ITRAMIN TOSYLATE

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H8O3S.C2H6N2O3
Molecular Weight	278.282
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCO[N+]([O-])=O.CC1=CC=C(C=C1)S(O)(=O)=O

InChI

InChIKey=HPPBBWMYZVALRK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6985697http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020845s016s017lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020215s024lbl.pdfhttps://www.drugs.com/pro/sodium-nitroprusside.html | https://www.ncbi.nlm.nih.gov/pubmed/7598246https://www.ncbi.nlm.nih.gov/pubmed/8644642 | https://www.ncbi.nlm.nih.gov/pubmed/7504768 | https://www.ncbi.nlm.nih.gov/pubmed/1724528 | https://adisinsight.springer.com/drugs/800001151https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19601018&CC=US&NR=2957021A&KC=A | https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=20020124&CC=WO&NR=0205795A2&KC=A2https://adisinsight.springer.com/drugs/800005482 | https://www.ncbi.nlm.nih.gov/pubmed/9845803https://www.ncbi.nlm.nih.gov/pubmed/19732062 | https://www.ncbi.nlm.nih.gov/pubmed/28988245 | https://www.ncbi.nlm.nih.gov/pubmed/24923291 | https://www.ncbi.nlm.nih.gov/pubmed/19563531http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019790s011lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021134s004lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/13426891 | https://www.ncbi.nlm.nih.gov/pubmed/13284675www.ncbi.nlm.nih.gov/pubmed/24071762
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/13106442

Pentaerythritol tetranitrate is an organic nitrate that has been used for the treatment of angina pectoris. Upon administration, the drug undergoes exstensive metabolism to NO which causes vasodilation and the relaxation of smooth muscle cells. The compound belongs to a familiy of explosive substances and may be used accordingly.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
liberation of NO 18 Target ID: liberation of NO Sources: http://www.ncbi.nlm.nih.gov/pubmed/2242448	Activator 1430
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: www.ncbi.nlm.nih.gov/pubmed/18574453	Activator 1430	0.1 µM [EC50]
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24560804	Activator 1430
Atrial natriuretic peptide receptor A 19 Target ID: CHEMBL1988 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12419094	Activator 1430
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10553632	Activator 1430
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021134s004lbl.pdf	Activator 1430
Soluble guanylate cyclase 34 Target ID: CHEMBL2111348 Sources: https://www.google.com/patents/EP2805730A1	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Hypertensive crises 18 Sources: https://www.drugs.com/pro/sodium-nitroprusside.html#s-34067-9	Primary	Approved 8429	NIPRIDE Approved Use Sodium Nitroprusside injection is indicated for the immediate reduction of blood pressure of adult and pediatric patients in hypertensive crises. Concomitant longer-acting antihypertensive medication should be administered so that the duration of treatment with Sodium Nitroprusside can be minimized. Sodium Nitroprusside injection is also indicated for producing controlled hypotension in order to reduce bleeding during surgery. Sodium Nitroprusside injection is also indicated for the treatment of acute congestive heart failure. Launch Date 1974
Heart failure 103 Sources: https://www.drugs.com/pro/sodium-nitroprusside.html#s-34067-9	Primary	Approved 8429	NIPRIDE Approved Use Sodium Nitroprusside injection is indicated for the immediate reduction of blood pressure of adult and pediatric patients in hypertensive crises. Concomitant longer-acting antihypertensive medication should be administered so that the duration of treatment with Sodium Nitroprusside can be minimized. Sodium Nitroprusside injection is also indicated for producing controlled hypotension in order to reduce bleeding during surgery. Sodium Nitroprusside injection is also indicated for the treatment of acute congestive heart failure. Launch Date 1974
Pulmonary hypertension 30 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020845s016s017lbl.pdf	Palliative	Approved 8429	INOMAX Approved Use INOmax is a vasodilator indicated to improve oxygenation and reduce the need for extracorporeal membrane oxygenation in term and near-term (>34 weeks gestation) neonates with hypoxic respiratory failure associated with clinical or echocardiographic evidence of pulmonary hypertension in conjunction with ventilatory support and other appropriate agents. Launch Date 1999
Angina pectoris 106 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019790s011lbl.pdf	Primary	Approved 8429	DILATRATE-SR Approved Use dilatrate®-SR sustained release capsules are indicated for the prevention of angina pectoris due to coronary artery disease. The onset of action of controlled-release oral isosorbide dinitrate is not sufficiently rapid for this product to be useful in aborting an acute anginal episode. Launch Date 1998
Angina pectoris 106 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020215s024lbl.pdf	Primary	Approved 8429	MONOKET Approved Use monoket® is indicated for the prevention and treatment of angina pectoris due to coronary artery disease. The onset of action of oral isosorbide mononitrate is not sufficiently rapid for this product to be useful in aborting an acute anginal episode. Launch Date 1993
Angina pectoris 106 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16644612	Primary	Approved 8429	Unknown Approved Use Unknown
Coronary heart disease 41 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2242448	Primary	Basic research	Unknown Approved Use Unknown
Angina 32 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8429	NITROSTAT Approved Use Acute relief of angina pectoris secondary to CAD; acute prophylactic management in situations likely to provoke angina attacks; and long-term prophylactic management of angina pectoris. Launch Date 2000
Myocardial infarction 121 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8429	NITROGLYCERIN Approved Use Management of patients with acute myocardial infarction (MI). Nitroglycerin is one of the principal initial therapies of MI. Launch Date 1981
Hypertension 567 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8429	NITROGLYCERIN Approved Use IV nitroglycerin is used to control BP in perioperative hypertension, especially hypertension associated with cardiovascular procedures; to control BP in patients with severe hypertension† or in hypertensive crises for the immediate reduction of BP in patients in whom such reduction is considered an emergency (hypertensive emergencies), especially those associated with coronary complications (e.g., coronary ischemia, acute coronary insufficiency, acute left ventricular failure, postoperative hypertension [especially following coronary bypass surgery]); and to produce controlled hypotension during surgical procedures. Launch Date 1981
Heart failure 103 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8429	NITROGLYCERIN Approved Use IV nitroglycerin has been used in the management of acutely decompensated (e.g., congestive) heart failure and other low cardiac-output states. Launch Date 1981
Angina pectoris 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4284102 https://www.ncbi.nlm.nih.gov/pubmed/13271134 https://www.ncbi.nlm.nih.gov/pubmed/13426891 https://www.ncbi.nlm.nih.gov/pubmed/13284675	Primary	Approved 8429	Metamine Approved Use https://www.ncbi.nlm.nih.gov/pubmed/13426891 \| https://www.ncbi.nlm.nih.gov/pubmed/13284675
Angina pectoris 106 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1952976/pdf/brmedj02877-0002.pdf	Primary	Approved 8429	PERITRATE Approved Use Unknown

