RANIMUSTINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H18ClN3O7
Molecular Weight	327.719
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@H]1O[C@H](CNC(=O)N(CCCl)N=O)[C@@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=AHHFEZNOXOZZQA-ZEBDFXRSSA-N

InChI=1S/C10H18ClN3O7/c1-20-9-8(17)7(16)6(15)5(21-9)4-12-10(18)14(13-19)3-2-11/h5-9,15-17H,2-4H2,1H3,(H,12,18)/t5-,6-,7+,8-,9+/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.genome.jp/dbget-bin/www_bget?D01760
Curator's Comment: Description was created based on several sources, including DOI: 10.1007/978-3-319-13278-5 Retrieved from Molecular Therapies of Cancer By Georg F. Weber, p.26 and http://www.ncbi.nlm.nih.gov/pubmed/2405779

Ranimustine (tradename Cymerin; also known as MCNU) is a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera. It has never been filed for FDA evaluation in the United States, where it is not marketed.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell growth 21 Target ID: GO:0016049 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9625826	Inhibitor 8297
DNA synthesis involved in DNA replication 7 Target ID: GO:0090592 Sources: http://www.genome.jp/dbget-bin/www_bget?D01760	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic myelogenous leukemia 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2817908	Primary		Approved 8429	Cymerin Approved Use Polycythemia vera treatment medicines Launch Date 2014
Polycythemia vera 15 Sources: http://drugs-about.com/drugs-c/cymerin.html	Primary		Approved 8429	Cymerin Approved Use Polycythemia vera treatment medicines Launch Date 2014

PubMed

Title	Date	PubMed
Detection of human herpesvirus 6 and JC virus in progressive multifocal leukoencephalopathy complicating follicular lymphoma.	2001 Jul	11391720
Reversible restrictive cardiomyopathy due to light-chain deposition disease.	2002 Feb	11838655
[A case of chronic thromboembolic pulmonary hypertension based on essential thrombocythemia].	2002 Jul	12382421
[A case of multiple myeloma with infiltration into skeletal muscle after injections of a granulocyte-colony stimulating-factor].	2002 Jul	12187809
Megakaryoblastic transformation of polycythemia vera with hypercalcemia.	2002 Nov	12454709
Combination chemotherapy of ranimustine, doxorubicine, and dexamethasone for relapsing multiple myeloma--a pilot study.	2003	17682310
Cardiac lymphoma successfully treated with high dose chemotherapy followed by autologous haematopoietic stem cell transplantation.	2003 Dec	14688007
Recombinant mutant human tumor necrosis factor-alpha (TNF-SAM2) immunotherapy with ranimustine chemotherapy and concurrent radiation therapy for malignant astrocytomas.	2003 Nov-Dec	14666736
Infrainguinal bypass surgery for chronic arterial occlusive disease associated with essential thrombocythemia: report of a case.	2004	15221564
[Focal segmental glomerulosclerosis in a patient with polycythemia vera].	2005	16296413
[Effective combination therapy of bortezomib and dexamethasone for two patients with refractory multiple myeloma].	2005 Apr	16444959
[Autologous hematopoietic stem cell transplantation for aggressive B-cell non-Hodgkin's lymphoma].	2005 Dec	16352929
[Trial of front-line intensive chemotherapy followed by peripheral blood stem cell transplantation in high-intermediate and high risk non-Hodgkin's lymphoma patients].	2005 May	16444968
Efficacy and feasibility of procarbazine, ranimustine and vincristine chemotherapy, and the role of surgical resection in anaplastic oligodendroglioma.	2005 Nov-Dec	16302731
Supratentorial primitive neuroectodermal tumor in an aged patient--case report--.	2005 Oct	16247240
Irinotecan therapy in a 12-year-old girl with recurrent brain stem glioma and without functional polymorphisms in UGT1A1 activity: case report.	2005 Sep	16187025
Successful chemotherapy for congenital malignant gliomas: a report of two cases.	2006	16714866
Multiple granulocytic sarcomas in essential thrombocythemia.	2006 Dec	17189221
[Development of acute type, CD 8 positive adult T-cell leukemia in a carrier of hepatitis B virus--possible therapeutic effect of lamivudine combined with chemotherapy].	2006 May	16685173
Evaluation of intratumoral administration of tumor necrosis factor-alpha in patients with malignant glioma.	2006 Nov-Dec	17195453
[Four cases of therapy-related leukemia in multiple myeloma].	2007 Jan	17220686
Genetically heterogeneous glioblastoma recurring with disappearance of 1p/19q losses: case report.	2007 Jul	17621007
Human T cell leukemia virus reactivation with progression of adult T-cell leukemia-lymphoma.	2009	19204798
Autologous stem cell transplantation using MEAM regimen for relapsed AIDS-related lymphoma patients who received highly active anti-retroviral therapy: a report of three cases.	2009	19145056
Long-term outcomes of autologous PBSCT for peripheral T-cell lymphoma: retrospective analysis of the experience of the Fukuoka BMT group.	2010 Feb	19597416
A pilot case-control study on the alveolar bone density measurement in risk assessment for bisphosphonate-related osteonecrosis of the jaw.	2010 May	19705049

Patents

Sample Use Guides

In Vivo Use Guide

oral administration of 50mg (one tablet)/body/day every 4-6 days was considered as one course, and this was repeated at 6-8-week intervals if possible

Route of Administration: Oral

In Vitro Use Guide

The SD10 (10% survival dose) of the cells to Ranimustine ranged from 4.3 uM (C6-2 cells) to 151.7 uM (T98G cells).

Name

Type

Language

RANIMUSTINE

Official Name

English

RANIMUSTINE [MART.]

Common Name

English

Ranimustine [WHO-DD]

Common Name

English

METHYL 6-(3-(2-CHLOROETHYL)-3-NITROSOUREIDO)-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSIDE

Common Name

English

RANIMUSTINE [JAN]

Common Name

English

RANIMUSTINE [MI]

Common Name

English

NSC-270516

Code

English

CYMERIN

Brand Name

English

ranimustine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C699