carzelesin: a cyclopropylpyrroloindole analog of U 73975; longer lasting than U 77779; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 3034013 |
| CHEMBL ID | 32911 |
| SCHEMBL ID | 7183293 |
| MeSH ID | M0205881 |
| Synonym |
|---|
| carzelesin |
| nsc-619029 |
| 119813-10-4 |
| u-80244 |
| carzelesin (usan/inn) |
| D03416 |
| 2-benzofurancarboxamide, n-(2-((1-(chloromethyl)-1,6-dihydro-8-methyl-5-(((phenylamino)carbonyl)oxy)benzo(1,2-b:4,3-b')dipyrrol-3(2h)-yl)carbonyl)-1h-indol-5-yl)-6-(diethylamino)-, (s)- |
| carzelesin [usan:inn] |
| nsc 619029 |
| u 80244 |
| 2-benzofurancarboxamide, n-(2-((1-(chloromethyl)-1,6-dihydro-8-methyl-5-(((phenylamino)carbonyl)oxy)benzo(1,2-b:4,3-b')dipyrrol-3(2h)-yl)carbonyl)-1h-idnol-5-yl)-6-(diethylamino)-, (s)- |
| n-(2-(((s)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo(1,2-b:4,3-b')dipyrrol-3(2h)-yl)carbonyl)indol-5-yl)-6-(diethylamino)-2-benzofurancarboxamide carbanilate (ester) |
| CHEMBL32911 |
| [8-(chloromethyl)-6-[5-[[6-(diethylamino)-1-benzofuran-2-carbonyl]amino]-1h-indole-2-carbonyl]-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indol-4-yl] n-phenylcarbamate |
| [(8s)-8-(chloromethyl)-6-[5-[[6-(diethylamino)-1-benzofuran-2-carbonyl]amino]-1h-indole-2-carbonyl]-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indol-4-yl] n-phenylcarbamate |
| 668uf07o1p , |
| unii-668uf07o1p |
| carzelesin [inn] |
| carzelesin [usan] |
| SCHEMBL7183293 |
| u80244;u-80244;u 80244 |
| DTXSID30152602 |
| Q27263977 |
Carzelesin is a novel cyclopropylpyrroloindole prodrug analogue that has recently been tested in Phase I clinical trials. It acts as a DNA-sequence-specific alkylating agent.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Carzelesin treatment produced 100% complete remissions (no palpable tumor mass at the termination of the experiment) in mice bearing early-stage human ovarian 2780." | ( Cytotoxicity and antitumor activity of carzelesin, a prodrug cyclopropylpyrroloindole analogue. DeKoning, TF; Kelly, RC; Krueger, WC; Li, LH; McGovren, JP; Ouding, RJ; Padbury, GE; Petzold, GL; Prairie, MD; Wallace, TL, 1992) | 1.27 |
We investigated the pharmacokinetic behavior of carzelesin in 31 patients receiving this drug by 10-min intravenous infusion in a Phase I clinical trial. The study was conducted at institutions in Nijmegen and Brussels.
