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CID 6918992

HCID 6918992
노트반응
기본 정보개요이름 및 식별자물성화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
148-82-3
표준 SMILES
[NH3+][C@@H](Cc1ccc(N(CCCl)CCCl)cc1)C(=O)[O-]
InChIKey
SGDBTWWWUNNDEQ-LBPRGKRZSA-N
분자식
C13H18Cl2N2O2
평균 분자량
305.2 g/mol
단동위원소 질량
304.0745332

개요

Melphalan 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.

이름 및 식별자

우선 이름
CID 6918992
IUPAC
(2S)-2-azaniumyl-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoate

데이터베이스 식별자

CAS
148-82-3
PubChem CID
6918992

물성

구조 계산 물성

XLogP
0.1
극성 표면적
71 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
7
무거운 원자 수
19
형식 전하
0
복잡도
260

실험 및 물리화학적 성질

LogP0.4
Solubility3.58e-01 g/L
Melting Point182.5 °C
Physical DescriptionSolid

화학 및 산업

약리 정보

Protein Binding · 1건

Protein 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.

Pharmacodynamics · 1건

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.

Mechanism of Action · 1건

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.

Biological Half-LifeIn patients given a single oral dose of 0.6 mg/kg of melphalan, the terminal elimination plasma half-life (± SD) was 1.5 ± 0.83 hours. Following intravenous administration, the terminal elimination half-life is approximately 75 minutes.
Metabolism/MetabolitesMelphalan primarily undergoes chemical hydrolysis to inactive metabolites, monohydroxymelphalan and dihydroxymelphalan. No other melphalan metabolites have been observed in humans.
Absorption, Distribution and Excretion · 4건

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.

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이 페이지에서기본 정보개요이름 및 식별자물성화학 및 산업관련 반응화합물 노트

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>.

Cellular LocationsCytoplasm