| Identification | More | [Name]
9-Aminocamptothecin | [CAS]
91421-43-1 | [Synonyms]
10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione
9-Amino-20-(S)-camptothecin
9-AMINO-CAMPTOTHECIN
CAMPTOTHECIN, 9-AMINO-
(20S)-9-AMINOCAMPTOTHECIN
9-Aminocamptothecin，9-Amino-20-(S)-camptothecin
(4S)-4α-Ethyl-4,12-dihydro-4-hydroxy-10-amino-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione
9-Amino-20(S)-camptothecine
NSC-603071 | [Molecular Formula]
C20H17N3O4 | [MDL Number]
MFCD00909855 | [Molecular Weight]
363.37 | [MOL File]
91421-43-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
142.0-145.0 °C | [Boiling point ]
819.6±65.0 °C(Predicted) | [density ]
1.55±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C(protect from light) | [solubility ]
≤1mg/ml in DMSO;1mg/ml in dimethyl formamide | [form ]
powder to crystal | [pka]
11.23±0.20(Predicted) | [color ]
Light yellow to Yellow to Orange | [Merck ]
14,431 | [InChI]
InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1 | [InChIKey]
FUXVKZWTXQUGMW-FQEVSTJZSA-N | [SMILES]
N1C2C(=C(N)C=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O | [CAS DataBase Reference]
91421-43-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the fruit of Camptotheca acuminata Decne., a plant of the Davidiaceae family. | [Uses]
9-Amino Camptothecin is a derivative of Camptothecin (C175150), as antitumor agent. | [Definition]
ChEBI: 9-Aminocamptothecin is a pyranoindolizinoquinoline. | [Biological Activity]
9-amino camptothecin is a topoisomerase i inhibitor [1][2].dna topoisomerases relax dna torsional strain generated during replication, transcription, recombination, repair, and chromosome condensation. the relaxation of dna supercoiling by topoisomerase i is enabled by a mechanism of controlled rotation around a transient dna single-strand break. camptothecin (cpt) is isolated from the bark of the chinese tree camptotheca accuminata [3].9-amino camptothecin, a water-soluble camptothecin analogue, is a topoisomerase i inhibitor. in human ht-29 colon adenocarcinoma, 9-amino camptothecin (9-ac) exhibited cytotoxicity with ic50 value of 19 nm. 9-ac also induced dna damage in whole cells and nuclei at a concenstration of 85 nm and 21 nm, respectively [1].9-amino camptothecin had greater activity than camptothecin against human tumour xenografts, including lewis lung carcinoma and b16 melanoma. 9-ac had entered phase ii trials. in patients with advanced solid tumours, 9-amino camptothecin exhibited anti-tumor activity [1][2]. | [in vivo]
9-Aminocamptothecin (9-Amino-CPT) inhibits tumor growth at the lowest oral dose (0.35 mg/kg/day), whereas higher oral doses (0.75 and 1 mg/kg/day) and s.c. administration (4 mg/kg/week) causes tumor regression. 9-Aminocamptothecin is well tolerated at all doses, with no toxic death or weight loss of more than 10% observed in any group[2]. 9-Aminocamptothecin induces complete remissions in 55 % of SCID mice engrafted with human myeloid leukemia. The oral and intravenous routes are equally effective. The results with this pre-clinical model support the evaluation of 9-Aminocamptothecin as antileukemic agent in a phase I trial in patients with AML[3]. | [IC 50]
Topoisomerase I | [References]
[1]. rothenberg, m.l. topoisomerase i inhibitors: review and update. annals of oncology 8(9), 837-855 (1997).
[2]. dancey j, eisenhauer ea. current perspectives on camptothecins in cancer treatment. br j cancer. 1996 aug;74(3):327-38.
[3]. drwal mn1, agama k, wakelin lp, et al. exploring dna topoisomerase i ligand space in search of novel anticancer agents. plos one. 2011;6(9):e25150. |
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