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60325-46-4,MFCD00216056
Catalog No.:AA01DP05

60325-46-4 | Sulprostone in 5mg/ml Methyl Acetate

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1mg
95%
in stock  
$138.00   $96.00
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5mg
95%
in stock  
$562.00   $393.00
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10mg
≥98%
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$1,093.00   $765.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA01DP05
Chemical Name:
Sulprostone in 5mg/ml Methyl Acetate
CAS Number:
60325-46-4
Molecular Formula:
C23H31NO7S
Molecular Weight:
465.5597
MDL Number:
MFCD00216056
SMILES:
O=C(NS(=O)(=O)C)CCCC=CCC1C(=O)CC([C@@H]1/C=C/C(COc1ccccc1)O)O
Properties
Computed Properties
 
Complexity:
766  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
12  
XLogP3:
1.5  

Literature

Title: Prostaglandin E2 EP3 receptor regulates cyclooxygenase-2 expression in the kidney.

Journal: American journal of physiology. Renal physiology 20120801

Title: Protein kinase C delta contributes to increase in EP3 agonist-induced contraction in mesenteric arteries from type 2 diabetic Goto-Kakizaki rats.

Journal: Pflugers Archiv : European journal of physiology 20120401

Title: [Severe hyperthermia and neurological disorders following prostaglandin treatment for uterine atonia after caesarean section].

Journal: Annales francaises d'anesthesie et de reanimation 20120301

Title: Postpartum hemorrhage: use of hemostatic combat gauze.

Journal: American journal of obstetrics and gynecology 20120101

Title: [Intracerebral haemorrhage and postpartum cerebral angiopathy associated with the administration of sulprostone and norepinephrine].

Journal: Annales francaises d'anesthesie et de reanimation 20120101

Title: Prostanoid receptors involved in regulation of the beating rate of neonatal rat cardiomyocytes.

Journal: PloS one 20120101

Title: Distinct PGE2-responder and non-responder phenotypes in human mast cell populations: 'all or nothing' enhancement of antigen-dependent mediator release.

Journal: Immunology letters 20111230

Title: [Lessons and impact of two audits on postpartum hemorrhages in 24 maternity hospitals of the network 'Sécurité Naissance - Naître Ensemble' in 'Pays-de-la-Loire' area].

Journal: Journal de gynecologie, obstetrique et biologie de la reproduction 20111101

Title: EP₃ receptors mediate PGE₂-induced hypothalamic paraventricular nucleus excitation and sympathetic activation.

Journal: American journal of physiology. Heart and circulatory physiology 20111001

Title: The role of PGE(2) in human atherosclerotic plaque on platelet EP(3) and EP(4) receptor activation and platelet function in whole blood.

Journal: Journal of thrombosis and thrombolysis 20110801

Title: Prostaglandin E2 analogue sulprostone for treatment of atonic postpartum hemorrhage.

Journal: Obstetrics and gynecology 20110801

Title: Differential reactivity of human mammary artery and saphenous vein to prostaglandin E(2) : implication for cardiovascular grafts.

Journal: British journal of pharmacology 20110601

Title: Capsaicin-induced vasodilatation in human nasal vasculature is mediated by modulation of cyclooxygenase-2 activity and abrogated by sulprostone.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20110601

Title: [Cardiac arrest associated with sulprostone use during cesarean section].

Journal: La Tunisie medicale 20110101

Title: Selexipag: a selective prostacyclin receptor agonist that does not affect rat gastric function.

Journal: The Journal of pharmacology and experimental therapeutics 20101001

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: EP1 prostanoid receptor coupling to G i/o up-regulates the expression of hypoxia-inducible factor-1 alpha through activation of a phosphoinositide-3 kinase signaling pathway.

Journal: Molecular pharmacology 20100601

Title: The EP3-agonist sulprostone, but not prostaglandin E2 potentiates platelet aggregation in human blood.

Journal: Thrombosis and haemostasis 20100601

Title: Differential regulation of the aggressive phenotype of inflammatory breast cancer cells by prostanoid receptors EP3 and EP4.

Journal: Cancer 20100601

Title: Cervical preparation for first trimester surgical abortion.

Journal: The Cochrane database of systematic reviews 20100217

Title: Participation of prostaglandin E2 receptor in nasal congestion of Brown Norway rats.

