| Identification | Back Directory | [Name]
(5Z,13E)-(9S,11S,15R)-9,15,DIHYDROXY-11-FLUORO-15-(2-INDANYL)-16,17,18,19,20,PENTANOR-5,13-PROSTADIENOIC ACID | [CAS]
246246-19-5 | [Synonyms]
AL 8810
WTYSXBKKVNOOIX-JTGCGUAKSA-N
AL-8810 >=98% (HPLC), solid
(5Z,13E)-(9S,11S,15R)-9,15,DIHYDROXY-11-FLUORO-15-(2-INDANYL)-16,17,18,19,20,PENTANOR-5,13-PROSTADIENOIC ACID
(5z, 13e)-(9s,11s,15r)-9,15,dihydroxy-11-fluoro-15-(2-indanyl)-16,17,18,19,20,pentanor-5,13-prostadienoic acid
9ALPHA,15R-DIHYDROXY-11BETA-FLUORO-15-(2,3-DIHYDRO-1H-INDEN-2-YL)-16,17,18, 19,20-PENTANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID
[1R-[1α(Z),2β(1E,3S*),3β,5α]]-7-[3-Fluoro-5-hydroxy-2-[3-hydroxy-4-[2-(2,3-dihydro-1H-indenyl)]-1-butenyl]cyclolpentyl]-5-heptenoic acid
5-Heptenoic acid, 7-[(1R,2R,3S,5S)-2-[(1E,3R)-3-(2,3-dihydro-1H-inden-2-yl)-3-hydroxy-1-propen-1-yl]-3-fluoro-5-hydroxycyclopentyl]-, (5Z)-
[1R-[1ALPHA(Z),2BETA(1E,3S*),3BETA,5ALPHA]]-7-[3-FLUORO-5-HYDROXY-2-[3-HYDROXY-4-[2-(2,3-DIHYDRO-1H-INDENYL)]-1-BUTENYL]CYCLOLPENTYL]-5-HEPTENOIC ACID
[1R-[1α(Z),2β(1E,3S*),3β,5α]]-7-[3-Fluoro-5-hydroxy-2-[3-hydroxy-4-[2-(2,3-dihydro-1H-indenyl)]-1-butenyl]cyclolpentyl]-5-heptenoic acid, (5Z, 13E)-(9S,11S,15R)-9,15,Dihydroxy-11-fluoro-15-(2-indanyl)-16,17,18,19,20,pentanor-5,13-prostadienoic acid | [Molecular Formula]
C24H31FO4 | [MDL Number]
MFCD04039992 | [MOL File]
246246-19-5.mol | [Molecular Weight]
402.5 |
| Chemical Properties | Back Directory | [Boiling point ]
594.6±50.0 °C(Predicted) | [density ]
1.21±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 10 mg/mL, soluble | [form ]
solid | [pka]
4.76±0.10(Predicted) | [color ]
white to off-white |
| Hazard Information | Back Directory | [Uses]
AL 8810 is an 11β-fluoro analog of PGF2α which acts as a potent and selective antagonist at the FP receptor. AL 8810 has weak intrinsic agonist activity on FP receptor preparations in the 200-300 nM range, yet it fully antagonizes the activity of the potent FP receptor agonist fluprostenol at this concentration, with EC50 values of approximately 430 nM. AL 8810 fully antagonized the bimatoprost-induced calcium mobilization in Swiss 3T3 fibroblasts at 100 μM, indicating that bimatoprost acts as an FP agonist in this preparation. The Ki for the inhibition of several potent agonists at the cloned human ciliary body FP receptor is in the range of 1-2 μM. | [Definition]
ChEBI: AL 8810 is a long-chain fatty acid. | [Biological Activity]
al-8810 is a novel prostaglandin f2α analog that acts as a selective antagonist of prostaglandin f2α (fp) receptor.prostaglandin receptors are a group of g-protein coupled receptor that exhibited a variety of functions in regulation of blood pressure and renal function; smooth muscle contraction; inhibition of plate aggregation; immune response etc.al-8810 has a ec50 of 261 ± 44 nm against fp receptor in the a7r5 rat thoracic aorta smooth muscle cells and a ec50 of 186 ± 63 nm in swiss mouse 3t3 fibroblasts. in addition, al-8810 antagonizes the response to 100 nm fluprostenol (ki = 426 ± 63 nm) in a concentration- dependent manner in a7r5 cells. [1]in the h-tm cells, al-8810 antagonizes the (±) fluprostenol-induced pi turn over responses concentration dependently (ki=2.56 ± 0.62 μm). al-8810 also antagonizes bimatoprost, travoprost acid, latanoprost acid and travoprost acid. [2] in hcm cells, 1 μm al-8810 blocks the 85% pgf2-induced mmp-2 secretion and 66% pgf2α-induced activation of erk1/2. [3] | [Biochem/physiol Actions]
AL-8810 is a novel prostaglandin F2α analog; selective FP prostanoid receptor antagonist. | [in vivo]
AL-8810 (1 or 10 mg/kg, intravenously) reduces ischemic brain injury and neurotoxicity in mice[2].
AL-8810 (10 mg/kg, intraperitoneal injection) can improve the prognosis after experimental traumatic brain injury in mice[5].
| Animal Model: | Stroke mouse model[2] | | Dosage: | 1 or 10 mg/kg | | Administration: | i.v. | | Result: | Reduced the cortical infarct volume and tape-removal times. |
| Animal Model: | Traumatic brain injury (TBI) model[5] | | Dosage: | 10 mg/kg | | Administration: | i.p. | | Result: | Improved neurological deficit scores (NDS) at 24 and 48 hours after controlled cortical impact (CCI). |
| [storage]
Store at -20°C | [References]
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):1278-84.2. husain s, jafri f, crosson ce. acute effects of pgf2alpha on mmp-2 secretion from human ciliary muscle cells: a pkc- and erk-dependent process. invest ophthalmol vis sci. 2005 may;46(5):1706-13.3. sharif na, kelly cr, crider jy. human trabecular meshwork cell responses induced by bimatoprost, travoprost, unoprostone, and other fp prostaglandin receptor agonist analogues. invest ophthalmol vis sci. 2003 feb;44(2):715-21. |
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