MELPHALAN

Search structure
Trade Names:
Synonyms:
Status: Approved (1964)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01AA03
UNII: Q41OR9510P

Structure
InChI Key SGDBTWWWUNNDEQ-LBPRGKRZSA-N
Smile N[C@@H](Cc1ccc(N(CCCl)CCCl)cc1)C(=O)O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H18Cl2N2O2
Molecular Weight 305.21
AlogP 1.93
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 8.0
Polar Surface Area 66.56
Molecular species ZWITTERION
Aromatic Rings 1.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -0.52 - EXP
Henry's Law Constant 4.20E-13 atm-m3/mole EST
Atmospheric OH Rate Constant 2.25E-10 cm3/molecule-sec EST
Melting Point 182.5 deg C EXP
Water Solubility 45.7 mg/L EST
Vapor Pressure 3.00E-10 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC03 and SLC07 families of heteromeric amino acid transporters (HATs) SLC07 Cationic amino acid transporter/glycoprotein-associated family
- - - 55000 -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 93750 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Multiple Myeloma 4 D009101 ClinicalTrials
Amyloidosis 3 D000686 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Amyloidosis, Familial 3 D028226 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Melanoma 3 D008545 ClinicalTrials
Smoldering Multiple Myeloma 3 D000075122 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Melanoma 3 D008545 ClinicalTrials
Retinoblastoma 3 D012175 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Anemia, Sickle Cell 3 D000755 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Plasmacytoma 2 D010954 ClinicalTrials
Stiff-Person Syndrome 2 D016750 ClinicalTrials
Waldenstrom Macroglobulinemia 2 D008258 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Leukemia, Hairy Cell 2 D007943 ClinicalTrials
Mycosis Fungoides 2 D009182 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 2 D015477 ClinicalTrials
Anemia, Aplastic 2 D000741 ClinicalTrials
Severe Combined Immunodeficiency 2 D016511 ClinicalTrials
Hemoglobinuria, Paroxysmal 2 D006457 ClinicalTrials
Ganglioneuroblastoma 2 D018305 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Lymphoma, T-Cell, Peripheral 2 D016411 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 2 D020529 ClinicalTrials
Testicular Neoplasms 2 D013736 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Adenoma, Islet Cell 2 D007516 ClinicalTrials
Leukemia, Myelomonocytic, Juvenile 2 D054429 ClinicalTrials
Inflammatory Breast Neoplasms 2 D058922 ClinicalTrials
Leukemia, Erythroblastic, Acute 2 D004915 ClinicalTrials
Thalassemia 2 D013789 ClinicalTrials
Histiocytosis 2 D015614 ClinicalTrials
Wiskott-Aldrich Syndrome 2 D014923 ClinicalTrials
Immunoblastic Lymphadenopathy 2 D007119 ClinicalTrials
Polycythemia Vera 2 D011087 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Lymphoma, T-Cell 2 D016399 ClinicalTrials
Leukemia, Large Granular Lymphocytic 2 D054066 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 2 D015459 ClinicalTrials
Granuloma, Lethal Midline 2 D006103 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Shwachman-Diamond Syndrome 2 D000081003 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Neuromyelitis Optica 2 D009471 ClinicalTrials
Myasthenia Gravis 2 D009157 ClinicalTrials
Polyradiculoneuropathy, Chronic Inflammatory Demyelinating 2 D020277 ClinicalTrials
Opsoclonus-Myoclonus Syndrome 2 D053578 ClinicalTrials
Bronchiectasis 2 D001987 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Carcinoma, Neuroendocrine 2 D018278 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Peritoneal Neoplasms 1 D010534 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Fallopian Tube Neoplasms 1 D005185 ClinicalTrials
Blast Crisis 1 D001752 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 1 D009373 ClinicalTrials
Chordoma 1 D002817 ClinicalTrials
beta-Thalassemia 1 D017086 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Neoplasms, Neuroepithelial 0 D018302 ClinicalTrials

Related Entries

MCS

Salt

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
12.0
General disorders and administration site conditions
8.04
Infections and infestations
8.0
Respiratory, thoracic and mediastinal disorders
7.53
Vascular disorders
7.49
Gastrointestinal disorders
6.53
Injury, poisoning and procedural complications
6.42
Eye disorders
5.21
Immune system disorders
4.7
Skin and subcutaneous tissue disorders
4.26
Nervous system disorders
4.22
Cardiac disorders
4.07
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.89
Renal and urinary disorders
3.3
Metabolism and nutrition disorders
3.23
Investigations
3.12
Musculoskeletal and connective tissue disorders
2.13
Hepatobiliary disorders
2.09

Cross References

Resources Reference
CAS NUMBER 148-82-3
ChEBI 28876
ChEMBL CHEMBL852
DrugBank DB01042
DrugCentral 1678
EPA CompTox DTXSID6020804
FDA SRS Q41OR9510P
Human Metabolome Database HMDB0015176
Guide to Pharmacology 7620
KEGG C07122
PubChem 460612
SureChEMBL SCHEMBL5872
ZINC ZINC000000001673
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