AL-8810 | CAS#246246-19-5 | PGF2α Analog

AL-8810
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531435

CAS#: 246246-19-5

Description: A novel analog of prostaglandin F(2alpha), AL-8810 has uniquely low efficacy (E(max)) at the endogenous prostaglandin F(2alpha) receptors (FP receptors) of A7r5 rat thoracic aorta smooth muscle cells and Swiss mouse 3T3 fibroblasts, as assayed by stimulation of phospholipase C activity. It is a selective antagonist at the prostaglandin F2 alpha (FP) receptor.

Chemical Structure

AL-8810

CAS# 246246-19-5

Instruction

Theoretical Analysis

MedKoo Cat#: 531435
Name: AL-8810
CAS#: 246246-19-5
Chemical Formula: C24H31FO4
Exact Mass: 402.22
Molecular Weight: 402.506
Elemental Analysis: C, 71.62; H, 7.76; F, 4.72; O, 15.90

Price and Availability

Size	Price	Availability
1mg	USD 300	2 Weeks
5mg	USD 780	2 Weeks
10mg	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: AL-8810, AL8810, AL 8810

IUPAC/Chemical Name: (Z)-7-[(1R,2R,3S,5S)-2-[(E,3R)-3-(2,3-dihydro-1H-inden-2-yl)-3-hydroxyprop-1-enyl]-3-fluoro-5-hydroxycyclopentyl]hept-5-enoic acid

InChi Key: WTYSXBKKVNOOIX-JTGCGUAKSA-N

InChi Code: InChI=1S/C24H31FO4/c25-21-15-23(27)20(9-3-1-2-4-10-24(28)29)19(21)11-12-22(26)18-13-16-7-5-6-8-17(16)14-18/h1,3,5-8,11-12,18-23,26-27H,2,4,9-10,13-15H2,(H,28,29)/b3-1-,12-11+/t19-,20-,21+,22+,23+/m1/s1

SMILES Code: O=C(O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](C2CC3=C(C=CC=C3)C2)O)[C@@H](F)C[C@@H]1O

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).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 402.51 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.

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:
In vitro protocol:
In vivo protocol:

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1: Griffin BW, Klimko P, Crider JY, Sharif NA. AL-8810: a novel prostaglandin F2 alpha analog with selective antagonist effects at the prostaglandin F2 alpha (FP) receptor. J Pharmacol Exp Ther. 1999 Sep;290(3):1278-84. PMID: 10454504.

2: Sharif NA. Discovery to Launch of Anti-allergy (Emadine; Patanol/Pataday/Pazeo) and Anti-glaucoma (Travatan; Simbrinza) Ocular Drugs, and Generation of Novel Pharmacological Tools Such as AL-8810. ACS Pharmacol Transl Sci. 2020 Nov 5;3(6):1391-1421. doi: 10.1021/acsptsci.0c00137. PMID: 33344909; PMCID: PMC7737327.

3: Sharif NA, Klimko PG. Prostaglandin FP receptor antagonists: discovery, pharmacological characterization and therapeutic utility. Br J Pharmacol. 2019 Apr;176(8):1059-1078. doi: 10.1111/bph.14335. Epub 2018 Jun 7. PMID: 29679483; PMCID: PMC6451070.

4: Sharif NA, McLaughlin MA, Kelly CR, Xu S, Crider JY, Williams GW, Parker JL. Preclinical pharmacology of AL-12182, a new ocular hypotensive 11-oxa prostaglandin analog. J Ocul Pharmacol Ther. 2006 Oct;22(5):291-309. doi: 10.1089/jop.2006.22.291. PMID: 17076623.

5: Deaver SE, Felix AM, Rhoads ML. Reproductive performance of lactating dairy cattle after intrauterine administration of a prostaglandin F2α receptor antagonist 4 days after insemination. Theriogenology. 2015 Mar 1;83(4):560-6. doi: 10.1016/j.theriogenology.2014.10.019. Epub 2014 Oct 30. PMID: 25488790.

6: Sharif NA, Crider JY, Davis TL. AL-3138 antagonizes FP prostanoid receptor- mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39. doi: 10.1211/0022357001777586. PMID: 11197083.

7: Goupil E, Wisehart V, Khoury E, Zimmerman B, Jaffal S, Hébert TE, Laporte SA. Biasing the prostaglandin F2α receptor responses toward EGFR-dependent transactivation of MAPK. Mol Endocrinol. 2012 Jul;26(7):1189-202. doi: 10.1210/me.2011-1245. Epub 2012 May 25. PMID: 22638073; PMCID: PMC5416999.

