Melphalan

Melphalan

Systematic (IUPAC) name
4-[bis(chloroethyl)amino]phenylalanine
Clinical data
Trade names	Alkeran
AHFS/Drugs.com	monograph
MedlinePlus	a682220
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral, intravenous
Pharmacokinetic data
Bioavailability	25% to 89%
Metabolism	hydrolysis
Half-life	1.5 ± 0.8 hours
Excretion	Renal, significantly metabolised
Identifiers
CAS number	148-82-3 Y
ATC code	L01AA03
PubChem	CID 4053
DrugBank	APRD00118
ChemSpider	405297 Y
UNII	Q41OR9510P Y
KEGG	D00369 Y
ChEBI	CHEBI:28876 N
ChEMBL	CHEMBL852 Y
Synonyms	2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid
Chemical data
Formula	C13H18Cl2N2O2
Mol. mass	305.2 g/mol
SMILES	eMolecules & PubChem
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 Y Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N Y
N(what is this?)  (verify)

Melphalan hydrochloride (trade name Alkeran) is a chemotherapy drug belonging to the class of nitrogen mustard alkylating agents.

An alkylating agent adds an alkyl group (C_nH_2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring.

Otherwise known as L-Phenylalanine Mustard, or L-PAM, melphalan is a phenylalanine derivative of mechlorethamine.

Uses

It is used to treat multiple myeloma^[1] 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.

Administration

Oral or intravenous; dosing varies by purpose and route of administration as well as patient weight.

Melphalan Prescribing Information: Alkeran^[2]

Melphalan Patient Information: MedlinePlus^[3]

Melphalan Material Safety Data Sheet (MSDS): Sequoia Research Products^[4]

Side effects

Common side effects include:

• Nausea and vomiting, and oral ulceration.
• Bone marrow suppression, including
  • Decreased white blood cell count causing increased risk of infection
  • Decreased platelet count causing increased risk of bleeding

Less common side effects include:

• Severe allergic reactions
• Pulmonary fibrosis (scarring of lung tissue) including fatal outcomes (usually only with prolonged use)
• Hair loss
• Interstitial pneumonitis
• Rash
• Itching
• Irreversible bone marrow failure due to melphalan not being withdrawn early enough.
• Cardiac arrest.

References

1. ^ Facon T, Mary JY, Hulin C, et al. (October 2007). "Melphalan and prednisone plus thalidomide versus melphalan and prednisone alone or reduced-intensity autologous stem cell transplantation in elderly patients with multiple myeloma (IFM 99-06): a randomised trial". Lancet 370 (9594): 1209–18. doi:10.1016/S0140-6736(07)61537-2. PMID 17920916. http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(07)61537-2. 
2. ^ celgene.com
3. ^ nlm.nih.gov
4. ^ seqchem.com

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.v · Categories: IARC Group 1 carcinogens Alkylating antineoplastic agents Nitrogen mustards Organochlorides Antineoplastic and immunomodulating drug stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем сделать НИР Cootehill Roman Čechmánek Look at other dictionaries: melphalan — melphalan. См. мелфалан. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь. melphalan — noun Etymology: probably from methanol + phenylalanine Date: 1960 an antineoplastic drug C13H18Cl2N2O2 …   New Collegiate Dictionary melphalan — noun A particular drug used in chemotherapy …   Wiktionary melphalan — l Phenylalanine mustard; l sarcolysine; l 3 [p [bis(2 chloroethyl)amino]phenyl]alanine; a phenylalanine derivative of nitrogen mustard; an alkalylating antineoplastic agent. * * * mel·pha·lan mel fə .lan n an antineoplastic drug C13H18Cl2N2O2… …   Medical dictionary melphalan — mel·pha·lan …   English syllables melphalan — n. a drug (an alkylating agent) used to treat various types of cancer, particularly myeloma but also including tumours of the breast and ovaries and Hodgkin s disease. It is administered by mouth or injection. Side effects include digestive… …   The new mediacal dictionary melphalan — A drug that is used to treat multiple myeloma and ovarian epithelial cancer and is being studied in the treatment of other types of cancer. It belongs to the family of drugs called alkylating agents. Also called Alkeran …   English dictionary of cancer terms melphalan — noun antineoplastic drug (trade name Alkeran) used to treat multiple myeloma and some other malignancies • Syn: ↑Alkeran • Usage Domain: ↑trade name (for: ↑Alkeran) • Hypernyms: ↑antineoplastic, ↑ …   Useful english dictionary Мелфалан (Melphalan) — лекарственное вещество; применяется для лечения различных видов злокачественных опухолей, в том числе злокачественной меланомы, опухолей молочной железы и яичников, а также болезни Ходжкина. Назначается внутрь или в инъекциях. Возможные побочные… …   Медицинские термины L-phenylalanine mustard — melphalan …   Medical dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”