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Prostaglandin E₁

Cayman Chemical Item Number 13010

Alprostadil; PGE₁ (CAS 745-65-3)

Prostaglandin E1 (CAS 745-65-3)

See more	Prostaglandins (517) Atherosclerosis (325) Cardiology (86) Hypertension (97)

Description

PGE₁ is the theoretical cyclooxygenase metabolite of dihomo-γ-linolenic acid (DGLA), but it is virtually undetectable in the plasma of normal humans or other animals.¹ Its pharmacology includes vasodilation, hypotension, and anti-platelet activities. The IC₅₀ of PGE₁ for the inhibition of ADP-induced human platelet aggregation is 40 nM.^2,3 The vasorelaxant and anti-hypertensive effects of PGE₁ are used to treat male erectile dysfunction and to provide emergency vasodilation of the patent ductus arteriosus in infants whose cardiac anomalies require pulmonary shunting for survival.^4,5 In human males, the intracavernosal effective dose range for PGE₁ is 2 to 80 µg, and the transurethral range is 125 to 1,000 µg.⁴

1 Cawello, W., Schweer, H., Dietrich, B., et al. Pharmacokinetics of prostaglandin E₁ and its main metabolites after intracavernous injection and short-term infusion of prostaglandin E₁ in patients with erectile dysfunction. J Urol 158 1403-1407 (1997).

2 Kobzar, G., Mardla, V., Järving, I., et al. Antiaggregating potency of E-type prostaglandins in human and rabbit platelets. Proc Est Acad Sci Chem 40 179-180 (1991).

3 Okada, F., Nukada, T., Yamauchi, Y., et al. The hypotensive effect of prostaglandin E₁ on hypertensive cases of various types. Prostaglandins 7 99-106 (1974).

4 Padma-Nathan, H., Hellstrom, W.J.G., Kaiser, F.E., et al. Treatment of men with erectile dysfunction with transurethral alprostadil. N Engl J Med 336 1-7 (1997).

5 Olley, P.M., and Coceani, F. Prostaglandins and the ductus arteriosus. Annu Rev Med 32 375-3785 (1981).

Synonyms	Alprostadil PGE1
Formal Name	9-oxo-11α,15S-dihydroxy-prost-13E-en-1-oic acid
CAS Number	745-65-3
Molecular Formula	C₂₀H₃₄O₅
Formula Weight	354.5
Formulation	A crystalline solid
Purity	>98%
Stability	2 years
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCCC(O)/C=C/[C@H]1C(O)CC(=O)C1CCCCCCC(=O)O

Background Reading

Virag, R., Shoukry, K., Floresco, J., et al. Intracavernous self-injection of vasoactive drugs in the treatment of impotence: 8-Year experience with 615 cases. J Urol 145 287-293 (1991).

Earle, C.M., Keogh, E.J., Wisniewski, Z.S., et al. Prostaglandin E₁ therapy for impotence, comparison with papaverine. J Urol 143 57-59 (1990).

Kobzar, G., Mardla, V., Järving, I., et al. Antiaggregating potency of E-type prostaglandins in human and rabbit platelets. Proc Est Acad Sci Chem 40 179-180 (1991).

Feld, S., Li, G., Amirian, J., et al. Enhanced thrombolysis, reduced coronary reocclusion and limitation of infarct size with liposomal prostaglandin E₁ in a canine thrombolysis model. J Am Coll Cardiol 24 1382-1390 (1994).

Anderson, K., and Wagner, G. Physiology of penile errection. Physiol Rev 75 191-236 (1995).

Okada, F., Nukada, T., Yamauchi, Y., et al. The hypotensive effect of prostaglandin E₁ on hypertensive cases of various types. Prostaglandins 7 99-106 (1974).

Wijkander, J., O'Flaherty, J.T., Nixon, A.B., et al. 5-Lipoxygenase products modulate the activity of the 85-kDa phospholipase A₂ in human neutrophils. J Biol Chem 270 26543-26549 (1995).

Olley, P.M., and Coceani, F. Prostaglandins and the ductus arteriosus. Annu Rev Med 32 375-3785 (1981).

Cawello, W., Schweer, H., Dietrich, B., et al. Pharmacokinetics of prostaglandin E₁ and its main metabolites after intracavernous injection and short-term infusion of prostaglandin E₁ in patients with erectile dysfunction. J Urol 158 1403-1407 (1997).

Ramwell, P.W., Shaw, J.E., Corey, E.J., et al. Biological activity of synthetic prostaglandins. Nature 221 1251-1253 (1969).

Egashira, T., Kim, Y.I., Takayama, F., et al. Lipo-PGE₁, prostaglandin E₁ incorporated in lipid microspheres, protects injury of the liver caused by warm ischemia reperfusion. Free Radic Biol Med 21 353-356 (1996).

Padma-Nathan, H., Hellstrom, W.J.G., Kaiser, F.E., et al. Treatment of men with erectile dysfunction with transurethral alprostadil. N Engl J Med 336 1-7 (1997).

Antoine, C., Murphy, R.C., Henson, P.M., et al. Time-dependent utilization of platelet arachidonic acid by the neutrophil in formation of 5-lipoxygenase products in platelet-neutrophil co-incubations. Biochim Biophys Acta 1128 139-146 (1992).

Van Hijfte, L., and Kolb, M. Towards a large scale preparation of mexiprostil. Tetrahedron 48 6393-6402 (1992).

Miledi, R., and Woodward, R.M. Membrane currents elicited by prostaglandins, atrial natriuretic factor and oxytocin in follicle-enclosed Xenopus oocytes. J Physiol 416 623-643 (1989).

Schweer, H., and Fischer, S. Negative ion chemical ionization and collisionally activated decomposition mass spectra of O-2,3,4,5,6-pentafluorobenzyloxime derivatives of prostaglandins. Biol Mass Spectrom 23 47-56 (1994).

Kobzar, G., Mardla, V., Järving, I., et al. Comparison of the inhibitory effect of E-prostaglandins in human and rabbit platelet-rich plasma and washed platelets. Comp Biochem Physiol 106(2) 489-494 (1993).

Kim, E.D., and McVary, K.T. Topical prostaglandin-E₁ for the treatment of erectile dysfunction. J Urol 153 1828-1830 (1995).

Jacobs, H.A., Okano, T., and Kim, S.W. Antithrombogenic surfaces: Characterization and bioactivity of surface immobilized PGE₁-heparin conjugate. J Biomed Mater Res 23 611-630 (1989).

Holcroft, J.W., Vassar, M.J., and Weber, C.J. Prostaglandin E₁ and survival in patients with the adult respiratory distress syndrome. Ann Surg 203 371-378 (1986).

Bergström, S., and Samuelsson, B. Isolation of prostaglandin E₁ from human seminal plasma. Prostaglandins and related factors 11. J Biol Chem 237 PC3005-PC3006 (1962).

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Prostaglandin E1 is available in the following screening libraries:

Size	Price	Quantity	Subtotal
1 mg	$15.00		$0.00
5 mg	$68.00		$0.00
10 mg	$120.00		$0.00
50 mg	$525.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Looking for cGMP Alprostadil? GMP API

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Prostaglandin E1