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MedKoo Cat#: 596514 | Name: Melphalan free base
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Description:

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

Melphalan (free base) is an alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.

Chemical Structure

Melphalan free base
Melphalan free base
CAS#148-82-3 (free base)

Theoretical Analysis

MedKoo Cat#: 596514

Name: Melphalan free base

CAS#: 148-82-3 (free base)

Chemical Formula: C13H18Cl2N2O2

Exact Mass: 304.0745

Molecular Weight: 305.20

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

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,450.00 Ready to Ship
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Related CAS #
148-82-3 (free base) 13045-94-8 (D-Melphalan) 3223-07-2 (HCl)
Synonym
Melphalan; Levopholan; NSC 8806; NSC-8806; NSC8806; Alkeran; L-Sarcolysine;
IUPAC/Chemical Name
(S)-2-amino-3-(4-(bis(2-chloroethyl)amino)phenyl)propanoic acid
InChi Key
SGDBTWWWUNNDEQ-LBPRGKRZSA-N
InChi Code
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
SMILES Code
N[C@@H](CC1=CC=C(N(CCCl)CCCl)C=C1)C(O)=O
Appearance
Solid powder
Purity
>97% (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
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Melphalan (free base) is an alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer.
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 305.20 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.
1: Noesslinger T, Panny M, Simanek R, Moestl M, Boehm A, Menschel E, Koller E, Keil F. High dose Bendamustine-EAM followed by autologous stem cell rescue results in long term remission rates in lymphoma patients, without renal toxicty. Eur J Haematol. 2018 May 25. doi: 10.1111/ejh.13102. [Epub ahead of print] PubMed PMID: 29799642. 2: Jain T, Kunze KL, Temkit M, Partain DK, Patnaik MS, Slack JL, Khera N, Hogan WJ, Roy V, Noel P, Leis JF, Sproat LZ, Fauble V, Mesa RA, Palmer J. Comparison of reduced intensity conditioning regimens used in patients undergoing hematopoietic stem cell transplantation for myelofibrosis. Bone Marrow Transplant. 2018 May 24. doi: 10.1038/s41409-018-0226-1. [Epub ahead of print] PubMed PMID: 29795431. 3: Adam Z, Ozábalová E, Němec P, Bedáňová H, Kuman M, Krejčí J, Špinarová L, Žampachová V, Čermáková Z, Pour L, Krejčí M, Sanecká V, Štork M, Pika T, Straub J, Adamová D, Stavařová Y, Král Z, Mayer J. [Heart transplantation and follow-up treatment with AL-amyloidosis in 5 patients]. Vnitr Lek. 2018 Spring;64(4):441-449. Czech. PubMed PMID: 29791180. 4: Aggarwal M, Agrawal N, Yadav N, Verma P, Ahmed R, Mehta P, Kapoor J, Bhurani D. Autologous stem cell transplantation in first remission is associated with better progression-free survival in multiple myeloma. Ann Hematol. 2018 May 21. doi: 10.1007/s00277-018-3370-1. [Epub ahead of print] PubMed PMID: 29781040. 5: Katsarelias D, Rådbo E, Ben-Shabat I, Mattsson J, Olofsson Bagge R. The Effect of Temperature and Perfusion Time on Response, Toxicity, and Survival in Patients with In-transit Melanoma Metastases Treated with Isolated Limb Perfusion. Ann Surg Oncol. 2018 May 15. doi: 10.1245/s10434-018-6459-9. [Epub ahead of print] PubMed PMID: 29766389. 6: Al Malki MM, Nathwani N, Yang D, Armenian S, Dadwal S, Salman J, Mokhtari S, Cao T, Sandhu K, Rouse M, Mei M, Ali H, Parker P, Alvarnas J, Smith E, Donnell MO, Marcucci G, Snyder D, Nademanee A, Forman SJ, Stein A, Nakamura R. Melphalan-Based Reduced-Intensity Conditioning Is Associated with Favorable Disease Control and Acceptable Toxicities in Patients Older Than 70 with Hematologic Malignancies Undergoing Allogeneic Hematopoietic Stem Cell Transplantation. Biol Blood Marrow Transplant. 2018 May 9. pii: S1083-8791(18)30250-7. doi: 10.1016/j.bbmt.2018.04.029. [Epub ahead of print] PubMed PMID: 29753158. 7: Dhakal B, D'Souza A, Lakshman A, Hamadani M, Chhabra S, Thompson R, Shah N, Pasquini M, Hari P. Pharmacokinetics of High-Dose Propylene Glycol-Free Melphalan in Multiple Myeloma Patients Undergoing Autologous Hematopoietic Cell Transplantation. Biol Blood Marrow Transplant. 2018 May 8. pii: S1083-8791(18)30249-0. doi: 10.1016/j.bbmt.2018.04.028. [Epub ahead of print] PubMed PMID: 29751116. 8: Endo T, Hamada T, Otake S, Nakagawa M, Uchino Y, Takahashi H, Miura K, Iriyama N, Koike T, Kurihara K, Sato H, Hatta Y, Takei M. [Achievement of a stringent complete response with low-dose pomalidomide monotherapy in a multiple myeloma patient]. Rinsho Ketsueki. 2018;59(4):395-400. doi: 10.11406/rinketsu.59.395. Japanese. PubMed PMID: 29743398. 