45 - 50 °C
5.1: hydrogenchloride / water / 12 h / 20 °C
View Scheme
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; dihydrogen peroxide / 8 h / 80 °C
2: sulfuric acid; water / 1,4-dioxane; acetonitrile / Inert atmosphere; Irradiation
3: dichloromethane / 6 h / 45 - 50 °C
4: hydrogenchloride / water / 12 h / 20 °C
View Scheme
7-Ethylcamptothecin 1-Oxide
86639-51-2

7-Ethylcamptothecin 1-Oxide

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid; water / 1,4-dioxane; acetonitrile / Inert atmosphere; Irradiation
2: dichloromethane / 6 h / 45 - 50 °C
3: hydrogenchloride / water / 12 h / 20 °C
View Scheme
N-(t-butoxycarbonyl)glycinal
89711-08-0

N-(t-butoxycarbonyl)glycinal

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

t-boc-glycine-irinotecan hydrochloride

t-boc-glycine-irinotecan hydrochloride

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 17℃; Inert atmosphere;95%
2-azidoacetic acid
18523-48-3

2-azidoacetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C35H39N7O7*ClH

C35H39N7O7*ClH

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; acetonitrile at 0 - 20℃; Inert atmosphere;95%
irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

14-azido-3,6,9,12-tetraoxa-1-tetradecanoic acid
201467-81-4

14-azido-3,6,9,12-tetraoxa-1-tetradecanoic acid

20-O-(14-azido-4,7,10,13-tetraoxattetradecanoyl)irinotecan

20-O-(14-azido-4,7,10,13-tetraoxattetradecanoyl)irinotecan

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane Inert atmosphere;90%
irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

irinotecan hydrochloride trihydrate
136572-09-3

irinotecan hydrochloride trihydrate

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol at 75 - 80℃;87%
With water In ethanol Heating / reflux;
triethylammonium sucrose octasulfate

triethylammonium sucrose octasulfate

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

irinotecan sucrosofate

irinotecan sucrosofate

Conditions
ConditionsYield
With hydrogenchloride In water at 65℃; for 0.0833333h;84%
C21H27FNO5P

C21H27FNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63FN5O10P

C54H63FN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;77.1%
2-(4-(((4-bromophenyl)(diethoxyphosphoryl)methyl)amino)phenyl)acetic acid

2-(4-(((4-bromophenyl)(diethoxyphosphoryl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59BrN5O10P

C52H59BrN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;76.7%
2-(4-(((3-bromophenyl)(diethoxyphosphoryl)methyl)amino)phenyl)acetic acid

2-(4-(((3-bromophenyl)(diethoxyphosphoryl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59BrN5O10P

C52H59BrN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;74.3%
C21H27BrNO5P

C21H27BrNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63BrN5O10P

C54H63BrN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;73.7%
2-(4-(((diethoxyphosphoryl)(4-fluorophenyl)methyl)amino)phenyl)acetic acid

2-(4-(((diethoxyphosphoryl)(4-fluorophenyl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59FN5O10P

C52H59FN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;73.5%
1,4-oxathiane-2,6-dione
3261-87-8

1,4-oxathiane-2,6-dione

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C37H42N4O9S

C37H42N4O9S

Conditions
ConditionsYield
Stage #1: irinotecan hydrochloirde With dmap In dichloromethane for 0.166667h;
Stage #2: 1,4-oxathiane-2,6-dione With dmap In dichloromethane at 20℃; for 19h;		73%
C21H27FNO5P

C21H27FNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63FN5O10P

C54H63FN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;72.8%
C21H27BrNO5P

C21H27BrNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63BrN5O10P

C54H63BrN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;71%
C19H23ClNO5P

C19H23ClNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59ClN5O10P

C52H59ClN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;70.5%
C19H23ClNO5P

C19H23ClNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59ClN5O10P

C52H59ClN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;69.5%
C22H30NO6P

C22H30NO6P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C55H66N5O11P

C55H66N5O11P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;69%
C21H27ClNO5P

C21H27ClNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63ClN5O10P

C54H63ClN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;67.6%
2-(4-(((diethoxyphosphoryl)(phenyl)methyl)amino)phenyl)acetic acid

2-(4-(((diethoxyphosphoryl)(phenyl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H60N5O10P

C52H60N5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;67.2%
6-azidohexanoic acid
79598-53-1

6-azidohexanoic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C39H47N7O7

C39H47N7O7

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; acetonitrile at 20℃;67%
C21H28NO5P

C21H28NO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H64N5O10P

C54H64N5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;66.7%
C22H30NO5P

C22H30NO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C55H66N5O10P

C55H66N5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;65.7%
C21H27ClNO5P

C21H27ClNO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C54H63ClN5O10P

C54H63ClN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;65.7%
2-(4-(((diethoxyphosphoryl)(4-methoxyphenyl)methyl)amino)phenyl)acetic acid

