Alprostadil
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MedKoo CAT#: 326671

CAS#: 745-65-3 (free acid),

Description: Alprostadil, also known as PGE1, is a vasodilator that can treat impotence. Alprostadil inhibits platelet aggregation and is a vasodilator in vivo. Alprostadil is a drug used in the continuous treatment of erectile dysfunction and has vasodilatory properties. Alprostadil is also used in maintaining a patent ductus arteriosus in newborns. Alprostadil is also used for critical limb ischemia. It increases blood flow by peripheral vasodilation within five minutes and induces angiogenesis.

Chemical Structure

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Alprostadil
CAS# 745-65-3 (free acid),
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326671
Name: Alprostadil
CAS#: 745-65-3 (free acid),
Chemical Formula: C20H34O5
Exact Mass: 354.24
Molecular Weight: 354.487
Elemental Analysis: C, 67.77; H, 9.67; O, 22.57

Price and Availability

Size Price Availability Quantity
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1350 2 Weeks
500mg USD 3950 2 Weeks
1g USD 4250 2 Weeks
2g USD 6450 2 Weeks
5g USD 9950 2 Weeks
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Related CAS #: 27930-45-6 (sodium)   745-65-3 (free acid),  

Synonym: l-PGE1; l-Prostaglandin E1; Lipoprost; Liprostin; Minprog; NSC 165559; ONO 1608; PGE-1; Promostan; Prostaglandin E1; Prostandin; Alprostadil; Topiglan; Vasaprostan. U 10136; U-10,136.

IUPAC/Chemical Name: 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoic acid

InChi Key: GMVPRGQOIOIIMI-DWKJAMRDSA-N

InChi Code: InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

SMILES Code: O=C(O)CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)CC1=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, not in water

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Prostaglandin E1 (PGE1) is a potent vasodilator and activates the prostaglandin E1 (EP) receptor.
In vitro activity: Cells were pretreated with different doses of alprostadil and then treated with 100 μg/l LPS for 3 h, 6 h, 12 h, and 24 h. This study found that cell viability was significantly restored by the pretreatment with alprostadil (Fig. 1). The cell viability gradually recovered in cells pretreated with 45 μg/l alprostadil for 12 and 24 h (p < 0.01; Fig. 2b). These results indicate that alprostadil protected H9c2 cells against LPS-induced injury; 45 μg/l alprostadil was chosen and used in the following experiments. Reference: Herz. 2020; 45(Suppl 1): 130–138. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7721679/
In vivo activity: Apoptosis assay was performed to explore the effect of Alp (Alprostadil) on liver cell apoptosis. It was found that the proportion of apoptotic liver cells in CLP group was considerably higher than that in Sham group and Alp group (p<0.05). Compared with CLP group, the proportion of apoptotic liver cells remarkably declined in Alp group (p<0.05) (Figure 2). These results suggest that Alp represses the apoptosis in rats with liver injury and promotes the recovery of liver function. Reference: Eur Rev Med Pharmacol Sci. 2021 Feb;25(3):1592-1599. https://pubmed.ncbi.nlm.nih.gov/33629328/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 73.7 207.82
DMF 100.0 282.10
Ethanol 59.7 169.36
Methanol 125.0 352.62
PBS (pH 7.2) 0.5 1.41

