DMPEN
DMPEN (4-demethylpenclomedine), the active metabolite of penclomedine [3,5-dichloro-4,6-dimethoxy-2-(trichloromethyl)pyridine], is a alkylation agent, and was demonstrated to have potent antitumor activity. DMPEN went Phase I clinical trials during 2000s. Currently no active clinical trials were reported.
1: Morgan LR, Struck RF, Waud WR, LeBlanc B, Rodgers AH, Jursic BS. Carbonate and carbamate derivatives of 4-demethylpenclomedine as novel anticancer agents. Cancer Chemother Pharmacol. 2009 Sep;64(4):829-35. Epub 2009 Mar 3. PubMed PMID: 19255760; PubMed Central PMCID: PMC2717391.
2: Struck RF, Waud WR. Thiolo-, thiono- and dithiocarbonate and thiocarbamate derivatives of demethylpenclomedine as novel anticancer agents. Cancer Chemother Pharmacol. 2006 Jan;57(2):180-4. Epub 2005 Aug 11. PubMed PMID: 16096790.
3: O'Reilly S, O'Hearn E, Struck RF, Rowinsky EK, Molliver ME. The alkylating agent penclomedine induces degeneration of purkinje cells in the rat cerebellum. Invest New Drugs. 2003 Aug;21(3):269-79. PubMed PMID: 14578677.
4: Struck RF, Tiwari A, Friedman HS, Keir S, Morgan LR, Waud WR. Acyl derivatives of demethylpenclomedine, an antitumor-active, non-neurotoxic metabolites of penclomedine. Cancer Chemother Pharmacol. 2001 Jul;48(1):47-52. PubMed PMID: 11488524.
5: Hartman NR, Leo KU, Brewer TG, Strong JM. The in vitro metabolism of penclomedine in mouse, rat, and human systems. Drug Metab Dispos. 1998 Jun;26(6):513-9. PubMed PMID: 9616185.
6: Waud WR, Tiwari A, Schmid SM, Shih TW, Strong JM, Hartman NR, O'Reilly S, Struck RF. 4-Demethylpenclomedine, an antitumor-active, potentially nonneurotoxic metabolite of penclomedine. Cancer Res. 1997 Mar 1;57(5):815-7. PubMed PMID: 9041177.
2: Struck RF, Waud WR. Thiolo-, thiono- and dithiocarbonate and thiocarbamate derivatives of demethylpenclomedine as novel anticancer agents. Cancer Chemother Pharmacol. 2006 Jan;57(2):180-4. Epub 2005 Aug 11. PubMed PMID: 16096790.
3: O'Reilly S, O'Hearn E, Struck RF, Rowinsky EK, Molliver ME. The alkylating agent penclomedine induces degeneration of purkinje cells in the rat cerebellum. Invest New Drugs. 2003 Aug;21(3):269-79. PubMed PMID: 14578677.
4: Struck RF, Tiwari A, Friedman HS, Keir S, Morgan LR, Waud WR. Acyl derivatives of demethylpenclomedine, an antitumor-active, non-neurotoxic metabolites of penclomedine. Cancer Chemother Pharmacol. 2001 Jul;48(1):47-52. PubMed PMID: 11488524.
5: Hartman NR, Leo KU, Brewer TG, Strong JM. The in vitro metabolism of penclomedine in mouse, rat, and human systems. Drug Metab Dispos. 1998 Jun;26(6):513-9. PubMed PMID: 9616185.
6: Waud WR, Tiwari A, Schmid SM, Shih TW, Strong JM, Hartman NR, O'Reilly S, Struck RF. 4-Demethylpenclomedine, an antitumor-active, potentially nonneurotoxic metabolite of penclomedine. Cancer Res. 1997 Mar 1;57(5):815-7. PubMed PMID: 9041177.
| Chemical | |
|---|---|
| CAS Num | 176046-79-0 |
| Chemical Formula | C7H4Cl5NO2 |
| Molecular Weight | 311.38 |
| IUPAC Chemical Name | 3,5-dichloro-2-methoxy-6-(trichloromethyl)pyridin-4-ol |
| Exact Mass | 308.86847 |
| Elemental Analysis | C, 27.00; H, 1.29; Cl, 56.93; N, 4.50; O, 10.28 |
| Synonym | DMPEN 4demethylpenclomedine; NSC682691NCI600295984Pyridinol 35dichloro2methoxy6(trichloromethyl)Clomet. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | OC1=C(Cl)C(OC)=NC(C(Cl)(Cl)Cl)=C1Cl |
| Biological | |
| Targets and Effects | N/A |
| Pathways | alkylating agent |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >5 years if stored properly |
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