melphalan

Modify Date: 2024-01-02 18:57:21

melphalan Structure
melphalan structure
 Common Name melphalan
CAS Number 148-82-3 Molecular Weight 305.200
Density 1.3±0.1 g/cm3 Boiling Point 473.1±45.0 °C at 760 mmHg
Molecular Formula C13H18Cl2N2O2 Melting Point ~180 °C
MSDS Chinese USA Flash Point 239.9±28.7 °C
Symbol GHS06 GHS08
GHS06, GHS08		 Signal Word Danger

 Use of melphalan


Melphalan is an effective DNA alkylating agent, with potent antitumor activity.

 Names

Name melphalan
Synonym More Synonyms

 melphalan Biological Activity

Description Melphalan is an effective DNA alkylating agent, with potent antitumor activity.
Related Catalog
Target

DNA Alkylator/Crosslinker[1]

In Vitro Melphalan is a DNA alkylating agent, used for multiple myeloma[1]. Melphalan-DNA adducts can be visualised in both cultured cells and solid tumour tissue[3].
In Vivo Melphalan (12 mg/kg, i.p.) increases pharmacological activity with heat in SD rats[2].
Cell Assay Melphalan cytotoxicity is determined by an MTT assay. The cells are seeded at 1000 cells per well in a 96-well microtitre plate in 100 μL culture medium to obtain approximately 4000 cells per well after 2 days at 37°C, 5% CO2. Then, the cells are washed and exposed to 0, 10, 25, 50, 100, 250 or 500 μM melphalan for 1 h at 37°C, 5% CO2. To control for cytotoxicity from hydrochloric acid, the solvent for melphalan, cells are also exposed to hydrochloric acid at a concentration adjusted to the highest concentration of melphalan (500 μM). After treatment the cells are washed twice with culture medium and 100 μL fresh culture medium is added. The day after exposure to melphalan another 100 μL fresh culture medium is added. After an additional 2 days the culture medium is removed and 200 μL fresh culture medium is added. At day 4 after treatment the culture medium is removed and cells are incubated for 4 h with 100 μL fresh culture medium and 10 μL MTT-labelling agent. Subsequently, 100 μL solubilisation solution (10% (v/v) in 0.01 M HCl) is added. After incubation overnight the absorbance at 590 nm is measured by a microtitre-plate reader[3].
Animal Admin Rats[2] Twenty rats are randomized into two groups according to the intraperitoneal temperature. The normothermic (NT) group receives intraperitoneal chemotherapy with intraperitoneal temperatures maintained between 32.5 and 34.5°C, and the hyperthermic (HT) group receives intraperitoneal chemotherapy with intraperitoneal temperatures maintained between 41.5 and 42.5°C. Melphalan at a dose of 12 mg/kg is diluted in 150 mL 0.9% NaCl solution immediately before administration. A closed perfusion system is utilized. The perfusate is heated in a tube coil in a thermostatically regulated water bath and infused into the peritoneal cavity with a roller pump at a rate of 80 mL/min for 90 min. Rhythmic massage of the abdomen is used to facilitate uniform heat distribution within the peritoneal cavity. When the proper temperature for the experiment is reached inside the peritoneal cavity, melphalan is added to the perfusate in the reservoir. For each animal, 0.5 mL peritoneal fluid and 0.5 mL blood are collected at 5, 15, 30, 60, and 90 min after the initiation of chemotherapy. The venous catheter is flushed with 0.2 mL of heparinized saline after each blood sampling. At the end of the procedure the rats are killed and tissues samples are taken[2].
References

[1]. BLUMBERG BS, et al. AN ALKYLATING AGENT FOR MULTIPLE MYELOMA: MELPHALAN. JAMA. 1965 Feb 15;191:547-9.

[2]. Glehen O, et al. Hyperthermia modifies pharmacokinetics and tissue distribution of intraperitoneal melphalan in a rat model. Cancer Chemother Pharmacol. 2004 Jul;54(1):79-84.