Preparing Stock Solutions

The following data is based on the product molecular weight 354.49 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
Formulation protocol: 1. Yu T, Dong D, Guan J, Sun J, Guo M, Wang Q. Alprostadil attenuates LPS-induced cardiomyocyte injury by inhibiting the Wnt5a/JNK/NF-κB pathway. Herz. 2020 Dec;45(Suppl 1):130-138. doi: 10.1007/s00059-019-4837-0. Epub 2019 Jul 16. PMID: 31312872; PMCID: PMC7721679. 2. Haider DG, Bucek RA, Giurgea AG, Maurer G, Glogar H, Minar E, Wolzt M, Mehrabi MR, Baghestanian M. PGE1 analog alprostadil induces VEGF and eNOS expression in endothelial cells. Am J Physiol Heart Circ Physiol. 2005 Nov;289(5):H2066-72. doi: 10.1152/ajpheart.00147.2005. Epub 2005 Jun 10. PMID: 15951350. 3. Wang M, Cai XF, Zhang SM, Xia SY, Du WH, Ma YL. Alprostadil alleviates liver injury in septic rats via TLR4/NF-κB pathway. Eur Rev Med Pharmacol Sci. 2021 Feb;25(3):1592-1599. doi: 10.26355/eurrev_202102_24869. PMID: 33629328. 4. Qin Z, Kong B, Zheng J, Wang X, Li L. Alprostadil Injection Attenuates Coronary Microembolization-Induced Myocardial Injury Through GSK-3β/Nrf2/HO-1 Signaling-Mediated Apoptosis Inhibition. Drug Des Devel Ther. 2020 Oct 22;14:4407-4422. doi: 10.2147/DDDT.S272877. PMID: 33122886; PMCID: PMC7588838.
In vitro protocol: 1. Yu T, Dong D, Guan J, Sun J, Guo M, Wang Q. Alprostadil attenuates LPS-induced cardiomyocyte injury by inhibiting the Wnt5a/JNK/NF-κB pathway. Herz. 2020 Dec;45(Suppl 1):130-138. doi: 10.1007/s00059-019-4837-0. Epub 2019 Jul 16. PMID: 31312872; PMCID: PMC7721679. 2. Haider DG, Bucek RA, Giurgea AG, Maurer G, Glogar H, Minar E, Wolzt M, Mehrabi MR, Baghestanian M. PGE1 analog alprostadil induces VEGF and eNOS expression in endothelial cells. Am J Physiol Heart Circ Physiol. 2005 Nov;289(5):H2066-72. doi: 10.1152/ajpheart.00147.2005. Epub 2005 Jun 10. PMID: 15951350.
In vivo protocol: 1. Wang M, Cai XF, Zhang SM, Xia SY, Du WH, Ma YL. Alprostadil alleviates liver injury in septic rats via TLR4/NF-κB pathway. Eur Rev Med Pharmacol Sci. 2021 Feb;25(3):1592-1599. doi: 10.26355/eurrev_202102_24869. PMID: 33629328. 2. Qin Z, Kong B, Zheng J, Wang X, Li L. Alprostadil Injection Attenuates Coronary Microembolization-Induced Myocardial Injury Through GSK-3β/Nrf2/HO-1 Signaling-Mediated Apoptosis Inhibition. Drug Des Devel Ther. 2020 Oct 22;14:4407-4422. doi: 10.2147/DDDT.S272877. PMID: 33122886; PMCID: PMC7588838.

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1: Jia Y, Liu LL, Su JL, Meng XH, Wang WX, Tian C. Effect of alprostadil in the treatment of intensive care unit patients with acute renal injury. World J Clin Cases. 2021 Feb 26;9(6):1284-1292. doi: 10.12998/wjcc.v9.i6.1284. PMID: 33644195; PMCID: PMC7896675.


2: Wang M, Cai XF, Zhang SM, Xia SY, Du WH, Ma YL. Alprostadil alleviates liver injury in septic rats via TLR4/NF-κB pathway. Eur Rev Med Pharmacol Sci. 2021 Feb;25(3):1592-1599. doi: 10.26355/eurrev_202102_24869. PMID: 33629328.


3: Taşkapu HH, Sönmez MG, Kılınç MT, Altınkaya N, Aydın A, Balasar M. Efficiency of intracavernosal alprostadil and oral clomiphene citrate combination treatment in penile vasculogenic erectile dysfunction patients accompanied by late-onset hypogonadism. Andrologia. 2020 Nov;52(10):e13759. doi: 10.1111/and.13759. Epub 2020 Jul 21. PMID: 33617097.


4: Lu Y, Yan Y, Liu X. Effects of alprostadil combined with tanshinone IIa injection on microcirculation disorder, outcomes, and cardiac function in AMI patients after PCI. Ann Palliat Med. 2021 Jan;10(1):97-103. doi: 10.21037/apm-20-2147. PMID: 33545751.


5: Garrido-Abad P, Senra-Bravo I, Manfredi C, Fernández-Pascual E, Linares- Espinós E, Fernández-Arjona M, Varillas-Delgado D, Martínez-Salamanca JI. Combination therapy with topical alprostadil and phosphodiesterase-5 inhibitors after failure of oral therapy in patients with erectile dysfunction: a prospective, two-arm, open-label, non-randomized study. Int J Impot Res. 2021 Jan 22. doi: 10.1038/s41443-020-00400-9. Epub ahead of print. PMID: 33483603.


6: Guan H, Ye M, Fang C, Zhang L, Han P, Qiu S, Fang X, Li L. The clinical effectiveness and safety of alprostadil combined with alpha lipoic acid in the treatment of diabetic peripheral neuropathy: A protocol for systematic review and meta-analysis. Medicine (Baltimore). 2020 Dec 11;99(50):e23507. doi: 10.1097/MD.0000000000023507. PMID: 33327292; PMCID: PMC7738071.


7: Shestakova KM, Moskaleva NE, Mesonzhnik NV, Kukharenko AV, Serkov IV, Lyubimov II, Fomina-Ageeva EV, Bezuglov VV, Akimov MG, Appolonova SA. In Vivo Targeted Metabolomic Profiling of Prostanit, a Novel Anti-PAD NO-Donating Alprostadil-Based Drug. Molecules. 2020 Dec 13;25(24):5896. doi: 10.3390/molecules25245896. PMID: 33322104; PMCID: PMC7764275.


