Details of the Drug

General Information of Drug (ID: DMDWU1S)

Drug Name
Rubitecan
Synonyms
9-Nitrocamptothecin; 91421-42-0; Orathecin; 9-nitro-20(S)-camptothecin; Camptogen; 9-NC; RFS 2000; RFS-2000; UNII-H19C446XXB; Nitrocamptothecin; H19C446XXB; CHEBI:90225; C20H15N3O6; (S)-4-Ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; NCGC00167969-01; (s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]-indolizino[1,2-b]quinoline-3,14(4h,12h)-dione; 9NC; Q-100889; (4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione; Inhaled Orathecin; L9NC; Rubitecan (inhaled); Aerosolized liposomal 9 nitro-20 (S) camptothecin; Rubitecan (inhaled), SuperGen; 9-Nitro-20(S)-camptothecin; 9-Nitrocamptothecin (9-NC)
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 393.3
Logarithm of the Partition Coefficient (xlogp) 0.8
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C20H15N3O6
IUPAC Name
(19S)-19-ethyl-19-hydroxy-8-nitro-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)-heptaene-14,18-dione
Canonical SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
InChI
InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
InChIKey
VHXNKPBCCMUMSW-FQEVSTJZSA-N
Cross-matching ID
PubChem CID
472335
ChEBI ID
CHEBI:90225
CAS Number
91421-42-0
DrugBank ID
DB06159
TTD ID
D0Y1FO
VARIDT ID
DR01438
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD 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 Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [4]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [4]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [4]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [5]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [4]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [4]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Human immunodeficiency virus infection
ICD Disease Classification 1C62
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
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 1.26E-03 -4.35E-01 -5.28E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00005869) Nitrocamptothecin Compared With Gemcitabine in Treating Patients With Unresectable Locally Advanced or Metastatic Pancreatic Cancer. U.S. National Institutes of Health.
2 Rubitecan. Expert Opin Investig Drugs. 2006 Jan;15(1):71-9.
3 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
4 Characterization of 9-nitrocamptothecin liposomes: anticancer properties and mechanisms on hepatocellular carcinoma in vitro and in vivo. PLoS One. 2011;6(6):e21064. doi: 10.1371/journal.pone.0021064. Epub 2011 Jun 9.
5 Analysis of ATP-binding cassette transporter expression in drug-selected cell lines by a microarray dedicated to multidrug resistance. Mol Pharmacol. 2004 Dec;66(6):1397-405. doi: 10.1124/mol.104.005009. Epub 2004 Sep 1.