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AB120095

AM404, Anandamide transport inhibitor

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(1 Publication)

MW 395.6 Da, Purity >99%. Competitive and selective anandamide transport inhibitor (IC50 = 1 μM). Active in vivo. Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate vanilloid receptors.

View Alternative Names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, 1,8-cineole 2-exo-monooxygenase, 15 LIPOXYGENASE RETICULOCYTE ARACHIDONATE, 15 LOX 1, 15 lipoxygenase 1, 15-LOX, 15-PGDH, 15-hydroxyprostaglandin dehydrogenase [NAD+], 70 kDa lysosomal alpha-glucosidase, AI838772, ALOX15, AW493413, Acid Maltase, Acid alpha glucosidase, Aglucosidase Alfa, Albendazole monooxygenase, Albendazole sulfoxidase, Alpha-glucosidase, Arachidonate 15-lipoxygenase, Arachidonate omega-6 lipoxygenase, CANN6, CB-R, CB1, CB1A, CB1K5, CB1R, CNR, CNR1_HUMAN, CNR2_HUMAN, CNRII, CP2C9_HUMAN, CP33, CP34, CP3A4_HUMAN, CPC9, CX 5, CYP2C, CYP2C10, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIC9, CYPIIIA3, CYPIIIA4, Cannabinoid receptor 1, Cannabinoid receptor 2, Cannabinoid receptor 2 macrophage, Capsaicin receptor, Central cannabinoid receptor, Cytochrome P-450MP, Cytochrome P450 2C9, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 NF-25, Cytochrome P450 PB-1, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-PCN1, DKFZp434K0220, FLJ11090, Glucocorticoid inducible P450, Glucosidase alpha, Glucosidase alpha acid, Glucosidase alpha acid (Pompe disease glycogen storage disease type II), HLP, Hpgd, Hydroxyprostaglandin dehydrogenase 15 (NAD), LOG15, LOX15_HUMAN, LYAG_HUMAN, Lysosomal Alpha-Glucosidase, MGC104252, MGC112732, MGC126680, MGC149605, MGC88320, Microsomal monooxygenase, NAD+ dependent 15 hydroxyprostaglandin dehydrogenase, NF 25, Nifedipine oxidase, OTRPC1, OTTHUMP00000016838, OTTHUMP00000020135, OTTHUMP00000214579, OTTHUMP00000218960, OTTHUMP00000219016, OTTHUMP00000219018, Osm-9-like TRP channel 1, P450 III steroid inducible, P450 MP, P450 PB 1, P450 PCN1, P450, family III, P450C3, P450IIC9, PGDH1, PGDH_HUMAN, PHOAR1, Prostaglandin dehydrogenase 1, Quinine 3-monooxygenase, RP24-311F12.2, S-mephenytoin 4-hydroxylase, SCAN1, SDR36C1, Short chain dehydrogenase/reductase family 36C member 1, TRPV1_HUMAN, TYDP, TYDP1_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Transient receptor potential cation channel subfamily V member 1, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, VR 1, Vanilloid receptor 1, Vanilloid receptor subtype 1, Xenobiotic monooxygenase, cytochrome P-450 S-mephenytoin 4-hydroxylase, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, flavoprotein-linked monooxygenase, hCB2, testis-dominant CNR2 isoform CB2

2 Images
Functional Studies - AM404, Anandamide transport inhibitor (AB120095)
  • FuncS

Unknown

Functional Studies - AM404, Anandamide transport inhibitor (AB120095)

SH-SY5Y cells were incubated at 37°C for 30 minutes with vehicle control (0 μM) and varied concentrations of AM404 (ab120095). Increased expression of c-Fos in SH-SY5Y cells correlates with an increase in AM404 concentration, as described in literature.

Whole cell lysates were prepared with RIPA buffer (containing protease inhibitors and sodium orthovanadate), 20 μg of each were loaded on the gel and the WB was run under reducing conditions. After transfer the membrane was blocked for an hour using 5% BSA before being incubated with ab7963 at 1 μg/ml and ab8227 at 1 μg/ml overnight at 4°C. Antibody binding was detected using an anti-rabbit antibody conjugated to HRP (ab97051) at 1/10000 dilution and visualised using ECL development solution.