Journal: Biological & pharmaceutical bulletin 20100101

Title: E Prostanoid-1 receptor regulates renal medullary alphaENaC in rats infused with angiotensin II.

Journal: Biochemical and biophysical research communications 20091113

Title: Intermolecular cross-talk between the prostaglandin E2 receptor (EP)3 of subtype and thromboxane A(2) receptor signalling in human erythroleukaemic cells.

Journal: British journal of pharmacology 20091001

Title: Incidence and management of postpartum haemorrhage following the dissemination of guidelines in a network of 16 maternity units in France.

Journal: International journal of obstetric anesthesia 20091001

Title: Acute myocardial infarction due to vasospasm induced by prostaglandin.

Journal: The Canadian journal of cardiology 20091001

Title: Practices for prevention, diagnosis and management of postpartum haemorrhage: impact of a regional multifaceted intervention.

Journal: BJOG : an international journal of obstetrics and gynaecology 20090901

Title: Prostaglandins compromise basal forebrain cholinergic neuron differentiation and survival: action at EP1/3 receptors results in AIF-induced death.

Journal: Brain research 20090818

Title: Prostaglandin regulation of gastric slow waves and peristalsis.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20090601

Title: Regulation of Nur77 gene expression by prostanoids in cementoblastic cells.

Journal: Archives of oral biology 20090501

Title: Pulmonary oedema after high infusion rate of sulprostone.

Journal: British journal of anaesthesia 20090201

Title: Alpha-1-adrenergic receptor agonist activity of clinical alpha-adrenergic receptor agonists interferes with alpha-2-mediated analgesia.

Journal: Anesthesiology 20090201

Title: Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys.

Journal: Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20090201

Title: Subcutaneous prostaglandin E(2) restrains airway mast cell activity in vivo and reduces lung eosinophilia and Th(2) cytokine overproduction in house dust mite-sensitive mice.

Journal: International archives of allergy and immunology 20090101

Title: Accelerated clearance of Plasmodium-infected erythrocytes in sickle cell trait and annexin-A7 deficiency.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20090101

Title: [Termination of pregnancy in the 2nd trimester: mifepriston/misoprostol preferable to sulprostone].

Journal: Nederlands tijdschrift voor geneeskunde 20090101

Title: DG-041 inhibits the EP3 prostanoid receptor--a new target for inhibition of platelet function in atherothrombotic disease.

Journal: Platelets 20081201

Title: Mifepristone and misoprostol versus Dilapan and sulprostone for second trimester termination of pregnancy.

Journal: The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians 20081101

Title: Increased cyclooxygenase-2 and thromboxane synthase expression is implicated in diosgenin-induced megakaryocytic differentiation in human erythroleukemia cells.

Journal: Analytical biochemistry 20080901

Title: EP4 and EP2 receptor subtypes involved in colonic secretion in rat.

Journal: Basic & clinical pharmacology & toxicology 20080901

Title: Broad modulation of neuropathic pain states by a selective estrogen receptor beta agonist.

Journal: European journal of pharmacology 20080820

Title: Detection of P2Y(14) protein in platelets and investigation of the role of P2Y(14) in platelet function in comparison with the EP(3) receptor.

Journal: Thrombosis and haemostasis 20080801

Title: Involvement of 15-lipoxygenase and prostaglandin EP receptors in aspirin-triggered 15-hydroxyeicosatetraenoic acid generation in aspirin-sensitive asthmatics.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20080701

Title: Characterization of prostanoid receptors present on adrenergic neurons innervating the porcine uterine longitudinal muscle.

Journal: Prostaglandins & other lipid mediators 20080601

Title: The role of prostaglandin E and thromboxane-prostanoid receptors in the response to prostaglandin E2 in the aorta of Wistar Kyoto rats and spontaneously hypertensive rats.

Journal: Cardiovascular research 20080401

Title: Trigeminal nociceptors express prostaglandin receptors.

Journal: Journal of dental research 20080301

Title: Transient allodynia pain models in mice for early assessment of analgesic activity.

Journal: British journal of pharmacology 20080201

Title: [Conservative versus radical management in cases of placenta accreta: a historical study].

Journal: Journal de gynecologie, obstetrique et biologie de la reproduction 20071101

Title: Prostaglandin E2 (PGE2) inhibits glutamatergic synaptic transmission in dorsolateral periaqueductal gray (dl-PAG).

