Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H16N2O2 |
| Molecular Weight | 304.3425 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=CC=C(O1)C2=NN(CC3=CC=CC=C3)C4=C2C=CC=C4
InChI
InChIKey=OQQVFCKUDYMWGV-UHFFFAOYSA-N
InChI=1S/C19H16N2O2/c22-13-15-10-11-18(23-15)19-16-8-4-5-9-17(16)21(20-19)12-14-6-2-1-3-7-14/h1-11,22H,12-13H2
Lificiguat (YC-1) [3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole], a chemically synthetic benzylindazole compound, is a direct soluble guanylate cyclase activator. It possessed antiplatelet activity. YC-1 inhibits Hypoxia-inducible factor-1 (HIF-1). YC-1 demonstrated antineoplastic potential both in vitro and in vivo in animal models.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12761342 | https://www.ncbi.nlm.nih.gov/pubmed/12761328
Curator's Comment: Lificiguat (YC-1) is CNS active in animals. No human data available.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Suppression of hypoxia inducible factor-1alpha (HIF-1alpha) by YC-1 is dependent on murine double minute 2 (Mdm2). | 2006-10-06 |
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| Carbon monoxide released by CORM-3 inhibits human platelets by a mechanism independent of soluble guanylate cyclase. | 2006-07-15 |
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| A domain responsible for HIF-1alpha degradation by YC-1, a novel anticancer agent. | 2006-07 |
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| YC-1 induces S cell cycle arrest and apoptosis by activating checkpoint kinases. | 2006-06-15 |
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| Penile erection requires association of soluble guanylyl cyclase with endothelial caveolin-1 in rat corpus cavernosum. | 2006-05 |
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| Molecular mechanisms underlying rat mesenteric artery vasorelaxation induced by the nitric oxide-independent soluble guanylyl cyclase stimulators BAY 41-2272 [5-cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine] and YC-1 [3-(5'-hydroxymethyl-2'-furyl)-1-benzyl Indazole]. | 2006-04 |
|
| Sulindac independently modulates extracellular signal-regulated kinase 1/2 and cyclic GMP-dependent protein kinase signaling pathways. | 2006-03 |
|
| YC-1-like potentiation of NO-dependent activation of soluble guanylate cyclase by derivatives of protoporphyrin IX. | 2006-03 |
|
| The design and synthesis of YC-1 analogues as probes for soluble guanylate cyclase. | 2006-02 |
|
| YC-1 [3-(5'-hydroxymethyl-2'-furyl)-1-benzyl indazole] inhibits neointima formation in balloon-injured rat carotid through suppression of expressions and activities of matrix metalloproteinases 2 and 9. | 2006-01 |
|
| Comparative relaxant effects of YC-1 and DEA/NO on the sheep sphincter of Oddi. | 2006 |
|
| BAY 41-2272, a potent activator of soluble guanylyl cyclase, stimulates calcium elevation and calcium-activated potassium current in pituitary GH cells. | 2005-12 |
|
| YC-1 suppresses constitutive nuclear factor-kappaB activation and induces apoptosis in human prostate cancer cells. | 2005-10 |
|
| Altered vascular reactivity in mice made hypertensive by nitric oxide synthase inhibition. | 2005-10 |
|
| Activation of protein kinase G up-regulates expression of 15-lipoxygenase-1 in human colon cancer cells. | 2005-09-15 |
|
| Interference of neutrophil-platelet interaction by YC-1: a cGMP-dependent manner on heterotypic cell-cell interaction. | 2005-09-05 |
|
| Enhanced responsiveness to nitric oxide, nitroxyl anions, and nitrergic transmitter by 3-(5'-hydroxymethyl-2'-furyl)-1-benzyl indazole in the rat anococcygeus muscle. | 2005-09 |
|
| Nitric oxide/cyclic guanosine monophosphate signaling in the central complex of the grasshopper brain inhibits singing behavior. | 2005-07-25 |
|
| Comparative relaxant effects of YC-1 and DETA/NO on spontaneous contractions and the levels of cGMP of isolated pregnant rat myometrium. | 2005-07-11 |
|
| YC-1-inhibited proliferation of rat mesangial cells through suppression of cyclin D1-independent of cGMP pathway and partially reversed by p38 MAPK inhibitor. | 2005-07-04 |
|
| Nitric oxide upregulates induction of PDGF receptor-alpha expression in rat renal mesangial cells and in anti-Thy-1 glomerulonephritis. | 2005-07 |
|
