94079-80-8,MFCD00865953
Catalog No.:AA006SL7

94079-80-8 | Cicaprost

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Purity
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1mg
≥98%
in stock  
$606.00   $424.00
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5mg
≥98%
in stock  
$2,538.00   $1,776.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA006SL7
Chemical Name:
Cicaprost
CAS Number:
94079-80-8
Molecular Formula:
C22H28O3
Molecular Weight:
340.4559
MDL Number:
MFCD00865953
SMILES:
CCC#CC[C@@H]([CH]C#C[C@H]1[CH]C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)C
Properties
Computed Properties
 
Complexity:
683  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
1  
Formal Charge:
0  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.1  

Literature

Title: A Prostacyclin Analog, Cicaprost, Exhibits Potent Anti-Inflammatory Activity in Human Primary Immune Cells and a Uveitis Model.

Journal: Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20170401

Title: Prostacyclin receptor-dependent inhibition of human erythroleukemia cell differentiation is STAT3-dependent.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20120301

Title: Prostaglandin I2 signaling drives Th17 differentiation and exacerbates experimental autoimmune encephalomyelitis.

Journal: PloS one 20120101

Title: PGI2 as a regulator of CD4+ subset differentiation and function.

Journal: Prostaglandins & other lipid mediators 20111101

Title: Glial cells isolated from dorsal root ganglia express prostaglandin E(2) (EP(4)) and prostacyclin (IP) receptors.

Journal: European journal of pharmacology 20110701

Title: Smooth muscle proliferation and role of the prostacyclin (IP) receptor in idiopathic pulmonary arterial hypertension.

Journal: American journal of respiratory and critical care medicine 20101101

Title: Activation of prostanoid EP receptors by prostacyclin analogues in rabbit iliac artery: implications for anti-restenotic potential.

Journal: European journal of pharmacology 20100901

Title: Cell-type- and cell-cycle-specific anti-mitogenesis by cicaprost.

Journal: Prostaglandins & other lipid mediators 20100901

Title: Dominant negative actions of human prostacyclin receptor variant through dimerization: implications for cardiovascular disease.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20100901

Title: Prostacyclin receptor suppresses cardiac fibrosis: role of CREB phosphorylation.

Journal: Journal of molecular and cellular cardiology 20100801

Title: Cyclooxygenase-2-dependent prostacyclin formation and blood pressure homeostasis: targeted exchange of cyclooxygenase isoforms in mice.

Journal: Circulation research 20100205

Title: Recycling of the human prostacyclin receptor is regulated through a direct interaction with Rab11a GTPase.

Journal: Cellular signalling 20081201

Title: Prostacyclin receptor-induced STAT3 phosphorylation in human erythroleukemia cells is mediated via Galpha(s) and Galpha(16) hybrid signaling.

Journal: Cellular signalling 20081101

Title: Agonist-dependent internalization and trafficking of the human prostacyclin receptor: a direct role for Rab5a GTPase.

Journal: Biochimica et biophysica acta 20081001

Title: Differential regulation of RhoA-mediated signaling by the TPalpha and TPbeta isoforms of the human thromboxane A2 receptor: independent modulation of TPalpha signaling by prostacyclin and nitric oxide.

Journal: Cellular signalling 20080801

Title: Prostaglandin I2 analogs inhibit Th1 and Th2 effector cytokine production by CD4 T cells.

Journal: Journal of leukocyte biology 20070301

Title: Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060717

Title: Lack of interaction between prostaglandin E2 receptor subtypes in regulating adenylyl cyclase activity in cultured rat dorsal root ganglion cells.

Journal: European journal of pharmacology 20060327

Title: Prostacyclin receptor induces STAT1 and STAT3 phosphorylations in human erythroleukemia cells: a mechanism requiring PTX-insensitive G proteins, ERK and JNK.

Journal: Cellular signalling 20060301

Title: Evidence that inward rectifier K+ channels mediate relaxation by the PGI2 receptor agonist cicaprost via a cyclic AMP-independent mechanism.

Journal: Cardiovascular research 20060101

Title: Augmented cardiac hypertrophy in response to pressure overload in mice lacking the prostaglandin I2 receptor.