Journal: Brain research 20070808

Title: Involvement of prostaglandin E receptor EP3 subtype in duodenal bicarbonate secretion in rats.

Journal: Life sciences 20070606

Title: Exploration of prostanoid receptor subtype regulating estradiol and prostaglandin E2 induction of spinophilin in developing preoptic area neurons.

Journal: Neuroscience 20070525

Title: [Place of the sulprostone in therapeutic interruptions of the pregnancy].

Journal: La Tunisie medicale 20070501

Title: Direct vasoconstrictor effect of prostaglandin E2 on renal interlobular arteries: role of the EP3 receptor.

Journal: American journal of physiology. Renal physiology 20070301

Title: Sulprostone reduces the need for manual removal of the placenta in patients with retained placenta: a randomized controlled trial.

Journal: American journal of obstetrics and gynecology 20070301

Title: The decrease of fibrinogen is an early predictor of the severity of postpartum hemorrhage.

Journal: Journal of thrombosis and haemostasis : JTH 20070201

Title: Prostaglandin E(2) protects human lung fibroblasts from cigarette smoke extract-induced apoptosis via EP(2) receptor activation.

Journal: Journal of cellular physiology 20070101

Title: Discovery of heteroaryl sulfonamides as new EP1 receptor selective antagonists.

Journal: Bioorganic & medicinal chemistry 20061001

Title: Investigation of the pronounced synergism between prostaglandin E2 and other constrictor agents on rat femoral artery.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20060601

Title: Prostaglandin F2alpha: French guidelines for uterine atony management.

Journal: International journal of obstetric anesthesia 20060401

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: Sulprostone reduces the need for the manual removal of the placenta in patients with retained placenta: a randomized controlled trial.

Journal: American journal of obstetrics and gynecology 20060201

Title: [Effect of guizhi decoction on PKA and PKC activities of hypothalamus in fever rats].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060101

Title: Prostaglandin E2 enhances neurotrophin-4 production via EP3 receptor in human keratinocytes.

Journal: The Journal of pharmacology and experimental therapeutics 20051101

Title: Stimulation of PGE receptors EP2 and EP4 protects cultured neurons against oxidative stress and cell death following beta-amyloid exposure.

Journal: The European journal of neuroscience 20051101

Title: Prostaglandin E2 receptor selective agonists E-prostanoid 2 and E-prostanoid 4 may have therapeutic effects on ovalbumin-induced bronchoconstriction.

Journal: Chest 20051101

Title: Duodenal secretion in humans mediated by the EP4 receptor subtype.

Journal: Acta physiologica Scandinavica 20051001

Title: Prostaglandin D2 and prostaglandin E2 accelerate the recovery of cutaneous barrier disruption induced by mechanical scratching in mice.

Journal: European journal of pharmacology 20050725

Title: Dual action of prostaglandin E2 on gastric acid secretion through different EP-receptor subtypes in the rat.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20050701

Title: [Anaphylactic shock and uterine atony: must we use sulprostone].

Journal: Annales francaises d'anesthesie et de reanimation 20050101

Title: [Sulprostone in the treatment of uterine inertia. Report of 60 cases].

Journal: La Tunisie medicale 20041001

Title: Medical management for termination of second and third trimester pregnancies: a comparison of strategies.

Journal: European journal of obstetrics, gynecology, and reproductive biology 20040910

Title: Low dose synthetic prostaglandin E2: always safe for pregnancy termination?

Journal: Lancet (London, England) 20040901

Title: [Rectal misoprostol for postpartum hemorrhage].

Journal: Gynecologie, obstetrique & fertilite 20040901

Title: [Pregnancy termination in the second trimester with vaginally administered dinoprostone followed by intravenous sulprostone, for the indication 'foetal congenital defects'; results of a retrospective study].

Journal: Nederlands tijdschrift voor geneeskunde 20040814

Title: Prostaglandin E2 induces IL-23 production in bone marrow-derived dendritic cells.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040801

Title: Role of EP3 and EP4 prostaglandin receptors in reorganization of the cytoskeleton in mature human osteoclasts.

Journal: The Journal of rheumatology 20040801

Title: PGE2 receptors rescue motor neurons in a model of amyotrophic lateral sclerosis.