C_max

Value	Dose	Analyte	Population
35 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
79 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1151 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
557 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
388 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
356 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.7 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208424s000lbl.pdf	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	NITROGLYCERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
17 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
187 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24851040	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
84 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/	13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered:	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
14241 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6979 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2524 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2647 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.3 pg × min/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208424s000lbl.pdf	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	NITROGLYCERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1458 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24851040	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3380 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/	13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered:	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2 min REVIEW https://pubmed.ncbi.nlm.nih.gov/6375932/	single, intravenous	NITROPRUSSIDE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	120 mg 1 times / day steady-state, oral dose: 120 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7614524/	60 mg 1 times / day steady-state, oral dose: 60 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6713775/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	ISOSORBIDE MONONITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208424s000lbl.pdf	800 μg single, sublingual dose: 800 μg route of administration: Sublingual experiment type: SINGLE co-administered:	NITROGLYCERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8573222/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
303 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24851040	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	ISOSORBIDE DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
50 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2111749/	13 mg single, oral dose: 13 mg route of administration: Oral experiment type: SINGLE co-administered:	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% EXPERIMENT https://www.sciencedirect.com/science/article/pii/B9780128012383967114			ISOSORBIDE DINITRATE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
ALDH2 19 P-gp 1461 MRP2 383 K+ channels 70 Ca2+ channels 57	ALDH2 19 CYP1A2 1054 CYP2A6 543 CYP2E1 667 CYP4A11 119	OCT1 35

