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Irinotecan

CAT: 0127-BUP15721-02Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0127-BUP15721-02Size:25 mg
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CAS Number
97682-44-5
Synonyms
CPT-11, Topotecin, (+) -Irinotecan
Purity
=98%
Smiles
CCc1c2Cn3c(cc4c(COC(=O)[C@]4(O)CC)c3=O)-c2nc2ccc(OC(=O)N3CCC(CC3)N3CCCCC3)cc12

Chemical Information

Irinotecan

Irinotecan is 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. It has a role as an antineoplastic agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It is a delta-lactone, a carbamate ester, a tertiary alcohol, a ring assembly, a N-acylpiperidine, a pyranoindolizinoquinoline and a tertiary amino compound. It is functionally related to a SN-38. It is a conjugate base of an irinotecan(1+).

CAS Number97682-44-5
PubChem CID60838
IUPAC Name[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate
Molecular FormulaC33H38N4O6
Molecular Weight586.7
XLogP3
Topological Polar Surface Area113
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Heavy Atom Count43
Formal Charge0
Complexity1200
SMILES
CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)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
Chemical Structure
2D Structure
2D structure of Irinotecan
CAS: 97682-44-5
CID: 60838
Formula: C33H38N4O6
MW: 586.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight586.7
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass586.27913494
Monoisotopic Mass586.27913494
Topological Polar Surface Area113 Ų
Heavy Atom Count43
Formal Charge0
Complexity1200
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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