(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt
![(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt Structure](StructureFile/ChemBookStructure7/GIF/CB2134383.gif)
- CAS No.
- 81496-19-7
- Chemical Name:
- (4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt
- Synonyms
- AH23848 CALCIUM SALT;AH23848 hemicalcium salt;COFQPJQSNPAAKY-LCCMWPRESA-M;(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt;(4Z)-7-[(rel-1S,2S,5R)-5-((1,1′-Biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]- 4-heptenoic acid hemicalcium salt
- CBNumber:
- CB2134383
- Molecular Formula:
- C29H37CaNO5
- Molecular Weight:
- 519.7
- MDL Number:
- MFCD05665139
- MOL File:
- Mol file
- MSDS File:
- SDS
- TDS File:
- TDS
(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt Properties
| storage temp. | -20°C |
|---|---|
| solubility | DMSO: 18 mg/mL at ≤60 °C |
| form | solid |
| color | off-white |
| InChIKey | JDEBIDDIERGZQY-XVFRBOAOSA-L |
| SMILES | O=C(C[C@@H](OCC1=CC=C(C2=CC=CC=C2)C=C1)[C@H]3CC/C=C\CCC(O[Ca]OC(CC/C=C\CC[C@@H]4[C@H](OCC5=CC=C(C6=CC=CC=C6)C=C5)CC([C@H]4N7CCOCC7)=O)=O)=O)[C@H]3N8CCOCC8 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| PPE | Eyeshields, Gloves, type N95 (US) |
|---|---|
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | A8227 | AH23848 hemicalcium salt ≥90% (HPLC), powder | 81496-19-7 | 5mg | $326 | 2026-04-30 | Buy |
| Sigma-Aldrich | A8227 | AH23848 hemicalcium salt ≥90% (HPLC), powder | 81496-19-7 | 25mg | $1130 | 2026-04-30 | Buy |
| Cayman Chemical | 19023 | AH 23848 (calcium salt) ≥90% | 81496-19-7 | 1mg | $91 | 2026-04-30 | Buy |
| Cayman Chemical | 19023 | AH 23848 (calcium salt) ≥90% | 81496-19-7 | 5mg | $293 | 2026-04-30 | Buy |
| Cayman Chemical | 19023 | AH 23848 (calcium salt) ≥90% | 81496-19-7 | 10mg | $539 | 2026-04-30 | Buy |
(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt Chemical Properties, Uses, Production
Uses
AH23848 has been used as an prostaglandin E2 receptor 4 (EP4) receptor antagonist to study its effect on cAMP accumulation in monocrotaline (MCT28d) rat pulmonary arterial smooth muscle cells (PASMCs) and human T cell enriched peripheral blood mononuclear cells (PBMC). It has also been used to study its effect on the expressions of collagen-I, metalloproteinase (MMP-1), MMP-3, and EP4 gene expression in human tendon fibroblasts following interleukin (IL)-1β treatment.
Definition
ChEBI: (1R,2R,5S)-AH23848 is a (4Z)-7-{5-[([1,1'-biphenyl]-4-yl)methoxy]-2-(morpholin-4-yl)-3-oxocyclopentyl}hept-4-enoic acid in which the stereocentres at positions 1, 2 and 5 have R-, R- and S-configuration respectively. It is a conjugate acid of a (1R,2R,5S)-AH23848(1-). It is an enantiomer of a (1S,2S,5R)-AH23848.
Biological Activity
ah 23848 (calcium salt) is a dual antagonist of tp1 and ep4 receptors [1][2].the thromboxane receptor (tp), also known as the prostanoid tp receptor, is activated by thromboxane a2 (txa2). txa2 is an exceptionally potent inducer of platelet aggregation and of contraction of vascular and respiratory smooth muscle [1]. prostaglandin e2 (pge2) subtype receptors (ep) are involved in cellular proliferation and tumor development. prostaglandin e2 (pge2) activates four ep receptors, ep1-4. the ep4 receptor is coupled to gs and mediates increases in camp concentration by activation of adenylyl cyclase [4].ah 23848 (calcium salt) is a dual antagonist of tp1 and ep4 receptors. ah 23848 is an orally active, potent and specific thromboxane receptor-blocking drug that has a long duration of action. ah 23848 inhibited txa2-induced platelet aggregation and antagonized the contraction of human bronchial smooth muscle induced by the tp agonist u-46619 with pa2 of 8.3 [1][3]. in 3t6 fibroblasts, ah-23848b induced accumulation of cells in early s phase and lowered cyclin a levels [4].in syngeneic balb/cbyj female mice injected with line 66.1 or 410.4 tumor cells, ah23848 inhibited the metastasis of line 66.1 and 410.4 cells [5].
Biochem/physiol Actions
AH23848 regulates nitric oxide (NO) production and reduces endogenous cAMP accumulation. This is carried out by declination of inducible nitric oxide synthase (iNOS) gene expression and acceleration of iNOS protein degradation in glomerular mesangial cells.
References
[1]. brittain rt, boutal l, carter mc, et al. ah23848: a thromboxane receptor-blocking drug that can clarify the pathophysiologic role of thromboxane a2. circulation. 1985 dec;72(6):1208-18.
[2]. coleman ra, grix sp, head sa, et al. a novel inhibitory prostanoid receptor in piglet saphenous vein. prostaglandins. 1994 feb;47(2):151-68.
[3]. coleman ra, sheldrick rl. prostanoid-induced contraction of human bronchial smooth muscle is mediated by tp-receptors. br j pharmacol. 1989 mar;96(3):688-92.
[4]. sanchez, t., and moreno, j.j. role of ep1 and ep4 pge2 subtype receptors in serum-induced 3t6 fibroblast cycle progression and proliferation. american journal of physiology.cell physiology 282, c280-c288 (2002).
[5]. ma x, kundu n, rifat s, et al. prostaglandin e receptor ep4 antagonism inhibits breast cancer metastasis. cancer res. 2006 mar 15;66(6):2923-7.
(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt Preparation Products And Raw materials
Raw materials
Preparation Products
(4Z)-7-[(rel-1S,2s,5r)-5-((1,1'-biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]-4-heptenoic acid calcium salt Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| BOC Sciences | 16314854226 | info@bocsci.com | United States | 9909 | 65 |
| BOC Sciences | 16314854226; +8616314854226 | inquiry@bocsci.com | United States | 19852 | 58 |
| ChemeGen(Shanghai) Biotechnology Co.,Ltd. | 18818260767 | sales@chemegen.com | China | 11123 | 58 |
| amyjet | 4006800868;027-59626688 18771149750 | sales@amyjet.com | China | 2909 | 58 |
| Shanghai Yifei Biotechnology Co. , Ltd. | 021-65675885 18964387627 | customer_service@efebio.com | China | 11963 | 58 |
| Guangzhou Ruidi Biotechnology Co., Ltd. | 020-82099279 18988941402 | sales@ubiochem.com | China | 9998 | 58 |
| Supplier | Advantage |
|---|---|
| Guangzhou Isun Pharmaceutical Co., Ltd | 55 |
| Sigma-Aldrich | 80 |
| BOC Sciences | 65 |
| BOC Sciences | 58 |
| ChemeGen(Shanghai) Biotechnology Co.,Ltd. | 58 |
| amyjet | 58 |
| Shanghai Yifei Biotechnology Co. , Ltd. | 58 |
| Guangzhou Ruidi Biotechnology Co., Ltd. | 58 |
