S-Ethylisothiouronium diethylphosphate

S-Ethylisothiouronium diethylphosphate
Clinical data
Trade names	Difetur
Identifiers
	IUPAC name S-Ethylisothiouronium diethylphosphate;
CAS Number	21704-46-1;
PubChem CID	11847634;
ChemSpider	182755;
UNII	CTD25O6OBI;
CompTox Dashboard (EPA)	DTXSID60176093 ;
Chemical and physical data
Formula	C7H19N2O4PS
Molar mass	258.27 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=P(OCC)(O)OCC.[N@H]=C(SCC)N;
	InChI InChI=1S/C4H11O4P.C3H8N2S/c1-3-7-9(5,6)8-4-2;1-2-6-3(4)5/h3-4H2,1-2H3,(H,5,6);2H2,1H3,(H3,4,5); Key:CSYSULGPHGCBQD-UHFFFAOYSA-N;

S-Ethylisothiouronium diethylphosphate (brand name Difetur) is an S-alkylisothiouronium derivative used as an antihypotensive drug. The S-alkylisothiouronium compounds are used in processes of treating acute hypotension, which may result, for example, from shock or hemorrhage, and in processes for treating hyperoxic conditions, for example, oxygen poisoning.[1]

Indications

It is used for increasing arterial blood pressure in cases of acute arterial hypotension due to surgical interference, trauma, poisoning, shock condition, hemorrhages; in conjunction with epidural anesthesia; in overdose of ganglion blockers, alpha-adrenergic blockers, neuroleptics, anesthetics; and in other conditions when adrenomimetics are contra-indicated or ineffective. Difetur was also found to possess oxygen protective activity and, thus, can be used as a medicament for protecting against oxygen poisoning conditions caused by hyperoxia.[1]

S-Ethylisothiouronium diethylphosphate is also used for the treatment of headaches, in particular, migraines, as well as for the prevention or treatment of nausea and vomiting, effective in preventing or alleviating emesis associated with migraines or other medical conditions such as chemotherapy or radiotherapy, as well as other symptoms of migraines including phonophobia and photophobia.[2]

Mechanism of action

S-Ethylisothiouronium diethylphosphate is a specific inhibitor of inducible NO synthase on hepatic NO production level.[3][4][5] S-Ethylisothiouronium diethylphosphate affects systemic hemodynamic indices in the following way: the peripheral vascular resistance increases, the stroke volume and central blood volume increase, and the work of the left ventricle improves. Other effects are: analgesic, uterotonic,[6] decongestive[7] and anti-inflammatory.[8]

In difetur’s antihypotensive effect unlike sympathomimetics there is no stimulation of the sympathetic system,thus does not cause tachycardia, nor alter the acid-base balance and electrolyte and does not cause hypotension secondary. These drugs have also sedative action, reduce body temperature and oxygen consumption.

Forms

Injectable solution 10%-1 ml in ampules N 10.

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References

WO application 9813036, "Pharmaceutical Compositions Comprising S-Alkylisothiouronium Derivatives", published 2 April 1998
US application 7148208, Barkan R, Mirimsky A, "Pharmaceutical compositions for headache, migraine, nausea and emesis", published 8 January 2004
Garvey EP, Oplinger JA, Tanoury GJ, Sherman PA, Fowler M, Marshall S, Harmon MF, Paith JE, Furfine ES (October 1994). "Potent and selective inhibition of human nitric oxide synthases. Inhibition by non-amino acid isothioureas" (PDF). The Journal of Biological Chemistry. 269 (43): 26669–76. PMID 7523409.
Proskuriakov SI, Ulianova LP, Skvotsov VG, Budagov RS (2005). "[The estimation of the nitric oxide role in the aggravation of combined radiation-thermal injuries]". Radiatsionnaia Biologiia, Radioecologiia (in Russian). 45 (3): 316–9. PMID 16080623.
Budagov RS, Ulianova LP, Proskuryakov SY (2006). "Nitric Oxide Level Increasing and Hyperfibrinogenemia in the Pathogenesis of Combined Radiation-Thermal Injuries". Cytokines & inflammation (1).
US application 2010305210, Barkan R, Ghicavii V, "S-Alkylisothiouronium Derivatives for Treating Abnormal Uterine Bleeding Disorders", published 2 December 2010, assigned to Barkan Pharma SRL
Sandu A. EUROINVENT 2009. Exhibition Catalogue (PDF). ISBN 978-973-702-641-5.
WO application 2007108004, "S-Alkylisothiouronium Derivatives for the Treatment of Inflammatory Diseases", published 27 September 2007, assigned to Barkan Pharma SRL

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[patent6160008-1] WO application 9813036, "Pharmaceutical Compositions Comprising S-Alkylisothiouronium Derivatives", published 2 April 1998

[2] US application 7148208, Barkan R, Mirimsky A, "Pharmaceutical compositions for headache, migraine, nausea and emesis", published 8 January 2004

[pmid7523409-3] Garvey EP, Oplinger JA, Tanoury GJ, Sherman PA, Fowler M, Marshall S, Harmon MF, Paith JE, Furfine ES (October 1994). "Potent and selective inhibition of human nitric oxide synthases. Inhibition by non-amino acid isothioureas" (PDF). The Journal of Biological Chemistry. 269 (43): 26669–76. PMID 7523409.

[pmid16080623-4] Proskuriakov SI, Ulianova LP, Skvotsov VG, Budagov RS (2005). "[The estimation of the nitric oxide role in the aggravation of combined radiation-thermal injuries]". Radiatsionnaia Biologiia, Radioecologiia (in Russian). 45 (3): 316–9. PMID 16080623.

[5] Budagov RS, Ulianova LP, Proskuryakov SY (2006). "Nitric Oxide Level Increasing and Hyperfibrinogenemia in the Pathogenesis of Combined Radiation-Thermal Injuries". Cytokines & inflammation (1).

[6] US application 2010305210, Barkan R, Ghicavii V, "S-Alkylisothiouronium Derivatives for Treating Abnormal Uterine Bleeding Disorders", published 2 December 2010, assigned to Barkan Pharma SRL

[7] Sandu A. EUROINVENT 2009. Exhibition Catalogue (PDF). ISBN 978-973-702-641-5.

[8] WO application 2007108004, "S-Alkylisothiouronium Derivatives for the Treatment of Inflammatory Diseases", published 27 September 2007, assigned to Barkan Pharma SRL