Details of the Drug

General Information of Drug (ID: DM6CHNJ)

Drug Name
Camptothecin
Synonyms
camptothecin; Camptothecine; 7689-03-4; (S)-(+)-Camptothecin; Campathecin; d-Camptothecin; (+)-Camptothecine; (+)-Camptothecin; 20(S)-Camptothecine; 21,22-Secocamptothecin-21-oic acid lactone; NSC94600; (S)-Camptothecin; Camptothecine (8CI); 20(S)-Camptothecin; Camptothecine (S,+); CHEMBL65; UNII-XT3Z54Z28A; MLS000766223; (4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; XT3Z54Z28A; CHEBI:27656; VSJKWCGYPAHWDS-FQEVSTJZSA-N; Camptothecin, Camptotheca acuminata; NSC-94600; Camptothecin derivat
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 348.4
Logarithm of the Partition Coefficient (xlogp) 1
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C20H16N2O4
IUPAC Name
(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
Canonical SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
InChI
InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
InChIKey
VSJKWCGYPAHWDS-FQEVSTJZSA-N
Cross-matching ID
PubChem CID
24360
ChEBI ID
CHEBI:27656
CAS Number
7689-03-4
DrugBank ID
DB04690
TTD ID
D09YDM
VARIDT ID
DR01383
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 Modulator [1]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [2]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [3]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
A-kinase anchor protein 13 (AKAP13) OTOZAR14 AKP13_HUMAN Drug Response [5]
A-kinase anchor protein 8 (AKAP8) OTK3EQAI AKAP8_HUMAN Gene/Protein Processing [6]
Activin receptor type-1B (ACVR1B) OT778HIQ ACV1B_HUMAN Post-Translational Modifications [7]
Adenomatous polyposis coli protein (APC) OTKV0TIK APC_HUMAN Post-Translational Modifications [7]
Agouti-related protein (AGRP) OT7XRHWU AGRP_HUMAN Drug Response [5]
Agrin (AGRN) OTWJENAZ AGRIN_HUMAN Gene/Protein Processing [8]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [9]
AMSH-like protease (STAMBPL1) OTI4CYTF STALP_HUMAN Post-Translational Modifications [7]
Annexin A4 (ANXA4) OTUCRYXL ANXA4_HUMAN Gene/Protein Processing [8]
Antigen peptide transporter 1 (TAP1) OTJL27PW TAP1_HUMAN Gene/Protein Processing [8]
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
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 1.02E-08 -5.12E-02 -2.22E-01
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 Topoisomerase I inhibitors: camptothecins and beyond. Nat Rev Cancer. 2006 Oct;6(10):789-802.
2 Pharmacogenetics of membrane transporters: an update on current approaches. Mol Biotechnol. 2010 Feb;44(2):152-67.
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 The beta-carboline alkaloid harmine inhibits BCRP and can reverse resistance to the anticancer drugs mitoxantrone and camptothecin in breast cancer cells. Phytother Res. 2010 Jan;24(1):146-9.
5 ATR inhibitors VE-821 and VX-970 sensitize cancer cells to topoisomerase i inhibitors by disabling DNA replication initiation and fork elongation responses. Cancer Res. 2014 Dec 1;74(23):6968-79.
6 Development and validation of the TGx-HDACi transcriptomic biomarker to detect histone deacetylase inhibitors in human TK6 cells. Arch Toxicol. 2021 May;95(5):1631-1645. doi: 10.1007/s00204-021-03014-2. Epub 2021 Mar 26.
7 Reduced camptothecin sensitivity of estrogen receptor-positive human breast cancer cells following exposure to di(2-ethylhexyl)phthalate (DEHP) is associated with DNA methylation changes. Environ Toxicol. 2019 Apr;34(4):401-414.
8 Characterization of DNA reactive and non-DNA reactive anticancer drugs by gene expression profiling. Mutat Res. 2007 Jun 1;619(1-2):16-29. doi: 10.1016/j.mrfmmm.2006.12.007. Epub 2007 Feb 8.
9 Albumin-binding prodrugs of camptothecin and doxorubicin with an Ala-Leu-Ala-Leu-linker that are cleaved by cathepsin B: synthesis and antitumor efficacy. Bioconjug Chem. 2007 May-Jun;18(3):702-16. doi: 10.1021/bc0602735. Epub 2007 Mar 23.