148-82-3[NH3+][C@@H](Cc1ccc(N(CCCl)CCCl)cc1)C(=O)[O-]SGDBTWWWUNNDEQ-LBPRGKRZSA-NMelphalan is a nitrogen mustard or bischloroethylamine type alkylating agent. It was first synthesized in the early 1950s by substituting L-phenylalanine for the methyl group on nitrogen mustard. Melphalan is used in the treatment of multiple myeloma and ovarian carcinoma. It is also used for high-conditioning before hematopoietic stem cell transplant. It is also used to treat uveal melanoma with unresectable hepatic metastases.
148-82-3Protein binding of melphalan ranges from 50% to 90%. Serum albumin is the major binding protein, accounting for approximately 40% to 60% of the plasma protein binding, while α1-acid glycoprotein accounts for about 20% of the plasma protein binding. Approximately 30% of melphalan is covalently and irreversibly bound to plasma proteins.
Melphalan possesses cytotoxic, immunosuppressive, and myeloablative activities. Melphalan produces chromosomal aberrations _in vitro_ and _in vivo_; thus, it is considered to be potentially leukemogenic in humans. It also causes dose-limiting bone marrow suppression. The peak mean heart rate increased by 20 bpm from baseline following melphalan 100 mg/m<sup>2</sup> for two consecutive days in multiple myeloma patients undergoing autologous stem cell transplantation.
Melphalan is an alkylating agent of the bischloroethylamine type. It is believed to be taken up by tumour cells via a neutral amino acid active pathway shared by leucine. Melphalan binds at the N7 position of guanine and induces inter-strand cross-links in DNA, disrupting DNA synthesis or transcription. It can also cause DNA-protein cross-linking and induce lesions in RNA, proteins, and lipids. Melphalan is cytotoxic in resting and rapidly dividing tumour cells.
The absorption of oral melphalan is highly variable concerning both the time to the first appearance of the drug in plasma (range: 0 to 6 hours) and peak plasma concentration (Cmax). The average absolute bioavailability of melphalan ranges from 56% to 93%. High variability in bioavailability may be due to incomplete intestinal absorption, variable first-pass hepatic metabolism, or rapid hydrolysis. Tmax was one hour in patients who received single oral doses of 0.2 mg/kg to 0.25 mg/kg of melphalan. Oral administration of melphalan with a high-fat meal may reduce melphalan exposure (AUC) by 36% to 54%. Mean (± SD) Cmax and AUC0-inf were 5.8 ± 1.5 mcg/mL and 451 ± 109 mcg x min/mL, respectively, following intravenous administration of 100 mg/m2 in multiple myeloma patients.
현재 필터 조건에 해당하는 반응 기록이 없습니다.
불러오는 중…
About 5.8% to 21.3% of melphalan is excreted in urine.
The volume of distribution of melphalan ranges from approximately 35.5 to 185.7 L/m<sup>2</sup>. Penetration into cerebrospinal fluid is low.
Average total body clearance (CL) ranges from approximately 250 to 325 mL/min/m<sup>2</sup>.