Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H39Cl2FN4O4S |
Molecular Weight | 629.614 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)[C@H](CCSC)NC(=O)[C@H](CC1=CC=CC(=C1)N(CCCl)CCCl)NC(=O)[C@@H](N)CC2=CC=C(F)C=C2
InChI
InChIKey=XPGDODOEEWLHOI-GSDHBNRESA-N
InChI=1S/C29H39Cl2FN4O4S/c1-3-40-29(39)25(11-16-41-2)34-28(38)26(35-27(37)24(33)18-20-7-9-22(32)10-8-20)19-21-5-4-6-23(17-21)36(14-12-30)15-13-31/h4-10,17,24-26H,3,11-16,18-19,33H2,1-2H3,(H,34,38)(H,35,37)/t24-,25-,26-/m0/s1
Ambamustine (PTT-119) is a bifunctional alkylating agent. Its antitumour effect is reported to mainly be through alkylation and interstrand cross-linkage of DNA. The drug was awaiting registration in Italy for the treatment of non-Hodgkin's lymphoma, and was also in phase-II clinical trial for small cell lung cancer, but was discontinued.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Phase II study of a new alkylating agent (PTT-119) in resistant-relapsed non-Hodgkin's lymphomas. | 1989 |
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Limiting dilution analysis of a novel tripeptide anticancer agent Ambamustine (PTT-119): effect on K-562, CCRF-SB and multidrug resistant LoVo-Dk cell lines. | 1994 Jun |
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Ambamustine in the second-line treatment of patients with small-cell lung cancer: a phase II Fonicap study. | 2000 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10683068
Small-cell lung cancer: Ambamustine was administered at the dose of 2 mg/kg as a 1-hour intravenous infusion on day 1 every 21 days. The dose was to be increased to 3 mg/kg if no grade IV toxicity and complete hematologic recovery had occurred by day 22.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8187848
Incubation with 50 ug/mL of Ambamustine (PTT-119) produced a total elimination of K-562 acute myelogenous blasts, whereas nearly 0.17 and 0.27 leukemic cells were still present in the cell mixtures after treatment with 5 and 25 ug/mL, respectively. When normal bone marrow was contaminated with CCRF-SB lymphoblastic cells, incubation with either 50 or 25 ug/mL of PTT-119 produced a complete clearing of leukemic cells, whereas with 5 ug/mL the leukemic cells in each well were 0.18. When PTT-119 was incubated with LoVo-DX, a colon cancer cell line which expresses the pleiotropic drug resistance MDR phenotype, virtually complete inhibition of clonogenic colonies was observed with as little as 5 ug/mL.
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C697
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ACTIVE MOIETY