| YC-1 [3-(5'-hydroxymethyl-2'-furyl)-1-benzyl indazole] inhibits endothelial cell functions induced by angiogenic factors in vitro and angiogenesis in vivo models. | 2005-07 |
|
| Dynamic association of nitric oxide downstream signaling molecules with endothelial caveolin-1 in rat aorta. | 2005-07 |
|
| The nitric oxide donor sodium nitroprusside stimulates the Na+-K+ pump in isolated rabbit cardiac myocytes. | 2005-06-15 |
|
| Resonance Raman and infrared spectroscopic studies of high-output forms of human soluble guanylyl cyclase. | 2005-04-06 |
|
| Enhancement of learning behaviour by a potent nitric oxide-guanylate cyclase activator YC-1. | 2005-03 |
|
| [Hypoxia-inducible factor 1: regulation, involvement in carcinogenesis and target for anticancer therapy]. | 2005-02 |
|
| CORM-A1: a new pharmacologically active carbon monoxide-releasing molecule. | 2005-02 |
|
| Soluble guanylyl cyclase during postnatal porcine pulmonary maturation. | 2005-01 |
|
| Nerve-induced release of nitric oxide from the rabbit corpus cavernosum is modulated by cyclic guanosine 3',5'-monophosphate. | 2005 |
|
| The blockade of cyclopiazonic acid-induced store-operated Ca2+ entry pathway by YC-1 in neutrophils. | 2004-11-15 |
|
| Activation of soluble guanylyl cyclase inhibits estradiol production and cyclic AMP accumulation from cultured rat granulosa cells. | 2004-10 |
|
| New anticancer strategies targeting HIF-1. | 2004-09-15 |
|
| An evolutionarily conserved mechanism for sensitization of soluble guanylyl cyclase reveals extensive nitric oxide-mediated upregulation of cyclic GMP in insect brain. | 2004-09 |
|
| YC-1-induced cyclooxygenase-2 expression is mediated by cGMP-dependent activations of Ras, phosphoinositide-3-OH-kinase, Akt, and nuclear factor-kappaB in human pulmonary epithelial cells. | 2004-09 |
|
| Soluble guanylyl cyclase is localised in the acinar cells and participates in amylase secretion in rat parotid gland. | 2004-09 |
|
| Downregulation of cGMP-dependent protein kinase expression by inflammatory cytokines in vascular smooth muscle cells. | 2004-07 |
|
| Resonance Raman study on synergistic activation of soluble guanylate cyclase by imidazole, YC-1 and GTP. | 2004-05 |
|
| Versatile pharmacological actions of YC-1: anti-platelet to anticancer. | 2004-04-15 |
|
| Inhibition of phosphodiesterase type 5 by the activator of nitric oxide-sensitive guanylyl cyclase BAY 41-2272. | 2004-04-13 |
|
| Inhibitory mechanisms of YC-1 and PMC in the induction of iNOS expression by lipoteichoic acid in RAW 264.7 macrophages. | 2004-04-01 |
|
| Microsomal prostaglandin E synthase-1 is overexpressed in inflammatory bowel disease. Evidence for involvement of the transcription factor Egr-1. | 2004-03-26 |
|
| Functional characterization of nitric oxide and YC-1 activation of soluble guanylyl cyclase: structural implication for the YC-1 binding site? | 2004-03-23 |
|
| Antiaggregating and antithrombotic activities of new 1, 2, 3-triazolecarboxamides. | 2004-03 |
|
| The inhibitory mechanism of YC-1, a benzyl indazole, on smooth muscle cell proliferation: an in vitro and in vivo study. | 2004-03 |
|
| Involvement of the cGMP signalling pathway in the regulation of viability in insulin-secreting BRIN-BD11 cells. | 2004-02-13 |
|
| Analysis of nitric oxide-sensitive guanylyl cyclase in human platelets before and after aggregation. | 2004-01-10 |
|
| YC-1, a nitric oxide-independent activator of soluble guanylate cyclase, inhibits the spontaneous contractions of isolated pregnant rat myometrium. | 2004-01 |
|
| Contribution of cGMP but not peroxynitrite to negative feedback regulation of penile erection elicited by nitric oxide in the hippocampal formation of the rat. | 2004-01 |
|
| The NO signaling pathway differentially regulates KCC3a and KCC3b mRNA expression. | 2003-11 |
Patents
Sample Use Guides
Lificiguat (YC-1) was tested on in vivo model of pulmonary arterial hypertension. To assess preventive or therapeutic effects, randomized mice were subjected to once daily i.p. injections of YC-1 for the entire hypoxic period (5 mg/kg) or for the last seven days of a 28-day hypoxic period (5 and 10 mg/kg).
Route of Administration:
Intraperitoneal
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C29707
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ACTIVE MOIETY
