Itramin tosilate

Chemical compound

Pharmaceutical compound

Itramin tosilate
Clinical data

Trade names	Nilatil
Other names	Itramin tosylate
ATC code	C01DX01 (WHO )
Identifiers
IUPAC name 2-aminoethyl nitrate; 4-methylbenzenesulfonic acid
CAS Number	13445-63-1 ^checkY
PubChem CID	26000
DrugBank	DBSALT002523
ChemSpider	24219
UNII	W9H0R50KY0
KEGG	D07157
ChEBI	CHEBI:136001
ChEMBL	ChEMBL2106780
CompTox Dashboard (EPA)	DTXSID30158705 Edit this at Wikidata
Chemical and physical data
Formula	C₉H₁₄N₂O₆S
Molar mass	278.28 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(C=C1)S(=O)(=O)O.C(CO[N+](=O)[O-])N
InChI InChI=1S/C7H8O3S.C2H6N2O3/c1-6-2-4-7(5-3-6)11(8,9)10;3-1-2-7-4(5)6/h2-5H,1H3,(H,8,9,10);1-3H2 Key:HPPBBWMYZVALRK-UHFFFAOYSA-N

Itramin tosilate (INN), or itramin tosylate (more commonly), is a vasodilator.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Batterman RC, Mouratoff GJ (June 1963). "Anginal syndrome. Treatment with a long-acting nitrate (itramin tosylate)". California Medicine. 98 (6): 318–9. PMC 1575756 . PMID 13966844.
^ McGrath JC (June 2013). "2-Aminoethylnitrate: Earlier investigation as a drug was missed by recent authors due to changes in nomenclature". British Journal of Pharmacology. 169 (4): 949–50. doi:10.1111/bph.12148. PMC 3687673 . PMID 23711023.
^ Ehrenberger W (August 1960). "[On the effects of 2-aminoethylnitrate p-toluenesulfonate (Nilatil) on coronary circulation disorders]". Wiener Zeitschrift für Innere Medizin und Ihre Grenzgebiete. 41: 323–4. PMID 13725976.
^ Fremont RE (May 1967). "Clinical and cardiographic evaluation of a new nitrate, itramin tosylate". Current Therapeutic Research, Clinical and Experimental. 9 (5): 235–46. PMID 4963057.
^ Kinnard WJ, Vogin EE, Aceto MD, Buckley JP (July 1964). "The Coronary Vasodilatory Effects of 2-Aminoethlynitrate p-Toluenesulfonate". Angiology. 15 (7): 312–5. doi:10.1177/000331976401500703. PMID 14177999. S2CID 29870356.
^ Takenaka F, Umeda T (July 1976). "Effects of propranolo, itramin tosylate and dipyridamole on myocardial phosphate metabolism in anoxic perfused rat hearts". Archives Internationales de Pharmacodynamie et de Therapie. 222 (1): 45–54. PMID 10860.

v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan ^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

sGC	Activators/stimulators: Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat Inhibitors: ODQ

nNOS	3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) N^ω-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS	1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N⁶-(1-Iminoethyl)-L-lysine (L-NIL) N^ω-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM
eNOS	Aminoguanidine (pimagedine) N⁵-(1-Iminoethyl)-L-ornithine (L-NIO) N^ω-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)
Unsorted	Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381