This HTML5 document contains 87 embedded RDF statements represented using HTML+Microdata notation.

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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00888
rdf:type
n5:Drug
n5:description
A vesicant and necrotizing irritant destructive to mucous membranes, mechlorethamine is an alkylating drug. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkin's disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem] The FDA granted marketing approval for the orphan drug Valchlor (mechlorethamine) gel on August 23, 2013 for the topical treatment of stage IA and IB mycosis fungoides-type cutaneous T-cell lymphoma (CTCL) in patients who have received prior skin-directed therapy. Each tube of Valchlor contains 0.016% of mechlorethamine which is equivalent to 0.02% mechlorethamine HCL.
n5:dosage
n13:271B588F-363D-11E5-9242-09173F13E4C5 n13:271B5890-363D-11E5-9242-09173F13E4C5
n5:generalReferences
# FDA label
n5:group
approved
n5:halfLife
15 minutes
n5:indication
For the palliative treatment of Hodgkin's disease (Stages III and IV), lymphosarcoma, chronic myelocytic or chronic lymphocytic leukemia, polycythemia vera, mycosis fungoides, and bronchogenic carcinoma. Also for the palliative treatment of metastatic carcinoma resulting in effusion.
n5:manufacturer
n11:271B588D-363D-11E5-9242-09173F13E4C5
owl:sameAs
n10:DB00888 n28:DB00888
dcterms:title
Mechlorethamine
adms:identifier
n4:Mechlorethamine n17:3893 n18:DB00888 n19:28925 n22:PA450336 n23:4033 n24:C07115 n25:46505784 n30:D07671 n31:66215-016-60
n5:mechanismOfAction
Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.
n5:packager
n11:271B588B-363D-11E5-9242-09173F13E4C5 n11:271B588C-363D-11E5-9242-09173F13E4C5
n5:patent
n12:8501818 n12:8501819 n12:7838564 n12:7872050 n12:8450375
n5:synonym
Mustine Bis(beta-chloroethyl)methylamine Bis(2-chloroethyl)methylamine beta,Beta'-dichlorodiethyl-N-methylamine Methylbis(2-chloroethyl)amine Nitrogen mustard N-methyl-bis(2-chloroethyl)amine N-Methyl-bis(beta-chloroethyl)amine 2,2'-dichloro-N-methyldiethylamine Chlormethine β,β'-dichlorodiethyl-N-methylamine Methylbis(beta-chloroethyl)amine Mechlorethamine
n5:toxicity
Symptoms of overexposure include severe leukopenia, anemia, thrombocytopenia, and a hemorrhagic diathesis with subsequent delayed bleeding may develop. Death may follow. The most common adverse reactions (≥5%) of the topical formulation are dermatitis, pruritus, bacterial skin infection, skin ulceration or blistering, and hyperpigmentation. The oral LD50 for a rat is 10 mg/kg.
n20:hasAHFSCode
n26:84-92 n26:10-00-00
n5:salt
n5:synthesisReference
Paul Siedlecki, "Preparation of nitrogen mustard derivatives." U.S. Patent US20030162990, issued August 28, 2003.
n14:hasConcept
n15:M0013168
foaf:page
n8:mechlorethamine.html n16:mustargen.htm
n5:IUPAC-Name
n6:271B5895-363D-11E5-9242-09173F13E4C5
n5:InChI
n6:271B589B-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n6:271B589A-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n6:271B5897-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n6:271B5898-363D-11E5-9242-09173F13E4C5
n5:SMILES
n6:271B5899-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n6:271B5893-363D-11E5-9242-09173F13E4C5 n6:271B58AA-363D-11E5-9242-09173F13E4C5
n5:logP
n6:271B5891-363D-11E5-9242-09173F13E4C5 n6:271B5894-363D-11E5-9242-09173F13E4C5 n6:271B58AD-363D-11E5-9242-09173F13E4C5
n5:logS
n6:271B5892-363D-11E5-9242-09173F13E4C5
n5:pKa
n6:271B58AE-363D-11E5-9242-09173F13E4C5
n20:hasATCCode
n21:L01AA05
n5:H-Bond-Acceptor-Count
n6:271B58A1-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n6:271B58A2-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n6:271B589C-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n6:271B589D-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n6:271B589F-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n6:271B589E-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n6:271B58A0-363D-11E5-9242-09173F13E4C5
n5:absorption
Partially absorbed following intracavitary administration, most likely due to rapid deactivation by body fluids. When it is topically administered, systemic exposure was undetectable.
n5:affectedOrganism
Humans and other mammals
n5:casRegistryNumber
51-75-2
n5:category
n5:containedIn
n29:271B588E-363D-11E5-9242-09173F13E4C5
n5:Bioavailability
n6:271B58A6-363D-11E5-9242-09173F13E4C5
n5:Boiling-Point
n6:271B58AC-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n6:271B58A8-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n6:271B58A9-363D-11E5-9242-09173F13E4C5
n5:Melting-Point
n6:271B58AB-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n6:271B58A5-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n6:271B58A4-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n6:271B58A7-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n6:271B5896-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n6:271B58A3-363D-11E5-9242-09173F13E4C5