Camptothecin

Category	Influenza Virus
CAS	7689-03-4
Description	Camptothecin (CPT) is a potent DNA enzyme topoisomerase I (topo I) inhibitor with an IC50 and IC70 of 50 nM and 0.225 μM for breast cancer cell line MDA-MB-231. Camptothecin is extratced from the barks of Camptotheca acuminata Decne. It can be used in cosmetics material. It is also an impurity of Irinotecan, a Topoisomerase I inhibitor used for the treatment of colon cancer and small cell lung cancer.

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Synonyms	camptothecin;7689-03-4;Camptothecine;(S)-(+)-Camptothecin;Campathecin;(+)-Camptothecin;(+)-Camptothecine;d-Camptothecin;20(S)-Camptothecine;21,22-Secocamptothecin-21-oic acid lactone;NSC94600;Camptothecine (S,+);CHEMBL65;(S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;NSC-94600;(4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;MLS000766223;XT3Z54Z28A;CHEBI:27656;MFCD00081076;(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;NSC 100880;(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione;(S)-Camptothecin;1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-;1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-;1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-;20(S)-Camptothecin;4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE;SR-01000075798;SR-01000597379;d-camptothecine;(s)-camptothecine;Camptothecin,(S);(4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE;(S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione;1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-;Prestwick_102;Camptothecine (8CI);Spectrum_000299;Tocris-1100;SpecPlus_000712;Prestwick0_000200;Prestwick1_000200;Prestwick2_000200;Prestwick3_000200;Spectrum2_000903;Spectrum3_001203;Spectrum4_000738;Spectrum5_001126;CAMPTOTHECIN [MI];Lopac-C-9911;SCHEMBL6038;UNII-XT3Z54Z28A;Lopac0_000341;BSPBio_000159;BSPBio_002586;KBioGR_001036;KBioSS_000779;KBioSS_002283;cid_24360;CAMPTOTHECIN [WHO-DD];DivK1c_000826;DivK1c_006808;SPECTRUM1502232;SPBio_000746;SPBio_002080;BPBio1_000175;CCRIS 8162;DTXSID0030956;HMS502J08;KBio1_000826;KBio1_001752;KBio2_000779;KBio2_003347;KBio2_005915;KBio3_002086;4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;NINDS_000826;Bio1_000400;Bio1_000889;Bio1_001378;GLXC-10346;HMS1568H21;HMS1921N08;HMS2089F08;HMS2095H21;HMS3261E03;HMS3414J17;HMS3654D13;HMS3678J15;HMS3712H21;BCP02857;Tox21_500341;AC-202;BBL033963;BDBM50008923;CCG-40255;GR-301;NSC 94600;s1288;STK801886;AKOS004119861;CS-1049;DB04690;KS-5235;LP00341;SDCCGMLS-0066688.P001;SDCCGSBI-0050329.P003;BRN 0631069;CAS-2114454;IDI1_000826;NCGC00015290-01;NCGC00016994-01;NCGC00016994-02;NCGC00016994-03;NCGC00016994-04;NCGC00016994-05;NCGC00016994-06;NCGC00016994-07;NCGC00016994-08;NCGC00016994-09;NCGC00016994-10;NCGC00016994-11;NCGC00016994-12;NCGC00016994-16;NCGC00016994-19;NCGC00016994-23;NCGC00016994-29;NCGC00024997-01;NCGC00024997-02;NCGC00024997-03;NCGC00024997-04;NCGC00024997-05;NCGC00024997-06;NCGC00178592-01;NCGC00178592-02;NCGC00261026-01;1ST40312;HY-16560;NCI60_042105;SMR000445686;SY010324;AI3-62475;EU-0100341;NS00011856;SW196414-3;C 9911;C01897;M01564;AB00052452-08;AB00052452-09;AB00052452_10;EN300-1725804;(S)-(+)-Camptothecin, >=90% (HPLC), powder;A838882;Q419964;Q-200785;SR-01000075798-1;SR-01000075798-4;SR-01000597379-1;SR-01000597379-3;BRD-K37890730-001-09-4;BRD-K37890730-001-10-2;BRD-K37890730-001-15-1;BRD-K37890730-001-16-9;BRD-K37890730-001-17-7;Z1741982070;(S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]florene-3,13-dione;(S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione;4-Ethyl-4-hydroxy-1H-pyrano-[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;4-Ethyl-4-hydroxy-1H-pyrano-[3[,4[:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione;(S)-4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(S)-(+)-Camptothecin;(S)-4-Ethyl-4-hydroxy-1H-pyrano[3 inverted exclamation mark ,4 inverted exclamation mark :6,7]indolizino[1,2-b]quinoline-3,14-(4H,12H)-dione;1H-Pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-;4(S)-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione;4-ethyl-4-hydroxy-(4S)-3,4,12,14-tetrahydro-1H-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-3,14-dione;4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin or CPT);4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (Camptothecin);4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (CPT, Camptothecin);
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
Molecular Weight	182.65
Molecular Formula	C6H14N2O2.ClH
Canonical SMILES	C(CCN)C[C@@H](C(=O)O)N.Cl
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
Boiling Point	757.0±60.0 °C at 760 mmHg
Melting Point	260 °C (dec.)(lit.)
Flash Point	411.6±32.9 °C
Purity	>98%
Density	1.5±0.1 g/cm3
Solubility	Soluble to 30 mg/ml (86 mm) in DMSO, not soluble in water
Appearance	Solid
Application	ADCs Cytotoxin
Shelf Life	≥12 months if stored properly
Storage	4°C, protect from light *In solvent : -80°C, 1 year; -20°C, 6 months (protect from light)
Complexity	742
Exact Mass	348.11100700
Index Of Refraction	1.746
In Vitro	[3H]BrCPT labeling of topoisomerase I is enhanced greatly by the presence of DNA; very little labeling of isolated topoisomerase I or isolated DNA occurrs. Even in the presence of DNA, [3H]BrCPT labeling of topoisomerase I is inhibited by camptothecin, suggesting that both CPT and BrCPT bind to the same site on the DNA-topoisomerase I binary complex. With increasing concentrations of camptothecin, closed circular pRR322 DNA (form I) is converted to nicked circular DNA (form 11). This apparent nicking activitv of camptothecin required DNA topoisomerase I.
In Vivo	Camptothecin (2 mg/kg every other day) treats mice, has developed numerous pulmonary metastases. Treatment with both kinase inhibitor of nuclear factor-kappaB-1 (KINK-1) and Camptothecin led to a statistically significant reduction in the number of pulmonary metastases.
PSA	81.42000
Target	Topoisomerase; ADC Cytotoxin; MicroRNA; Influenza Virus; Apoptosis; Fungal
Vapor Pressure	0.0±2.7 mmHg at 25°C
XLogP3-AA	1