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Details

Stereochemistry ACHIRAL
Molecular Formula C21H24N4O
Molecular Weight 348.4415
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INTOPLICINE

SMILES

CN(C)CCCNC1=C2C(NC3=CC=C4C=C(O)C=CC4=C23)=C(C)C=N1

InChI

InChIKey=QROONAIPJKQFMC-UHFFFAOYSA-N
InChI=1S/C21H24N4O/c1-13-12-23-21(22-9-4-10-25(2)3)19-18-16-7-6-15(26)11-14(16)5-8-17(18)24-20(13)19/h5-8,11-12,24,26H,4,9-10H2,1-3H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C21H24N4O
Molecular Weight 348.4415
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Intoplicine is a pyrido[4,3-b]indole derivative patented by Rhone-Poulenc Sante as an antitumor agent. Intoplicine acts via inhibiting DNA nicking and closing reactions by stabilizing the cleavable complex, a transient intermediate in the religation reaction involving topoisomerase I and II and DNA. Intoplicine was active in a range of solid tumors in mice, including colon adenocarcinoma 51, MA16/C, MA14/A, MA13/C, early-stage pancreatic ductal adenocarcinoma 03, Glasgow osteogenic sarcoma and B16 melanoma. In Phase I clinical studies using a 24-h infusion, the maximum tolerated dose was established as 270 mg/m2 every 3 weeks, with hepatotoxicity rather than myelosuppression being dose-limiting, although cardiac toxicity was also seen. Preclinical cytotoxic concentrations were not achieved at the dose levels studied and clinical development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibitors of human immunodeficiency virus integrase.
1993 Mar 15
Patents

Patents

Sample Use Guides

640 mg/m2
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:34:52 UTC 2023
Edited
by admin
on Wed Jul 05 23:34:52 UTC 2023
Record UNII
FB2CIN6HMI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INTOPLICINE
INN   WHO-DD  
INN  
Official Name English
RP-60475 FREE BASE
Code English
Intoplicine [WHO-DD]
Common Name English
11-((3-(DIMETHYLAMINO)PROPYL)AMINO)-8-METHYL-7H-BENZO(E)PYRIDO(4,3-B)INDOL-3-OL
Systematic Name English
RP 60475
Code English
intoplicine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C582
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
NCI_THESAURUS C1748
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
Code System Code Type Description
PUBCHEM
65954
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
NCI_THESAURUS
C1495
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL1908351
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
INN
6947
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
DRUG CENTRAL
1446
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
MESH
C081834
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
SMS_ID
100000083400
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
DRUG BANK
DB12868
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
FDA UNII
FB2CIN6HMI
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
EVMPD
SUB08200MIG
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
CAS
125974-72-3
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID80155022
Created by admin on Wed Jul 05 23:34:52 UTC 2023 , Edited by admin on Wed Jul 05 23:34:52 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY