Compound Detail

CHEMBL852

MELPHALAN

💊 Approved Drug

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💊 Approved Drug

N[C@@H](Cc1ccc(N(CCCl)CCCl)cc1)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL852
Name	MELPHALAN
Phase	Approved
Structure Type	MOL
InChI Key	SGDBTWWWUNNDEQ-LBPRGKRZSA-N
Therapeutic	✓ Yes

Known Names

Alanine nitrogen mustard Alkeran CB 3025 CB-3025 L-pam L-phenylalanine mustard L-sarcolysin Melfalan Melphalan NCI-C04853 NSC-241286 NSC-8806 +4 more

Targets

265

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

305.2

MW (Da)

1.93

ALogP

HBA

HBD

66.6

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1964
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Year

1963

Extended Properties

Molecular Formula	C13H18Cl2N2O2
MW	305.21
Aromatic Rings	1
Heavy Atoms	19
NP-Likeness	-0.07

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
DNA inhibitor	INHIBITOR	DNA	✓	✓

Indications

Carcinoma Multiple Myeloma Neoplasms Neoplasms Amyloidosis, Familial Anemia, Sickle Cell Breast Neoplasms Colorectal Neoplasms Ganglioneuroblastoma Immunoglobulin Light-chain Amyloidosis Leukemia Leukemia, Myeloid, Acute Lymphoma Lymphoma, Follicular Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Mantle-Cell Melanoma Melanoma Myelodysplastic Syndromes