8: Jain A, Iqbal OA. Alprostadil. 2020 Dec 15. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 31194374.


9: De Basagoiti A, Katsumiti A, Abascal S, Bustinza A, López-Giménez LR, Pascual P, De Miguel M, Campino A. Physical compatibility of alprostadil with selected drugs commonly used in the neonatal intensive care units. Eur J Pediatr. 2021 Apr;180(4):1169-1176. doi: 10.1007/s00431-020-03854-7. Epub 2020 Oct 31. PMID: 33128625.


10: Qin Z, Kong B, Zheng J, Wang X, Li L. Alprostadil Injection Attenuates Coronary Microembolization-Induced Myocardial Injury Through GSK-3β/Nrf2/HO-1 Signaling-Mediated Apoptosis Inhibition. Drug Des Devel Ther. 2020 Oct 22;14:4407-4422. doi: 10.2147/DDDT.S272877. PMID: 33122886; PMCID: PMC7588838.


11: Zhao JQ, Gao YX, Wu C, Sun WL, Hu Y, Wang ZQ, Chen XX, Yu CA, Kong W, Zheng JG. [Effects of alprostadil in β-aminopropanitrile induced aortic dissection in a murine model]. Zhonghua Xin Xue Guan Bing Za Zhi. 2020 Aug 24;48(8):682-688. Chinese. doi: 10.3760/cma.j.cn112148-20190925-00592. PMID: 32847325.


12: Cheng X, Zhan JH, Luo JH, Zheng GY. [Effect of alprostadil in early wound healing of rats with deep partial-thickness scald]. Zhonghua Shao Shang Za Zhi. 2020 Apr 20;36(4):317-322. Chinese. doi: 10.3760/cma.j.cn501120-20190125-00017. PMID: 32340424.


13: Seftel AD. Re: Is Topical Alprostadil an Usable and Reliable Alternative to Intracavernous Injection for Penile Dynamic Duplex Ultrasonography? J Urol. 2020 Jul;204(1):169. doi: 10.1097/JU.0000000000001047.02. Epub 2020 Apr 15. PMID: 32293955.


14: Higgins KL, Buck ML. Caffeine Citrate for the Prevention of Apnea Associated With Alprostadil Infusions. J Pediatr Pharmacol Ther. 2020;25(3):235-240. doi: 10.5863/1551-6776-25.3.235. PMID: 32265607; PMCID: PMC7134579.


15: Xu X, Pan X, Li S. Prospective analysis of the efficacy of beraprost sodium combined with alprostadil on diabetic nephropathy and influence on rennin- angiotensin system and TNF-α. Exp Ther Med. 2020 Jan;19(1):639-645. doi: 10.3892/etm.2019.8265. Epub 2019 Dec 2. PMID: 31885702; PMCID: PMC6913236.


16: Li R, Qi C, Feng Q, Ding P, Kang L, Chi J. Alprostadil alleviates myocardial fibrosis in rats with diabetes mellitus through TGF-β1/Smad signaling pathway. Minerva Endocrinol. 2020 Sep;45(3):270-273. doi: 10.23736/S0391-1977.19.03114-6. Epub 2019 Dec 3. PMID: 31797656.


17: Tu JH, Xu Y, Dai Y, Dang L. Effect of alprostadil on myocardial fibrosis in rats with diabetes mellitus via TGF-β1/Smad signaling pathway. Eur Rev Med Pharmacol Sci. 2019 Nov;23(21):9633-9641. doi: 10.26355/eurrev_201911_19457. PMID: 31773714.


18: Arcaniolo D, Bellastella G, Manfredi C, Terribile M, Giordano DR, Quattrone C, La Rocca R, De Sio M, Verze P, Mirone V. Is topical alprostadil an usable and reliable alternative to intracavernous injection for penile dynamic duplex ultrasonography? Andrologia. 2020 Mar;52(2):e13480. doi: 10.1111/and.13480. Epub 2019 Nov 11. PMID: 31710398.


19: Duan T, Zhang J, Xiang D, Song R, Kong R, Xu D. Effectiveness and safety of intracoronary papaverine, alprostadil, and high dosages of nicorandil and adenosine triphosphate for measurement of the index of coronary microcirculatory resistance in a pig model. Adv Clin Exp Med. 2019 Oct;28(10):1409-1418. doi: 10.17219/acem/104541. PMID: 31638745.


20: Fei S, Li W, Xiang L, Xie X, Zhang L. Protective Effect of Alprostadil on Acute Pancreatitis in Rats via Inhibiting Janus Kinase 2 (JAK2)/STAT3 Signal Transduction Pathway. Med Sci Monit. 2019 Oct 13;25:7694-7701. doi: 10.12659/MSM.919148. PMID: 31606729; PMCID: PMC6807527.