1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-(2-chloroethyl)-3-nitrosourea hydrochloride

• ChemBase ID: 155648
• Molecular Formular: C9H14Cl2N6O2
• Molecular Mass: 309.15246
• Monoisotopic Mass: 308.05552908
• SMILES: Cc1ncc(c(n1)N)CNC(=O)N(CCCl)N=O.Cl
• Canonical SMILES: ClCCN(C(=O)NCc1cnc(nc1N)C)N=O.Cl
• InChI: InChI=1S/C9H13ClN6O2.ClH/c1-6-12-4-7(8(11)14-6)5-13-9(17)16(15-18)3-2-10;/h4H,2-3,5H2,1H3,(H,13,17)(H2,11,12,14);1H
• InChIKey: KPMKNHGAPDCYLP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-(2-chloroethyl)-3-nitrosourea hydrochloride
• IUPAC Traditional name: nimustine hydrochloride; 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-(2-chloroethyl)-3-nitrosourea hydrochloride
• Synonyms: N′-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-N-(2-chloroethyl)-N-nitrosourea hydrochloride; Nimustine hydrochloride; Nidran

Database IDs

• CAS Number: 55661-38-6
• MDL Number: MFCD01676942
• PubChem SID: 162249786; 24278598
• PubChem CID: 91657

CALCULATED PROPERTIES

• Acid pKa: 12.579354
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.18515736
• LogD (pH = 7.4): 0.5956762
• Log P: 0.6260267
• Molar Refractivity: 68.5516 cm^3
• Polarizability: 24.24491 Å^3
• Polar Surface Area: 113.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• RTECS: YR8450000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Mechanism of Action: Alkylating agent

Product Information

• Salt Data: HCl
• Application(s): Antineoplastic (antileukaemic) agent
• Empirical Formula (Hill Notation): C9H13ClN6O2

DETAILS

Sigma Aldrich - N8659

Application
Nimustine hydrochloride is an antineoplastic.

REFERENCES

• Ger. Pat., 1973, Sankyo, 2 257 360; CA, 79, 53186c, (synth, pharmacol)
• Shimizu, F. et al., Gann, 1975, 66, 149, (pharmacol)
• Tatsuhara, T. et al., J. Chromatogr., 1990, 526, 507, (hplc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 496
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ALF500; NDY800