Melphalan is an alkylating antineoplastic agent used to treat multiple myeloma and ovarian carcinoma.

Brand Names
Alkeran, Evomela
Generic Name
DrugBank Accession Number

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.

Small Molecule
Average: 305.2
Monoisotopic: 304.074533244
Chemical Formula
  • 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine
  • 3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine
  • 4-(Bis(2-chloroethyl)amino)-L-phenylalanine
  • L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine
  • L-PAM
  • L-Phenylalanine mustard
  • L-Sarcolysine
  • Melfalano
  • Melphalan
  • Melphalanum
  • p-Bis(beta-chloroethyl)aminophenylalanine
  • p-Di-(2-chloroethyl)amino-L-phenylalanine
  • p-L-Sarcolysin
  • p-N-Bis(2-chloroethyl)amino-L-phenylalanine
  • p-N,N-bis(2-chloroethyl)amino-L-phenylalanine
  • Phenylalanine mustard
  • Phenylalanine nitrogen mustard
External IDs
  • CB 3025
  • CB-3025
  • NCI-C04853
  • NSC-241286
  • NSC-8806
  • SK 15673
  • SK-15673



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.

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Melphalan is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.

Mechanism of action

Melphalan attaches alkyl groups to the N-7 position of guanine and N-3 position of adenine, leading to the formation of monoadducts, and DNA fragmenting when repair enzymes attempt to correct the error.4,5 It can also cause DNA cross-linking from the N-7 position of one guanine to the N-7 position of another, preventing DNA strands from separating for synthesis or transcription.4,5 Finally, melphalan can induce a number of different mutations.4


Incomplete, variable, 25-89% post oral dose

Volume of distribution
  • 0.5 L/kg
Protein binding

Moderate to high (60 to 90%), primarily to albumin and, to a lesser extent, alpha 1-acid glycoprotein. 30% is irreversibly bound.


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% ± 4.5%, suggesting that renal clearance is not a major route of elimination of parent drug.


1.5 (±0.83) hours


Not Available

Adverse Effects
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Vomiting, ulceration of the mouth, diarrhea, and hemorrhage of the gastrointestinal tract; The principal toxic effect is bone marrow suppression. LD50=11.2 mg/kg (orally in rat)

Not Available
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
AbataceptThe risk or severity of adverse effects can be increased when Melphalan is combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Melphalan.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Melphalan.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Melphalan.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Melphalan.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Melphalan.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Melphalan.
AlefaceptThe risk or severity of adverse effects can be increased when Alefacept is combined with Melphalan.
AlemtuzumabThe risk or severity of adverse effects can be increased when Alemtuzumab is combined with Melphalan.
Allogeneic processed thymus tissueThe therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Melphalan.
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Food Interactions
  • Drink plenty of fluids.
  • Take on an empty stomach. Food decreases absorption and decreases bioavailabilty by approximately 30%.


Drug product information from 10+ global regions
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Product Ingredients
IngredientUNIICASInChI Key
Melphalan hydrochloride1VXP4V453T3223-07-2OUUYBRCCFUEMLH-YDALLXLXSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlkeranTablet2 mg/1OralCelgene1993-03-162009-11-02US flag
AlkeranKit50 mg/10mLIntravenousGlaxo Operations UK Ltd2011-01-012018-02-13US flag
AlkeranTablet2 mgOralAspen Pharmacare Canada Inc.1964-12-31Not applicableCanada flag
AlkeranKit50 mg/10mLIntravenousGlaxosmithkline Inc1993-03-162012-05-31US flag
AlkeranKit50 mg/10mLIntravenousApoPharma USA, Inc.2011-01-01Not applicableUS flag
AlkeranTablet, film coated2 mg/1OralPhysicians Total Care, Inc.2005-08-152012-06-30US flag
AlkeranKit50 mg/10mLIntravenousCelgene1993-03-162009-11-02US flag
AlkeranTablet, film coated2 mg/1OralGlaxosmithkline Inc1984-05-102012-04-30US flag
AlkeranTablet, film coated2 mg/1OralApoPharma USA, Inc.2011-01-01Not applicableUS flag
EvomelaInjection, powder, lyophilized, for solution50 mg/10mLIntravenousAcrotech Biopharma Llc2016-03-31Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Melphalan50 mg/50mgIntravenousBpi Labs Llc2020-09-30Not applicableUS flag
MelphalanTablet2 mg/1OralAlvogen Inc.2017-03-22Not applicableUS flag
Melphalan50 mg/10mLIntravenousFresenius Kabi USA, LLC2017-12-22Not applicableUS flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousActavis Pharma, Inc.2017-01-13Not applicableUS flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousDr.Reddy's Laboratories Inc2021-04-26Not applicableUS flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousGenera Medix Inc.2009-10-27Not applicableUS flag
Melphalan hydrochlorideKit50 mg/10mLIntravenousGland Pharma Limited2019-06-10Not applicableUS flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousSagent Pharmaceuticals2017-03-152020-04-30US flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousMylan Institutional LLC2014-09-29Not applicableUS flag
Melphalan HydrochlorideKit50 mg/10mLIntravenousAthenex Pharmaceutical Division, Llc.2019-07-30Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AlkeranMelphalan (50 mg)Kit; Powder, for solution; SolutionIntra-arterial; IntravenousAspen Pharmacare Canada Inc.1995-12-31Not applicableCanada flag
Melphalan for InjectionMelphalan (50 mg)Kit; Powder, for solution; SolutionIntravenousApotex Corporation2018-11-20Not applicableCanada flag
Melphalan for InjectionMelphalan (50 mg)Kit; Powder, for solution; SolutionIntra-arterial; IntravenousMarcan Pharmaceuticals Inc2018-06-18Not applicableCanada flag
Taro-melphalanMelphalan (50 mg)Kit; Powder, for solutionIntra-arterial; IntravenousTaro Pharmaceuticals, Inc.2021-01-25Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ALKERAN 2 MG TABLET, 25 ADETMelphalan (2 mg)TabletOralVLD DANIŞMANLIK TIBBİ ÜRÜNLER VE TANITIM HİZMETLERİ LTD. ŞTİ.2020-08-14Not applicableTurkey flag


