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Details

Stereochemistry RACEMIC
Molecular Formula C21H18N2O4
Molecular Weight 362.3786
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of E-HOMOCAMPTOTHECIN, (±)-

SMILES

CCC1(O)CC(=O)OCC2=C1C=C3N(CC4=CC5=CC=CC=C5N=C34)C2=O

InChI

InChIKey=PAEZRCINULFAGO-UHFFFAOYSA-N
InChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3

HIDE SMILES / InChI

Molecular Formula C21H18N2O4
Molecular Weight 362.3786
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

E-Homocamptothecin, (±)- (also known as BN 80245) is an E-ring modified analog of camptothecin. This compound is more stable than camptothecin, remains a potent inhibitor of both cell growth and topoisomerase I. Homocamptothecin exhibited high in vitro cytotoxicities and good in vivo efficacy, thus that compound could be a promising template for the preparation of improved anticancer agents.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11387|||Q9UJN0
Gene ID: 7150.0
Gene Symbol: TOP1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogues.
1998 Dec 31
Homocamptothecin, an E-ring modified camptothecin with enhanced lactone stability, retains topoisomerase I-targeted activity and antitumor properties.
1999 Jun 15

Sample Use Guides

The mouse L1210 lymphoblastic leukemia cells were maintained by serial i.p. passage in DBA/2 mice: when injected i.p. daily for 4 days, racemic homocamptothecin (dl-hCPT) increased the life span of the mice (untreated animals died between day 9 and day 14 posttumor-cell injection) treated at doses ranging from 0.32 to 2.5 mg/kg, with maximal efficacy at 1.25 mg/kg.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:30 GMT 2023
Edited
by admin
on Sat Dec 16 08:35:30 GMT 2023
Record UNII
33SH2P87CX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
E-HOMOCAMPTOTHECIN, (±)-
Common Name English
BN-80245
Common Name English
(±)-E-HOMOCAMPTOTHECIN
Brand Name English
3H,15H-OXEPINO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,15-DIONE, 5-ETHYL-1,4,5,13-TETRAHYDRO-5-HYDROXY-
Systematic Name English
Code System Code Type Description
PUBCHEM
9863779
Created by admin on Sat Dec 16 08:35:30 GMT 2023 , Edited by admin on Sat Dec 16 08:35:30 GMT 2023
PRIMARY
FDA UNII
33SH2P87CX
Created by admin on Sat Dec 16 08:35:30 GMT 2023 , Edited by admin on Sat Dec 16 08:35:30 GMT 2023
PRIMARY
CAS
186668-40-6
Created by admin on Sat Dec 16 08:35:30 GMT 2023 , Edited by admin on Sat Dec 16 08:35:30 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY