Metoprine
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Basic information
- CAS
7761-45-7- Standard SMILES
Cc1nc(N)nc(N)c1-c1ccc(Cl)c(Cl)c1- InChIKey
VQJHOPSWBGJHQS-UHFFFAOYSA-N- Molecular formula
- C11H10Cl2N4
- Average molar mass
- 269.13 g/mol
- Monoisotopic mass
- 268.0282517
Overview
Metoprine is a diaminopyrimidine folate antagonist with potential antineoplastic activity. Metoprine inhibits dihydrofolate reductase, resulting in decreased cellular folate metabolism and cell growth; it also inhibits histamine-N-methyltransferase, resulting in decreased histamine catabolism. Lipid-soluble metoprine is capable of crossing the blood-brain barrier. (NCI04)
Names & identifiers
- Preferred name
- Metoprine
- IUPAC
- 5-(3,4-dichlorophenyl)-6-methylpyrimidine-2,4-diamine
- English name
- Metoprine
- Molecular formula
- C11H10Cl2N4
- Molecular weight
- 269.13
Names & synonyms
METOPRINE7761-45-7MethodichlorophenDDMP5-(3,4-DICHLOROPHENYL)-6-METHYLPYRIMIDINE-2,4-DIAMINENSC-19494BW-197UTCMDC-123931NSC73642,4-Diamino-5-(3,4-dichlorophenyl)-6-methylpyrimidineDTXSID00578312,4-Pyrimidinediamine, 5-(3,4-dichlorophenyl)-6-methyl-
Show more names
U-197SK 5265NSC 7364BW-50-197Metoprine, 10 mM in DMSO
NSC-73642L9RKX796QBW 197UNSC19494DTXCID1031620RefChem:1583892,4-diamino-5-(3',4'-dichlorophenyl)-6-methylpyrimidineMetoprine [USAN]
Database identifiers
- CAS
7761-45-7- PubChem CID
- 24466
- DTXSID
DTXSID0057831- ChEMBL
CHEMBL264373- UNII
- 2L9RKX796Q
- Nikkaji
- J9.654G
Properties
Computed structural propertiesFilling in
- XLogP
- 2.8
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 266
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.8
Physicochemical properties
- Melting point
- 275 · 275-276℃
- Boiling point
- 418.42 °C · 418.42°C (rough estimate)
- Density
- 1.447 · 1.447
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
- form
- Solid
- pka
- 6.8 · 6.80±0.10(Predicted)
- color
- Off-White to Light Yellow
- Stability
- Hygroscopic
- FDA UNII
- 2 L9RKX796Q · 2L9RKX796Q
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319
- Precautionary statements
- P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033)
Applications
UsesA 2,4-Diaminopyrimidine derivative as antimalarial agent.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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