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

Molecular Formula	C10H18ClN3O7
Molecular Weight	327.719
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
[Syndrome of inappropriate secretion of antidiuretic hormone and neurotoxicity induced by vincristine and alkylating agents during chemotherapy for malignant lymphoma of thyroid gland].	1998 Apr	9571977
Prophylactic effect of interferon-alpha for exacerbation of hepatitis B after high-dose chemotherapy.	2001	11713383
[Perioperative management for radical esophagectomy in a patient with polycythemia vera].	2001 Dec	11797364
L-asparaginase induced durable remission of relapsed nasal NK/T-cell lymphoma after autologous peripheral blood stem cell transplantation.	2001 Dec	11794702
[Gross spreading multiple extramedullary plasmacytomas to the skin in the terminal stage of multiple myeloma].	2001 Jul	11524846
Planning of hyperthermic treatment for malignant glioma using computer simulation.	2001 Mar-Apr	11252356
A new G-CSF-supported combination chemotherapy, LSG15, for adult T-cell leukaemia-lymphoma: Japan Clinical Oncology Group Study 9303.	2001 May	11380402
Leukemic transformation with trisomy 8 in essential thrombocythemia: a report of four cases.	2002 Feb	12061320
Reversible restrictive cardiomyopathy due to light-chain deposition disease.	2002 Feb	11838655
Megakaryoblastic transformation of polycythemia vera with hypercalcemia.	2002 Nov	12454709
[A case of primary malignant lymphoma of the pararectal space].	2002 Sep	12402484
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
Infrainguinal bypass surgery for chronic arterial occlusive disease associated with essential thrombocythemia: report of a case.	2004	15221564
[Pneumocystis carinii pneumonia complicating brain tumor].	2004 Feb	15031973
Phase III study of ranimustine, cyclophosphamide, vincristine, melphalan, and prednisolone (MCNU-COP/MP) versus modified COP/MP in multiple myeloma: a Japan clinical oncology group study, JCOG 9301.	2004 Feb	15005346
[Granulocyte-colony stimulating factor-producing myeloma with clinical manifestations mimicking chronic neutrophilic leukemia].	2004 Mar	15103937
[Multiple myeloma of the IgD-lambda type invading CNS].	2004 Oct	15553049
[CD56-positive peripheral T-cell lymphoma primarily presenting with tonsillar swelling].	2004 Oct	15553048
[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
[A case of high grade astrocytoma arising in the hand area of precentral gyrus].	2005 Jun	16026048
[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
VCAP-AMP-VECP compared with biweekly CHOP for adult T-cell leukemia-lymphoma: Japan Clinical Oncology Group Study JCOG9801.	2007 Dec 1	17968021
[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
Chemotherapeutic choice of ranimustine or nimustine on the basis of regional polyamine levels in rat brain.	2008 Mar	18560626
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
Changes in serum tryptophan catabolism as an indicator of disease activity in adult T-cell leukemia/lymphoma.	2009 Aug	19544139
Interferon-beta, MCNU, and conventional radiotherapy for pediatric patients with brainstem glioma.	2009 Jul	19260101
[Long-term remission of non-Hodgkin lymphoma secondary to the treatment for essential thrombocythemia].	2009 Mar	19352088
Successful treatment with autologous peripheral blood stem cell transplantation for acquired immunodeficiency syndrome (AIDS)-related malignant lymphoma.	2009 Nov	20009441
Long-term outcomes of autologous PBSCT for peripheral T-cell lymphoma: retrospective analysis of the experience of the Fukuoka BMT group.	2010 Feb	19597416
Aortic thrombus in a patient with myeloproliferative thrombocytosis, successfully treated by pharmaceutical therapy: a case report.	2010 Jul 21	20663173
Treatment of atypical central neurocytoma in a child with high dose chemotherapy and autologous stem cell rescue.	2010 May	19924515
A pilot case-control study on the alveolar bone density measurement in risk assessment for bisphosphonate-related osteonecrosis of the jaw.	2010 May	19705049
A nonradiation-containing, intermediate-dose methotrexate regimen for elderly patients with primary central nervous system lymphoma.	2010 Nov	20967518
[Plasmacytoma of chest wall].	2010 Sep	20845698

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).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:20:06 GMT 2023` Edited by `admin` on `Sat Dec 16 16:20:06 GMT 2023`
Record UNII	RYH2T97J77
Record Status	`Validated (UNII)`
Record Version

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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