TENITRAMINE

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H20N6O12
Molecular Weight	416.2988
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O

InChI

InChIKey=DLDKCSIJFIPYRK-UHFFFAOYSA-N

InChI=1S/C10H20N6O12/c17-13(18)25-7-3-11(4-8-26-14(19)20)1-2-12(5-9-27-15(21)22)6-10-28-16(23)24/h1-10H2

HIDE SMILES / InChI

Molecular Formula	C10H20N6O12
Molecular Weight	416.2988
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19538173https://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=A2http://www.ncbi.nlm.nih.gov/pubmed/6985697https://www.ncbi.nlm.nih.gov/pubmed/13426891 | https://www.ncbi.nlm.nih.gov/pubmed/13284675http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021134s004lbl.pdfhttps://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/19563531https://adisinsight.springer.com/drugs/800005482 | https://www.ncbi.nlm.nih.gov/pubmed/9845803http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020845s016s017lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020215s024lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019790s011lbl.pdfwww.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 20 Target ID: liberation of NO Sources: http://www.ncbi.nlm.nih.gov/pubmed/2242448	Activator 1447
Soluble guanylate cyclase 36 Target ID: CHEMBL2111348 Sources: www.ncbi.nlm.nih.gov/pubmed/18574453	Activator 1447	0.1 µM [EC50]
nitric oxide mediated signal transduction 20 Target ID: GO:0007263 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23927471	Activator 1447
Soluble guanylate cyclase 36 Target ID: CHEMBL2111348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24560804	Activator 1447
Atrial natriuretic peptide receptor A 21 Target ID: CHEMBL1988 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12419094	Activator 1447
Soluble guanylate cyclase 36 Target ID: CHEMBL2111348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10553632	Activator 1447
Soluble guanylate cyclase 36 Target ID: CHEMBL2111348 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021134s004lbl.pdf	Activator 1447
Soluble guanylate cyclase 36 Target ID: CHEMBL2111348 Sources: https://www.google.com/patents/EP2805730A1	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12700285	Primary	Preclinical	Unknown Approved Use Unknown
Hypertensive crises 20 Sources: https://www.drugs.com/pro/sodium-nitroprusside.html#s-34067-9	Primary	Approved 8583	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 106 Sources: https://www.drugs.com/pro/sodium-nitroprusside.html#s-34067-9	Primary	Approved 8583	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 32 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020845s016s017lbl.pdf	Palliative	Approved 8583	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 110 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/019790s011lbl.pdf	Primary	Approved 8583	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 110 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020215s024lbl.pdf	Primary	Approved 8583	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 110 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16644612	Primary	Approved 8583	Unknown Approved Use Unknown
Coronary heart disease 43 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2242448	Primary	Basic research	Unknown Approved Use Unknown
Angina 34 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8583	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 125 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8583	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 575 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8583	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 106 Sources: https://www.drugs.com/monograph/nitroglycerin.html	Primary	Approved 8583	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 110 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 8583	Metamine Approved Use https://www.ncbi.nlm.nih.gov/pubmed/13426891 \| https://www.ncbi.nlm.nih.gov/pubmed/13284675
Angina pectoris 110 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1952976/pdf/brmedj02877-0002.pdf	Primary	Approved 8583	PERITRATE Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
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
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
15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3838399/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
29.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
17.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.89 ng/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.03 ng/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.26 ng/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.08 ng/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
32 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
37 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
32 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
34 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
8 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10 μg/L EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
106.5 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
31.7 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.2 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.4 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
17.54 ng × h/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.5 ng × h/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
0.46 ng × h/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.11 ng × h/mL/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
311 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
423 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
60 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
61 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
335 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
310 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
49 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
70 ng × h/mL EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
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
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
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
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
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
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
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
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
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
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
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3838399/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1955198/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1777378/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
12 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
12 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg 1 times / day multiple, oral dose: 16 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.7 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.2 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
6.6 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.8 h EXPERIMENT https://link.springer.com/article/10.2165/00137696-200402020-00005	16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered:	LINSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

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
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3838399/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		MOLSIDOMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 MRP2 499 K+ channels 73 Ca2+ channels 59 ALDH2 21	ALDH2 21 CYP1A2 1197 CYP2A6 626 CYP2E1 729 CYP4A11 137	OCT1 39