ATC Classification

L01AA03

melphalan

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning

hematological toxicity

Country: United States

Black Box Warning

teratogenicity

Country: United States

Activity Summary

IC50 259 meas. best 6.66

EC50 4 meas. best 5.7

Ki 2 meas. best 4.26

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
P388 CHEMBL389	IC50	6.66	6.66	220.0	7
MOLT-3 CHEMBL614176	IC50	6.52	6.52	300.0	1
MCF7S CHEMBL614328	IC50	6.52	6.52	300.0	1
5637 CHEMBL612565	IC50	6.51	6.195	310.0	2
HL-60(TB) CHEMBL4296429	IC50	6.42	6.055	380.0	2
Unchecked CHEMBL612545	IC50	6.41	5.4429	389.8	7
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.3	5.1497	500.0	34
SAOS-2 CHEMBL614894	IC50	6.17	6.17	680.0	1
U2OS CHEMBL615023	IC50	6.17	6.17	680.0	1
MC3T3-E1 CHEMBL4296463	IC50	6.17	6.17	680.0	1
MDA-MB-468 CHEMBL614335	IC50	6.09	5.1775	810.0	4
L1210 CHEMBL386	IC50	6.01	5.4353	980.5	36
SISO CHEMBL613527	IC50	6.0	6.0	1000.0	1
M4Beu cell line CHEMBL612270	IC50	5.92	5.92	1200.0	1
SW-620 CHEMBL612262	IC50	5.91	4.9083	1220.0	6
CCRF-CEM CHEMBL382	IC50	5.85	5.5929	1400.0	28
HeLa CHEMBL399	IC50	5.77	5.3563	1700.0	8
SR CHEMBL614300	IC50	5.73	5.65	1860.0	3
Unchecked CHEMBL612545	EC50	5.7	5.7	2000.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	5.7	5.7	2000.0	1
HL-60 CHEMBL383	IC50	5.69	5.315	2040.0	2
ADMET CHEMBL612558	IC50	5.69	4.8133	2040.0	3
Jurkat CHEMBL397	IC50	5.66	5.66	2200.0	2
Homo sapiens CHEMBL372	IC50	5.66	5.335	2200.0	4
B16 CHEMBL381	IC50	5.66	5.66	2200.0	1
DAN-G CHEMBL614033	IC50	5.58	5.58	2650.0	2
DLD-1 CHEMBL614285	IC50	5.52	5.52	3000.0	1
U-251 CHEMBL615022	IC50	5.52	5.52	3000.0	1
A549 CHEMBL392	IC50	5.52	4.605	3000.0	4
PANC-1 CHEMBL614139	IC50	5.52	5.52	3000.0	1
HT-29 CHEMBL384	IC50	5.52	4.7267	3000.0	3
PBMC CHEMBL613107	EC50	5.52	5.52	3000.0	2
HCT-116 CHEMBL394	IC50	5.52	4.752	3000.0	5
MOLT-4 CHEMBL614177	IC50	5.5	5.4925	3200.0	4
FM3A CHEMBL614297	IC50	5.44	5.44	3600.0	2
MCF7 CHEMBL387	IC50	5.43	4.8267	3710.0	6
LoVo CHEMBL614721	IC50	5.39	5.35	4090.0	2
RT-112 CHEMBL614145	IC50	5.33	5.33	4690.0	1
H2981 cell line CHEMBL614802	IC50	5.3	5.3	5000.0	1
A-427 CHEMBL614515	IC50	5.29	5.29	5130.0	1
SH-SY5Y CHEMBL614910	IC50	5.26	5.26	5500.0	1
YAPC CHEMBL612815	IC50	5.22	5.22	5950.0	1
D283 Med CHEMBL614476	IC50	5.17	4.98	6800.0	2
KYSE-510 CHEMBL613868	IC50	5.09	5.09	8180.0	1
RPMI-8226 CHEMBL614882	IC50	5.05	4.3975	8900.0	4
Plasmodium falciparum CHEMBL364	IC50	5.0	4.9286	10000.0	7
C6 CHEMBL614657	IC50	4.96	4.6633	11000.0	3
D341 cell line CHEMBL614478	IC50	4.91	4.595	12400.0	2
RT-4 CHEMBL614884	IC50	4.85	4.85	14250.0	1
RG2 CHEMBL614001	IC50	4.82	4.82	15200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	7.0	mL.min-1.kg-1	Homo sapiens
CL	7.0	mL.min-1.kg-1	Homo sapiens
F	71.0	%	Homo sapiens
F	71.0	%	Homo sapiens
Fu	0.14	-	Homo sapiens
MRT	1.1	hr	Homo sapiens
T1/2	2.0	hr	-
T1/2	0.7667	hr	-
T1/2	0.8667	hr	-
T1/2	-	hr	-
T1/2	1.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
P388	IC50	=	220.0	nM	6.66	Cytotoxicity against murine P388 cells.	11170648
P388	IC50	=	220.0	nM	6.66	Inhibitory activity against Murine P388 cells	12086496
P388	IC50	=	220.0	nM	6.66	Cytotoxicity evaluated against P388 cells.	9767639
P388	IC50	=	220.0	nM	6.66	Concentration required to inhibit 50% of cell growth on murine P388 D1 cells.	11052798
P388	IC50	=	220.0	nM	6.66	Inhibitory activity was tested against P388 cells	10212121
P388	IC50	=	220.0	nM	6.66	Inhibition of proliferation of murine P388 cells	9544201
P388	IC50	=	220.0	nM	6.66	Cytotoxicity against mouse P388 cells assessed as inhibition of cell growth incu...	30114660
MCF7S	IC50	=	300.0	nM	6.52	In vitro cytotoxicity activity against MCF-7	11985479
MOLT-3	IC50	=	300.0	nM	6.52	Antitumor activity against human MOLT3 cells in presence of Penicillin-G-amidase...	17416532
5637	IC50	=	310.0	nM	6.51	Cytotoxicity against human 5637 cells after 96 hrs by microtiter assay	18187237
HL-60(TB)	IC50	=	380.0	nM	6.42	Antileukemic activity against human HL-60(TB) cells assessed as inhibition of tu...	24657568
Unchecked	IC50	=	389.79	nM	6.41	PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator...	-
NON-PROTEIN TARGET	IC50	=	500.0	nM	6.3	In vitro cytotoxicity activity against M4 Dau by colony forming assay	11985479
SAOS-2	IC50	=	680.0	nM	6.17	Cytotoxicity against human SAOS-2 cells assessed as cell growth inhibition	35665692
U2OS	IC50	=	680.0	nM	6.17	Cytotoxicity against human U2OS cells assessed as cell growth inhibition	35665692
MC3T3-E1	IC50	=	680.0	nM	6.17	Cytotoxicity against mouse MC3T3-E1 cells assessed as cell growth inhibition	35665692
MDA-MB-468	IC50	=	810.0	nM	6.09	Cytotoxicity against human MDA-MB-468 cells incubated for 4 hrs under hypoxic co...	30885680
L1210	IC50	=	980.5	nM	6.01	In vitro cytotoxicity against L1210 murine leukemia cells	10937717
MDA-MB-468	IC50	=	1000.0	nM	6.0	Cytotoxicity against human MDA-MB-468 cells incubated for 4 hrs under aerobic co...	30885680
SISO	IC50	=	1000.0	nM	6.0	Cytotoxicity against human SISO cells after 96 hrs by microtiter assay	18187237

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	152
-	10.5281/zenodo.13943903	ADMET	54
1992140	10.1021/jm00105a007	P388	24
16472241	10.2174/1570163043334794	Hepatotoxicity	18
28238612	10.1016/j.bmcl.2017.02.016	Unchecked	16
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
21122952	10.1016/j.ejmech.2010.11.007	NON-PROTEIN TARGET	8
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
26727215	10.1021/acs.jmedchem.5b01706	NON-PROTEIN TARGET	5
12086496	10.1021/jm010559p	L1210	5
11052798	10.1021/jm000058o	Homo sapiens	5
27162123	10.1016/j.ejmech.2016.04.068	NON-PROTEIN TARGET	5
27073056	10.1016/j.bmc.2016.03.056	NON-PROTEIN TARGET	4
24657568	10.1016/j.ejmech.2014.03.009	NON-PROTEIN TARGET	4
10212121	10.1021/jm9806695	Jurkat	4
18426954	10.1124/dmd.108.020479	ADMET	4
11170648	10.1021/jm0002580	L1210	4
592323	10.1021/jm00222a009	Ehrlich	4

Data from ChEMBL 36 via Core Engine