ATC Codes
L01AA03 — Melphalan
Drug Categories
Chemical TaxonomyProvided by Classyfire
This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These 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.
Organic compounds
Super Class
Organic acids and derivatives
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
Phenylpropanoic acids / Amphetamines and derivatives / L-alpha-amino acids / Aniline and substituted anilines / Dialkylarylamines / Nitrogen mustard compounds / Aralkylamines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids
show 7 more
3-phenylpropanoic-acid / Alkyl chloride / Alkyl halide / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic homomonocyclic compound
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organochlorine compound, non-proteinogenic L-alpha-amino acid, L-phenylalanine derivative, nitrogen mustard (CHEBI:28876)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

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


Synthesis Reference
General References
  1. Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. doi: 10.1021/tx7004508. Epub 2008 Feb 14. [Article]
  2. Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. [Article]
  3. Moscow JA, Swanson CA, Cowan KH: Decreased melphalan accumulation in a human breast cancer cell line selected for resistance to melphalan. Br J Cancer. 1993 Oct;68(4):732-7. [Article]
  4. Povirk LF, Shuker DE: DNA damage and mutagenesis induced by nitrogen mustards. Mutat Res. 1994 Dec;318(3):205-26. doi: 10.1016/0165-1110(94)90015-9. [Article]
  5. Lawley PD, Phillips DH: DNA adducts from chemotherapeutic agents. Mutat Res. 1996 Aug 17;355(1-2):13-40. doi: 10.1016/0027-5107(96)00020-6. [Article]
Human Metabolome Database
KEGG Compound
PubChem Compound
PubChem Substance
Therapeutic Targets Database
RxList Drug Page Drug Page
FDA label
Download (175 KB)

Clinical Trials

Clinical Trials
4CompletedTreatmentMultiple Myeloma (MM)1
4RecruitingTreatmentMultiple Myeloma (MM)1
4TerminatedTreatmentMultiple Myeloma (MM)1
3Active Not RecruitingTreatmentAuto Stem Cell Transplant / Multiple Myeloma (MM)1
3Active Not RecruitingTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma / Smoldering Plasma Cell Myeloma1
3Active Not RecruitingTreatmentEwing's Sarcoma1
3Active Not RecruitingTreatmentMultiple Myeloma (MM)8
3Active Not RecruitingTreatmentMultiple Myeloma (MM) / Newly Diagnosed Patients1
3Active Not RecruitingTreatmentOcular Melanoma1
3Active Not RecruitingTreatmentRelapsed or Refractory Systemic Light Chain Amyloidosis1