9: Jindahra P, Dejthevaporn C, Niparuck P, Waisayarat J, Cheecharoen P, Threetong T, Petpiroon P, Sujirakul T, Poonyathalang A, Vanikieti K. Atypical central retinal artery occlusion as the first presentation of POEMS syndrome: a case report. BMC Neurol. 2018 May 8;18(1):64. doi: 10.1186/s12883-018-1071-y. PubMed PMID: 29739345; PubMed Central PMCID: PMC5938810. 10: Fan FS, Yang CF. Complete response to orally administered melphalan in malignant pleural effusion from an occult female genital organ primary neoplasm with BRCA1/2 mutations: a case report. J Med Case Rep. 2018 May 6;12(1):122. doi: 10.1186/s13256-018-1674-3. PubMed PMID: 29729664; PubMed Central PMCID: PMC5936624. 11: Hishiki T, Matsumoto K, Ohira M, Kamijo T, Shichino H, Kuroda T, Yoneda A, Soejima T, Nakazawa A, Takimoto T, Yokota I, Teramukai S, Takahashi H, Fukushima T, Kaneko T, Hara J, Kaneko M, Ikeda H, Tajiri T, Nakagawara A; Japan Childhood Cancer Group Neuroblastoma Committee (JNBSG). Results of a phase II trial for high-risk neuroblastoma treatment protocol JN-H-07: a report from the Japan Childhood Cancer Group Neuroblastoma Committee (JNBSG). Int J Clin Oncol. 2018 Apr 26. doi: 10.1007/s10147-018-1281-8. [Epub ahead of print] PubMed PMID: 29700636. 12: Hathi D, DeLassus E, Achilefu S, McConathy J, Shokeen M. Imaging melphalan therapy response in preclinical extramedullary myeloma with (18)F-FDOPA and (18)F-FDG PET. J Nucl Med. 2018 Apr 26. pii: jnumed.118.208744. doi: 10.2967/jnumed.118.208744. [Epub ahead of print] PubMed PMID: 29700126. 13: Singh N, Ecker GF. Insights into the Structure, Function, and Ligand Discovery of the Large Neutral Amino Acid Transporter 1, LAT1. Int J Mol Sci. 2018 Apr 24;19(5). pii: E1278. doi: 10.3390/ijms19051278. Review. PubMed PMID: 29695141. 14: Funes S, Sampor C, Villasante F, Fandiño A, Manzitti J, Sgroi M, Neira P, Peralta L, Lagomarsino E, Schaiquevich P, Ceciliano A, Chantada GL. Feasibility and results of an intraarterial chemotherapy program for the conservative treatment of retinoblastoma in Argentina. Pediatr Blood Cancer. 2018 Apr 25:e27086. doi: 10.1002/pbc.27086. [Epub ahead of print] PubMed PMID: 29693791. 15: Kubota H, Umeda K, Kagehiro K, Tanaka K, Daifu T, Hamabata T, Nodomi S, Kato I, Hiramatsu H, Arakawa Y, Mizowaki T, Adachi S. High-dose chemotherapy with autologous stem cell transplantation spares re-irradiation for recurrent intracranial germinoma. Pediatr Blood Cancer. 2018 Apr 25:e27104. doi: 10.1002/pbc.27104. [Epub ahead of print] PubMed PMID: 29693779. 16: Borrelli C, Ricci B, Vulpis E, Fionda C, Ricciardi MR, Petrucci MT, Masuelli L, Peri A, Cippitelli M, Zingoni A, Santoni A, Soriani A. Drug-induced senescent Multiple Myeloma cells elicit NK cell proliferation by direct or exosome-mediated IL-15 trans-presentation. Cancer Immunol Res. 2018 Apr 24. pii: canimm.0604.2017. doi: 10.1158/2326-6066.CIR-17-0604. [Epub ahead of print] PubMed PMID: 29691234. 17: Scordo M, Morjaria SM, Littmann ER, Bhatia A, Chung HH, Maloy M, DeAngelis LM, Giralt SA, Taur Y, Sauter CS. Distinctive Infectious Complications in Patients with Central Nervous System Lymphoma Undergoing Thiotepa, Busulfan, and Cyclophosphamide-Conditioned Autologous Stem Cell Transplantation. Biol Blood Marrow Transplant. 2018 Apr 18. pii: S1083-8791(18)30194-0. doi: 10.1016/j.bbmt.2018.04.013. [Epub ahead of print] PubMed PMID: 29679773. 18: Badar T, Hari P, Chhabra S, Dhakal B, Drobyski WR, Fenske TS, Hamadani M, Pasquini M, Saber W, Shah NN, Shaw BE, D'Souza A. Use of propylene glycol-free melphalan conditioning in light-chain amyloidosis patients undergoing autologous hematopoietic cell transplantation is well tolerated and effective. Bone Marrow Transplant. 2018 Apr 20. doi: 10.1038/s41409-018-0178-5. [Epub ahead of print] PubMed PMID: 29679076. 19: Fridthjof KS, Kampmann P, Dünweber A, Gørløv JS, Nexø C, Friis LS, Nørskov KH, Welinder PC, Moser C, Kjeldsen L, Møller T. Systematic patient involvement for homebased outpatient administration of complex chemotherapy in acute leukemia and lymphoma. Br J Haematol. 2018 Jun;181(5):637-641. doi: 10.1111/bjh.15249. Epub 2018 Apr 20. PubMed PMID: 29676445. 20: Jodele S, Dandoy CE, Myers K, Wallace G, Lane A, Teusink-Cross A, Weiss B, Davies SM. High-dose Carboplatin/Etoposide/Melphalan increases risk of thrombotic microangiopathy and organ injury after autologous stem cell transplantation in patients with neuroblastoma. Bone Marrow Transplant. 2018 Apr 19. doi: 10.1038/s41409-018-0159-8. [Epub ahead of print] PubMed PMID: 29674658.