Journal: Circulation 20050705

Title: The effect of the farnesyl protein transferase inhibitor SCH66336 on isoprenylation and signalling by the prostacyclin receptor.

Journal: The Biochemical journal 20050215

Title: Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins.

Journal: Circulation research 20050107

Title: Dimerization of the human receptors for prostacyclin and thromboxane facilitates thromboxane receptor-mediated cAMP generation.

Journal: The Journal of biological chemistry 20041217

Title: Reduced IP receptors in STZ-induced diabetic rat kidneys and high-glucose-treated mesangial cells.

Journal: American journal of physiology. Renal physiology 20041001

Title: Activation of IP prostanoid receptors prevents cardiomyocyte hypertrophy via cAMP-dependent signaling.

Journal: American journal of physiology. Heart and circulatory physiology 20040901

Title: Mechanism of cicaprost-induced desensitization in rat pulmonary artery smooth muscle cells involves a PKA-mediated inhibition of adenylyl cyclase.

Journal: American journal of physiology. Lung cellular and molecular physiology 20040801

Title: Antimitogenesis linked to regulation of Skp2 gene expression.

Journal: The Journal of biological chemistry 20040709

Title: Agonists can discriminate between cloned human and mouse prostacyclin receptors.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20040501

Title: Characterization of the PGI2/IP system in cultured rat mesangial cells.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20040501

Title: Excitatory action of prostanoids on the ferret isolated vagus nerve preparation.

Journal: European journal of pharmacology 20040426

Title: Prostacyclin receptor-mediated activation of extracellular signal-regulated kinases 1 and 2.

Journal: Cellular signalling 20040401

Title: Induction of hyaluronic acid synthase 2 (HAS2) in human vascular smooth muscle cells by vasodilatory prostaglandins.

Journal: Circulation research 20040319

Title: Comparative analysis of the in vivo angiogenic properties of stable prostacyclin analogs: a possible role for peroxisome proliferator-activated receptors.

Journal: Journal of molecular and cellular cardiology 20040301

Title: Asymmetric synthesis of the highly potent anti-metastatic prostacyclin analogue cicaprost and its isomer isocicaprost.

Journal: Journal of the American Chemical Society 20030813

Title: Prostacylin receptor activation inhibits proliferation of aortic smooth muscle cells by regulating cAMP response element-binding protein- and pocket protein-dependent cyclin a gene expression.

Journal: Molecular pharmacology 20030801

Title: Protein kinase A-dependent coupling of mouse prostacyclin receptors to Gi is cell-type dependent.

Journal: European journal of pharmacology 20030801

Title: Long-term-desensitization of prostacyclin receptors is independent of the C-terminal tail.

Journal: Biochemical pharmacology 20030615

Title: Prostanoid-induced modulation of neuropeptide Y and noradrenaline release from the rat mesenteric bed.

Journal: Autonomic & autacoid pharmacology 20030401

Title: Facilitation by endogenous prostaglandins of capsaicin-induced gastric protection in rodents through EP2 and IP receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20030301

Title: Cyclooxygenase-2 acts as an endogenous brake on endothelin-1 release by human pulmonary artery smooth muscle cells: implications for pulmonary hypertension.

Journal: Molecular pharmacology 20021101

Title: Investigation of the mechanisms of G protein: effector coupling by the human and mouse prostacyclin receptors. Identification of critical species-dependent differences.

Journal: The Journal of biological chemistry 20020726

Title: In vitro pharmacological characterization of the prostanoid receptor population in the non-pregnant porcine myometrium.

Journal: European journal of pharmacology 20020503

Title: Investigation of a functional requirement for isoprenylation by the human prostacyclin receptor.

Journal: European journal of biochemistry 20020301

Title: Differential effects of stable prostacyclin analogs on smooth muscle proliferation and cyclic AMP generation in human pulmonary artery.

Journal: American journal of respiratory cell and molecular biology 20020201

Title: Central nociceptive role of prostacyclin (IP) receptor induced by peripheral inflammation.

Journal: Neuroreport 20020121

Title: Prostacyclin receptor-independent inhibition of phospholipase C activity by non-prostanoid prostacyclin mimetics.