| Excerpt | Reference | Relevance |
|---|---|---|
| "We investigated the pharmacokinetic behavior of carzelesin in 31 patients receiving this drug by 10-min intravenous infusion in a Phase I clinical trial, which was conducted at institutions in Nijmegen (institution 1) and Brussels (institution 2)." | ( A clinical pharmacokinetics study of carzelesin given by short-term intravenous infusion in a phase I study. Awada, A; Beijnen, JH; Groot, Y; Henrar, RE; Nooijen, WJ; Piccart, MJ; Punt, CJ; Schaaf, LJ; van Tellingen, O; Wagener, DJ, 1998) | 0.83 |
| " In this Phase I study, carzelesin was given daily for 5 consecutive days to (a) determine the maximum tolerable dose (MTD) and the pattern of toxicity of this schedule; (b) define the pharmacokinetic profile of the parent, as was done for the intermediate compound U-76073 and the DNA-reactive agent U-76074; and (c) document any antitumor activity observed." | ( Phase I clinical and pharmacokinetic study of carzelesin (U-80244) given daily for five consecutive days. Beijnen, JH; Bench, K; Bruntsch, U; Cavalli, F; de Jong, J; Groot, Y; Sessa, C; van Tellingen, O; Wanders, J; Wolff, I, 1996) | 0.86 |
Carzelesin was less potent in terms of in vitro cytotoxicity and in vivo optimal dosage. It was therapeutically more efficacious against mouse L1210 leukemia than was U-76074 or adozelesin (U-73975)
| Excerpt | Relevance | Reference |
|---|---|---|
| " Although carzelesin was less potent in terms of in vitro cytotoxicity and in vivo optimal dosage and showed low affinity for binding to DNA, it was therapeutically more efficacious against mouse L1210 leukemia than was U-76074 or adozelesin (U-73975), another cyclopropylpyrroloindole analogue which is currently in phase I clinical trials." | ( Cytotoxicity and antitumor activity of carzelesin, a prodrug cyclopropylpyrroloindole analogue. DeKoning, TF; Kelly, RC; Krueger, WC; Li, LH; McGovren, JP; Ouding, RJ; Padbury, GE; Petzold, GL; Prairie, MD; Wallace, TL, 1992) | 0.96 |
| "The aim of this study was to design a parenteral dosage form for the investigational cytotoxic drug carzelesin." | ( Pharmaceutical development of a parenteral formulation of the novel anti-tumor agent carzelesin (U-80,244). Beijnen, JH; Bult, A; de Graaff-Teulen, MJ; Henrar, RE; Jonkman-de Vries, JD; Kettenes-van den Bosch, JJ, 1994) | 0.73 |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID122159 | In vivo antitumor activity (0.584 mg/kg) is the measure of tumor growth inhibition of human tumor xenograft WiDr (colon) implanted sc in mice. | 1999 | Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8 | Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups. |
| AID122156 | In vivo antitumor activity (0.584 mg/kg) is the measure of tumor growth inhibition of human tumor xenograft DLD-1 (colon) implanted sc in mice. | 1999 | Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8 | Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups. |
| AID88790 | The myelotoxicity was tested in vitro on human granulocyte macrophage colony forming units (CFU-GM) cord blood derived hematopoietic cells (1 hr exposure) | 2004 | Journal of medicinal chemistry, May-06, Volume: 47, Issue:10 | Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. |
| AID89265 | Cytotoxicity was determined after 1 hr exposure against six different human tumor cells lines | 2004 | Journal of medicinal chemistry, May-06, Volume: 47, Issue:10 | Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. |
| AID122158 | In vivo antitumor activity (0.584 mg/kg) is the measure of tumor growth inhibition of human tumor xenograft NUGC-3 (stomach) implanted sc in mice. | 1999 | Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8 | Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups. |
| AID122157 | In vivo antitumor activity (0.584 mg/kg) is the measure of tumor growth inhibition of human tumor xenograft HCT116 (colon) implanted sc in mice. | 1999 | Journal of medicinal chemistry, Apr-22, Volume: 42, Issue:8 | Novel cyclopropapyrroloindole derivative (AT-3510) bearing methoxycarbonyl and trifluoromethyl groups. |
| AID90917 | Ratio between IC50 on human bone marrow progenitors (CFUGM) and tumor cells. | 2004 | Journal of medicinal chemistry, May-06, Volume: 47, Issue:10 | Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. |
| AID690852 | Half life in human plasma at 1 ug/mL at pH 7 by HPLC analysis | 2012 | Journal of medicinal chemistry, Jun-28, Volume: 55, Issue:12 | A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 15 (78.95) | 18.2507 |
| 2000's | 3 (15.79) | 29.6817 |
| 2010's | 1 (5.26) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (16.15) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 4 (20.00%) | 5.53% |
| Reviews | 1 (5.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 15 (75.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||