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
CHEMBL77305
CAS Number
91421-42-0
UNII
H19C446XXB
DrugBank ID
DB06159
TTD ID
D0Y1FO
VARIDT ID
DR01438
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_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.