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MedKoo Cat#: 100580 | Name: Melphalan HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Melphalan is an orally available phenylalanine derivative of nitrogen mustard with antineoplastic activity. Melphalan alkylates DNA at the N7 position of guanine and induces DNA inter-strand cross-linkages, resulting in the inhibition of DNA and RNA synthesis and cytotoxicity against both dividing and non-dividing tumor cells.

Chemical Structure

Melphalan HCl
Melphalan HCl
CAS#3223-07-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 100580

Name: Melphalan HCl

CAS#: 3223-07-2 (HCl)

Chemical Formula: C13H19Cl3N2O2

Exact Mass: 0.0000

Molecular Weight: 341.66

Elemental Analysis: C, 51.16; H, 5.94; Cl, 23.23; N, 9.18; O, 10.48

Price and Availability

Size Price Availability Quantity
100mg USD 950.00 2 Weeks
200mg USD 1,450.00 2 Weeks
500mg USD 2,150.00 2 Weeks
1g USD 3,450.00 2 Weeks
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Related CAS #
148-82-3 (free base) 13045-94-8 (D-Melphalan) 3223-07-2 (HCl)
Synonym
Lsarcolysine; phenylalanine mustard; Alkeran. Alkerana; Melfalan; Melphalanum; Sarkolysin. LPAM. CB3025; WR19813 .
IUPAC/Chemical Name
(S)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanoic acid hydrochloride
InChi Key
OUUYBRCCFUEMLH-YDALLXLXSA-N
InChi Code
InChI=1S/C13H18Cl2N2O2.ClH/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);1H/t12-;/m0./s1
SMILES Code
O=C(O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
M elphalan  is used to treat multiple myeloma and ovarian cancer, and occasionally malignant melanoma. The agent was first investigated as a possible drug for use in melanoma. It was not found to be effective, but has been found to be effective in the treatment of myeloma. Adminstration: oral or intravenous; dosing varies by purpose and route of administration as well as patient weight.   DRUG 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 that is active against selected human neoplastic diseases. It is known chemically as 4-[bis(2-chloroethyl)amino]-L-phenylalanine. The molecular formula is C13H18Cl2N2O2 and the molecular weight is 305.20. Melphalan is the active L-isomer of the compound and was first synthesized in 1953 by Bergel and Stock; the D-isomer, known as medphalan, is less active against certain animal tumors, and the dose needed to produce effects on chromosomes is larger than that required with the L-isomer. The racemic (DL-) form is known as merphalan or sarcolysin. Melphalan is practically insoluble in water and has a pKa1 of ~2.5. ALKERAN for Injection is supplied as a sterile, nonpyrogenic, freeze-dried powder. Each single-use vial contains melphalan hydrochloride equivalent to 50 mg melphalan and 20 mg povidone. ALKERAN for Injection is reconstituted using the sterile diluent provided. Each vial of sterile diluent contains sodium citrate 0.2 g, propylene glycol 6.0 mL, ethanol (96%) 0.52 mL, and Water for Injection to a total of 10 mL. ALKERAN for Injection is administered intravenously.      
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Melphalan is an orally available phenylalanine derivative of nitrogen mustard with antineoplastic activity.
In vitro activity:
The ability of conjugates of melphalan and FSHβ peptides to kill murine testicular cells was first tested in vitro in a three-dimensional testicular cell coculture system. In this system, melphalan caused considerable cell death as measured both by increases in lactate dehydrogenase concentrations in the culture supernatant and direct visualization of the cultures. Of the conjugates tested, melphalan conjugated to a 20-amino acid peptide derived from human FSHβ consisting of amino acids 33 to 53 (FSHβ (33-53)-melphalan) was very potent, with cell cytotoxicity and lactate dehydrogenase release roughly one-half that of melphalan. Reference: Theriogenology. 2014 Jul 1;82(1):152-9. https://pubmed.ncbi.nlm.nih.gov/24746827/
In vivo activity:
Male Wistar rats were treated with 4-8 mg/kg melphalan intravenously. Melphalan 5 mg/kg caused self-limiting intestinal injury, severe neutropenia and fever while impairing the microbial metabolome, prompting expansion of enteric pathogens. Reference: Cancer Chemother Pharmacol. 2021 Aug;88(2):173-188. https://pubmed.ncbi.nlm.nih.gov/33877390/

