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MedKoo Cat#: 205860 | Name: Nitroarginine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nitroarginine, or Nω-nitro-L-arginine, is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase and hence a vaso-constrictor and coronary constrictor. As such, it finds widespread use as a biochemical tool in the study of nitric oxide and its biological effects. Nitroarginine has been used in research studying coronary constriction, in the presence of midazolam vasodilatation was unaffected by nitroarginine. Nitroarginine is currently in clinical trials for treating patients with advanced solid tumors.

Chemical Structure

Nitroarginine
CAS#2149-70-4

Theoretical Analysis

MedKoo Cat#: 205860

Name: Nitroarginine

CAS#: 2149-70-4

Chemical Formula: C6H13N5O4

Exact Mass: 219.0968

Molecular Weight: 219.20

Elemental Analysis: C, 32.88; H, 5.98; N, 31.95; O, 29.20

Price and Availability

Size Price Availability Quantity
5g USD 300.00
25g USD 550.00 2 Weeks
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Synonym
Nitroarginine; N5(nitroamidino)LOrnithine; (+)NGNitroarginine; NGnitroLArginine LNGNitroarginine; LNNA; LNOARG; NGNitroLarginine; NGNitroarginine; NOLA; NSC 53662; NitroLarginine; NNitroLarginine; NNitroLarginine; NitroLarginine; Nitroarginine.
IUPAC/Chemical Name
(S)-2-amino-5-(3-nitroguanidino)pentanoic acid
InChi Key
MRAUNPAHJZDYCK-BYPYZUCNSA-N
InChi Code
InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
SMILES Code
O=C(O)[C@@H](N)CCCNC(N[N+]([O-])=O)=N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
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Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nitroarginine, or Nω-nitro-L-arginine, is a nitro derivative of the amino acid arginine. It is an inhibitor of nitric oxide synthase.
In vitro activity:
Inhibition of nitric oxide (NO) synthase activity by L-NG-Nitroarginine (NO2Arg) in brain preparations is not reversed by dialysis and is enhanced by prolonged preincubation of NO2Arg with the enzyme. By contrast, the weaker inhibition by NO2Arg of macrophage NO synthase is fully reversible. Reference: Biochem Biophys Res Commun. 1991 May 15;176(3):1136-41. https://pubmed.ncbi.nlm.nih.gov/1710109/
In vivo activity:
Feeding rats a diet containing 0.2 g/kg L-NNA for 5 weeks elevated serum concentrations of triglyceride, cholesterol, phospholipid, and free fatty acid and reduced serum nitrate (an oxidation product of NO). L-NNA treatment caused significantly higher activity of hepatic microsomal phosphatidate phosphohydrolase (the rate-limiting enzyme in triglyceride synthesis) and lower activity of hepatic carnitine palmitoyltransferase (the rate-limiting enzyme in fatty acid oxidation). Reference: J Nutr Biochem. 1999 May;10(5):274-8. https://pubmed.ncbi.nlm.nih.gov/15539300/