Drug as perpetrator

Target	Modality	Activity
ALDH2 19	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15331769/	no
K+ channels 70	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S001429990800616X Page: abstract	no
Ca2+ channels 60	inhibitor 3277 Sources: https://link.springer.com/article/10.1007/BF00497774 Page: abstract	yes
MRP2 475	inhibitor 3277 Sources: https://www.ingentaconnect.com/content/ben/dml/2011/00000005/00000001/art00009 Page: abstract	yes
OCT1 543	inducer 1573 Sources: https://www.sciencedirect.com/science/article/abs/pii/S1056871913002578 Page: abstract	yes
P-gp 1650	inhibitor 3277 Sources: https://www.nature.com/articles/aps201225 Page: abstract	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1737	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	major
CYP1A2 1054	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2A6 543	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2C9 1037	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2D6 1217	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2E1 667	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP4A11 119	substrate 3367 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
ALDH2 19	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15331769/	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-4956	http://www.3bsc.com/index/pro_info.php?id=79896
3B Scientific (Wuhan) Corp	3B3-046180	http://www.3bsc.com/index/pro_info.php?id=82779
AA Blocks	AA00ILEO	https://www.aablocks.com/goods/Goods/detail?id=AA00ILEO
ABI Chem	AC1L1MPG
ABI Chem	AC1Q21X4
AHH Chemical co.,ltd	MT-57727	http://www.ahhchemical.com/product/MT-57727.html
AN PharmaTech	AN-23936
Aaron Chemicals	AR00IM6G	http://www.aaronchem.com/1302-78-9
Alfa Chemistry	7077-34-1	https://www.alfa-chemistry.com/cas_7077-34-1.htm
Ambinter	Amb17672903	http://www.ambinter.com/reference/17672903
BioSynth	W-111015	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-111015.html
ChEBI	CHEBI:28787	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28787
ChEBI	CHEBI:6061	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6061
ChEBI	CHEBI:6062	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6062
ChEBI	CHEBI:7596	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7596
ChemMol	49416736	http://www.chemmol.com/chemmol/49416736.html
ChemMol	99151477	http://www.chemmol.com/chemmol/99151477.html
Chemhere	Achem162548
ChemicalBook	CB2145318	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2145318
ChemicalBook	CB2226929	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2226929
ChemicalBook	CB3256697	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3256697
Chemieliva Pharmaceutical Co., Ltd	PBCM0000174
Chemspace	CSSB00016996527	https://chem-space.com/CSSB00016996527
Clearsynth	CS-O-00951	http://www.clearsynth.com/en/CSO00951.html
Compound Cloud	6518
Hangzhou Yuhao Chemical Technology	LL0106
LGC Standards	DRE-LA15589000AL	https://www.lgcstandards.com/US/en/p/DRE-LA15589000AL
Lab Network	LN02049364	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02049364
MolPort	MolPort-003-848-286	https://www.molport.com/shop/molecule-link/MolPort-003-848-286
NovoSeek	6518
Oakwood	94458	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=79632&ExtHyperLink=1
SelectLab Chemicals GmbH	Ex187
Sigma Aldrich	ERP-109S
Sigma Aldrich	P-037
Sigma-Aldrich	ERP-109S_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/erp109s?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P-037_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/p037?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S567259	https://www.smolecule.com/products/s567259
Smolecule	S585822	https://www.smolecule.com/products/s585822
THE BioTek	bt-433598	https://www.thebiotek.com/product/others/bt-433598
Tetrahedron	TS61261
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0472
Yuhao Chemical	LL0106	http://www.chemyuhao.com/78-11-5.html
ZINC	ZINC000001849548	http://zinc15.docking.org/substances/ZINC000001849548
ZINC	ZINC000008101167	http://zinc15.docking.org/substances/ZINC000008101167
ZINC	ZINC000008214625	http://zinc15.docking.org/substances/ZINC000008214625
ZINC	ZINC000018089317	http://zinc15.docking.org/substances/ZINC000018089317
eMolecules	10397191	https://www.emolecules.com/cgi-bin/more?vid=10397191
eMolecules	30154680	https://www.emolecules.com/cgi-bin/more?vid=30154680
eMolecules	30488208	https://www.emolecules.com/cgi-bin/more?vid=30488208
eMolecules	33507015	https://www.emolecules.com/cgi-bin/more?vid=33507015
eMolecules	36753592	https://www.emolecules.com/cgi-bin/more?vid=36753592
eMolecules	524496	https://www.emolecules.com/cgi-bin/more?vid=524496
eMolecules	713614	https://www.emolecules.com/cgi-bin/more?vid=713614