Preparing Stock Solutions

The following data is based on the product molecular weight 341.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Liu R, Li D, Sun F, Rampoldi A, Maxwell JT, Wu R, Fischbach P, Castellino SM, Du Y, Fu H, Mandawat A, Xu C. Melphalan induces cardiotoxicity through oxidative stress in cardiomyocytes derived from human induced pluripotent stem cells. Stem Cell Res Ther. 2020 Nov 5;11(1):470. doi: 10.1186/s13287-020-01984-1. PMID: 33153480; PMCID: PMC7643439. 2. Amory JK, Hong S, Yu X, Muller CH, Faustman E, Goldstein A. Melphalan, alone or conjugated to an FSH-β peptide, kills murine testicular cells in vitro and transiently suppresses murine spermatogenesis in vivo. Theriogenology. 2014 Jul 1;82(1):152-9. doi: 10.1016/j.theriogenology.2014.03.014. Epub 2014 Mar 27. PMID: 24746827; PMCID: PMC4079550. 3. Wardill HR, de Mooij CEM, da Silva Ferreira AR, van de Peppel IP, Havinga R, Harmsen HJM, Tissing WJE, Blijlevens NMA. Translational model of melphalan-induced gut toxicity reveals drug-host-microbe interactions that drive tissue injury and fever. Cancer Chemother Pharmacol. 2021 Aug;88(2):173-188. doi: 10.1007/s00280-021-04273-7. Epub 2021 Apr 20. PMID: 33877390; PMCID: PMC8236460. 4. Chai RC, McDonald MM, Terry RL, Kovačić N, Down JM, Pettitt JA, Mohanty ST, Shah S, Haffari G, Xu J, Gillespie MT, Rogers MJ, Price JT, Croucher PI, Quinn JMW. Melphalan modifies the bone microenvironment by enhancing osteoclast formation. Oncotarget. 2017 Jul 10;8(40):68047-68058. doi: 10.18632/oncotarget.19152. PMID: 28978095; PMCID: PMC5620235.
In vitro protocol:
1. Liu R, Li D, Sun F, Rampoldi A, Maxwell JT, Wu R, Fischbach P, Castellino SM, Du Y, Fu H, Mandawat A, Xu C. Melphalan induces cardiotoxicity through oxidative stress in cardiomyocytes derived from human induced pluripotent stem cells. Stem Cell Res Ther. 2020 Nov 5;11(1):470. doi: 10.1186/s13287-020-01984-1. PMID: 33153480; PMCID: PMC7643439. 2. Amory JK, Hong S, Yu X, Muller CH, Faustman E, Goldstein A. Melphalan, alone or conjugated to an FSH-β peptide, kills murine testicular cells in vitro and transiently suppresses murine spermatogenesis in vivo. Theriogenology. 2014 Jul 1;82(1):152-9. doi: 10.1016/j.theriogenology.2014.03.014. Epub 2014 Mar 27. PMID: 24746827; PMCID: PMC4079550.
In vivo protocol:
1. Wardill HR, de Mooij CEM, da Silva Ferreira AR, van de Peppel IP, Havinga R, Harmsen HJM, Tissing WJE, Blijlevens NMA. Translational model of melphalan-induced gut toxicity reveals drug-host-microbe interactions that drive tissue injury and fever. Cancer Chemother Pharmacol. 2021 Aug;88(2):173-188. doi: 10.1007/s00280-021-04273-7. Epub 2021 Apr 20. PMID: 33877390; PMCID: PMC8236460. 2. Chai RC, McDonald MM, Terry RL, Kovačić N, Down JM, Pettitt JA, Mohanty ST, Shah S, Haffari G, Xu J, Gillespie MT, Rogers MJ, Price JT, Croucher PI, Quinn JMW. Melphalan modifies the bone microenvironment by enhancing osteoclast formation. Oncotarget. 2017 Jul 10;8(40):68047-68058. doi: 10.18632/oncotarget.19152. PMID: 28978095; PMCID: PMC5620235.