Journal: British journal of pharmacology 20011201

Title: Factors affecting prostacyclin receptor agonist efficacy in different cell types.

Journal: Cellular signalling 20011101

Title: Protein kinase A-mediated phosphorylation of serine 357 of the mouse prostacyclin receptor regulates its coupling to G(s)-, to G(i)-, and to G(q)-coupled effector signaling.

Journal: The Journal of biological chemistry 20010907

Title: Distinction between relaxations induced via prostanoid EP(4) and IP(1) receptors in pig and rabbit blood vessels.

Journal: British journal of pharmacology 20010901

Title: A functional study on prostanoid receptors involved in cultured human iridal melanocyte stimulation.

Journal: Experimental eye research 20010701

Title: Regulation of prostacyclin and prostaglandin E(2) receptor mediated responses in adult rat dorsal root ganglion cells, in vitro.

Journal: British journal of pharmacology 20010501

Title: Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation.

Journal: Journal of leukocyte biology 20010401

Title: Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.

Journal: Journal of physiology, Paris 20010101

Title: The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.

Journal: Biochimica et biophysica acta 20000117

Title: The effect of indomethacin and prostacyclin agonists on blood pressure in a rat model of preeclampsia.

Journal: American journal of obstetrics and gynecology 19990501

Title: Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.

Journal: British journal of pharmacology 19970901

Title: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.

Journal: British journal of pharmacology 19970901

Title: Relaxant actions of nonprostanoid prostacyclin mimetics on human pulmonary artery.

Journal: Journal of cardiovascular pharmacology 19970401

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Tags:94079-80-8 Molecular Formula|94079-80-8 MDL|94079-80-8 SMILES|94079-80-8 Cicaprost
Catalog No.: AA006SL7
94079-80-8,MFCD00865953
94079-80-8 | Cicaprost
Pack Size: 1mg
Purity: ≥98%
in stock
$606.00 $424.00
Pack Size: 5mg
Purity: ≥98%
in stock
$2,538.00 $1,776.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA006SL7
Chemical Name: Cicaprost
CAS Number: 94079-80-8
Molecular Formula: C22H28O3
Molecular Weight: 340.4559
MDL Number: MFCD00865953
SMILES: CCC#CC[C@@H]([CH]C#C[C@H]1[CH]C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)C
Properties
Complexity: 683  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 6  
Defined Bond Stereocenter Count: 1  
Formal Charge: 0  
Heavy Atom Count: 27  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 6  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.1  
Literature fold

Title: A Prostacyclin Analog, Cicaprost, Exhibits Potent Anti-Inflammatory Activity in Human Primary Immune Cells and a Uveitis Model.

Journal: Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics20170401

Title: Prostacyclin receptor-dependent inhibition of human erythroleukemia cell differentiation is STAT3-dependent.

Journal: Prostaglandins, leukotrienes, and essential fatty acids20120301

Title: Prostaglandin I2 signaling drives Th17 differentiation and exacerbates experimental autoimmune encephalomyelitis.

Journal: PloS one20120101

Title: PGI2 as a regulator of CD4+ subset differentiation and function.

Journal: Prostaglandins & other lipid mediators20111101

Title: Glial cells isolated from dorsal root ganglia express prostaglandin E(2) (EP(4)) and prostacyclin (IP) receptors.

Journal: European journal of pharmacology20110701

Title: Smooth muscle proliferation and role of the prostacyclin (IP) receptor in idiopathic pulmonary arterial hypertension.

Journal: American journal of respiratory and critical care medicine20101101

Title: Activation of prostanoid EP receptors by prostacyclin analogues in rabbit iliac artery: implications for anti-restenotic potential.

Journal: European journal of pharmacology20100901

Title: Cell-type- and cell-cycle-specific anti-mitogenesis by cicaprost.

Journal: Prostaglandins & other lipid mediators20100901

Title: Dominant negative actions of human prostacyclin receptor variant through dimerization: implications for cardiovascular disease.

Journal: Arteriosclerosis, thrombosis, and vascular biology20100901

Title: Prostacyclin receptor suppresses cardiac fibrosis: role of CREB phosphorylation.