Not Available
  • Antibioticos Ltd.
  • Bioniche Pharma
  • Cardinal Health
  • Catalent Pharma Solutions
  • Generamedix Inc.
  • GlaxoSmithKline Inc.
  • Nerviano Medical Science S.R.L.
  • Oso Biopharmaceuticals Manufacturing LLC
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
Dosage Forms
Injection, powder, for solutionParenteral50 MG/10ML
Kit; powder, for solution; solutionIntra-arterial; Intravenous
TabletOral2 mg
TabletOral2 mg/1
TabletOral5 MG
Tablet, film coatedOral2 mg/1
Tablet, film coatedOral
Injection, powder, lyophilized, for solutionIntravenous
Tablet, film coatedOral2.00 mg
Tablet, film coatedOral2 mg
Injection, powder, lyophilized, for solutionParenteral50 mg
InjectionIntravenous50 mg
Injection, powder, lyophilized, for solutionIntravenous50 mg/10mL
Injection, powder, for solution
Injection, powder, for solutionIntravenous
Injection, powder, for solutionParenteral50 MG
Kit; powder, for solutionIntravenous50 mg / vial
Kit; powder, for solution; solutionIntravenous
KitIntravenous50 mg/10mL
KitIntravenous50 mg/15mL
Injection, powder, for solutionParenteral
Injection, powder, lyophilized, for solutionIntravenous50 mg
Injection, powder, for solutionIntravenous200 mg
Injection, powder, for solutionIntravenous50 mg
PowderIntravenous200 MG
PowderIntravenous50 MG
Kit; powder, for solutionIntra-arterial; Intravenous
PowderIntravenous50 mg/1vial
Tablet, coatedOral2 mg
Unit descriptionCostUnit
Alkeran 50 mg vial1971.72USD vial
Melphalan hcl 50 mg vial1845.6USD vial
Alkeran 2 mg tablet5.65USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA1341114No2000-10-102017-10-10Canada flag
US8410077No2013-04-022029-03-13US flag
US9200088No2015-12-012029-03-13US flag
US9493582No2016-11-152033-02-27US flag
US10040872No2018-08-072034-01-30US flag
US10864183No2020-12-152030-05-28US flag
US10940128No2021-03-092030-06-14US flag
US11020363No2010-05-282030-05-28US flag


Experimental Properties
melting point (°C)182.5 °CPhysProp
water solubility< 0.1 g/100 mL at 22 °CNot Available
logP-0.52SANGSTER,J (1994) @pH=7.4
Predicted Properties
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.56 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.23 m3·mol-1ChemAxon
Polarizability31.38 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Human Intestinal Absorption+0.9523
Blood Brain Barrier-0.6073
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.983
P-glycoprotein inhibitor IINon-inhibitor0.9192
Renal organic cation transporterNon-inhibitor0.811
CYP450 2C9 substrateNon-substrate0.8457
CYP450 2D6 substrateNon-substrate0.7432
CYP450 3A4 substrateNon-substrate0.7553
CYP450 1A2 substrateInhibitor0.779
CYP450 2C9 inhibitorNon-inhibitor0.9348
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9193
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9863
Ames testAMES toxic0.9108
BiodegradationNot ready biodegradable0.9746
Rat acute toxicity3.9179 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8187
hERG inhibition (predictor II)Non-inhibitor0.8488
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000w-2930000000-b95beb5e9c3e61b7687f


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insights and accelerate drug research.
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Pharmacological action
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Monahan SD, Subbotin VM, Budker VG, Slattum PM, Neal ZC, Herweijer H, Wolff JA: Rapidly reversible hydrophobization: an approach to high first-pass drug extraction. Chem Biol. 2007 Sep;14(9):1065-77. [Article]
  4. Lee PC, Kakadiya R, Su TL, Lee TC: Combination of bifunctional alkylating agent and arsenic trioxide synergistically suppresses the growth of drug-resistant tumor cells. Neoplasia. 2010 May;12(5):376-87. [Article]
  5. Wang F, Li F, Ganguly M, Marky LA, Gold B, Egli M, Stone MP: A bridging water anchors the tethered 5-(3-aminopropyl)-2'-deoxyuridine amine in the DNA major groove proximate to the N+2 C.G base pair: implications for formation of interstrand 5'-GNC-3' cross-links by nitrogen mustards. Biochemistry. 2008 Jul 8;47(27):7147-57. doi: 10.1021/bi800375m. Epub 2008 Jun 13. [Article]
  6. Vasquez KM: Targeting and processing of site-specific DNA interstrand crosslinks. Environ Mol Mutagen. 2010 Jul;51(6):527-39. doi: 10.1002/em.20557. [Article]
  7. Dimopoulos MA, Souliotis VL, Anagnostopoulos A, Bamia C, Pouli A, Baltadakis I, Terpos E, Kyrtopoulos SA, Sfikakis PP: Melphalan-induced DNA damage in vitro as a predictor for clinical outcome in multiple myeloma. Haematologica. 2007 Nov;92(11):1505-12. [Article]
  8. Chen Q, Van der Sluis PC, Boulware D, Hazlehurst LA, Dalton WS: The FA/BRCA pathway is involved in melphalan-induced DNA interstrand cross-link repair and accounts for melphalan resistance in multiple myeloma cells. Blood. 2005 Jul 15;106(2):698-705. Epub 2005 Mar 31. [Article]
  9. Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. [Article]
  10. Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. doi: 10.1021/tx7004508. Epub 2008 Feb 14. [Article]


Pharmacological action
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
  1. Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [Article]
Pharmacological action
General Function
Peptide antigen binding
Specific Function
Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
Gene Name
Uniprot ID
Uniprot Name
Large neutral amino acids transporter small subunit 1
Molecular Weight
55009.62 Da
  1. Moscow JA, Swanson CA, Cowan KH: Decreased melphalan accumulation in a human breast cancer cell line selected for resistance to melphalan. Br J Cancer. 1993 Oct;68(4):732-7. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 28, 2021 11:56