2-(4-(((diethoxyphosphoryl)(4-methoxyphenyl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C53H62N5O11P

C53H62N5O11P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;63.8%
C22H30NO6P

C22H30NO6P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C55H66N5O11P

C55H66N5O11P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;60.5%
2-(4-(((diethoxyphosphoryl)(3-fluorophenyl)methyl)amino)phenyl)acetic acid

2-(4-(((diethoxyphosphoryl)(3-fluorophenyl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C52H59FN5O10P

C52H59FN5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;60.3%
2-(4-(((diethoxyphosphoryl)(3-methoxyphenyl)methyl)amino)phenyl)acetic acid

2-(4-(((diethoxyphosphoryl)(3-methoxyphenyl)methyl)amino)phenyl)acetic acid

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C53H62N5O11P

C53H62N5O11P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;57.8%
C20H26NO5P

C20H26NO5P

irinotecan hydrochloirde
100286-90-6

irinotecan hydrochloirde

C53H62N5O10P

C53H62N5O10P

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30℃;57.4%

Irinotecan hydrochloride Consensus Reports

In 2004, a clinical study was performed that both validated prospectively the association of the variant with greater toxicity and the ability of genetic testing in predicting that toxicity before chemotherapy administration.
In 2005, the FDA made changes to the labelling of irinotecan to add pharmacogenomics recommendations that patients with polymorphisms in UGT1A1 gene, specifically the variant, should perhaps receive reduced drug doses. Irinotecan is one of the first widely-used chemotherapy agents that is dosed for each patient according to his genotype.

Irinotecan hydrochloride Specification

1. Introduction of Irinotecan hydrochloride
Irinotecan hydrochloride is yellow crystalline powder or white or off-white crystalline powder. Its systematic name is called (4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 1,4'-bipiperidine-1'-carboxylate hydrochloride (1:1). Irinotecan hydrochloride belongs to product categories of Active Pharmaceutical Ingredients; Antineoplastic; Antitumors for Research and Experimental Use; Biochemistry; Chiral Reagents; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Irinotecan.

This chemical is a yellow crystalline powder and should be sealed in a cool, dry place at the temperature of 2-8 °C. Besides, its Classification Code is Antineoplastic Agents; Antineoplastic Agents, Phytogenic; Drug / Therapeutic Agent; Enzyme Inhibitors; Mutation data; Radiation-Sensitizing Agents; Reproductive Effect; Topoisomerase I Inhibitors; Topoisomerase Inhibitors. Irinotecan hydrochloride Solubility is DMSO (50 mg/ml).

2. Properties of Irinotecan hydrochloride
Physical properties about Irinotecan hydrochloride are:
(1)ACD/LogP: 4.18; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.09; (4)ACD/LogD (pH 7.4): 2.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 19.89; (7)ACD/KOC (pH 5.5): 3.63; (8)ACD/KOC (pH 7.4): 100.73; (9)#H bond acceptors: 10; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 101.51 Å2; (13)Flash Point: 482 °C; (14)Enthalpy of Vaporization: 132.98 kJ/mol; (15)Boiling Point: 873.4 °C at 760 mmHg; (16)Vapour Pressure: 1.31E-32 mmHg at 25 °C.

3. Structure Descriptors of Irinotecan hydrochloride
You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O=C7OCC=6C(=O)N2C(\c1nc5c(c(c1C2)CC)cc(OC(=O)N4CCC(N3CCCCC3)CC4)cc5)=C/C=6[C@@]7(O)CC
(2) InChI: InChI=1S/C33H38N4O6.ClH/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2;/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;1H/t33-;/m0./s1
(3) InChIKey: GURKHSYORGJETM-WAQYZQTGSA-N

4. Toxicity of Irinotecan hydrochloride
The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 40mg/kg (40mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse LD50 intraperitoneal 177mg/kg (177mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
mouse LD50 intravenous 132mg/kg (132mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.
mouse LD50 oral 765mg/kg (765mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
rat LD50 intravenous 83600ug/kg (83.6mg/kg)   Cancer Research. Vol. 47, Pg. 5944, 1987.
rat LD50 oral 867mg/kg (867mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 7185, 1990.

5. Preparation of Irinotecan hydrochloride
Irinotecan hydrochloride is prepared by irinotecan with HCl. The reaction needs solvent ethanol at the temperature of 20 °C. Product is obtained by concentration and recrystallization. The yield is about 65.2%.

Irinotecan hydrochloride is prepared by reaction of irinotecan with HCl.


6. Uses of Irinotecan hydrochloride
Irinotecan hydrochloride is a DNA topoisomerase inhibitor. What's more, Irinotecan hydrochloride is used as DNA topoisomerase inhibitor and antineoplastic. It can inhibitor of DNA topoisomerase I that displays antitumor activity against a range of tumor types.

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