Ranimustine: Difference between revisions

Ranimustine
Clinical data
Trade names	Cymerin
Other names	1-(2-chloroethyl)-1-nitroso-3-([(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl)urea
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV
ATC code	L01AD07 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name Methyl 6-({[(2-chloroethyl)(nitroso)amino]carbonyl}amino)-6-deoxy-α-D-glucopyranoside;
CAS Number	58994-96-0 ;
PubChem CID	71741;
ChemSpider	64785;
UNII	RYH2T97J77;
CompTox Dashboard (EPA)	DTXSID501015584 ;
Chemical and physical data
Formula	C10H18ClN3O7
Molar mass	327.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CNC(=O)N(CCCl)N=O)O)O)O;
	InChI 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; Key:AHHFEZNOXOZZQA-ZEBDFXRSSA-N;
	(verify)

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Revision as of 14:03, 8 July 2024

Ranimustine (INN, marketed under the tradename Cymerin; also known as MCNU) is a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia^[1] and polycythemia vera.^[2]

It has never been filed for FDA evaluation in the United States, where it is not marketed.

Synthesis

Ranimustine is made by reacting the primary amine of a pyranose sugar (2) with o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (1) to form the nitrosourea group.^[3] ^[4]

References

^ Kitajima K, Adachi T, Takahashi I, et al. (November 1989). "[Chemotherapy of chronic myelogenous leukemia—VP(M) regimen initiated during its chronic phase, and evaluation of MCNU in the phase of blastic crisis]". Gan To Kagaku Ryoho (in Japanese). 16 (11): 3573–9. PMID 2817908.
^ Nagai M, Tasaka T, Kamano H, et al. (December 1988). "[Therapeutic effect of ranimustine (MCNU) on essential thrombocythemia and polycythemia vera]". Gan To Kagaku Ryoho (in Japanese). 15 (12): 3267–70. PMID 3196045.
^ US patent 4156777, Goro Kimura, "Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein", issued 1979-05-29, assigned to Tokyo Tanabe Co Ltd
^ Sosnovsky, George; Rao, Nuti Uma Maheshwara (1991). "In the Search for New Anticancer Drugs. XXIII: Exploration of a Predictive Design for Anticancer Drugs of Carbohydrates Containing N-Nitrosochloroethylamino, N-Nitrosomethyl, and N-Nitrosoaminoxyl Components". Journal of Pharmaceutical Sciences. 80 (7): 693–699. doi:10.1002/jps.2600800717. PMID 1658297.

External links

(in Japanese) Cymerin サイメリン (PDF) Mitsubishi Tanabe Pharma. October 2007.

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

[pmid2817908-1] Kitajima K, Adachi T, Takahashi I, et al. (November 1989). "[Chemotherapy of chronic myelogenous leukemia—VP(M) regimen initiated during its chronic phase, and evaluation of MCNU in the phase of blastic crisis]". Gan To Kagaku Ryoho (in Japanese). 16 (11): 3573–9. PMID 2817908.

[pmid3196045-2] Nagai M, Tasaka T, Kamano H, et al. (December 1988). "[Therapeutic effect of ranimustine (MCNU) on essential thrombocythemia and polycythemia vera]". Gan To Kagaku Ryoho (in Japanese). 15 (12): 3267–70. PMID 3196045.

[3] US patent 4156777, Goro Kimura, "Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein", issued 1979-05-29, assigned to Tokyo Tanabe Co Ltd

[4] Sosnovsky, George; Rao, Nuti Uma Maheshwara (1991). "In the Search for New Anticancer Drugs. XXIII: Exploration of a Predictive Design for Anticancer Drugs of Carbohydrates Containing N-Nitrosochloroethylamino, N-Nitrosomethyl, and N-Nitrosoaminoxyl Components". Journal of Pharmaceutical Sciences. 80 (7): 693–699. doi:10.1002/jps.2600800717. PMID 1658297.

[1]

@@ Line 52: / Line 52: @@
 It has never been filed for [[Food and Drug Administration|FDA]] evaluation in the [[United States]], where it is not marketed.
 ==Synthesis==
+:[[File:Ranimustine synthesis.svg|upright=2]]
-[[File:Ranimustine synthesis.svg|thumb|center|400px|[https://www.chemdrug.com/article/8/3285/16420009.html ChemDrug] Synthesis:<ref>Prous, J.; Castaer, J.; Ranimustine. Drugs Fut 1986, 11, 9, 762.</ref> Patent:<ref>Goro Kimura, {{US patent|4156777}} (1979 to Tokyo Tanabe Co Ltd).</ref> 42% (Cmp#34)<ref>Sosnovsky, George; Rao, Nuti Uma Maheshwara (1991). "In the Search for New Anticancer Drugs. XXIII: Exploration of a Predictive Design for Anticancer Drugs of Carbohydrates Containing N-Nitrosochloroethylamino, N-Nitrosomethyl, and N-Nitrosoaminoxyl Components". Journal of Pharmaceutical Sciences. 80 (7): 693–699. doi:10.1002/jps.2600800717.</ref>]]
+Ranimustine is made by reacting the [[primary amine]] of a [[pyranose]] sugar (2) with ''o''-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (1) to form the [[nitrosourea]] group.<ref>{{cite patent |country=US |number=4156777 |inventor=Goro Kimura  |title=Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein |status=patent |gdate=1979-05-29 |fdate=1978-01-26 |assign1=Tokyo Tanabe Co Ltd}}</ref>
-*o-nitrophenyl N-(2-chloroethyl)N-nitrosocarbamate, PC13231923 (1)
+<ref>{{cite journal |doi=10.1002/jps.2600800717 |title=In the Search for New Anticancer Drugs. XXIII: Exploration of a Predictive Design for Anticancer Drugs of Carbohydrates Containing N-Nitrosochloroethylamino, N-Nitrosomethyl, and N-Nitrosoaminoxyl Components |date=1991 |last1=Sosnovsky |first1=George |last2=Rao |first2=Nuti Uma Maheshwara |journal=Journal of Pharmaceutical Sciences |volume=80 |issue=7 |pages=693–699 |pmid=1658297 }}</ref>
-*(2R,3S,4S,5R,6S)-2-(aminomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol [5155-47-5] (2)
 ==References==
 {{Reflist}}
+==External links==
 * {{in lang|ja}} [https://web.archive.org/web/20110814142718/http://di.mt-pharma.co.jp/file/dc/cmr_a.pdf Cymerin サイメリン] (PDF) Mitsubishi Tanabe Pharma. October 2007.