Viprostol

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

MedKoo CAT#: 584328

CAS#: 73621-92-8

Description: Viprostol is a prostaglandin antihypertensive.


Price and Availability

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Viprostol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584328
Name: Viprostol
CAS#: 73621-92-8
Chemical Formula: C23H36O5
Exact Mass: 392.2563
Molecular Weight: 392.536
Elemental Analysis: C, 70.38; H, 9.24; O, 20.38


Synonym: Viprostol; CL 115,347

IUPAC/Chemical Name: Prosta-5,13-dien-1-oic acid, 16-ethenyl-11,16-dihydroxy-9-oxo-, methyl ester, (5Z,11alpha,13E)-

InChi Key: TWCQWABAGCMHLL-ROVQGQOSSA-N

InChi Code: InChI=1S/C23H36O5/c1-4-6-15-23(27,5-2)16-11-13-19-18(20(24)17-21(19)25)12-9-7-8-10-14-22(26)28-3/h5,7,9,11,13,18-19,21,25,27H,2,4,6,8,10,12,14-17H2,1,3H3/b9-7-,13-11+/t18-,19-,21-,23?/m1/s1

SMILES Code: CCCCC(O)(C=C)C/C=C/[C@@H]1[C@H](C(C[C@H]1O)=O)C/C=C\CCCC(OC)=O


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:
>2 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).

Harmonized System Code:
293490


References

1: Chan PS, Cervoni P, Scully PA, Ronsberg MA, Accomando RC. Mechanism of action of a new prostaglandin antihypertensive, viprostol [CL 115 347; (dl)-15-deoxy-16-hydroxy-16(alpha/beta)-vinyl-prostaglandin E2 methyl ester]: (I). Vasodilation. J Hypertens. 1986 Dec;4(6):741-7. PubMed PMID: 3029218.

2: Chan PS, Cervoni P, Accomando RC, Quirk GJ, Ronsberg MA. Mechanism of action of a new prostaglandin antihypertensive, viprostol [CL 115 347; (dl)-15-deoxy-16-hydroxy-16(alpha/beta)-vinyl-prostaglandin E2 methyl ester]: (II). Effects on the adrenergic nervous system. J Hypertens. 1986 Dec;4(6):749-57. PubMed PMID: 2880911.

3: Olsen EA, DeLong E. Transdermal viprostol in the treatment of male pattern baldness. J Am Acad Dermatol. 1990 Sep;23(3 Pt 1):470-2. PubMed PMID: 2212146.

4: Nicolau G, Cosulich DB, Tonelli A, Chen SM, Pruzinsky MS, Blum D. Metabolism of viprostol--a synthetic vasodilator PGE2 analog. Prostaglandins. 1986 Apr;31(4):811-27. PubMed PMID: 3088678.

5: Cervoni P, Chan PS. Synthetic stable orally and transdermally long-acting prostaglandin E2 (PGE2) congener (viprostol; CL 115,347) and prostacyclin congener (CL 115,999) as antihypertensive agents. Adv Prostaglandin Thromboxane Leukot Res. 1989;19:331-4. PubMed PMID: 2526492.

6: Olivari MT, Levine TB, Cohn JN. Evidence for a direct renal stimulating effect of prostaglandin E2 on renin release in patients with congestive heart failure. Circulation. 1986 Dec;74(6):1203-7. PubMed PMID: 3536150.

7: Belch JJ, O'Dowd A, Forbes CD, Sturrock RD. Platelet sensitivity to a prostacyclin analogue in systemic sclerosis. Br J Rheumatol. 1985 Nov;24(4):346-50. PubMed PMID: 2415199.

8: Lai FM, Tanikella TK, Cervoni P. The vasorelaxant effect of (+/-)-15-deoxy-16-hydroxy-16(alpha/beta)-vinyl-prostaglandin E2 (CL 115, 129) and its methyl ester (CL 115, 347) on the isolated ductus arteriosus preparation. Life Sci. 1984 May 7;34(19):1861-6. PubMed PMID: 6588286.

9: Lai FM, Cobuzzi A, Tanikella T, Cervoni P. Relaxant actions of viprostol and prostaglandin E2 on tracheal muscle and their effects on calcium influx. Prostaglandins. 1988 Jul;36(1):115-23. PubMed PMID: 3175022.

10: Chatziantoniou C, Arendshorst WJ. Prostaglandin interactions with angiotensin, norepinephrine, and thromboxane in rat renal vasculature. Am J Physiol. 1992 Jan;262(1 Pt 2):F68-76. PubMed PMID: 1733298.

11: Dunger DB, Dillon MJ, Daman-Willems C, Cooke ED, Bowcock SA. Treatment of childhood Raynaud's disease by transdermal prostaglandin E2 analogue. Lancet. 1985 Jul 6;2(8445):50. PubMed PMID: 2861505.

12: Birnbaum JE, Chan PS, Cervoni P, Dessy F, Van Humbeeck L. Cutaneous erythema and blood pressure lowering effects of topically applied 16-vinylprostaglandins. Prostaglandins. 1982 Feb;23(2):185-99. PubMed PMID: 7079519.

13: Crandall DL, Vu V, Lizzo FH, Davis BA, Cervoni P. Antilipolytic activity of viprostol, a transdermally active antihypertensive PGE2 analog. Prostaglandins. 1987 May;33(5):767-73. PubMed PMID: 2438724.

14: Burns EC, Dunger DB, Dillon MJ. Raynaud's disease. Arch Dis Child. 1985 Jun;60(6):537-41. PubMed PMID: 3160308; PubMed Central PMCID: PMC1777375.

15: Cervoni P, Chan PS, Lai FM, Birnbaum JE. CL 115,347 (DHV-PGE2 ME): a new orally and topically active prostaglandin antihypertensive agent. Fed Proc. 1983 Feb;42(2):157-61. PubMed PMID: 6571821.

16: Nicolau G, Baughman RA, Tonelli A, McWilliams W, Schiltz J, Yacobi A. Deposition of viprostol (a synthetic PGE2 vasodilator) in the skin following topical administration to laboratory animals. Xenobiotica. 1987 Sep;17(9):1113-20. PubMed PMID: 3120427.

17: Crandall DL, Goldstein BM, Gabel R, Lizzo FH, Cervoni P. Effects of the antihypertensive prostaglandin analog CL 115,347 on cardiac output distribution in the spontaneously hypertensive rat. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):996-1002. PubMed PMID: 2413314.

18: Chatziantoniou C, Arendshorst WJ. Vascular interactions of prostaglandins with thromboxane in kidneys of rats developing hypertension. Am J Physiol. 1993 Aug;265(2 Pt 2):F250-6. PubMed PMID: 8396345.

19: Nicolau G, Dahlin DC, Kohlbrenner M, Chan PS, Ronsberg MA, Saunders TK, Yacobi A, Cervoni P. Skin metabolism and transdermal absorption of viprostol, a synthetic PGE2 analog, in the rat: effect of vehicle. Skin Pharmacol. 1989;2(1):22-9. PubMed PMID: 2627412.

20: Chatziantoniou C, Arendshorst WJ. Impaired ability of prostaglandins to buffer renal vasoconstriction in genetically hypertensive rats. Am J Physiol. 1992 Oct;263(4 Pt 2):F573-80. PubMed PMID: 1329556.