Journal: Journal of molecular and cellular cardiology20100801

Title: Cyclooxygenase-2-dependent prostacyclin formation and blood pressure homeostasis: targeted exchange of cyclooxygenase isoforms in mice.

Journal: Circulation research20100205

Title: Recycling of the human prostacyclin receptor is regulated through a direct interaction with Rab11a GTPase.

Journal: Cellular signalling20081201

Title: Prostacyclin receptor-induced STAT3 phosphorylation in human erythroleukemia cells is mediated via Galpha(s) and Galpha(16) hybrid signaling.

Journal: Cellular signalling20081101

Title: Agonist-dependent internalization and trafficking of the human prostacyclin receptor: a direct role for Rab5a GTPase.

Journal: Biochimica et biophysica acta20081001

Title: Differential regulation of RhoA-mediated signaling by the TPalpha and TPbeta isoforms of the human thromboxane A2 receptor: independent modulation of TPalpha signaling by prostacyclin and nitric oxide.

Journal: Cellular signalling20080801

Title: Prostaglandin I2 analogs inhibit Th1 and Th2 effector cytokine production by CD4 T cells.

Journal: Journal of leukocyte biology20070301

Title: Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20060717

Title: Lack of interaction between prostaglandin E2 receptor subtypes in regulating adenylyl cyclase activity in cultured rat dorsal root ganglion cells.

Journal: European journal of pharmacology20060327

Title: Prostacyclin receptor induces STAT1 and STAT3 phosphorylations in human erythroleukemia cells: a mechanism requiring PTX-insensitive G proteins, ERK and JNK.

Journal: Cellular signalling20060301

Title: Evidence that inward rectifier K+ channels mediate relaxation by the PGI2 receptor agonist cicaprost via a cyclic AMP-independent mechanism.

Journal: Cardiovascular research20060101

Title: Augmented cardiac hypertrophy in response to pressure overload in mice lacking the prostaglandin I2 receptor.

Journal: Circulation20050705

Title: The effect of the farnesyl protein transferase inhibitor SCH66336 on isoprenylation and signalling by the prostacyclin receptor.

Journal: The Biochemical journal20050215

Title: Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins.

Journal: Circulation research20050107

Title: Dimerization of the human receptors for prostacyclin and thromboxane facilitates thromboxane receptor-mediated cAMP generation.

Journal: The Journal of biological chemistry20041217

Title: Reduced IP receptors in STZ-induced diabetic rat kidneys and high-glucose-treated mesangial cells.

Journal: American journal of physiology. Renal physiology20041001

Title: Activation of IP prostanoid receptors prevents cardiomyocyte hypertrophy via cAMP-dependent signaling.

Journal: American journal of physiology. Heart and circulatory physiology20040901

Title: Mechanism of cicaprost-induced desensitization in rat pulmonary artery smooth muscle cells involves a PKA-mediated inhibition of adenylyl cyclase.

Journal: American journal of physiology. Lung cellular and molecular physiology20040801

Title: Antimitogenesis linked to regulation of Skp2 gene expression.

Journal: The Journal of biological chemistry20040709

Title: Agonists can discriminate between cloned human and mouse prostacyclin receptors.

Journal: Prostaglandins, leukotrienes, and essential fatty acids20040501

Title: Characterization of the PGI2/IP system in cultured rat mesangial cells.

Journal: Prostaglandins, leukotrienes, and essential fatty acids20040501

Title: Excitatory action of prostanoids on the ferret isolated vagus nerve preparation.

Journal: European journal of pharmacology20040426

Title: Prostacyclin receptor-mediated activation of extracellular signal-regulated kinases 1 and 2.

Journal: Cellular signalling20040401

Title: Induction of hyaluronic acid synthase 2 (HAS2) in human vascular smooth muscle cells by vasodilatory prostaglandins.

Journal: Circulation research20040319

Title: Comparative analysis of the in vivo angiogenic properties of stable prostacyclin analogs: a possible role for peroxisome proliferator-activated receptors.

