Drug Information

General Information
Drug ID
DR00044
Drug Name
Topotecan
Synonyms
(4S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; (S)-10-((Dimethylamino)methyl)-4-ethyl-4,9-dihydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione; (S)-10-[(DIMETHYLAMINO)METHYL]-4-ETHYL-4,9-DIHYDROXY-1H-PYRANO[3',4':6,7]INOLIZINO[1,2-B]-QUINOLINE-3,14(4H,12H)-DIONE; (S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]-quinoline-3,14(4H,12H)-dione; (S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 9-Dimethylaminomethyl-10-hydroxycamptothecin; Hycamptamine; Hycamptin; Hycamtamine; Hycamtin; Hycamtin (TN); SK&F-104864-A; SKF 104864; SKF-104864-A; SKF-S 104864; TOPOTECAN, HYCAMTIN; Topotecan (BAN); Topotecan Monohydrochloride, (S)-Isomer; Topotecan [INN:BAN]; Topotecan lactone; Topotecane; Topotecane [INN-French]; Topotecanum; Topotecanum [INN-Latin]
Drug Type
Small molecular drug
Indication Ovarian cancer [ICD11:2C73] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C23H23N3O5
Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O
InChI
InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
InChIKey
UCFGDBYHRUNTLO-QHCPKHFHSA-N
CAS Number
CAS 119413-54-6
Pharmaceutical Properties Molecular Weight 421.4 Topological Polar Surface Area 103
Heavy Atom Count 31 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
XLogP
0.5
PubChem CID
60700
PubChem SID
103170619 ,103922004 ,103942242 ,104321416 ,11409161 ,11459078 ,11461196 ,117586312 ,124878927 ,124878928 ,126631363 ,126682466 ,129347572 ,13340 ,134337938 ,135026276 ,135610141 ,136342520 ,136376449 ,137007926 ,137275799 ,142090317 ,144220376 ,14807035 ,14904851 ,152106211 ,152198470 ,160660968 ,160964365 ,24769902 ,43118056 ,46505204 ,47348955 ,47499101 ,47572929 ,48242924 ,50028360 ,50123362 ,53790588 ,56311903 ,57314070 ,581639 ,606579 ,78527173 ,7890901 ,7980817 ,8187013 ,92309036 ,92710943 ,96025302
ChEBI ID
CHEBI:63632
TTD Drug ID
D02PMO
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MATE1 Transporter Info Multidrug and toxin extrusion protein 1 Substrate [3]
MATE2 Transporter Info Multidrug and toxin extrusion protein 2 Substrate [3]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [4]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [6]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BCRP Transporter Info Km =213 microM Madin-Darby canine kidney cells (MDCKII)-BCRP [6]
MATE1 Transporter Info Km =70 microM Human embryonic kidney cells (HEK293)-MATE1 [3]
MATE2 Transporter Info Km =60 microM Human embryonic kidney cells (HEK293)-MATE2K [3]
MRP4 Transporter Info Km =1.66 microM Human liver cancer cells (HepG2)-MRP4 [5]
P-GP Transporter Info Km =78.3 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [6]
P-GP Transporter Info Km =102 microM Madin-Darby canine kidney cells (MDCKII)-MDR1 [6]
References
1 Topotecan was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Differential inhibition of murine Bcrp1/Abcg2 and human BCRP/ABCG2 by the mycotoxin fumitremorgin C. Eur J Pharmacol. 2010 Oct 10;644(1-3):41-8.
3 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
4 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
5 Topotecan is a substrate for multidrug resistance associated protein 4. Curr Drug Metab. 2006 Jan;7(1):105-18.
6 Involvement of P-glycoprotein, multidrug resistance protein 2 and breast cancer resistance protein in the transport of belotecan and topotecan in Caco-2 and MDCKII cells. Pharm Res. 2008 Nov;25(11):2601-12.

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