Drug as perpetrator

Target	Modality	Activity
ALDH2 21	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15331769/	no
K+ channels 73	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/S001429990800616X Page: abstract	no
Ca2+ channels 62	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/BF00497774 Page: abstract	yes
MRP2 625	inhibitor 4027 Sources: https://www.ingentaconnect.com/content/ben/dml/2011/00000005/00000001/art00009 Page: abstract	yes
OCT1 656	inducer 1966 Sources: https://www.sciencedirect.com/science/article/abs/pii/S1056871913002578 Page: abstract	yes
P-gp 1932	inhibitor 4027 Sources: https://www.nature.com/articles/aps201225 Page: abstract	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	major
CYP1A2 1197	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2A6 626	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2C9 1193	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2D6 1388	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP2E1 729	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
CYP4A11 137	substrate 4014 Sources: https://febs.onlinelibrary.wiley.com/doi/full/10.1016/S0014-5793%2899%2900612-2	minor
ALDH2 21	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15331769/	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6061	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6061
ChemicalBook	CB2226929	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2226929
eMolecules	30154680	https://www.emolecules.com/cgi-bin/more?vid=30154680
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
ZINC	ZINC000018089317	http://zinc15.docking.org/substances/ZINC000018089317
ChEBI	CHEBI:6062	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6062
ChemicalBook	CB3256697	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3256697
eMolecules	30488208	https://www.emolecules.com/cgi-bin/more?vid=30488208
eMolecules	713614	https://www.emolecules.com/cgi-bin/more?vid=713614
MolPort	MolPort-003-848-286	https://www.molport.com/shop/molecule-link/MolPort-003-848-286
ZINC	ZINC000001849548	http://zinc15.docking.org/substances/ZINC000001849548
ChEBI	CHEBI:28787	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28787
ChemicalBook	CB2145318	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2145318
ZINC	ZINC000008214625	http://zinc15.docking.org/substances/ZINC000008214625
AA Blocks	AA00ILEO	https://www.aablocks.com/goods/Goods/detail?id=AA00ILEO
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
Chemspace	CSSB00016996527	https://chem-space.com/CSSB00016996527
Clearsynth	CS-O-00951	http://www.clearsynth.com/en/CSO00951.html
Lab Network	LN02049364	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02049364
Oakwood	94458	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=79632&ExtHyperLink=1
Smolecule	S585822	https://www.smolecule.com/products/s585822
THE BioTek	bt-433598	https://www.thebiotek.com/product/others/bt-433598
ChEBI	CHEBI:7596	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7596
eMolecules	10397191	https://www.emolecules.com/cgi-bin/more?vid=10397191
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
ABI Chem	AC1L1MPG
ABI Chem	AC1Q21X4
AHH Chemical co.,ltd	MT-57727	http://www.ahhchemical.com/product/MT-57727.html
AN PharmaTech	AN-23936
Chemhere	Achem162548
Chemieliva Pharmaceutical Co., Ltd	PBCM0000174
ChemMol	49416736	http://www.chemmol.com/chemmol/49416736.html
ChemMol	99151477	http://www.chemmol.com/chemmol/99151477.html
Compound Cloud	6518
Hangzhou Yuhao Chemical Technology	LL0106
LGC Standards	DRE-LA15589000AL	https://www.lgcstandards.com/US/en/p/DRE-LA15589000AL
NovoSeek	6518
SelectLab Chemicals GmbH	Ex187
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
Sigma Aldrich	ERP-109S
Sigma Aldrich	P-037
Smolecule	S567259	https://www.smolecule.com/products/s567259
Tetrahedron	TS61261
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0472
Yuhao Chemical	LL0106	http://www.chemyuhao.com/78-11-5.html
ZINC	ZINC000008101167	http://zinc15.docking.org/substances/ZINC000008101167

