DMPEN

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200880

CAS#: 176046-79-0

Description: 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.


Chemical Structure

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DMPEN
CAS# 176046-79-0

Theoretical Analysis

MedKoo Cat#: 200880
Name: DMPEN
CAS#: 176046-79-0
Chemical Formula: C7H4Cl5NO2
Exact Mass: 308.86847
Molecular Weight: 311.38
Elemental Analysis: C, 27.00; H, 1.29; Cl, 56.93; N, 4.50; O, 10.28

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: DMPEN 4demethylpenclomedine; NSC682691NCI600295984Pyridinol 35dichloro2methoxy6(trichloromethyl)Clomet.

IUPAC/Chemical Name: 3,5-dichloro-2-methoxy-6-(trichloromethyl)pyridin-4-ol

InChi Key: GUYGGZGIKZIRFO-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H4Cl5NO2/c1-15-6-3(9)4(14)2(8)5(13-6)7(10,11)12/h1H3,(H,13,14)

SMILES Code: OC1=C(Cl)C(OC)=NC(C(Cl)(Cl)Cl)=C1Cl

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).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 311.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.



Additional Information

According to http://www.ncbi.nlm.nih.gov/pubmed/9041177, penclomedine [3,5-dichloro-4,6-dimethoxy-2-(trichloromethyl)pyridine], an antitumor agent, was in clinical trials during 2000s, and was believed to be a prodrug. In these studies, cerebellar effects had been dose limiting. Previous studies identified 4-demethylpenclomedine (4-DM-PEN) as the major plasma metabolite in rodents and humans. 4-DM-PEN was demonstrated to be an antitumor-active metabolite of penclomedine in vivo when evaluated against the penclomedine-sensitive MX-1 human breast tumor xenograft implanted either s.c. or intracerebrally and is believed to be on the metabolic activation pathway of penclomedine. Because earlier studies revealed an absence of neurotoxic cerebellar effects for 4-DM-PEN in contrast to penclomedine in a rat model, this metabolite may be a candidate for an alternative to penclomedine in the clinic for treatment of breast cancer or brain tumors, if the cerebellar effects of penclomedine preclude its further clinical development. Because neither penclomedine nor 4-DM-PEN were very active in vitro, the metabolism of penclomedine was also investigated using rat liver microsomes in an attempt to identify the ultimate active form of the drug. Metabolites and putative metabolites were prepared by chemical synthesis for antitumor evaluation in vitro and in vivo. A reductive metabolite, alpha,alpha-didechloro-PEN, was observed to be much more cytotoxic than penclomedine or 4-DM-PEN in vitro, but evaluation of this and the other metabolites and putative metabolites in vivo against the MX-1 tumor failed to identify any active metabolite among the structures evaluated other than 4-DM-PEN. The limited activity of 4-DM-PEN in vitro indicates that it, like penclomedine, is also a prodrug, demonstrating a need for additional studies on the metabolic activation of penclomedine to identify the ultimate active form of the drug.
 
Current developer:    Xanthus Pharmaceuticals Inc