Symmetric dimethylarginine

Symmetric dimethylarginine
Names
	IUPAC name (2S)-2-amino-5-[(N,N'-dimethylcarbamimidoyl)amino]pentanoic acid
	Other names Nω,Nω'-dimethyl-L-arginine
Identifiers
CAS Number	30344-00-4;
3D model (JSmol)	Interactive image;
Beilstein Reference	973080
ChEBI	CHEBI:25682;
ChemSpider	147942;
DrugBank	DB02302;
PubChem CID	169148;
UNII	49787G1ULV;
CompTox Dashboard (EPA)	DTXSID00952691 ;
	InChI InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1 Key: HVPFXCBJHIIJGS-LURJTMIESA-N;
	SMILES C(C[C@@H](C(=O)O)N)CNC(=NC)NC;
Properties
Chemical formula	C8H18N4O2
Molar mass	202.258 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Symmetric dimethylarginine (SDMA) is produced during catabolism of proteins. It consists of an arginine core, with one methyl group on each of the two terminal side-chain nitrogen atoms.

Dimethylation of arginine in proteins is mediated by various enzymes, including protein arginine methyltransferase 5^[1] as part of a regulatory pathway of transcription.

SDMA has been explored as a possible biomarker for kidney disease in cats^[2]^[3] and dogs.^[4]

References

^ Stopa, Nicole; Krebs, Jocelyn E.; Shechter, David (2015). "The PRMT5 arginine methyltransferase: Many roles in development, cancer and beyond". Cellular and Molecular Life Sciences. 72 (11): 2041–2059. doi:10.1007/s00018-015-1847-9. PMC 4430368. PMID 25662273.
^ Paltrinieri, Saverio; Giraldi, Marco; Prolo, Amanda; Scarpa, Paola; Piseddu, Eleonora; Beccati, Massimo; Graziani, Benedetta; Bo, Stefano (2018). "Serum symmetric dimethylarginine and creatinine in Birman cats compared with cats of other breeds". Journal of Feline Medicine and Surgery. 20 (10): 905–912. doi:10.1177/1098612X17734066. PMC 11129243. PMID 28994640.
^ Braff, J.; Obare, E.; Yerramilli, M.; Elliott, J.; Yerramilli, M. (2014). "Relationship between Serum Symmetric Dimethylarginine Concentration and Glomerular Filtration Rate in Cats". Journal of Veterinary Internal Medicine. 28 (6): 1699–1701. doi:10.1111/jvim.12446. PMC 4895615. PMID 25272985.
^ Nabity, M.B.; Lees, G.E.; Boggess, M.M.; Yerramilli, M.; Obare, E.; Yerramilli, M.; Rakitin, A.; Aguiar, J.; Relford, R. (2015). "Symmetric Dimethylarginine Assay Validation, Stability, and Evaluation as a Marker for the Early Detection of Chronic Kidney Disease in Dogs". Journal of Veterinary Internal Medicine. 29 (4): 1036–1044. doi:10.1111/jvim.12835. PMC 4895368. PMID 26079532.

[1] Stopa, Nicole; Krebs, Jocelyn E.; Shechter, David (2015). "The PRMT5 arginine methyltransferase: Many roles in development, cancer and beyond". Cellular and Molecular Life Sciences. 72 (11): 2041–2059. doi:10.1007/s00018-015-1847-9. PMC 4430368. PMID 25662273.

[2] Paltrinieri, Saverio; Giraldi, Marco; Prolo, Amanda; Scarpa, Paola; Piseddu, Eleonora; Beccati, Massimo; Graziani, Benedetta; Bo, Stefano (2018). "Serum symmetric dimethylarginine and creatinine in Birman cats compared with cats of other breeds". Journal of Feline Medicine and Surgery. 20 (10): 905–912. doi:10.1177/1098612X17734066. PMC 11129243. PMID 28994640.

[3] Braff, J.; Obare, E.; Yerramilli, M.; Elliott, J.; Yerramilli, M. (2014). "Relationship between Serum Symmetric Dimethylarginine Concentration and Glomerular Filtration Rate in Cats". Journal of Veterinary Internal Medicine. 28 (6): 1699–1701. doi:10.1111/jvim.12446. PMC 4895615. PMID 25272985.

[4] Nabity, M.B.; Lees, G.E.; Boggess, M.M.; Yerramilli, M.; Obare, E.; Yerramilli, M.; Rakitin, A.; Aguiar, J.; Relford, R. (2015). "Symmetric Dimethylarginine Assay Validation, Stability, and Evaluation as a Marker for the Early Detection of Chronic Kidney Disease in Dogs". Journal of Veterinary Internal Medicine. 29 (4): 1036–1044. doi:10.1111/jvim.12835. PMC 4895368. PMID 26079532.

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