8: Woodward DF, Krauss AH, Wang JW, Protzman CE, Nieves AL, Liang Y, Donde Y, Burk RM, Landsverk K, Struble C. Identification of an antagonist that selectively blocks the activity of prostamides (prostaglandin-ethanolamides) in the feline iris. Br J Pharmacol. 2007 Feb;150(3):342-52. doi: 10.1038/sj.bjp.0706989. Epub 2006 Dec 18. PMID: 17179945; PMCID: PMC2013905.

9: Glushakov AV, Robbins SW, Bracy CL, Narumiya S, Doré S. Prostaglandin F2α FP receptor antagonist improves outcomes after experimental traumatic brain injury. J Neuroinflammation. 2013 Oct 30;10:132. doi: 10.1186/1742-2094-10-132. PMID: 24172576; PMCID: PMC3907016.

10: Sharif NA. Neuroaxonal and cellular damage/protection by prostanoid receptor ligands, fatty acid derivatives and associated enzyme inhibitors. Neural Regen Res. 2023 Jan;18(1):5-17. doi: 10.4103/1673-5374.343887. PMID: 35799502; PMCID: PMC9241399.

11: Cao Y, Liu Y, Dong Q, Wang T, Niu C. Alterations in the gut microbiome and metabolic profile in rats acclimated to high environmental temperature. Microb Biotechnol. 2022 Jan;15(1):276-288. doi: 10.1111/1751-7915.13772. Epub 2021 Feb 23. PMID: 33620148; PMCID: PMC8719808.

12: Dimitrova DZ, Dimitrov SD, Iliev I, Mladenov MI, Hristov KL, Mihov DN, Duridanova DB, Gagov HS. Ghrelin signaling in human mesenteric arteries. J Physiol Pharmacol. 2010 Aug;61(4):383-90. PMID: 20814065.

13: Nicotra LL, Vu M, Harvey BS, Smid SD. Prostaglandin ethanolamides attenuate damage in a human explant colitis model. Prostaglandins Other Lipid Mediat. 2013 Jan;100-101:22-9. doi: 10.1016/j.prostaglandins.2013.01.003. Epub 2013 Feb 1. PMID: 23380599.

14: Schaafsma D, Gosens R, Ris JM, Zaagsma J, Meurs H, Nelemans SA. Insulin induces airway smooth muscle contraction. Br J Pharmacol. 2007 Jan;150(2):136-42. doi: 10.1038/sj.bjp.0706985. Epub 2006 Dec 11. PMID: 17160007; PMCID: PMC2042899.

15: Roddy GW, Rinkoski TA, Monson KJ, Chowdhury UR, Fautsch MP. Stanniocalcin-1 (STC-1), a downstream effector molecule in latanoprost signaling, acts independent of the FP receptor for intraocular pressure reduction. PLoS One. 2020 May 4;15(5):e0232591. doi: 10.1371/journal.pone.0232591. PMID: 32365129; PMCID: PMC7197809.

16: Kim YT, Moon SK, Maruyama T, Narumiya S, Doré S. Prostaglandin FP receptor inhibitor reduces ischemic brain damage and neurotoxicity. Neurobiol Dis. 2012 Oct;48(1):58-65. doi: 10.1016/j.nbd.2012.06.003. Epub 2012 Jun 16. PMID: 22709986; PMCID: PMC3415285.

17: Obara K, Inaba R, Kawakita M, Murata A, Yoshioka K, Tanaka Y. Effects of NP-1815-PX, a P2X4 Receptor Antagonist, on Contractions in Guinea Pig Tracheal and Bronchial Smooth Muscles. Biol Pharm Bull. 2022;45(8):1158-1165. doi: 10.1248/bpb.b22-00234. PMID: 35908896.

18: Sharif NA. Synthetic FP-prostaglandin-induced contraction of rat uterus smooth muscle in vitro. Prostaglandins Leukot Essent Fatty Acids. 2008 Mar;78(3):199-207. doi: 10.1016/j.plefa.2008.01.005. Epub 2008 Mar 28. PMID: 18375109.

19: Maehara T, Higashitarumi F, Kondo R, Fujimori K. Prostaglandin F2α receptor antagonist attenuates LPS-induced systemic inflammatory response in mice. FASEB J. 2020 Nov;34(11):15197-15207. doi: 10.1096/fj.202001481R. Epub 2020 Sep 28. PMID: 32985737.

20: More AS, Kim HM, Zhao R, Khang G, Hildebrandt T, Bernlöhr C, Doods H, Lee D, Lee SH, Vanhoutte PM, Wu D. COX-2 mediated induction of endothelium-independent contraction to bradykinin in endotoxin-treated porcine coronary artery. J Cardiovasc Pharmacol. 2014 Sep;64(3):209-17. doi: 10.1097/FJC.0000000000000105. PMID: 25192543.

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AL-8810 featured