Ranimustine

Base Information

• Chemical Name: Ranimustine
• CAS No.: 58994-96-0
• Molecular Formula: C₁₀H₁₈ClN₃O₇
• Molecular Weight: 327.722
• UNII: RYH2T97J77
• DSSTox Substance ID: DTXSID501015584
• Nikkaji Number: J22.805B
• Wikipedia: Ranimustine
• Wikidata: Q7293058
• NCI Thesaurus Code: C1515
• Metabolomics Workbench ID: 154610
• ChEMBL ID: CHEMBL2105348
• Mol file: 58994-96-0.mol

Synonyms:MCNU;methyl 6-((((2-chloroethyl)nitrosoamino)carbonyl) amino)-6-deoxy-alpha-D-glucopyranoside;methyl 6-(3-(2-chloroethyl)-3-nitrosoiureido)-6-deoxy-alpha-D-glucopyranoside;methyl 6-(3-(2-chloroethyl)-3-nitrosoureido)-6-deoxy-alpha-D-glucopyranoside;ranimustine;ranimustine, (beta)-(D)-isomer

Chemical Property of Ranimustine

Chemical Property:

• Melting Point: 111-112°
• Refractive Index: 1.616
• PSA: 140.92000
• Density: 1.69 g/cm³
• LogP: -1.23690
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 327.0833276
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

99% ^*data from raw suppliers

Ranimustine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CNC(=O)N(CCCl)N=O)O)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CNC(=O)N(CCCl)N=O)O)O)O
• Recent NIPH Clinical Trials: Dose-intensified pirarubicin-cyclophosphamide, vincristine and prednisolone regimen (Double-THP-COP) followed by consolidative high-dose chemotherapy for peripheral T-cell lymphomas: a prospective phase II trial.
• Description: Ranimustine, a new nitrosourea derivative, is a water soluble antitumor agent with low hematological toxicity and diabetogenic effect. It is reportedly effective in the treatment of hematologic malignancies, especially the myeloproliferative disorders.
• Uses: Glucocorticoid with low systemic absorption anti-inflammatory agent

Technology Process of Ranimustine

There total 3 articles about Ranimustine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

1-(2-chloroethyl)-3-(1-methyl-6-deoxy-α-D-glucopyranse-6-yl)urea (58994-95-9) → Ranimustine (58994-96-0)

Guidance literature:

With hydrogenchloride; sodium nitrite; In ethanol; water; 1.) 0 deg C, 30 min, 2.) 25 deg C, 1.5 h;

DOI:10.1002/jps.2600800717

Reference yield:

ethanol-n-hexane + methyl 6-amino-6-deoxy-α-D-glucopyranoside (5155-47-5,68396-86-1,68422-61-7,79695-15-1,83334-22-9,83377-36-0,104714-43-4,104714-44-5,496811-81-5) + o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (68396-84-9) → Ranimustine (58994-96-0)

Guidance literature:

With formic acid; In tetrahydrofuran; 1,4-dioxane; methanol;

Reference yield:

methyl 6-deoxy-α-D-glucopyranoside (5155-43-1) → Ranimustine (58994-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / 1M aq. NaOH / CHCl₃; diethyl ether / 3 h / 0 °C

2: 42 percent / NaNO₂, HCl / ethanol; H₂O / 1.) 0 deg C, 30 min, 2.) 25 deg C, 1.5 h

With hydrogenchloride; sodium hydroxide; sodium nitrite; In diethyl ether; ethanol; chloroform; water;

DOI:10.1002/jps.2600800717

upstream raw materials:

1-(2-chloroethyl)-3-(1-methyl-6-deoxy-α-D-glucopyranse-6-yl)urea

methyl 6-deoxy-α-D-glucopyranoside

methyl 6-amino-6-deoxy-α-D-glucopyranoside

o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate

Refernces

• 1、 -. "Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein". . . Retrieved 2008/06/13.