NAV

4-O-Demethylpenclomedine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
4-O-Demethylpenclomedine
DrugBank Accession Number
DB06331
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 311.36
Monoisotopic: 308.8684669
Chemical Formula
C7H4Cl5NO2
Synonyms
  • 4-Demethylpenclomedine
  • 4-Dm-pen
  • 4-Dmpen
  • DM-PEN
  • DMPEN
External IDs
  • NSC-682691
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Pharmacology

Indication

Investigated for use/treatment in solid tumors.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

DMPEN (4,o-demethylpenclomedine) is the highly reactive principal alkylating metabolite of Penclomedine (PEN), a multichlorinated alpha-picoline derivative. DM-PEN’s proposed mechanism of action begins with activation by free radical formation in the liver, where it is then transported to tumor cells via the circulation system. The free radical moiety forms an adduct with DNA, and interstrand crosslinking occurs through the 5-chloro moiety. The 5-chloro moiety is then activated by keto-enol tautomerism, producing the alkylating group, an alpha-haloketo function.

TargetActionsOrganism
UDNANot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Clomet (Xanthus Pharmaceuticals Inc.)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as polyhalopyridines. These are organic compounds containing a pyridine ring substituted at two or more positions by a halogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Halopyridines
Direct Parent
Polyhalopyridines
Alternative Parents
Dihydropyridines / Alkyl aryl ethers / Aryl chlorides / Vinylogous esters / Vinylogous amides / Heteroaromatic compounds / Cyclic ketones / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 4 more
Substituents
Alkyl aryl ether / Alkyl chloride / Alkyl halide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Cyclic ketone / Dihydropyridine / Ether
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
XUK71J2M0Q
CAS number
176046-79-0
InChI Key
GUYGGZGIKZIRFO-UHFFFAOYSA-N
InChI
InChI=1S/C7H4Cl5NO2/c1-15-6-3(9)4(14)2(8)5(13-6)7(10,11)12/h1H3,(H,13,14)
IUPAC Name
3,5-dichloro-2-methoxy-6-(trichloromethyl)-1,4-dihydropyridin-4-one
SMILES
[H]N1C(OC)=C(Cl)C(=O)C(Cl)=C1C(Cl)(Cl)Cl

References

General References
  1. 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. [Article]
  2. 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. [Article]
ChemSpider
344015
ChEMBL
CHEMBL11122

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00205 mg/mLALOGPS
logP3.68ALOGPS
logP3.26Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)6.28Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area38.33 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity74.25 m3·mol-1Chemaxon
Polarizability24.53 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-024i-1492000000-3380d4b5e61d02ecf261
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-05c2489bc4365c89878c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-924157a951543bd2e782
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-2e1e77e1a3bd1ce95a91
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0029000000-c24cee48f5cf36d0f31d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-4009000000-949b220c88400a889083
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-1941000000-cee69c5434a0e2f88a09
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-154.52287
predicted
DeepCCS 1.0 (2019)
[M+H]+156.88087
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.97403
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Drug created at March 19, 2008 16:24 / Updated at June 12, 2020 16:52