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Substance Name: Bendamustine [INN:BAN]
RN: 16506-27-7
UNII: 9266D9P3PQ
InChIKey: YTKUWDBFDASYHO-UHFFFAOYSA-N

Note

  • NCI: Bendamustine hydrochloride ... The hydrochloride salt of bendamustine, a bifunctional mechlorethamine derivative with alkylator and antimetabolite activities. Bendamustine possesses three active moieties: an alkylating group; a benzimidazole ring, which may act as a purine analogue; and a butyric acid side chain. Although its exact mechanism of action is unknown, this agent appears to act primarily as an alkylator. Bendamustine metabolites alkylate and crosslink macromolecules, resulting in DNA, RNA and protein synthesis inhibition, and, subsequently, apoptosis. Bendamustine may differ from other alkylators in that it may be more potent in activating p53-dependent stress pathways and inducing apoptosis; it may induce mitotic catastrophe; and it may activate a base excision DNA repair pathway rather than an alkyltransferase DNA repair mechanism. Accordingly, this agent may be more efficacious and less susceptible to drug resistance than other alkylators. (NCI Thesaurus)

Molecular Formula

  • C16-H21-Cl2-N3-O2

Molecular Weight

  • 358.2669
 

Classification Codes

  • Alkylating Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Noxae

Names and Synonyms

Name of Substance

  • Bendamustine
  • Bendamustine [INN:BAN]

Synonyms

  • 5-(Bis(2-chloroethyl)amino)-1-methyl-2-benzimidazolebutyric acid
  • Bendamustina
  • Bendamustina [Spanish]
  • Bendamustine
  • Bendamustinum
  • Bendamustinum [Latin]
  • Bendeka
  • HSDB 7763
  • SDX 105
  • SDX-105
  • UNII-9266D9P3PQ

Systematic Names

  • 1H-Benzimidazole-2-butanoic acid, 5-(bis(2-chloroethyl)amino)-1-methyl-
  • 2-Benzimidazolebutyric acid, 5-(bis(2-chloroethyl)amino)-1-methyl-
  • 5-(Bis(2-chloroethyl)amino)-1-methyl-2-benzimidazolebutyric acid
  • omega-(1-Methyl-5-bis(beta-chloroethyl)aminobenzimidazole-(2)-butyric acid

Registry Numbers

CAS Registry Number

  • 16506-27-7

FDA UNII

  • 9266D9P3PQ

Related Registry Number

  • 3543-75-7 (hydrochloride)

System Generated Number

  • 0016506277

Structure Descriptors

InChI

1S/C16H21Cl2N3O2/c1-20-14-6-5-12(21(9-7-17)10-8-18)11-13(14)19-15(20)3-2-4-16(22)23/h5-6,11H,2-4,7-10H2,1H3,(H,22,23)

InChIKey

YTKUWDBFDASYHO-UHFFFAOYSA-N

Smiles

c12n(C)c(CCCC(=O)O)nc1cc(N(CCCl)CCCl)cc2