Irinotecan hydrochloride

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Names

[ CAS No. ]:
100286-90-6

[ Name ]:
Irinotecan hydrochloride

[Synonym ]:
Campto hydrochloride
Campto
[1,4'-Bipiperidine]-1'-carboxylic acid, (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, hydrochloride (1:1)
[1,4'-bipiperidine]-1'-carboxylic acid, (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
1,4'-bipipéridine-1'-carboxylate de (4S)-4,11-diéthyl-4-hydroxy-3,14-dioxo-3,4,12,14-tétrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoléin-9-yle chlorhydrate
Camptothecin 11 hydrochloride
Irinotecan hydrochloride
CPT-11 hydrochloride
Topotecin
(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
irinotecan hydrochloride (anhydrous)
Irinotecan Hcl
CPT 11
(4s)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1h-pyrano[3',4':6,7]indolizino[1,2-b]chinolin-9-yl-1,4'-bipiperidin-1'-carboxylathydrochlorid
(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)
Camptothecin analog
MFCD01862255
Irinotecan (hydrochloride)

Chemical & Physical Properties

[ Boiling Point ]:
257 °C

[ Melting Point ]:
250-256°C (dec.)

[ Molecular Formula ]:
C33H39ClN4O6

[ Molecular Weight ]:
623.139

[ Flash Point ]:
482ºC

[ Exact Mass ]:
622.255798

[ PSA ]:
114.20000

[ LogP ]:
4.76890

[ Vapour Pressure ]:
1.31E-32mmHg at 25°C

[ Index of Refraction ]:
67.7 ° (C=1, H2O)

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DW1061000
CAS REGISTRY NUMBER :
100286-90-6
LAST UPDATED :
199806
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C33-H38-N4-O6.Cl-H
MOLECULAR WEIGHT :
623.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
867 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
83600 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
765 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
177 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
132 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
728 mg/kg/26W-C
TOXIC EFFECTS :
Endocrine - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in other cell count (unspecified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
112 mg/kg/4W-I
TOXIC EFFECTS :
Endocrine - changes in thymus weight Blood - pigmented or nucleated red blood cells Blood - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
700 mg/kg/14D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from small intestine Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
44800 ug/kg/28D-C
TOXIC EFFECTS :
Endocrine - changes in spleen weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in other cell count (unspecified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
66 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
66 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
66 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
66 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
78 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
78 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
78 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
78 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Leukocyte
DOSE/DURATION :
100 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 51,4187,1991

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DW1060750

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 4-Piperidinopiperidine
  • 7-Ethyl-10-hydroxycamptothecin
  • Irinotecan
  • 1-CHLOROCARBONYL-4-PIPERIDINOPIPERIDINE
  • 1-(2-Amino-5-hydroxyphenyl)-1-propanone
  • (S)-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
  • 1-(5-fluoro-2-nitrophenyl)propan-1-one
  • 1-(5-hydroxy-2-nitrophenyl)propan-1-one
  • 3-Fluorobenzaldehyde
  • 3-fluorobenzaldoxime

DownStream

  • 7-Ethyl-10-hydroxycamptothecin
  • Irinotecan HCI Trihydrate

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Related Compounds

  • Irinotecan Hydrochloride Trihydrate
  • Irinotecan-d10 (hydrochloride)
  • carnitine hydrochloride
  • Losoxantrone hydrochloride [USAN]
  • Triprolidine hydrochloride
  • Tyrocidine, hydrochloride
  • 4-Chloro-5-hydroxy-3-(trifluoromethoxy)pyridine-2-carboxamide
  • 4-Cyano-3-(difluoromethyl)-2-iodo-6-(trifluoromethoxy)pyridine
  • 4-Cyano-3-difluoromethoxy-2-(trifluoromethoxy)benzenesulfonyl chloride
  • 4-Chloro-6-(difluoromethyl)-3-methoxypyridine-2-carbonyl chloride
  • 4-Fluoro-3-hydroxypyridine-2-sulfonyl chloride
  • 4-Cyano-3-difluoromethyl-5-(hydroxymethyl)phenylacetic acid
  • 4-Fluoro-2-hydroxypyridine-5-sulfonyl chloride
  • 4-Bromo-3-(difluoromethyl)-2-methylpyridine-5-methanol
  • 4-Cyano-3-methoxy-6-(trifluoromethoxy)pyridine-2-sulfonyl chloride
  • 4-Bromo-3-(difluoromethyl)-6-(trifluoromethoxy)pyridine-2-carboxaldehyde
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