PubMed

Title	Date	PubMed
[The classic anti-anginal agents and molsidomine].	1983 Feb	6407452
Prostaglandin I2 and the nitric oxide donor molsidomine have synergistic effects on thromboresistance in man.	1992 Mar	1576049
Nitric oxide donors antagonize N-nitro-L-arginine and haloperidol catalepsy: potential implication for the treatment of Parkinsonism?	1997 Aug	9437770
Nitric oxide (NO) pathway and locomotor hyperactivity towards dopaminomimetics in rats.	1997 Sep-Oct	9566027
[The effect of nitric oxide administration on pateints with pulmonary hypertension: a dose-response study].	1998 Feb	10923418
L-arginine partially reverses established adrenocorticotrophin-induced hypertension and nitric oxide deficiency in the rat.	2000	11193135
Sodium nitroprusside-induced seizure and taurine release from rat hippocampus.	2000	11140358
Vascular effects of endothelin-1 in essential hypertension: relationship with cyclooxygenase-derived endothelium-dependent contracting factors and nitric oxide.	2000	10976779
Angiotensin in the nucleus tractus solitarii contributes to neurogenic hypertension caused by chronic nitric oxide synthase inhibition.	2000 Aug	10948087
Nitric oxide induces thymocyte apoptosis via a caspase-1-dependent mechanism.	2000 Aug 1	10903723
Nitric oxide metabolites, prostaglandins and trigeminal vasoactive peptides in internal jugular vein blood during spontaneous migraine attacks.	2000 Dec	11304026
Residual pulmonary hypertension in children after treatment with inhaled nitric oxide: a follow-up study regarding cardiopulmonary and neurological symptoms.	2000 Dec	11195228
Glyceryl trinitrate induced headache in migraineurs - relation to attack frequency.	2000 Jul	10971600
Cytokines induce apoptosis in beta-cells isolated from mice lacking the inducible isoform of nitric oxide synthase (iNOS-/-).	2000 Jul	10909967
Protective effect of bilobalide against nitric oxide-induced neurotoxicity in PC12 cells.	2000 May	11324438
The neurogenic vasodilator response to endothelin-1: a study in human skin in vivo.	2000 Nov	11187978
Inhibition of nitric oxide synthase enhances the myocardial toxicity of phenylpropanolamine.	2000 Nov	11098973
Role of nitric oxide in adrenocorticotrophin-induced hypertension: L-arginine effects reversed by N-nitro-L-arginine.	2000 Nov	11071304
Female sex steroids: effects upon microglial cell activation.	2000 Nov 1	11063824
Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway.	2000 Nov 15	11020457
Inhibition of inducible nitric oxide synthase gene expression by indomethacin or ibuprofen in beta-amyloid protein-stimulated J774 cells.	2000 Nov 17	11080519
Endothelins and endothelin receptor antagonists: therapeutic considerations for a novel class of cardiovascular drugs.	2000 Nov 7	11067800
High-calcium diet enhances vasorelaxation in nitric oxide-deficient hypertension.	2000 Sep	10993766
Nitric oxide-induced headache in patients with chronic tension-type headache.	2000 Sep	10960046
Regulation of diaphragmatic nitric oxide synthase expression during hypobaric hypoxia.	2000 Sep	10956627
Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages.	2001	11500931
Beneficial effect of 1,25 dihydroxyvitamin D3 on cytokine-treated human pancreatic islets.	2001 Apr	11250657
Induction of JAB/SOCS-1/SSI-1 and CIS3/SOCS-3/SSI-3 is involved in gp130 resistance in cardiovascular system in rat treated with cardiotrophin-1 in vivo.	2001 Apr 13	11304496
Stimulation of cyclooxygenase-2-activity by nitric oxide-derived species in rat chondrocyte: lack of contribution to loss of cartilage anabolism.	2001 Apr 15	11286988
Lipopolysaccharide and interferon-gamma-induced nitric oxide production and protein oxidation in mouse peritoneal macrophages are affected by glutathione peroxidase-1 gene knockout.	2001 Aug 15	11498278
Role for endothelin-1-induced superoxide and peroxynitrite production in rebound pulmonary hypertension associated with inhaled nitric oxide therapy.	2001 Aug 17	11509453
Effects of molsidomine on scopolamine-induced amnesia and hypermotility in the rat.	2001 Aug 31	11527544
Interleukin-1beta down-regulates the expression of glucuronosyltransferase I, a key enzyme priming glycosaminoglycan biosynthesis: influence of glucosamine on interleukin-1beta-mediated effects in rat chondrocytes.	2001 Feb	11229466
The phosphodiesterase inhibitors pentoxifylline and rolipram suppress macrophage activation and nitric oxide production in vitro and in vivo.	2001 Feb	11161985
Comparison of the effects of nitric oxide, nitroprusside, and nifedipine on hemodynamics and right ventricular contractility in patients with chronic pulmonary hypertension.	2001 Jan	11157594
Gastric mucosal resistance to acute injury in experimental portal hypertension.	2001 Jan	11156591
Ethanol inhibits cytokine-induced iNOS and sPLA2 in immortalized astrocytes: evidence for posttranscriptional site of ethanol action.	2001 Jan-Feb	11173986
15-Deoxy-delta12,14-PGJ2, but not troglitazone, modulates IL-1beta effects in human chondrocytes by inhibiting NF-kappaB and AP-1 activation pathways.	2001 Jul 13	11457450
Effects of Ginkgo biloba extract (EGb 761) and quercetin on lipopolysaccharide-induced release of nitric oxide.	2001 Jul 31	11518563
Prostaglandins and nitric oxide mediate superoxide-induced myocardial contractile dysfunction in isolated rat hearts.	2001 Jun	11444916
Nitric oxide inhalation increases alveolar gas exchange by decreasing deadspace volume.	2001 Jun	11395602
Neonatal pulmonary hypertension--urea-cycle intermediates, nitric oxide production, and carbamoyl-phosphate synthetase function.	2001 Jun 14	11407344
Calcitonin gene-related peptide levels during nitric oxide-induced headache in patients with chronic tension-type headache.	2001 Mar	11284996
Expression of inducible nitric oxide synthase in primary culture of rat bladder smooth muscle cells by plasma from cyclophosphamide-treated rats.	2001 Mar 23	11282106
Sildenafil (viagra) facilitates weaning of inhaled nitric oxide following placement of a biventricular-assist device.	2001 May	11377161
Nitric oxide and chronic HCV and HIV infections.	2001 May	11341651
Acetylcholine and bradykinin enhance hypotension and affect the function of remodeled conduit arteries in SHR and SHR treated with nitric oxide donors.	2005 Jun	15933791
The nitric oxide (NO) donor molsidomine antagonizes scopolamine and L-NAME-induced performance deficits in a spatial memory task in the rat.	2009 Jun 8	19373981
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.	2011 Jun	21641380
Pharmacological screening using an FXN-EGFP cellular genomic reporter assay for the therapy of Friedreich ataxia.	2013	23418481