Journal: Annals of neurology 20040801

Title: Participation of prostaglandin E receptor EP4 subtype in duodenal bicarbonate secretion in rats.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040701

Title: [Pregnancy termination in the second trimester with vaginally administered dinoprostone followed by intravenous sulprostone, for the indication 'foetal congenital defects'; results of a retrospective study].

Journal: Nederlands tijdschrift voor geneeskunde 20040626

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

Journal: European journal of pharmacology 20040426

Title: Prostaglandin E2 is a potent regulator of interleukin-12- and interleukin-18-induced natural killer cell interferon-gamma synthesis.

Journal: Immunology 20040301

Title: E-ring 8-isoprostanes inhibit ACh release from parasympathetic nerves innervating guinea-pig trachea through agonism of prostanoid receptors of the EP3-subtype.

Journal: British journal of pharmacology 20040201

Title: [Induction of labour: which method to use?].

Journal: Minerva ginecologica 20031201

Title: [Effect of guizhi tang and its active components on the fever induced by EP3 agonist].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20031101

Title: Pharmacological characterization of pre- and postsynaptic prostanoid receptors in pig gastric fundus.

Journal: Neuropharmacology 20031001

Title: Morphological changes in the anterior eye segment after long-term treatment with different receptor selective prostaglandin agonists and a prostamide.

Journal: Investigative ophthalmology & visual science 20031001

Title: Functional prostaglandin E (EP) receptors in human penile corpus cavernosum.

Journal: International journal of impotence research 20031001

Title: Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats.

Journal: The journal of pain : official journal of the American Pain Society 20030901

Title: The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho.

Journal: Journal of cell science 20030815

Title: Involvement of Rho-kinase in contraction of guinea-pig aorta induced by prostanoid EP3 receptor agonists.

Journal: British journal of pharmacology 20030802

Title: Induction of adherent activity in mastocytoma P-815 cells by the cooperation of two prostaglandin E2 receptor subtypes, EP3 and EP4.

Journal: The Journal of biological chemistry 20030516

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

Journal: Autonomic & autacoid pharmacology 20030401

Title: Agonist concentration-dependent differential responsivity of a human platelet purinergic receptor: pharmacological and kinetic studies of aggregation, deaggregation and shape change responses mediated by the purinergic P2Y1 receptor in vitro.

Journal: Platelets 20030101

Title: Differential peristaltic motor effects of prostanoid (DP, EP, IP, TP) and leukotriene receptor agonists in the guinea-pig isolated small intestine.

Journal: British journal of pharmacology 20021201

Title: Stimulatory effects of prostaglandin E2 on neurogenesis in the dentate gyrus of the adult rat.

Journal: Zoological science 20021101

Title: Complete recovery after 2 h of cardiopulmonary resuscitation following high-dose prostaglandin treatment for atonic uterine haemorrhage.

Journal: Acta anaesthesiologica Scandinavica 20021001

Title: [Chest pain and sulprostone during postpartum hemorrhage].

Journal: Annales francaises d'anesthesie et de reanimation 20021001

Title: Contribution of prostaglandin EP(2) receptors to renal microvascular reactivity in mice.

Journal: American journal of physiology. Renal physiology 20020901

Title: Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.

Journal: The Journal of pharmacy and pharmacology 20020401

Title: Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes.

Journal: Hypertension (Dallas, Tex. : 1979) 20020201

Title: Prostaglandin E(2) induces caspase-dependent apoptosis in rat cortical cells.

Journal: Neuroscience letters 20020111

Title: Augmentation of receptor-mediated adenylyl cyclase activity by Gi-coupled prostaglandin receptor subtype EP3 in a Gbetagamma subunit-independent manner.

Journal: Biochemical and biophysical research communications 20020111

Title: Sulprostone for pregnancy termination in women with severe (pre-) eclampsia.

Journal: Hypertension in pregnancy 20020101

Title: Synergism between prostanoids and other vasoactive agents.

Journal: Journal of cardiac surgery 20020101

Title: Prostanoid EP(1)- and TP-receptors involved in the contraction of human pulmonary veins.

Journal: British journal of pharmacology 20011201

Title: Low dose sulprostone for termination of second and third trimester pregnancies.

Journal: European journal of obstetrics, gynecology, and reproductive biology 20011201

Title: Medical management of cervical pregnancy--a report of two cases.

