Nimustine Hydrochloride

Names

[ Name ]:
Nimustine Hydrochloride

[Synonym ]:
EINECS 255-838-1
NIMUSTINE
1-(2-chloroethyl)-1-nitroso-3-[(2-methyl-4-aminopyrimidine-5-yl)methyl]urea
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-1-(2-chloroethyl)-1-nitrosourea
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-1-(2-chloro-ethyl)-1-nitroso-urea
MFCD01676942
Nimustina
Nimustin
Nimustinum [INN-Latin]
1-(2-chloro-ethyl)-3-(4-amino-2-methyl-5-pyrimidinyl)methyl-1-nitrosourea
Nimustina [INN-Spanish]
Nimustine [INN]
Nimustinum

Biological Activity

[Description]:

Nimustine is a nitrosourea alkylating agent. Nimustine induces cell apoptosis, and activates DNA damage response and MAPK signaling. Nimustine shows anti-cancer effects, it can be used for the research of cancer[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

Nimustine (50 μM; 72-120 h) causes cell death by inducing cell apoptosis[1]. Nimustine (50 μM; 24-96 h) activates the DNA damage response pathway[1]. Nimustine (50 μM; 24-120 h) activates MAPK signaling in glioma cells[1]. Apoptosis Analysis[1] Cell Line: LN-229 cell line Concentration: 50 μM Incubation Time: 72-120 hours Result: Time-dependently induced apoptosis. Western Blot Analysis[1] Cell Line: LN-229 and glioma cell lines Concentration: 50 μM Incubation Time: 24-120 hours Result: Induced cleavage of caspase-8 and -9 and the effector caspase-3. Increased phosphorylation of ERK kinase and H2AX. Decreased phosphorylation of JNK

[In Vivo]

Nimustine (15 four times a week and 30 mg/kg twice with an interval of 2 weeks; i.v.) effectively inhibits tumor growth and the higher dose is more effective[2]. Animal Model: Female C3H/HeN mice with solid FM3A tumors[2] Dosage: 15 and 30 mg/kg Administration: Intravenous injection; 15 (4 times a week) and 30 mg/kg (twice with an interval of 2 weeks) Result: The intermittent large-dose injections resulted in better inhibition of tumor growth than did the fractionated small-dose injections.

Chemical & Physical Properties

[ Density]:
1.52g/cm3

[ Molecular Formula ]:
C₉H₁₃ClN₆O₂

[ Molecular Weight ]:
272.69200

[ Exact Mass ]:
272.07900

[ PSA ]:
113.57000

[ LogP ]:
1.77110

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YR8449000

CHEMICAL NAME :: Urea, N'-((4-amino-2-methyl-5-pyrimidinyl)methyl)-N-(2-chlo roethyl)-N-nitroso-

CAS REGISTRY NUMBER :: 42471-28-3

BEILSTEIN REFERENCE NO. :: 0685903

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C9-H13-Cl-N6-O2

MOLECULAR WEIGHT :: 272.73

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 3 mg/kg

SEX/DURATION :: multigeneration

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - rat Cells - not otherwise specified

DOSE/DURATION :: 2 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 149,95,1985

Safety Information

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
YR8450000

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%