ContaminantDB: Melphalan

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 02:05:38 UTC

Update Date

2026-04-05 10:47:27 UTC

Accession Number

CHEM003660

Identification

Common Name

Melphalan

Class

Small Molecule

Description

An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - melphalan, the racemic mixture - merphalan, and the dextro isomer - medphalan; toxic to bone marrow, but little vesicant action; potential carcinogen.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
IARC Carcinogens Group 1
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Drug
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine	ChEBI
3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine	ChEBI
4-(Bis(2-chloroethyl)amino)-L-phenylalanine	ChEBI
L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine	ChEBI
L-PAM	ChEBI
L-Phenylalanine mustard	ChEBI
L-Sarcolysine	ChEBI
Melfalano	ChEBI
Melphalanum	ChEBI
p-Bis(beta-chloroethyl)aminophenylalanine	ChEBI
p-Di-(2-chloroethyl)amino-L-phenylalanine	ChEBI
p-L-Sarcolysin	ChEBI
p-N,N-Bis(2-chloroethyl)amino-L-phenylalanine	ChEBI
p-N-Bis(2-chloroethyl)amino-L-phenylalanine	ChEBI
Phenylalanine mustard	ChEBI
Phenylalanine nitrogen mustard	ChEBI
Alkeran	Kegg
p-Bis(b-chloroethyl)aminophenylalanine	Generator
p-Bis(β-chloroethyl)aminophenylalanine	Generator
4-(Bis(2-chloroethyl)amino)phenylalanine	HMDB
Medphalan	HMDB
Merphalan	HMDB
Sarcolysine	HMDB
Sarkolysin	HMDB
Mustard, phenylalanine	HMDB

Chemical Formula

C₁₃H₁₈Cl₂N₂O₂

Average Molecular Mass

305.200 g/mol

Monoisotopic Mass

304.075 g/mol

CAS Registry Number

148-82-3

IUPAC Name

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

Traditional Name

melphalan

SMILES

N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O

InChI Identifier

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

InChI Key

SGDBTWWWUNNDEQ-LBPRGKRZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Nitrogen mustard
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Tertiary amine
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Primary amine
Carbonyl group
Organopnictogen compound
Alkyl halide
Amine
Organic oxygen compound
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:28876 )
non-proteinogenic L-alpha-amino acid (CHEBI:28876 )
L-phenylalanine derivative (CHEBI:28876 )
nitrogen mustard (CHEBI:28876 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	182.5°C
Boiling Point	Not Available
Solubility	< 0.1 g/100 mL at 22°C

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	-0.22	ALOGPS
logP	0.25	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.29	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.56 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	78.23 m³·mol⁻¹	ChemAxon
Polarizability	31.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-3890000000-153ff87813e7a797c73b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01c3-8295000000-421b0e52574345db725f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000w-2930000000-b95beb5e9c3e61b7687f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000w-2930000000-b95beb5e9c3e61b7687f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0093000000-78045bae5e6c1e79e22d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1490000000-3b1f7009692b1139989b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-3930000000-b0f45ffda87388d4384a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0049000000-8c401366ace5d7fc1f08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4i-1192000000-fd136d877921c8afed95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9530000000-511158435cb1ef063085	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0095000000-3f3242a1d9debe0c8315	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bi-0090000000-91067233804f48cd760a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-0930000000-af3e37be6b85ec7f144b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-7090000000-6793f4f7ed0a2c22f972	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-c2fa753da65a4bac80a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-ed9c052b92676bc8a30b	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Incomplete, variable, 25-89% post oral dose

Mechanism of Toxicity

Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases (primarily at the N-7 position of guanine and to a lesser extent, at the N-3 position of adenine), forming monoadducts and 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.

Metabolism

Melphalan is not actively metabolised, it spontaneously degrades to mono and dihydroxy products. Route of Elimination: The 24-hour urinary excretion of parent drug in these patients was 10% Њ± 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug. Half Life: 1.5 (±0.83) hours

Toxicity Values

LD₅₀=11.2 mg/kg (orally in rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (4)

Uses/Sources

For the palliative treatment of multiple myeloma and for the palliation of non-resectable epithelial carcinoma of the ovary. Has also been used alone or as part of various chemotherapeutic regimens as an adjunct to surgery in the treatment of breast cancer, alone or in combination regimens for palliative treatment of locally recurrent or unresectable in-transit metastatic melanoma of the extremities, as well as for the treatment of amyloidosis with prednisone.

Minimum Risk Level

Not Available

Health Effects

The principal toxic effect is bone marrow suppression.

Symptoms

Vomiting, ulceration of the mouth, diarrhea, and hemorrhage of the gastrointestinal tract.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID