Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H13N3O |
Molecular Weight | 227.2618 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(C=C1)C(=O)NC2=CC=CC=C2N
InChI
InChIKey=QGMGHALXLXKCBD-UHFFFAOYSA-N
InChI=1S/C13H13N3O/c14-10-7-5-9(6-8-10)13(17)16-12-4-2-1-3-11(12)15/h1-8H,14-15H2,(H,16,17)
Dinaline represents a group of pharmacologically active lipophilic substances with a relatively simple structure derived from N-acyl-o-phenylenediamine. It has been found to exhibit high antineoplastic activity in a series of slowly growing tumors such as chemically induced rat mammary and colorectal carcinomas, osteosarcoma C22LR and Brown Norway myeloid leukemia. The drug was inactive against many of the typically hypersensitive signal tumors, i.e. mouse leukemias P388 and L1210, sarcoma 180 and Yoshida sarcoma. Colon carcinoma cells exposed to dinaline demonstrate distinct but reversible changes in amino acid transport, protein metabolism, DNA synthesis and cell proliferation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669814 |
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Target ID: GO:0051320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669814 |
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Target ID: GO:0071897 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669814 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effectiveness of P-aminobenzoyl-O-phenylenediamine (Goe 1734) against mouse, rat, and human tumour cells. | 1985 |
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Synthesis, toxicity, and therapeutic efficacy of 4-amino-N-(2'-aminophenyl)-benzamide: a new compound preferentially active in slowly growing tumors. | 1985 Dec |
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Autochthonous, acetoxymethylmethylnitrosamine-induced colorectal cancer in rats: a useful tool in selecting new active antineoplastic compounds? | 1986 Oct |
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Dinaline: a new oral drug against leukemia? Preclinical studies in a relevant rat model for human acute myelocytic leukemia (BNML). | 1988 Apr |
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New cytostatics--more activity and less toxicity. | 1990 Sep |
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Acetyldinaline: a new oral cytostatic drug with impressive differential activity against leukemic cells and normal stem cells--preclinical studies in a relevant rat model for human acute myelocytic leukemia. | 1993 Jul 1 |
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Combination treatment based on metabolic effects of dinaline. | 1995 |
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Dinaline inhibits amino acid transport and proliferation of colon carcinoma cells in vitro. | 1995 Nov-Dec |
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Application of alpha-aminoisobutyric acid, L-methionine, thymidine and 2-fluoro-2-deoxy-D-glucose to monitor effects of chemotherapy in a human colon carcinoma cell line. | 1996 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8943683
Rat: 10, 7.7 and 5.9 mg/kg 5 days per week
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3859382
An in vitro clonogenic assay did not reveal any activity of Goe 1734 when mouse osteosarcoma or human tumour cells were exposed for only 1 h. However, continuous exposure led to 70% or greater inhibition of colony formation at concentrations of 0.1-1 ug/ml (osteosarcoma) or 0.2-2 ug/ml (human tumours).
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C1946
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ACTIVE MOIETY