Arabinopyranosyl-N-methyl-N-nitrosourea

Arabinopyranosyl-N-methyl-N-nitrosourea

Clinical data
Trade names	Aranose
AHFS/Drugs.com	Monograph
Pregnancy category	D
Routes of administration	Intravenously
ATC code	L01
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	100%
Protein binding	50%
Metabolism	Hepatic
Identifiers
IUPAC name 1-Methyl-1-nitroso-3-[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]urea
Synonyms	Arabinopyranosyl methylnitrosourea; 3-(α-L-Arabinopyranosyl)-1-methyl-1-nitrosourea
CAS Number	167396-23-8 Y
PubChem CID	208900
ChemSpider	180998 Y
UNII	7149VX7891
Chemical and physical data
Formula	C7H13N3O6
Molar mass	235.194595
3D model (JSmol)	Interactive image
SMILES CN(C(=O)NC1C(C(C(CO1)O)O)O)N=O
InChI InChI=1S/C7H13N3O6/c1-10(9-15)7(14)8-6-5(13)4(12)3(11)2-16-6/h3-6,11-13H,2H2,1H3,(H,8,14)/t3-,4-,5+,6+/m0/s1 Y Key:BADMGRJDJPQBLS-UNTFVMJOSA-N Y

Arabinopyranosyl-N-methyl-N-nitrosourea, also known as Aranose (Араноза) is a cytostatic anticancer chemotherapeutic drug of an alkylating type. Chemically it is a nitrosourea derivative. It was developed in the Soviet Union in the 1970s. It was claimed by its developers that its advantages over other nitrosoureas are a relatively low hematological toxicity (compared to other nitrosoureas available at that time) and a wider therapeutic index, which allows for its outpatient administration.

It was first synthesized in late 1970s in the Laboratory of Organic Synthesis of Soviet Cancer Research Institute (which belonged to Academy of Medical Sciences of the USSR). Its first clinical trials in USSR were conducted in the late 1980s. Those trials confirmed its potential clinical efficacy in melanoma and better relative safety & improved tolerability over other nitrosourea antineoplastic compounds available at that time. In 1996 the compound obtained an Russian Pharmacologic Committee (a Russian analog of the U.S. Food and Drug Administration (FDA) and EMA in the European Community) regulatory approval for its use in melanoma under the trade name Aranoza.

The compound is basically a conjugate between the well-known cytotoxic and mutagenic residue of N-nitroso-N-methylurea and the sugar L-arabinose. The L-arabinose is a well-known component of some other effective anticancer drug molecules, including cytarabine (cytosine arabinoside) and fludarabine (2-fluoro-arabinoside of the nucleoside adenosine). The presence of L-arabinoside residue in the molecule greatly improves its penetration into malignant cells and its blood–brain barrier penetration and, while maintaining or even increasing anticancer activity, reduces the toxicity for normally fast dividing cells (bone marrow cells and mucosa of the gastro-intestinal system), improving the concentration ratio "tumor / normal tissue".