Journal: Singapore medical journal 20011101

Title: Prostaglandin E(2) (EP(1)) receptor agonist-induced DNA synthesis and proliferation in primary cultures of adult rat hepatocytes: the involvement of TGF-alpha.

Journal: Endocrinology 20011001

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: PGE2 triggers recovery of transmucosal resistance via EP receptor cross talk in porcine ischemia-injured ileum.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20010801

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

Journal: Experimental eye research 20010701

Title: Altered growth response to prostaglandin E2 and its receptor signaling in mesangial cells from stroke-prone spontaneously hypertensive rats.

Journal: Journal of hypertension 20010601

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: Variable responses to prostaglandin E(2) in human non-pregnant myometrium.

Journal: European journal of pharmacology 20010323

Title: Direct activation of rat spinal dorsal horn neurons by prostaglandin E2.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010301

Title: [Cardiac arrest during the concomitant administration of sulprostone and noradrenaline].

Journal: Annales francaises d'anesthesie et de reanimation 20010301

Title: Mechanisms involved in prostaglandin-induced increase in bone resorption in neonatal mouse calvaria.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20010201

Title: Effects of tetramethylpyrazine on prostaglandin E(2)- and prostaglandin E(2) receptor agonist-induced disruption of blood-aqueous barrier in pigmented rabbits.

Journal: Japanese journal of ophthalmology 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: Developmental regulation of endothelial nitric oxide synthase in cerebral vessels of newborn pig by prostaglandin E(2).

Journal: The Journal of pharmacology and experimental therapeutics 19991101

Title: Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression.

Journal: Journal of lipid research 19990601

Title: Characterization of a prostanoid EP3-receptor in guinea-pig aorta: partial agonist action of the non-prostanoid ONO-AP-324.

Journal: British journal of pharmacology 19981101

Title: Pharmacology of [3H]prostaglandin E1/[3H]prostaglandin E2 and [3H]prostaglandin F2alpha binding to EP3 and FP prostaglandin receptor binding sites in bovine corpus luteum: characterization and correlation with functional data.

Journal: The Journal of pharmacology and experimental therapeutics 19980801

Title: Cardiac arrest associated with sulprostone use during caesarean section.

Journal: Anaesthesia and intensive care 19980601

Title: [Acute myocardial infarct following sulprostone administration].

Journal: Nederlands tijdschrift voor geneeskunde 19980124

Title: [Circulatory arrest following sulprostone administration in postpartum hemorrhage].

Journal: Nederlands tijdschrift voor geneeskunde 19980124

Title: Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.

Journal: European journal of pharmacology 19971211

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: Effect of NMDA receptor antagonists on prostaglandin E2-induced hyperalgesia in conscious mice.

Journal: Brain research 19950417

Title: RU486: the French experience.

Journal: Human reproduction (Oxford, England) 19940601

Title: SC-46275: a potent and highly selective agonist at the EP3 receptor.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 19931201

Title: [Prolonged angina after the administration of a synthetic PGE2 derivative].

Journal: Giornale italiano di cardiologia 19930701

Title: [Cardiocirculatory arrest after administration of combined mifepristone (Mifegyne) and sulprostone (Nalador) for induced abortion. Possible role of coronary vasospasm].

Journal: Archives des maladies du coeur et des vaisseaux 19920101

Title: A prostaglandin analogue as a probable cause of myocardial infarction in a young woman.

Journal: BMJ (Clinical research ed.) 19910216

Title: [Cardio-circulatory arrest with mifepristone sulprostone combination for pregnancy interruption].

Journal: Therapie 19910101

Title: Convulsions in epileptic women after administration of prostaglandin E2 derivative.

Journal: Lancet (London, England) 19901103

Title: S Narumiya, et al. Prostanoid receptors: structures, properties, and functions. Physiol Rev. 1999 Oct;79(4):1193-226.

Title: Jenny Bulgarelli, et al. Skewing effect of sulprostone on dendritic cell maturation compared with dinoprostone. Cytotherapy. 2018 Jun;20(6):851-860.

Title: Yifan Shi, et al. Bioanalysis of sulprostone, a prostaglandin E 2 analogue and selective EP 3 agonist, in monkey plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Aug 15;1092:51-57.

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