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Melflufen (hydrochloride)

CAT: 0804-HY-105019A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-105019A-01Size:5 mg
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Description
Melflufen (Melphalan flufenamide) hydrochloride, a dipeptide proagent of Melphalan, is an alkylating agent. Melflufen hydrochloride shows antitumor activity against multiple myeloma (MM) cells and inhibits angiogenesis. Melflufen hydrochloride induces irreversible DNA damage and cytotoxicity in MM cells[1][2][3].
CAS Number
380449-54-7
Product Name Alternative
Melphalan flufenamide (hydrochloride)
UNSPSC
12352005
Hazard Statement
H300, H315, H340, H350, H361
Target
Apoptosis; DNA Alkylator/Crosslinker
Type
Reference compound
Related Pathways
Apoptosis; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/melflufen-hydrochloride.html
Purity
98.06
Solubility
DMSO : 33.33 mg/mL (ultrasonic) |H2O : 1 mg/mL (ultrasonic)
Smiles
O=C(OCC)[C@H](CC1=CC=C(F)C=C1)NC([C@H](CC2=CC=C(N(CCCl)CCCl)C=C2)N)=O.[H]Cl
Molecular Formula
C24H31Cl3FN3O3
Molecular Weight
534.88
Precautions
H300, H315, H340, H350, H361
References & Citations
[1]Chauhan D, et al. In vitro and in vivo antitumor activity of a novel alkylating agent, melphalan-flufenamide, against multiple myeloma cells. Clin Cancer Res. 2013;19 (11) :3019-3031.|[2]Ray A, et al. A novel alkylating agent Melflufen induces irreversible DNA damage and cytotoxicity in multiple myeloma cells. Br J Haematol. 2016;174 (3) :397-409.|[3]McAndrews KM, et, al. Mechanisms associated with biogenesis of exosomes in cancer. Mol Cancer. 2019 Mar 30;18 (1) :52.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Melphalan Flufenamide Hydrochloride

Melphalan Flufenamide Hydrochloride is the hydrochloride salt form of melphalan flufenamide, a peptide-drug conjugate composed of a peptide conjugated, via an aminopeptidase-targeting linkage, to the alkylating agent melphalan, with potential antineoplastic and anti-angiogenic activities. Upon administration, the highly lipophilic melphalan flufenamide penetrates cell membranes and enters cells. In aminopeptidase-positive tumor cells, melphalan flufenamide is hydrolyzed by peptidases to release the hydrophilic alkylating agent melphalan. This results in the specific release and accumulation of melphalan in aminopeptidase-positive tumor cells. Melphalan alkylates DNA at the N7 position of guanine residues and induces DNA intra- and inter-strand cross-linkages. This results in the inhibition of DNA and RNA synthesis and the induction of apoptosis, thereby inhibiting tumor cell proliferation. Peptidases are overexpressed by certain cancer cells. The administration of melphalan flufenamide allows for enhanced efficacy and reduced toxicity compared to melphalan.

CAS Number380449-54-7
PubChem CID70675838
IUPAC Nameethyl (2S)-2-[[(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoyl]amino]-3-(4-fluorophenyl)propanoate;hydrochloride
Molecular FormulaC24H31Cl3FN3O3
Molecular Weight534.9
Topological Polar Surface Area84.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count14
Heavy Atom Count34
Formal Charge0
Complexity579
SMILES
CCOC(=O)[C@H](CC1=CC=C(C=C1)F)NC(=O)[C@H](CC2=CC=C(C=C2)N(CCCl)CCCl)N.Cl
InChI
InChI=1S/C24H30Cl2FN3O3.ClH/c1-2-33-24(32)22(16-18-3-7-19(27)8-4-18)29-23(31)21(28)15-17-5-9-20(10-6-17)30(13-11-25)14-12-26;/h3-10,21-22H,2,11-16,28H2,1H3,(H,29,31);1H/t21-,22-;/m0./s1
InChIKey
ZCMWSKHHXLCVHI-VROPFNGYSA-N
Chemical Structure
2D Structure
2D structure of Melphalan Flufenamide Hydrochloride
CAS: 380449-54-7
CID: 70675838
Formula: C24H31Cl3FN3O3
MW: 534.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight534.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count14
Exact Mass533.141503
Monoisotopic Mass533.141503
Topological Polar Surface Area84.7 Ų
Heavy Atom Count34
Formal Charge0
Complexity579
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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