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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18Cl2N2O2
Molecular Weight 305.2
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELPHALAN

SMILES

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

InChI

InChIKey=SGDBTWWWUNNDEQ-LBPRGKRZSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H18Cl2N2O2
Molecular Weight 305.2
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Melphalan, also known as L-phenylalanine mustard, phenylalanine mustard, L-PAM, or L-sarcolysin, is a phenylalanine derivative of nitrogen mustard. Melphalan is a bifunctional alkylating agent which produces a number of DNA adducts with the DNA interstrand crosslink (ICL) considered to be the critical cytotoxic lesion. Melphalan is used to treat different cancers including myeloma, melanoma and ovarian cancer.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Prolonged apnea after succinylcholine in a case treated with cytostatics for cancer.
1972 Sep-Oct
[Diagnosis and treatment of plasma cell leukemia].
1973 Apr 27
Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma.
1976 Oct 4
[Refractory anemia with partial myeloblastosis in multiple myeloma treated with melphalan].
1977 Apr 9-16
Lymphocyte transformation studies in drug hypersensitivity.
1979 May 5
Drug testing using a soft agar stem cell assay on patient and xenograft tumor material.
1984 Sep
Melphalan-resistant multiple myeloma: results of treatment according to the M-2 protocol.
1985
Syndrome of inappropriate antidiuretic hormone secretion. A complication of high-dose intravenous melphalan.
1985 Jan 1
Cyclophosphamide-associated carcinoma of urothelium: modalities for prevention.
1991 Nov
Deletion 5q31 in patients with stable, melphalan-treated multiple myeloma.
1999 Aug
Encephalopathy complicating high-dose melphalan.
1999 Nov
Acute left ventricular failure following melphalan and fludarabine conditioning.
2001 Jul
Ifosfamide and etoposide are superior to vincristine and melphalan for pediatric metastatic rhabdomyosarcoma when administered with irradiation and combination chemotherapy: a report from the Intergroup Rhabdomyosarcoma Study Group.
2001 May
Phase II trial of sequential high-dose chemotherapy with paclitaxel, melphalan and cyclophosphamide, thiotepa and carboplatin with peripheral blood progenitor support in women with responding metastatic breast cancer.
2002 Aug
Expression of rat liver glutathione-S-transferase GSTA5 in cell lines provides increased resistance to alkylating agents and toxic aldehydes.
2002 May 20
Melphalan antitumor efficacy and hepatotoxicity: the effect of variable infusion duration in the hepatic artery.
2003 Jun
Cross-talk between DNA damage and cell survival checkpoints during G2 and mitosis: pharmacologic implications.
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
In vivo therapeutic responses contingent on Fanconi anemia/BRCA2 status of the tumor.
2005 Oct 15
[White blood cell lysis syndrome after autologous peripheral blood stem cell transplantation in the treatment of renal AL amyloidosis. Case report].
2006 Jun
Bortezomib-dexamethasone combination in a patient with refractory multiple myeloma and impaired renal function.
2006 Jun
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Heterogeneity of human glioblastoma: glutathione-S-transferase and methylguanine-methyltransferase.
2008 Jul
Cardiac toxicity of high-dose cyclophosphamide and melphalan in patients with multiple myeloma treated with tandem autologous hematopoietic stem cell transplantation.
2008 Sep
Cutaneous involvement in multiple myeloma and bortezomib.
2009 Nov
Excessive toxicity of once daily i.v. BU, melphalan and thiotepa followed by auto SCT on patients with non-Hodgkin's lymphoma.
2010 Apr
Efficacy and safety of once-weekly bortezomib in multiple myeloma patients.
2010 Dec 2
Uptake of 3-[125I]iodo-alpha-methyl-L-tyrosine into colon cancer DLD-1 cells: characterization and inhibitory effect of natural amino acids and amino acid-like drugs.
2010 Feb
Increased expression of VDAC1 sensitizes carcinoma cells to apoptosis induced by DNA cross-linking agents.
2012 May 1
Corticosteroid treatment inhibits airway hyperresponsiveness and lung injury in a murine model of chemical-induced airway inflammation.
2012 Nov 15
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Sample Use Guides

In Vivo Use Guide
6 mg (3 tablets) daily
Route of Administration: Oral
In Vitro Use Guide
10 uM or 100 uM
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:49:06 UTC 2019
Edited
by admin
on Tue Oct 22 00:49:06 UTC 2019
Record UNII
Q41OR9510P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MELPHALAN
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
MELPHALAN [INN]
Common Name English
L-SARCOLYSIN
Common Name English
NSC-241286
Code English
MELPHALAN [MI]
Common Name English
MELPHALAN [MART.]
Common Name English
NCI-C04853
Code English
MELPHALAN [JAN]
Common Name English
SK 15673
Code English
MELPHALAN [USAN]
Common Name English
L-3-(P-(BIS(2-CHLOROETHYL)AMINO)PHENYL)ALANINE
Common Name English
SARCOLYCIN, L-
Common Name English
MELPHALAN [ORANGE BOOK]
Common Name English
MELPHALAN [WHO-DD]
Common Name English
MELPHALAN [USP]
Common Name English
L-PHENYLALANINE MUSTARD
Common Name English
MELPHALAN [IARC]
Common Name English
PHENYLALANINE MUSTARD
Common Name English
L-PHENYLALANINE, 4-(BIS(2-CHLOROETHYL)AMINO)-
Systematic Name English
MELPHALAN [HSDB]
Common Name English
L-PAM
Common Name English
NSC-8806
Code English
MELPHALAN [VANDF]
Common Name English
ALKERAN
Brand Name English
CB-3025
Code English
CB 3025
Code English
SK-15673
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 485515
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
NDF-RT N0000000236
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
NCI_THESAURUS C697
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
FDA ORPHAN DRUG 64291
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
WHO-ATC L01AA03
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
NDF-RT N0000175558
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
WHO-VATC QL01AA03
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
FDA ORPHAN DRUG 60991
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
FDA ORPHAN DRUG 378112
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
FDA ORPHAN DRUG 270008
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
LIVERTOX 596
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
Code System Code Type Description
PUBCHEM
460612
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
MESH
D008558
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
EVMPD
SUB08728MIG
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
RXCUI
6718
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
MELPHALAN
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
CAS
148-82-3
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
DRUG BANK
DB01042
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
NCI_THESAURUS
C633
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
IUPHAR
7620
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-726-3
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
EPA CompTox
148-82-3
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
MERCK INDEX
M7166
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY Merck Index
HSDB
148-82-3
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
ChEMBL
CHEMBL852
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
INN
745
Created by admin on Tue Oct 22 00:49:06 UTC 2019 , Edited by admin on Tue Oct 22 00:49:06 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC