WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 585314
CAS#: 56985-32-1
Description: U 44069 has a contractile effect on rat pulmonary veins and arteries, and is a thromboxane-A2 mimetic.
MedKoo Cat#: 585314
Name: U 44069
CAS#: 56985-32-1
Chemical Formula: C21H34O4
Exact Mass: 350.2457
Molecular Weight: 350.499
Elemental Analysis: C, 71.96; H, 9.78; O, 18.26
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
The following data is based on the product molecular weight 350.499 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.
| 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 |
1: Loutzenhiser R, Epstein M, Horton C, Sonke P. Reversal of renal and smooth muscle actions of the thromboxane mimetic U-44069 by diltiazem. Am J Physiol. 1986 Apr;250(4 Pt 2):F619-26. PubMed PMID: 3963201.
2: Holmquist F, Hedlund H, Andersson KE. Pre- and postjunctional effects of some prostanoids in human isolated vas deferens. Am J Physiol. 1991 Apr;260(4 Pt 2):R792-7. PubMed PMID: 1707245.
3: Ho WK, Nakao K, Shibata S. The inhibitory action of two thrombin inhibitors (TI-189 and TI-233) on the contractile responses to 5-hydroxytryptamine and prostaglandin endoperoxide analogue (U-44069) in isolated vascular strips. Br J Pharmacol. 1980;71(2):399-405. PubMed PMID: 7225193; PubMed Central PMCID: PMC2044436.
4: Loutzenhiser R, van Breemen C. Mechanism of activation of isolated rabbit aorta by PGH2 analogue U-44069. Am J Physiol. 1981 Nov;241(5):C243-9. PubMed PMID: 6795928.
5: Alemayehu A, Chou CC. 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.
