Alprostadil sodium

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MedKoo CAT#: 412671

CAS#: 27930-45-6 (sodium)

Description: Alprostadil, also known as and 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 sodium
CAS# 27930-45-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 412671
Name: Alprostadil sodium
CAS#: 27930-45-6 (sodium)
Chemical Formula: C20H33NaO5
Exact Mass: 354.2406
Molecular Weight: 376.4688
Elemental Analysis: C, 63.81; H, 8.84; Na, 6.11; O, 21.25

Price and Availability

Size Price Availability Quantity
1.0g USD 4250.0 1 month
2.0g USD 6250.0 1 month
5.0g USD 9950.0 1 month
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Related CAS #: 27930-45-6 (sodium)   745-65-3 (free acid)  

Synonym: Alprostadil sodium; PGE1; Prostaglandin E1; 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: sodium 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)heptanoate

InChi Key: BMHCMWOSEOFUFU-HZTJSMSYSA-M

InChi Code: InChI=1S/C20H34O5.Na/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);/q;+1/p-1/b13-12+;/t15-,16+,17+,19+;/m0./s1

SMILES Code: O=C1[C@@H]([C@H]([C@@H](C1)O)/C=C/[C@@H](O)CCCCC)CCCCCCC(O[Na])=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 ethanol

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in ethanol

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 17.72 50.0

Preparing Stock Solutions

The following data is based on the product molecular weight 376.4688 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

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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.