[3]. Rothbarth J, et al. Immunohistochemical detection of melphalan-DNA adducts in colon cancer cells in vitro and human colorectal liver tumours in vivo. Biochem Pharmacol. 2004 May 1;67(9):1771-8.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 473.1±45.0 °C at 760 mmHg
Melting Point ~180 °C
Molecular Formula C13H18Cl2N2O2
Molecular Weight 305.200
Flash Point 239.9±28.7 °C
Exact Mass 304.074524
PSA 66.56000
LogP 1.79
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.597
Storage condition -20?C Freezer
Water Solubility 95% ethanol and 1 drop 6 N HCl: 0.05 g/mL, clear | <0.1 g/100 mL at 22 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AY3675000
CHEMICAL NAME :
Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-
CAS REGISTRY NUMBER :
148-82-3
BEILSTEIN REFERENCE NO. :
2816456
LAST UPDATED :
199712
DATA ITEMS CITED :
95
MOLECULAR FORMULA :
C13-H18-Cl2-N2-O2
MOLECULAR WEIGHT :
305.23
WISWESSER LINE NOTATION :
QVYZ1R DN2G2G -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Rinsed with water
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
700 mg/kg/7D
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
1200 ug/kg/5D-I
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
4500 mg/kg
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
8140 mg/kg
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - agranulocytosis Blood - thrombocytopenia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4484 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD10 - Lethal Dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
32 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20800 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
3 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Blood - normocytic anemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14 mg/kg/7D-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Immunological Including Allergic - decrease in humoral immune response Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
80 ug/kg/D-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - other changes Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
57 ug/kg/D-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - other changes Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
26 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
70 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Tumorigenic - tumors at site of application
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
58 mg/kg/9W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Skin and Appendages - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 mg/kg/6W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
66 mg/kg/4Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
34 mg/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
12 mg/kg/3Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
23 mg/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
17 mg/kg/4Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3750 ug/kg
SEX/DURATION :
female 25 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
8800 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - other effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
5946 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Dominant lethal test
TYPE OF TEST :
Heritable translocation test

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
2500 nmol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 368,235,1996 *** REVIEWS *** IARC Cancer Review:Human Sufficient Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,239,1987 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 9,167,1975 IARC Cancer Review:Group 1 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,239,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4742 No. of Facilities: 140 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 2418 (estimated) No. of Female Employees: 974 (estimated)

 Safety Information

Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H300-H310-H330-H350-H361
Precautionary Statements P201-P260-P264-P280-P284-P302 + P350
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T+:Verytoxic;
Risk Phrases R45;R46;R26/27/28;R63
Safety Phrases S53-S22-S36/37/39-S45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS AY3675000
Packaging Group II
Hazard Class 6.1(a)
HS Code 2922499990

 Synthetic Route

methyl 2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoate structure

methyl 2-amino-...

CAS#:62978-52-3

~%

melphalan Structure

melphalan

CAS#:148-82-3

Literature: US2012/116117 A1, ; Page/Page column 2 ;
N-Boc-4-[bis(2-hydroxyethyl)amino]-L-phenylalanine Methyl Ester structure

N-Boc-4-[bis(2-...

CAS#:1217651-06-3

~%

melphalan Structure

melphalan

CAS#:148-82-3

Literature: US2012/116117 A1, ;

 Customs

HS Code 2922499990
Summary HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

 Articles161

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 Synonyms

4-[Bis(2-chloroethyl)amino]-L-phenylalanine
L-3-[p-[Bis(2-chloroethyl)amino]phenyl]alanine
melphalan
L-Phenylalanine, 4-(bis(2-chloroethyl)amino)-
2-Amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
MFCD00057717
Alanine, 3-(p-(bis(2-chloroethyl)amino)phenyl)-, L-
(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
L-Phenylalanine, 4-[bis(2-chloroethyl)amino]-
Sarcoclorin
3025 C.B.
L-Phenylalanine mustard
EINECS 205-726-3
p-Di(2-chloroethyl)amino-L-phenylalanine
3-(4-bis(2-chloroethyl)aminophenyl)-L-alanine
3-[p-[Bis(2-chloroethyl)amino]phenyl]-L-alanine
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Related Compounds: More...
D-Melphalan
13045-94-8
boc-melphalan
79145-92-9
Hydroxymelphalan
61733-01-5
isopropyl melphalan
57675-29-3
Dihydroxy Melphalan
72143-20-5
Melphalan Impurity 3
896715-19-8
Melphalan Impurity 2
1270153-04-2
Melphalan Impurity 11
660-68-4
melphalan methylester
88457-23-2
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
N-(2,2-dimethoxyethyl)cyclopropanamine
1245531-40-1
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
4-Benzyl 1-(tert-butyl) 2-(3-phenyl-2-propynoyl)-1,4-piperazinedicarboxylate
1353506-88-3
(4R)-4-methyl-2-phenyl-5H-1,3-thiazole-4-carboxylic acid
941714-77-8
2-Methyl-3-[methyl(1,2,4-oxadiazol-3-ylmethyl)amino]propanoic acid
1249312-31-9
3-(Thiazol-2-ylamino)tetrahydro-2H-thiopyran 1,1-dioxide
1341117-68-7
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
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