Chemical Structure - AM404, Anandamide transport inhibitor (AB120095)
  • Chemical Structure

Lab

Chemical Structure - AM404, Anandamide transport inhibitor (AB120095)

2D chemical structure image of ab120095, AM404, Anandamide transport inhibitor

Key facts

CAS number

183718-77-6

Purity

>99%

Form

Solid

form

Molecular weight

395.6 Da

Molecular formula

C<sub>2</sub><sub>6</sub>H<sub>3</sub><sub>7</sub>NO<sub>2</sub>

PubChem

6604822

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Soluble in ethanol to 50 mM

Biochemical name

N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide

Biological description

Competitive and selective anandamide transport inhibitor (IC50 = 1 μM). Active in vivo. Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate vanilloid receptors.

Canonical smiles

CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(C=C1)O

Isomeric smiles

CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O

InChi

InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-

InChiKey

IJBZOOZRAXHERC-DOFZRALJSA-N

IUPAC Name

(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

TRPV1 also known as the Transient Receptor Potential Vanilloid 1 is a protein that functions as an ion channel. It is activated by heat and capsaicin the compound that makes chili peppers hot. The protein has a mass of approximately 95 kDa. TRPV1 is widely expressed in sensory neurons where it plays a role in pain perception. Cannabinoid Receptor I (CB1) and Cannabinoid Receptor II (CB2) are part of the endocannabinoid system. They are G protein-coupled receptors located in the central nervous system and peripheral tissues. Cytochrome P450 3A4 abbreviated CYP3A4 is an enzyme known for its role in drug metabolism expressed mostly in the liver. TDP1 a tyrosyl-DNA phosphodiesterase facilitates DNA repair. CYP2C9 also contributes to drug metabolism similar to CYP3A4. 15-PGDH (15-hydroxyprostaglandin dehydrogenase) is involved in prostaglandin degradation and 15 Lipoxygenase 1 plays a role in fatty acid metabolism. GAA or Acid Alpha-Glucosidase is necessary for glycogen breakdown.
Biological function summary

TRPV1 channels are central to detecting and regulating body temperature. They participate in inflammatory pain signaling. CB1 and CB2 receptors modulate neurotransmitter release and immune cell function. Both receptors have roles in the endocannabinoid system which includes endogenous cannabinoids like anandamide. CYP3A4 is critical for metabolizing xenobiotics and endogenous compounds affecting drug clearance rates. TDP1 helps in fixing DNA double-strand breaks working with other proteins in a complex. CYP2C9 is responsible for the oxidative metabolism of various substances including several drugs. 15-PGDH regulates prostaglandin levels and 15 Lipoxygenase 1 is involved in producing inflammatory mediators. GAA functions in lysosomes to convert glycogen to glucose.

Pathways

TRPV1 is part of the pain and sensory pathways including those associated with inflammatory responses. It interacts with proteins like calcineurin in pain signaling pathways. CB1 and CB2 receptors are integral to cannabinoid signaling pathways. They regulate the endocannabinoid system and affect pathways related to mood and appetite. CYP3A4 and CYP2C9 enzymes participate in the metabolic pathways of drug detoxification. 15-PGDH participates in arachidonic acid metabolism relating to the pathway of prostaglandin degradation. 15 Lipoxygenase 1 associated with linoleic acid metabolism contributes to leukotriene production. GAA is significant in glycogen metabolism pathways related to energy release processes.

TRPV1 is associated with chronic pain conditions like neuropathy and inflammatory pain. Its dysregulation impacts pain signaling where calcineurin also plays an important role. CB1 and CB2 receptors are linked to disorders such as anxiety and multiple sclerosis due to their role in the endocannabinoid system affecting neurological functions. CYP3A4 and CYP2C9 alterations can influence drug reactions contributing to adverse drug events and vitamin D deficiency. 15-PGDH is relevant in cancer progression due to its role in prostaglandin metabolism. 15 Lipoxygenase 1 associates with inflammatory diseases like atherosclerosis. GAA deficiency causes Pompe disease a glycogen storage disorder impacting muscle and respiratory functions.

Product protocols

Publications (1)

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Nature neuroscience 13:592-600 PubMed20348918

2010

Reduction in endocannabinoid tone is a homeostatic mechanism for specific inhibitory synapses.

Applications

Unspecified application

Species

Unspecified reactive species

Jimok Kim,Bradley E Alger
View all publications

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