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Ranimustine

Ranimustine structure

CAS No:
58994-96-0
Formula:
C10H18ClN3O7
Chemical Name:
Ranimustine
Synonyms:
α-D-Glucopyranoside,methyl 6-[[[(2-chloroethyl)nitrosoamino]carbonyl]amino]-6-deoxy-;Methyl 6-[[[(2-chloroethyl)nitrosoamino]carbonyl]amino]-6-deoxy-α-D-glucopyranoside;MCNU;Cymerin;Cymerine;Ranimustine;NSC 270516
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Ranimustine is an organic molecular entity.|Ranimustine is a chloroethylnitrosourea derivative that inhibits proliferation and growth of tumor cells by alkylation and cross-linkage of DNA strands of tumor cells. (NCI)

Ranimustine Basic Attributes

Molecular Weight：

327.72

Exact Mass：

327.72

UNII：

RYH2T97J77

NCI Thesaurus Code：

C1515

ATC Code：

L - Antineoplastic and immunomodulating agents

Characteristics

PSA：

141

XLogP3：

-1.7

Density：

1.69 g/cm3

Melting Point：

111 °C

Refractive Index：

1.616

Toxicity：

LD50 in male rats (mg/kg): 42 i.p., 42 i.v., 50 orally (Kimura)

Specific rotation：

D20 +93.2° (c = 0.5 in methanol) (Kimura); D25 +73.2° (c = 0.3 in methanol) (Kimura, Sekine)

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

R25:Toxic if swallowed. R41:Risk of serious damage to eyes. R43:May cause sensitization by skin contact.

safety instructions：

S26-S36/37/39-S45

RTECS Number：

XU7700000

Marks：

Drug Information

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

MCNU

Ranimustine Use and Manufacturing

Methods of Manufacturing

Isocyanate method: Dissolve methyl-6-amino-6-deoxy-2-D-glucopyranoside in water and isopropanol, add (2-chloroethyl) isocyanate dropwise with stirring, proceed reaction. The reaction solution was concentrated under reduced pressure, and the residue was repeatedly crystallized in absolute ethanol to obtain a light yellow-white crystalline intermediate in a yield of 57.3%. Add sodium nitrite powder to the above intermediate solution in acetic acid at 28-29°C with good agitation. After the reaction, Amberlite IR-120 (H+ type) was added to absorb sodium ions. Filter and wash thoroughly with glacial acetic acid. The washing liquid and the filtrate were combined and concentrated under reduced pressure. The residue was recrystallized with isopropanol to obtain ramustine in 90.5% yield. Active ester method: first make the active ester of nitrosamine, and then react with methyl-6-amino-6-deoxy-D-glucopyranoside to obtain ramustine.

Uses

Glucocorticoid with low systemic absorption anti-inflammatory agent

Computed Properties

Molecular Weight:327.72
XLogP3:-1.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:327.0833276
Monoisotopic Mass:327.0833276
Topological Polar Surface Area:141
Heavy Atom Count:21
Complexity:362
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes