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irinotecan

CHEBI:CHEBI_80630

Definition

A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active.

Chemical Information

Molecular Formula
C33H38N4O6
Molecular Mass
586.679
Charge
0
SMILES
C1(=CC=C2C(=C1)C(=C3C(=N2)C=4N(C3)C(C5=C(C4)[C@](C(OC5)=O)(CC)O)=O)CC)OC(=O)N6CCC(CC6)N7CCCCC7
InChI
InChI=1S/C33H38N4O6/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/t33-/m0/s1
InChIKey
UWKQSNNFCGGAFS-XIFFEERXSA-N

Alternative Names

  • (+)-Irinotecan
  • (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
  • HSDB 7607
  • Irinophore C
  • irinotecan
  • Irinotecan lactone
  • Irinotecan mylan
  • irinotecanum

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
51499
oboInOwl#hasDbXref
Wikipedia:Irinotecan
core#notation
CHEBI:80630

Additional References

Wikipedia:Irinotecan

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
51499
oboInOwl#hasDbXref
Wikipedia:Irinotecan
oboInOwl#id
CHEBI:80630
core#notation
CHEBI:80630
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_50276
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#has_functional_parent
http://purl.obolibrary.org/obo/CHEBI_8988
chebi#is_conjugate_base_of
http://purl.obolibrary.org/obo/CHEBI_90895
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_6728
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect35899
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_90895
owl#annotatedSource
t300592
owl#someValuesFrom
t2988941