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MedKoo Cat#: 461869 | Name: Enisoprost

Description:

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

Enisoprost is a synthetic PGE1 analogue and has been shown to have antisecretory and antipeptic effects.

Chemical Structure

Enisoprost
Enisoprost
CAS#81026-63-3

Theoretical Analysis

MedKoo Cat#: 461869

Name: Enisoprost

CAS#: 81026-63-3

Chemical Formula: C22H36O5

Exact Mass: 380.2563

Molecular Weight: 380.52

Elemental Analysis: C, 69.44; H, 9.54; O, 21.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Enisoprost; Enisoprostum; SC 34301; SC-34301; SC34301;
IUPAC/Chemical Name
methyl (Z)-7-((1R,2R,3R)-3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl)hept-4-enoate
InChi Key
CIBHDGPIOICRGX-ZQCHCGQNSA-N
InChi Code
InChI=1S/C22H36O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h6-7,10,12,17-18,20,24,26H,4-5,8-9,11,13-16H2,1-3H3/b7-6-,12-10+/t17-,18-,20-,22?/m1/s1
SMILES Code
CCCCC(C)(O)C/C=C/[C@@H]1[C@H](C(C[C@H]1O)=O)CC/C=C\CCC(OC)=O
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 380.52 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
1: Adams MB. Enisoprost in renal transplantation. The Enisoprost Renal Transplant Study Group. Transplantation. 1992 Feb;53(2):338-45. Erratum in: Transplantation 1992 Sep;54(3):571. PubMed PMID: 1738927. 2: Thomson AB, McCullough HN, Kirdeikis P, Zuk L, Simpson I, Cook DJ, Wildeman RA, Brunet K, Fisher D, Pinchbeck B, et al. Twenty-four-hour intragastric measurements in twenty healthy subjects: effect of enisoprost, a novel and potent antisecretory and antipeptic synthetic E1 prostaglandin. Aliment Pharmacol Ther. 1988 Aug;2(4):325-36. PubMed PMID: 2979255. 3: Howden CW, Burget DW, Silletti C, Van Eeden A, Tomkins KB, Hunt RH. Marked suppression of stimulated gastric acid and pepsin secretion by enisoprost, a new PGE1 analogue. Aliment Pharmacol Ther. 1987 Aug;1(4):305-13. PubMed PMID: 2979675. 4: Gianotti L, Alexander JW, Pyles T, Fukushima R, Babcock GF. Prostaglandin E1 analogues misoprostol and enisoprost decrease microbial translocation and modulate the immune response. Circ Shock. 1993 Aug;40(4):243-9. PubMed PMID: 8375025. 5: Hibbins M, Chapman JR. In vitro assessment of triple-therapy immunosuppression and prostaglandin analogues enisoprost and misoprostol. Transplant Proc. 1992 Feb;24(1):224-6. PubMed PMID: 1539257. 6: Allan LM, Hawkins AJ, Vose CW, Firth J, Brownsill RD, Steiner JA. Disposition of 3H-enisoprost, a gastric antisecretory prostaglandin, in healthy humans. Xenobiotica. 1987 Oct;17(10):1233-46. PubMed PMID: 3424870. 7: Fabrega AJ, Blanchard J, Rivas PA, Moran SM, Pollak R. Prolongation of rat heart allograft survival using cyclosporine and enisoprost, a prostaglandin E1 analog. Transplantation. 1992 Jun;53(6):1363-4. PubMed PMID: 1604492. 8: Pollak R, Knight R, Mozes MF, Maddux M, Veremis S, Van Buren C, Lewis R, Scott E, Cole M, Hyndman V, et al. A trial of the prostaglandin E1 analogue, enisoprost, to reverse chronic cyclosporine-associated renal dysfunction. Am J Kidney Dis. 1992 Oct;20(4):336-41. PubMed PMID: 1415200. 9: Collins PW, Shone RL, Perkins WE, Gasiecki AF, Kalish VJ, Kramer SW, Bianchi RG. Synthesis and structure-activity relationships of acyclic omega chain conjugated diene analogues of enisoprost. J Med Chem. 1992 Feb 21;35(4):694-704. PubMed PMID: 1542096. 10: Weir MR, Li XW, Gomolka D, Peppler R, O'Bryan-Tear CG, Moran MA. The immunosuppressive properties of enisoprost and a 5-lipoxygenase inhibitor (SC-45662). Transplantation. 1991 Dec;52(6):1053-7. PubMed PMID: 1750068. 11: Mitchell SV, Dumble LJ, Plenter RJ, Millar RJ, Moran M, Clunie GJ. Cyclosporine-sparing influence of the synthetic PGE1 analogue enisoprost in rabbit cardiac allograft recipients. Transplant Proc. 1992 Feb;24(1):229-30. PubMed PMID: 1539259. 12: Weir MR, Li XW, Gomolka D, Peppler R, O'Bryan-Tear G, Moran M. Immunosuppressive properties of enisoprost and a 5-lipoxygenase inhibitor (SC 45662). Transplant Proc. 1991 Feb;23(1 Pt 2):1074-7. PubMed PMID: 1989152. 13: Collins PW, Gasiecki AF, Perkins WE, Gullikson GW, Jones PH, Bauer RF. 18-cycloalkyl analogues of enisoprost. J Med Chem. 1989 May;32(5):1001-6. PubMed PMID: 2709370. 14: Kasim SE, Moran M, Khilnani S, West MA, Jen KL. Effect of the prostaglandin E1 analog enisoprost on glucose and lipid metabolism in patients with type II diabetes mellitus. Horm Metab Res. 1992 Apr;24(4):176-80. PubMed PMID: 1601393. 15: Johnson BH, Dean RR, Moran SM, Thompson EB. Glucocorticoid, interleukin-2, and prostaglandin interactions in a clonal human leukemic T-cell line. J Steroid Biochem Mol Biol. 1992 Mar;42(1):1-9. PubMed PMID: 1558815. 16: Collins PW, Gasiecki AF, Perkins WE, Gullikson GW, Bianchi RG, Kramer SW, Ng JS, Yonan EE, Swenton L, Jones PH, et al. Chemistry and structure-activity relationships of C-17 unsaturated 18-cycloalkyl and cycloalkenyl analogues of enisoprost. Identification of a promising new antiulcer prostaglandin. J Med Chem. 1990 Oct;33(10):2784-93. PubMed PMID: 2213831. 17: Ismail T, Ayres R, Kiff P, McMaster P, Neuberger J. Enisoprost in liver transplantation. Transplantation. 1995 May 15;59(9):1298-301. PubMed PMID: 7762065. 18: Pulkkinen MO, Cohen H, Vuento M. Oral administration of the prostaglandin enisoprost induces uterine activity and softens the cervix during first trimester pregnancy. Acta Obstet Gynecol Scand. 1989;68(2):149-52. PubMed PMID: 2686340. 19: Fukushima R, Alexander JW, Gianotti L, Pyles T, Ogle CK. Bacterial translocation-related mortality may be associated with neutrophil-mediated organ damage. Shock. 1995 May;3(5):323-8. PubMed PMID: 7648332. 20: Collins PW, Kramer SW, Gullikson GW. Synthesis and gastrointestinal pharmacology of the 4-fluoro analogue of enisoprost. J Med Chem. 1987 Nov;30(11):1952-5. PubMed PMID: 3669004.

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