(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid

• ChemBase ID: 128251
• Molecular Formular: C13H18Cl2N2O2
• Molecular Mass: 305.20022
• Monoisotopic Mass: 304.07453319
• SMILES: c1cc(ccc1C[C@@H](C(=O)O)N)N(CCCl)CCCl
• Canonical SMILES: ClCCN(c1ccc(cc1)C[C@@H](C(=O)O)N)CCCl
• InChI: InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
• InChIKey: SGDBTWWWUNNDEQ-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
• IUPAC Traditional name: melphalan
• Brand Name: Alkeran
• Synonyms: p-Di-(2-chloroethyl)amino-L-phenylalanine; Alanine Nitrogen Mustard; Melfalan; Alkeran; Sarcoclorin; 2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid; Melphalan; 4-[Bis(2-chloroethyl)amino]-L-phenylalanine; L-PAM; L-Phenylalanine mustard; Melphalan

Database IDs

• CAS Number: 148-82-3
• EC Number: 205-726-3
• MDL Number: MFCD00057717
• Beilstein Number: 2816456
• PubChem SID: 162222560; 24278538
• PubChem CID: 4053; 460612
• CHEBI ID: 28876
• ATC CODE: L01AA03
• CHEMBL: 852
• Chemspider ID: 405297
• DrugBank ID: DB01042
• KEGG ID: D00369
• Unique Ingredient Identifier: Q41OR9510P
• Wikipedia Title: Melphalan
• Medline Plus: a682220

CALCULATED PROPERTIES

• Acid pKa: 1.2884431
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.25192413
• LogD (pH = 7.4): 0.2493237
• Log P: 0.25219622
• Molar Refractivity: 78.2315 cm^3
• Polarizability: 30.09238 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 95% ethanol and 1 drop 6 N HCl: soluble0.05 g/mL, clear; DMSO; Ethanol; Methanol; Propylene Glycol
• Apperance: Off-White Solid; white powder
• Melting Point: ~180 °C; 165-167°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: AY3675000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 45-46-26/27/28-63; 45-46-63-26/27/28
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H350-H361
• GHS Precautionary statements: P201-P260-P264-P280-P284-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: 25% to 89%
• Excretion: Renal, significantly metabolised
• Half Life: 1.5 ± 0.8 hours
• Metabolism: hydrolysis
• Legal Status: Rx-only

Product Information

• Purity: ≥90% (TLC)
• Impurities: ≤10% water
• Empirical Formula (Hill Notation): C13H18Cl2N2O2

DETAILS

Sigma Aldrich - M2011

Biochem/physiol Actions
Melphalan is an antineoplastic agent.1,2 It forms DNA intrastrand crosslinks by bifunctional alkylation in 5′-GGC sequences.3

Sigma Aldrich - 63648

Other Notes
Mechanisms of DNA sequence selective alkylation of guanine-N7 positions by nitrogen mustards1; Review2

Toronto Research Chemicals - M216900

Antineoplastic.

REFERENCES

• Ross, W.C.J., et al.: Biochem. Pharmacol., 13, 969 (1964)
• Donelli, M.G., et al.: J. Pharm. Pharmacol., 18, 760 (1964)
• Furner, R.L., et al.: Cancer Treat. Rep., 64, 559 (1964)