Discuss This Drug

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

product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
listing_expiration_date
20241231
marketing_start_date
20030731
dosage_form
INJECTION
labeler_name
Sichuan Xieli Pharmaceutical Co., Ltd.
route
INTRAVENOUS
application_number
NDA020571
spl_id
b2a88610-838d-477c-8a7c-c3f0c5d14337
package_ndc
65129-1025-0
package_marketing_start_date
31-JUL-03
package_description
5.5 kg in 1 BAG (65129-1025-0)
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
51499
oboInOwl#hasDbXref
Wikipedia:Irinotecan
oboInOwl#id
CHEBI:80630
generic_name
Irinotecan HCl
brand_name
Camptosar
brand_name_base
Camptosar
product_ndc
65129-1025
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
core#notation
CHEBI:80630
rxcui
1726335
manufacturer_name
Xiromed LLC
active_ingredient_strength
4.3 mg/mL
brand_name_suffix
40 mg/2 mL
active_ingredient_name
IRINOTECAN HYDROCHLORIDE
unii
042LAQ1IIS
spl_set_id
b26e5d27-dba5-7538-9e7b-48b358998cbb
upc
0370700169223
pharm_class
Topoisomerase Inhibitors [MoA]
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