Patents

Sample Use Guides

In Vivo Use Guide

twice-daily 8-mg tablet

Route of Administration: Intravenous

In Vitro Use Guide

Was studied the action of the biologically active metabolite of molsidomine, N-morpholino-N-nitrosoamino-acetonitrile (SIN), on eicosanoid formation and functional behavior of bovine coronary arteries and human platelets in vitro. Molsidomine itself was inactive

Name

Type

Language

ITRAMIN TOSYLATE

Common Name

English

ITRAMIN TOSYLATE [MI]

Common Name

English

2-AMINOETHANOL NITRATE MONO-P-TOLUENESULFONATE

Common Name

English

ITRAMIN TOSILATE

Official Name

English

itramin tosilate [INN]

Common Name

English

2-AMINOETHANOL NITRATE (ESTER) P-TOLUENESULPHONATE

Common Name

English

2-AMINOETHANOL NITRATE (ESTER) P-TOLUENESULFONATE

Common Name

English

2-NITRATOETHYLAMINOTOLUENE-P-SULPHONATE

Common Name

English

2-AMINOETHANOL NITRATE MONO(4-METHYLBENZENESULPHONATE)

Systematic Name

English

2-AMINOETHANOL NITRATE MONO-P-TOLUENESULPHONATE

Common Name

English

2-AMINOETHANOL NITRATE MONO(4-METHYLBENZENESULFONATE)

Systematic Name

English

2-NITRATOETHYLAMINOTOLUENE-P-SULFONATE

Common Name

English

Itramin tosilate [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC01DX01