Journal: Journal of molecular and cellular cardiology20040301

Title: Asymmetric synthesis of the highly potent anti-metastatic prostacyclin analogue cicaprost and its isomer isocicaprost.

Journal: Journal of the American Chemical Society20030813

Title: Prostacylin receptor activation inhibits proliferation of aortic smooth muscle cells by regulating cAMP response element-binding protein- and pocket protein-dependent cyclin a gene expression.

Journal: Molecular pharmacology20030801

Title: Protein kinase A-dependent coupling of mouse prostacyclin receptors to Gi is cell-type dependent.

Journal: European journal of pharmacology20030801

Title: Long-term-desensitization of prostacyclin receptors is independent of the C-terminal tail.

Journal: Biochemical pharmacology20030615

Title: Prostanoid-induced modulation of neuropeptide Y and noradrenaline release from the rat mesenteric bed.

Journal: Autonomic & autacoid pharmacology20030401

Title: Facilitation by endogenous prostaglandins of capsaicin-induced gastric protection in rodents through EP2 and IP receptors.

Journal: The Journal of pharmacology and experimental therapeutics20030301

Title: Cyclooxygenase-2 acts as an endogenous brake on endothelin-1 release by human pulmonary artery smooth muscle cells: implications for pulmonary hypertension.

Journal: Molecular pharmacology20021101

Title: Investigation of the mechanisms of G protein: effector coupling by the human and mouse prostacyclin receptors. Identification of critical species-dependent differences.

Journal: The Journal of biological chemistry20020726

Title: In vitro pharmacological characterization of the prostanoid receptor population in the non-pregnant porcine myometrium.

Journal: European journal of pharmacology20020503

Title: Investigation of a functional requirement for isoprenylation by the human prostacyclin receptor.

Journal: European journal of biochemistry20020301

Title: Differential effects of stable prostacyclin analogs on smooth muscle proliferation and cyclic AMP generation in human pulmonary artery.

Journal: American journal of respiratory cell and molecular biology20020201

Title: Central nociceptive role of prostacyclin (IP) receptor induced by peripheral inflammation.

Journal: Neuroreport20020121

Title: Prostacyclin receptor-independent inhibition of phospholipase C activity by non-prostanoid prostacyclin mimetics.

Journal: British journal of pharmacology20011201

Title: Factors affecting prostacyclin receptor agonist efficacy in different cell types.

Journal: Cellular signalling20011101

Title: Protein kinase A-mediated phosphorylation of serine 357 of the mouse prostacyclin receptor regulates its coupling to G(s)-, to G(i)-, and to G(q)-coupled effector signaling.

Journal: The Journal of biological chemistry20010907

Title: Distinction between relaxations induced via prostanoid EP(4) and IP(1) receptors in pig and rabbit blood vessels.

Journal: British journal of pharmacology20010901

Title: A functional study on prostanoid receptors involved in cultured human iridal melanocyte stimulation.

Journal: Experimental eye research20010701

Title: Regulation of prostacyclin and prostaglandin E(2) receptor mediated responses in adult rat dorsal root ganglion cells, in vitro.

Journal: British journal of pharmacology20010501

Title: Differential effects of 15-deoxy-delta(12,14)-prostaglandin J2 and a peroxisome proliferator-activated receptor gamma agonist on macrophage activation.

Journal: Journal of leukocyte biology20010401

Title: Role of endogenous prostacyclin in gastric ulcerogenic and healing responses--a study using IP-receptor knockout mice.

Journal: Journal of physiology, Paris20010101

Title: The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.

Journal: Biochimica et biophysica acta20000117

Title: The effect of indomethacin and prostacyclin agonists on blood pressure in a rat model of preeclampsia.

Journal: American journal of obstetrics and gynecology19990501

Title: Characterization of the prostanoid receptor(s) on human blood monocytes at which prostaglandin E2 inhibits lipopolysaccharide-induced tumour necrosis factor-alpha generation.

Journal: British journal of pharmacology19970901

Title: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.

Journal: British journal of pharmacology19970901

Title: Relaxant actions of nonprostanoid prostacyclin mimetics on human pulmonary artery.

Journal: Journal of cardiovascular pharmacology19970401

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