Preparing Stock Solutions

The following data is based on the product molecular weight 219.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Dwyer MA, Bredt DS, Snyder SH. Nitric oxide synthase: irreversible inhibition by L-NG-nitroarginine in brain in vitro and in vivo. Biochem Biophys Res Commun. 1991 May 15;176(3):1136-41. doi: 10.1016/0006-291x(91)90403-t. PMID: 1710109. 2. Abraham P, K I, K D. Nitro-arginine methyl ester, a non-selective inhibitor of nitric oxide synthase reduces ibuprofen-induced gastric mucosal injury in the rat. Dig Dis Sci. 2005 Sep;50(9):1632-40. doi: 10.1007/s10620-005-2908-y. PMID: 16133962. 3. Goto T, Ohnomi S, Khedara A, Kato N, Ogawa H, Yanagita T. Feeding the nitric oxide synthase inhibitor L-N(omega)nitroarginine elevates serum very low density lipoprotein and hepatic triglyceride synthesis in rats. J Nutr Biochem. 1999 May;10(5):274-8. doi: 10.1016/s0955-2863(99)00008-x. PMID: 15539300.
In vitro protocol:
1. Dwyer MA, Bredt DS, Snyder SH. Nitric oxide synthase: irreversible inhibition by L-NG-nitroarginine in brain in vitro and in vivo. Biochem Biophys Res Commun. 1991 May 15;176(3):1136-41. doi: 10.1016/0006-291x(91)90403-t. PMID: 1710109.
In vivo protocol:
1. Abraham P, K I, K D. Nitro-arginine methyl ester, a non-selective inhibitor of nitric oxide synthase reduces ibuprofen-induced gastric mucosal injury in the rat. Dig Dis Sci. 2005 Sep;50(9):1632-40. doi: 10.1007/s10620-005-2908-y. PMID: 16133962. 2. Goto T, Ohnomi S, Khedara A, Kato N, Ogawa H, Yanagita T. Feeding the nitric oxide synthase inhibitor L-N(omega)nitroarginine elevates serum very low density lipoprotein and hepatic triglyceride synthesis in rats. J Nutr Biochem. 1999 May;10(5):274-8. doi: 10.1016/s0955-2863(99)00008-x. PMID: 15539300.
1: Moon IJ, Kim KR, Chu HS, Kim SH, Chung WH, Cho YS, Hong SH. N-acetylcysteine and N-nitroarginine methyl ester attenuate Carboplatin-induced ototoxicity in dissociated spiral ganglion neuron cultures. Clin Exp Otorhinolaryngol. 2011 Mar;4(1):11-7. Epub 2011 Mar 17. PubMed PMID: 21461057; PubMed Central PMCID: PMC3062221. 2: Delgado E, Marques-Neves C, Rocha I, Sales-Luís J, Silva-Carvalho L. L-arginine and L-nitroarginine methylester effects on vasomotion in isolated rabbit eyes. Ophthalmic Res. 2010;43(3):113-21. Epub 2009 Oct 29. PubMed PMID: 19887876. 3: Ozel H, Yuksel BC, Berkem H, Avsar FM, Guler G, Iskit AB, Guc MO, Hengirmen S. The effects of L-NG-nitroarginine in a zymosan-induced multiple organ dysfunction syndrome model. Eur Surg Res. 2009;43(2):211-8. Epub 2009 Jun 24. PubMed PMID: 19556797. 4: Le Nguyen YH, Winkler JR, Gray HB. Probing heme coordination states of inducible nitric oxide synthase with a ReI(imidazole-alkyl-nitroarginine) sensitizer-wire. J Phys Chem B. 2007 Jun 21;111(24):6628-33. Epub 2007 May 31. PubMed PMID: 17536854; PubMed Central PMCID: PMC2596599. 5: Fontana L, Souza AS, Del Bel EA, Oliveira RM. Ginkgo biloba leaf extract (EGb 761) enhances catalepsy induced by haloperidol and L-nitroarginine in mice. Braz J Med Biol Res. 2005 Nov;38(11):1649-54. Epub 2005 Oct 26. PubMed PMID: 16258634. 6: Goto T, Ohnomi S, Khedara A, Kato N, Ogawa H, Yanagita T. Feeding the nitric oxide synthase inhibitor L-N(omega)nitroarginine elevates serum very low density lipoprotein and hepatic triglyceride synthesis in rats. J Nutr Biochem. 1999 May;10(5):274-8. PubMed PMID: 15539300. 7: Flinspach M, Li H, Jamal J, Yang W, Huang H, Silverman RB, Poulos TL. Structures of the neuronal and endothelial nitric oxide synthase heme domain with D-nitroarginine-containing dipeptide inhibitors bound. Biochemistry. 2004 May 11;43(18):5181-7. PubMed PMID: 15122883. 8: Wang LJ, Zhou SX, Sun CK. [Effects of L-nitroarginine on the recovery of traumatic facial paralysis]. Zhonghua Kou Qiang Yi Xue Za Zhi. 2003 Nov;38(6):447-9. Chinese. PubMed PMID: 14703481. 9: Riganti C, Aldieri E, Bergandi L, Miraglia E, Costamagna C, Bosia A, Ghigo D. Nitroarginine methyl ester and canavanine lower intracellular reduced glutathione. Free Radic Biol Med. 2003 Nov 15;35(10):1210-6. PubMed PMID: 14607520. 10: Huang H, Martásek P, Roman LJ, Silverman RB. Synthesis and evaluation of dipeptide amides containing N omega-nitroarginine and D-2,4-diaminobutyric acids as inhibitors of neuronal nitric oxide synthase. J Enzyme Inhib. 2001;16(3):233-9. PubMed PMID: 11697043.