PubMed

Title	Date	PubMed
[The effects of sodiumnitroprusside and trimethaphan induced hypotension on haemodynamics and myocardial oxygen consumption (author's transl)].	1976 Jan	1259127
Venodilator effects of adenosine triphosphate and sodium nitroprusside; comparisons during controlled hypotension.	1987 Sep 1	15235850
Rat renal papillary release of hypotensive substances in vitro.	1991 Aug	1655886
Effects of fenoldopam on renal blood flow and systemic hemodynamics during isoflurane anesthesia.	1991 Feb	1678284
ACTH and vasopressin responses to insulin-induced hypoglycemia in intact and neurohypophysectomized conscious dogs.	1991 Jan	1646414
Blood pressure, pulse, and neurohumoral responses to nitroprusside-induced hypotension in normotensive aging men.	1991 Jul	1677019
Comparative cardiovascular effects of SNP, ATP and phentolamine during norepinephrine-induced hypertension in dogs.	1991 Oct	15278610
Effect of hypotension and hyperosmolality on vasopressin and ACTH responses to hypoglycemia in conscious dogs.	1992 Aug	1324617
Bradykinin-induced activation of nociceptors: receptor and mechanistic studies on the neonatal rat spinal cord-tail preparation in vitro.	1992 Dec	1334751
Cardiovascular function during induced hypotension by fenoldopam or sodium nitroprusside in anesthetized dogs.	1992 Jan	1346487
The ATP-sensitive K+ channel mediates hypotension in endotoxemia and hypoxic lactic acidosis in dog.	1992 Jun	1602014
[Effects of deliberate hypotension on the ischemic heart during isoflurane anesthesia--a comparison of prostaglandin E1 and sodium nitroprusside].	1992 Sep	1433870
[The effects of sodium nitroprusside-induced hypotension at different levels on cerebral blood flow and metabolism: a clinical study].	2000 Aug	12903451
Serotonin(3) receptor stimulation in the nucleus tractus solitarii activates non-catecholaminergic neurons in the rat ventrolateral medulla.	2002	12088752
Elevated vascular resistance after labetalol during resection of a pheochromocytoma (brief report).	2002 Feb	11823392
Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity.	2002 Oct	12433056
JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity.	2003 Apr	12700285
Internal thoracic artery flow competition: studies in a canine H-graft model.	2003 Jan	12493505
A-350619: a novel activator of soluble guanylyl cyclase.	2003 Jan 17	12495780
Sodium nitroprusside-induced deliberate hypotension to facilitate patent ductus arteriosus ligation in dogs.	2003 Jul-Aug	12865995
Cocaine- and amphetamine-regulated transcript is present in hypothalamic neuroendocrine neurones and is released to the hypothalamic-pituitary portal circuit.	2003 Mar	12588509
Differential toxicity of nitric oxide, aluminum, and amyloid beta-peptide in SN56 cholinergic cells from mouse septum.	2003 Mar	12470706
Hypothermia does not alter somatosensory evoked potential amplitude and global cerebral oxygen extraction during marked sodium nitroprusside-induced arterial hypotension.	2003 May	12717132
Zinc released from metallothionein-iii may contribute to hippocampal CA1 and thalamic neuronal death following acute brain injury.	2003 Nov	14637104
Receptor activity modifying protein 2 distribution in the rat central nervous system and regulation by changes in blood pressure.	2003 Sep	12899678
The role of endogenous heme synthesis and degradation domain cysteines in cellular iron-dependent degradation of IRP2.	2003 Sep-Oct	12972033
Esmolol attenuates hepatic blood flow responses during sodium nitroprusside-induced hypotension in dogs.	2004 Apr	15064263
Nitric oxide donor sodium nitroprusside dilates rat small arteries by activation of inward rectifier potassium channels.	2004 Apr	14993195
Additive antinociceptive effect of the combination of diazoxide, an activator of ATP-sensitive K+ channels, and sodium nitroprusside and dibutyryl-cGMP.	2004 Apr 5	15063156
Diminished baroreflex control of heart rate responses in otoconia-deficient C57BL/6JEi head tilt mice.	2004 Aug	15059776
Relationship between carbamoyl-phosphate synthetase genotype and systemic vascular function.	2004 Feb	14718356
Intrapericardial delivery enhances cardiac effects of sotalol and atenolol.	2004 Jul	15175557
Effects of TNF-alpha and IFN-gamma on nitric oxide-induced neurotoxicity in the mouse brain.	2004 Jun 1	15153526
Down-regulation of survivin in nitric oxide-induced cell growth inhibition and apoptosis of the human lung carcinoma cells.	2004 May 7	14988404
The inhibitory effect of sodium nitroprusside on HIF-1 activation is not dependent on nitric oxide-soluble guanylyl cyclase pathway.	2004 Nov 5	15465035
Regulation of cytoplasmic stress granules by apoptosis-inducing factor.	2004 Sep 1	15316071
Intracavernous sodium nitroprusside (SNP) versus papaverine/phentolamine in erectile dysfunction: a comparative study of short-term efficacy and side-effects.	2005 Jan	16422914
Dynamic beat-to-beat modeling of the QT-RR interval relationship: analysis of QT prolongation during alterations of autonomic state versus human ether a-go-go-related gene inhibition.	2005 Jan	15306635
Effects of sodium nitroprusside, a nitric oxide donor, on gamma-aminobutyric acid concentration in the brain and on picrotoxin-induced convulsions in combination with phenobarbitone in rats.	2005 Mar	15740777
Effect of nitric oxide on mitochondrial respiratory activity of human articular chondrocytes.	2005 Mar	15708893
Nitric oxide induces oral squamous cell carcinoma cells apoptosis with p53 accumulation.	2005 Sep	15979383
Antitumor activity of JS-K [O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O2-aryl diazeniumdiolates in vitro and in vivo.	2006 Jul 13	16821795
Labetalol pretreatment reduces blood pressure instability during surgical resection of pheochromocytoma.	2006 Mar	16520833
Iron released by sodium nitroprusside contributes to heme oxygenase-1 induction via the cAMP-protein kinase A-mitogen-activated protein kinase pathway in RAW 264.7 cells.	2006 May	16439612
Inhibitors of inducible nitric oxide (NO) synthase are more effective than an NO donor in reducing carbon-tetrachloride induced acute liver injury.	2006 Nov	16874658
Ablation of NK1 receptor bearing neurons in the nucleus of the solitary tract blunts cardiovascular reflexes in awake rats.	2006 Nov 13	16982039
JS-K, a nitric oxide prodrug, induces cytochrome c release and caspase activation in HL-60 myeloid leukemia cells.	2006 Oct	16439016
Cytotoxicity of nitric oxide is alleviated by zinc-mediated expression of antioxidant genes.	2006 Oct	17018880
Melittin inhibits inflammatory target gene expression and mediator generation via interaction with IkappaB kinase.	2007 Jan 15	17067557
JS-K, a GST-activated nitric oxide generator, induces DNA double-strand breaks, activates DNA damage response pathways, and induces apoptosis in vitro and in vivo in human multiple myeloma cells.	2007 Jul 15	17384201

