Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

AM-251 (drug)

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AM-251
Identifiers
  • 1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidyl)pyrazole-3-carboxamide
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.162.062Edit this at Wikidata
Chemical and physical data
FormulaC22H21Cl2IN4O
Molar mass555.24 g·mol−1
3D model (JSmol)
  • O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(I)cc3)c4C
  • InChI=1S/C22H21Cl2IN4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-7-16(23)13-18(19)24)21(14)15-5-8-17(25)9-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30) checkY
  • Key:BUZAJRPLUGXRAB-UHFFFAOYSA-N checkY
  (verify)

AM-251 is aninverse agonist at theCB1cannabinoid receptor. AM-251 is structurally very close torimonabant; both arebiarylpyrazolecannabinoid receptor antagonists. In AM-251, thep-chloro group attached to thephenyl substituent at C-5 of thepyrazole ring is replaced with ap-iodo group. The resulting compound exhibits slightly betterbinding affinity for theCB1 receptor (with a Ki value of 7.5 nM) than rimonabant, which has a Ki value of 11.5 nM, AM-251 is, however, about two-fold more selective for the CB1 receptor when compared to rimonabant.[1] Like rimonabant, it is additionally a μ-opioid receptor antagonist[2] that attenuates analgesic effects.[3]

AM251 has shown anin vitro antimelanoma activity againstpancreatic andcolon cancer cells.[4]

See also

[edit]

References

[edit]
  1. ^Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, et al. (February 1999). "Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists".Journal of Medicinal Chemistry.42 (4):769–776.doi:10.1021/jm980363y.PMID 10052983.
  2. ^Seely KA, Brents LK, Franks LN, Rajasekaran M, Zimmerman SM, Fantegrossi WE, Prather PL (October 2012)."AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies".Neuropharmacology.63 (5):905–915.doi:10.1016/j.neuropharm.2012.06.046.PMC 3408547.PMID 22771770.
  3. ^Seely KA, Brents LK, Franks LN, Rajasekaran M, Zimmerman SM, Fantegrossi WE, Prather PL (October 2012)."AM-251 and rimonabant act as direct antagonists at mu-opioid receptors: implications for opioid/cannabinoid interaction studies".Neuropharmacology.63 (5):905–915.doi:10.1016/j.neuropharm.2012.06.046.PMC 3408547.PMID 22771770.
  4. ^Carpi S, Fogli S, Romanini A, Pellegrino M, Adinolfi B, Podestà A, et al. (August 2015)."AM251 induces apoptosis and G2/M cell cycle arrest in A375 human melanoma cells"(PDF).Anti-Cancer Drugs.26 (7):754–762.doi:10.1097/CAD.0000000000000246.hdl:11568/750318.PMID 25974027.S2CID 205526223.Archived(PDF) from the original on July 2, 2021.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-3-tetrahydrocannabinols
Delta-4-tetrahydrocannabinols
Delta-7-tetrahydrocannabinols
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Delta-11-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Receptor
(ligands)
CB1Tooltip Cannabinoid receptor type 1
Agonists
(abridged,
full list)
Inverse agonists
Antagonists
CB2Tooltip Cannabinoid receptor type 2
Agonists
Antagonists
NAGly
(GPR18)
Agonists
Antagonists
GPR55
Agonists
Antagonists
GPR119
Agonists
Transporter
(modulators)
eCBTsTooltip Endocannabinoid transporter
Enzyme
(modulators)
FAAHTooltip Fatty acid amide hydrolase
MAGL
ABHD6
ABHD12
Others
  • Others:2-PG(directly potentiates activity of 2-AG at CB1 receptor)
  • ARN-272(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
Stub icon

Thiscannabinoid related article is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=AM-251_(drug)&oldid=1279840217"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp