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MedKoo Cat#: 585314 | Name: U 44069
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

U-44069 is a stable prostaglandin H₂ analogue that acts as a potent vasoconstrictor by stimulating thromboxane A₂ (TXA₂) receptors, also known as TP receptors. It induces calcium influx in preglomerular vessels, leading to vasoconstriction. Additionally, U-44069 stimulates shape change in human platelets without a measurable increase in intracellular calcium concentration. These properties make U-44069 a valuable tool for studying vascular function and platelet aggregation.

Chemical Structure

U 44069
U 44069
CAS#56985-32-1

Theoretical Analysis

MedKoo Cat#: 585314

Name: U 44069

CAS#: 56985-32-1

Chemical Formula: C21H34O4

Exact Mass: 350.2457

Molecular Weight: 350.50

Elemental Analysis: C, 71.96; H, 9.78; O, 18.26

Price and Availability

Size Price Availability Quantity
1mg USD 450.00
5mg USD 1,000.00
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Related CAS #
No Data
Synonym
U 44069; U44069; U-44069
IUPAC/Chemical Name
(Z)-7-[(1S,4R,5S,6R)-5-[(E,3S)-3-hydroxyoct-1-enyl]-2-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
InChi Key
DJKDIKIDYDXHDD-IGUVKOCZSA-N
InChi Code
InChI=1S/C21H34O4/c1-2-3-6-9-17(22)12-13-18-16-14-20(25-15-16)19(18)10-7-4-5-8-11-21(23)24/h4,7,12-13,16-20,22H,2-3,5-6,8-11,14-15H2,1H3,(H,23,24)/b7-4-,13-12+/t16-,17-,18-,19+,20-/m0/s1
SMILES Code
O=C(O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)[C@]2([H])CO[C@@]1([H])C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 350.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Differences in vascular response to thromboxane between intestinal mucosa and muscularis. Prostaglandins. 1993 May;45(5):447-57. PubMed PMID: 8321914. 6: Imura Y, Terashita Z, Shibouta Y, Inada Y, Nishikawa K. Antagonistic action of AA-2414 on thromboxane A2/prostaglandin endoperoxide receptor in platelets and blood vessels. Jpn J Pharmacol. 1990 Jan;52(1):35-43. PubMed PMID: 2137886. 7: Bylund J, Hidestrand M, Ingelman-Sundberg M, Oliw EH. Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. J Biol Chem. 2000 Jul 21;275(29):21844-9. PubMed PMID: 10791960. 8: Mené P, Dunn MJ. Contractile effects of TxA2 and endoperoxide analogues on cultured rat glomerular mesangial cells. Am J Physiol. 1986 Dec;251(6 Pt 2):F1029-35. PubMed PMID: 3538903. 9: Elliott GR, Van Batenburg MJ, Bonta IL. Differential regulation of the cyclooxygenase pathway in starch elicited rat peritoneal macrophages by prostaglandin E2, U-44069, a stable endoperoxide analogue and dibutyryl-cyclic AMP. Eur J Pharmacol. 1985 Aug 7;114(1):71-4. PubMed PMID: 2995076. 10: Scotland R, Vallance P, Ahluwalia A. On the regulation of tone in vasa vasorum. Cardiovasc Res. 1999 Jan;41(1):237-45. PubMed PMID: 10325971. 11: Carrier R, Cragoe EJ, Ethier D, Ford-Hutchinson AW, Girard Y, Hall RA, Hamel P, Rokach J, Share NN, Stone CA, et al. Studies on L-640,035: a novel antagonist of contractile prostanoids in the lung. Br J Pharmacol. 1984 Jun;82(2):389-95. PubMed PMID: 6428502; PubMed Central PMCID: PMC1987036. 12: Hall RA, Gillard J, Guindon Y, Letts G, Champion E, Ethier D, Evans J, Ford-Hutchinson AW, Fortin R, Jones TR, et al. Pharmacology of L-655,240 (3-[1-(4-chlorobenzyl)-5-fluoro-3-methyl-indol-2-yl]2,2-dimethylpro pan oic acid); a potent, selective thromboxane/prostaglandin endoperoxide antagonist. Eur J Pharmacol. 1987 Mar 17;135(2):193-201. PubMed PMID: 3582493. 13: Hall RA, Rokach JR, Bélanger P, Bianchi L, Ethier D, Ford-Hutchinson AW, Girard Y, Hamel P, Hamel R, Lord A, et al. L-641,953 (R-8-fluoro-dibenzo[b, f]thiepin-3-carboxylic acid-5-oxide): a novel thromboxane-prostaglandin endoperoxide antagonist. Can J Physiol Pharmacol. 1987 Apr;65(4):509-14. PubMed PMID: 3607600. 14: Hood JS, Nossaman BD, Ibrahim IN, McMahon TJ, Babycos CR, Kadowitz PJ. Daltroban blocks thromboxane responses in the pulmonary vascular bed of the cat. J Appl Physiol (1985). 1992 Jun;72(6):2305-10. PubMed PMID: 1385804. 15: Bennett A, Sanger GJ. Pinane thromboxane A2 analogues are non-selective prostanoid antagonists in rat and human stomach muscle. Br J Pharmacol. 1982 Dec;77(4):591-6. PubMed PMID: 6758907; PubMed Central PMCID: PMC2044671. 16: Das A, Varma SS, Mularczyk C, Meling DD. Functional investigations of thromboxane synthase (CYP5A1) in lipid bilayers of nanodiscs. Chembiochem. 2014 Apr 14;15(6):892-9. doi: 10.1002/cbic.201300646. Epub 2014 Mar 12. PubMed PMID: 24623680. 17: Sirois MG, Plante GE, Braquet P, Sirois P. Role of eicosanoids in PAF-induced increases of the vascular permeability in rat airways. Br J Pharmacol. 1990 Dec;101(4):896-900. PubMed PMID: 2085713; PubMed Central PMCID: PMC1917852. 18: Jones TR, Zamboni R, Belley M, Champion E, Charette L, Ford-Hutchinson AW, Frenette R, Gauthier JY, Leger S, Masson P, et al. Pharmacology of L-660,711 (MK-571): a novel potent and selective leukotriene D4 receptor antagonist. Can J Physiol Pharmacol. 1989 Jan;67(1):17-28. PubMed PMID: 2540892. 19: Jones TR, Labelle M, Belley M, Champion E, Charette L, Evans J, Ford-Hutchinson AW, Gauthier JY, Lord A, Masson P, et al. Pharmacology of montelukast sodium (Singulair), a potent and selective leukotriene D4 receptor antagonist. Can J Physiol Pharmacol. 1995 Feb;73(2):191-201. Erratum in: Can J Physiol Pharmacol 1995 Jun;73(6):747. PubMed PMID: 7621356. 20: Saad MH, Burka JF. Effects of immunological sensitization on the responses and sensitivity of guinea pig airways to bronchoconstrictors. Modulation by selective inhibition of arachidonic acid metabolism. Can J Physiol Pharmacol. 1983 Aug;61(8):876-87. PubMed PMID: 6414680.