U 44069
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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.


Price and Availability

Size Price Shipping out time Quantity
1mg USD 310 2 Weeks
5mg USD 855 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-09-23. Prices are subject to change without notice.

U 44069, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

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


Technical Data

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


References

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.