Details of the Drug

General Information of Drug (ID: DMRQV8I)

Drug Name
BECATECARIN
Synonyms
BMS-181176; Becatecarin < USAN; DEAE-Rebeccamycin; XL-119; BMY-27557-01 (HCl); BMY-27557-14 (tartrate); 1,11-Dichloro-6-[2-(diethylamino)ethyl]-12-(4-O-methyl-beta-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Discontinued in Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 669.5
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C33H34Cl2N4O7
IUPAC Name
5,21-dichloro-13-[2-(diethylamino)ethyl]-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
Canonical SMILES
CCN(CC)CCN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)NC3=C5C(=C2C1=O)C6=C(N5[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)OC)O)O)C(=CC=C6)Cl
InChI
InChI=1S/C33H34Cl2N4O7/c1-4-37(5-2)12-13-38-31(43)22-20-15-8-6-10-17(34)24(15)36-25(20)27-21(23(22)32(38)44)16-9-7-11-18(35)26(16)39(27)33-29(42)28(41)30(45-3)19(14-40)46-33/h6-11,19,28-30,33,36,40-42H,4-5,12-14H2,1-3H3/t19-,28-,29-,30-,33-/m1/s1
InChIKey
JSKFWUPVIZYJMR-UDOAKELVSA-N
Cross-matching ID
PubChem CID
101524
CAS Number
119673-08-4
UNII
A60X6MBU6G
DrugBank ID
DB06362
TTD ID
D0N1FR
VARIDT ID
DR01415
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
DNA topoisomerase I (TOP1) TTGTQHC TOP1_HUMAN Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
DNA topoisomerase I (TOP1) DTT TOP1 6.65E-01 0.2 0.39
Breast cancer resistance protein (ABCG2) DTP BCRP 3.87E-47 -1.28E+00 -1.63E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of Exelixis.
2 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
3 Becatecarin (rebeccamycin analog, NSC 655649) is a transport substrate and induces expression of the ATP-binding cassette transporter, ABCG2, in lung carcinoma cells. Cancer Chemother Pharmacol. 2009 Aug;64(3):575-83.