Syrosingopine

Syrosingopine is a drug, derived from reserpine. It is used (since about 1960) to treat hypertension.[1][2]

Syrosingopine
Clinical data
Trade namesSingoserp
ATC code
Identifiers
IUPAC name
  • Methyl (3β,16β,17α,18β,20α)-18-({4-[(Ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyl}oxy)-11,17-dimethoxyyohimban-16-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC35H42N2O11
Molar mass666.724 g·mol−1
3D model (JSmol)
SMILES
  • CCOC(=O)Oc1c(cc(cc1OC)C(=O)O[C@@H]2C[C@@H]3CN4CCc5c6ccc(cc6[nH]c5[C@H]4C[C@@H]3[C@@H]([C@H]2OC)C(=O)OC)OC)OC
InChI
  • InChI=1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3/t19-,23+,25-,28-,29+,32+/m1/s1
  • Key:ZCDNRPPFBQDQHR-SSYATKPKSA-N

Research

A combination of the diabetes drug metformin and syrosingopine killed tumor cells in blood samples from leukemia patients, while it did not damage blood cells in samples from healthy patients. The combination of metformin and syrosingopine also reduced or eliminated tumors in mice with malignant liver cancer.[3] The drugs interfere with the cancer cells' glucose (i.e. energy) supply and utilization. Cancer cells have much higher energy requirements than normal cells, making them vulnerable when there is a reduction in the available energy supply. Syrosingopine inhibits the degradation of sugars within the cells.[4]

References
  1. Shelburne PF, Orgain ES (March 1963). "Comparison of syrosingopine and reserpine in the treatment of ambulatory hypertensive patients". The American Journal of the Medical Sciences. 245: 304–10. doi:10.1097/00000441-196303000-00013. PMID 13977067.
  2. Bartels CC (October 1959). "Syrosingopine: a new rauwolfia preparation". The New England Journal of Medicine. 261 (16): 785–8. doi:10.1056/NEJM195910152611603. PMID 13797201.
  3. Benjamin D, Colombi M, Hindupur SK, Betz C, Lane HA, El-Shemerly MY, et al. (December 2016). "Syrosingopine sensitizes cancer cells to killing by metformin". Science Advances. 2 (12): e1601756. Bibcode:2016SciA....2E1756B. doi:10.1126/sciadv.1601756. PMC 5182053. PMID 28028542. We report that the anticancer activity of the widely used diabetic drug metformin is strongly potentiated by syrosingopine. Synthetic lethality elicited by combining the two drugs is synergistic and specific to transformed cells.
  4. "Treating cancer with drugs for diabetes and hypertension". Science Daily. December 27, 2016. Retrieved 18 January 2017. The antihypertensive drug syrosingopine potentiates the anti-cancer efficacy of metformin.
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