Patents

Sample Use Guides

In Vivo Use Guide

mice were treated three times a week for 3 weeks with intravenous tail vein injections of either vehicle (2.25% Pluronic P123 in PBS) or JS-K (6 μmol/kg in the vehicle).

Route of Administration: Intravenous

In Vitro Use Guide

Human U87 cells (HTB-14), fibroblasts (CRL-1634), and astrocytes (CRL-8621; ATCC) were cultured in Dulbecco’s Minimal Essential Eagle Medium (DMEM; Gibco, USA) supplemented with 10% fetal calf serum (FCS) and penicillin (100U/mL)/streptomycin (100mg/mL) under normoxic conditions (95% air, 5% CO2, and 37°C). The nitric oxide donor JS-K (O2-(2.4-dinitrophenyl) 1-[(4-ethoxycarbonyl) piperazin-1-yl] diazen-1-ium1,2-diolate, CAS 7054 32-12-8) was dissolved in 100% dimethyl sulfoxide (DMSO) in a concentration of 5.2mM. U87 was incubated with JS-K doses of 0–15µM for 4 h. The JS-K solvent control (DMSO≤1%) was adjusted to the highest JS-K concentration used in these experiments. A cesium source emitting γ-radiation was used for radiotherapy (RT; 3×2Gy) with a 24-h interval between each RT dose (Isotopen Diagnostik CIS, Germany).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:53:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:53:52 GMT 2025`
Record UNII	CKB16BAQ3S
Record Status	`Validated (UNII)`
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Name

Type

Language

2-(2-BIS(2-NITROOXYETHYL)AMINO)ETHYL-(2-NITROOXYETHYL)AMINO)ETHYL NITRATE

Preferred Name

English

TENITRAMINE

Common Name

English

TENITRAMINE [MART.]

Common Name

English

ETHANOL, 2,2',2'',2'''-(ETHYLENEDINITRILO)TETRA-, TETRANITRATE (ESTER)

Common Name

English

ETHANOL, 2,2',2'',2'''-(1,2-ETHANEDIYLDINITRILO)TETRAKIS-, 1,1',1'',1'''-TETRANITRATE

Common Name

English

ETHANOL, 2,2',2'',2'''-(ETHYLENEDINITRILO)TETRA-, TETRANITRATE

Systematic Name

English

ETHANOL, 2,2',2'',2'''-(1,2-ETHANEDIYLDINITRILO)TETRAKIS-, TETRANITRATE (ESTER)

Common Name

English

Tenitramine [WHO-DD]

Common Name

English

N,N,N',N'-TETRAKIS(HYDROXYETHYL)ETHYLENEDIAMINE TETRANITRATE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC01DA38