Basic information
- CAS
13909-02-9- Standard SMILES
O=NN(CCCl)C(=O)NC1CCC(=O)NC1=O- InChIKey
KHWIRCOLWPNBJP-UHFFFAOYSA-N- Molecular formula
- C8H11ClN4O4
- Average molar mass
- 262.65 g/mol
- Monoisotopic mass
- 262.0468825
Overview
PCNU is a chloroethylnitrosourea compound and an alkylating agent with antineoplastic property. PCNU inhibits DNA synthesis by alkylating DNA and causing DNA cross links, thereby inducing apoptosis. In addition, this agent may be associated with pulmonary, hepatic, and hematologic toxicities. Unlike other nitrosoureas, PCNU has strong alkylating while weak carbamoylating activity.
Names & identifiers
- Preferred name
- 1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidinyl)-1-nitrosourea
- IUPAC
- 1-(2-chloroethyl)-3-(2,6-dioxopiperidin-3-yl)-1-nitrosourea
- English name
- 1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitrosourea
- Molecular formula
- C8H11ClN4O4
- Molecular weight
- 262.65034
Names & synonyms
1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitrosourea13909-02-9NSC-95466NSC-95,466UNII-AZW59V4Q3BUrea, N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitroso-AZW59V4Q3BNSC 95466BRN 0431046N-(2-Chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitrosoureaUrea, 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)-1-nitroso-AI3-52898
Show more names
1-(2-Chloroethyl)-3-(2,6-dioxo-3-piperidinyl)-1-nitrosoureaRefChem:74109Urea, N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)-N-nitroso-(9CI)PCNUNSC954661-(2-Chloroethyl)3-(2,6-dioxo-3-piperidyl)-1-nitrosoureaCHEMBL12200SCHEMBL845062
Database identifiers
- CAS
13909-02-9- PubChem CID
- 26328
- DTXSID
DTXSID10864453- ChEMBL
CHEMBL12200- UNII
- AZW59V4Q3B
- Nikkaji
- J15.712K
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 348
Experimental & physicochemical properties
LogP0.37
Solubility
Water < 1 (mg/mL)
Water pH 4 < 1 (mg/mL)
Water pH 9 2-3 (mg/mL)
10% EtOH < 1 (mg/mL)
95% EtOH 2-3 (mg/mL)
McOH 3-4 (mg/mL)
Stability/Shelf Life
Bulk: A sample stored at 60° C for 10 days decomposed 18% (UV). The compound was found to be stable in bulk form at room temperature exposed to lab light through 60 days (UV, TLC and ionic chloride). For long -term storage the bulk compound should be protected from moisture and stored at -15° C. Solution: The compound dissolved in 3% methanol/ water decomposed 4% in one hour, 6.5% in three hours 15% in six hours, and 38% in 24 hours (UV). There was no formation of ionic chloride during the 24 hours. Solutions should be prepared immediately before use.
Physicochemical properties
- Density
- 1.8525 · 1.8525 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- FDA UNII
- 59 V4Q3B · AZW59V4Q3B
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Data
Mouse(po): LD50 35700 lug/kg
Mouse(iv): LD50 22 mg/kg
Dog(iv): LDLo, 3 mg/kg
Monkey(iv): LDLo 10 mg/kg
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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