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Anisodamine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Anisodamine
Clinical data
Other names7β-hydroxyhyoscyamine
ATC code
  • None
Identifiers
  • [(1S,3S,5S,7S)-7-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
CAS Number
PubChemCID
ChemSpider
UNII
ECHA InfoCard100.164.962Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO4
Molar mass305.374 g·mol−1
3D model (JSmol)
  • O=C(O[C@@H]1C[C@@H]2N(C)[C@H](C1)C[C@@H]2O)[C@@H](c3ccccc3)CO
  • InChI=1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13+,14-,15+,16+/m1/s1 checkY
  • Key:WTQYWNWRJNXDEG-LEOABGAYSA-N checkY
  (verify)

Anisodamine, also known as7β-hydroxyhyoscyamine, is a mAChRanticholinergic andα1 adrenergicreceptor antagonist used in the treatment of acutecirculatory shock inChina.[1] It is given orally or byinjection, as a racemic mixture (racanisodamine) or as a hydrobromide salt of the natural enantiometer.[2] Eye drops at 0.5% concentration for slowing the progression of myopia is also available in China.[3]

Anisodamine is anaturally occurringtropanealkaloid found in some plants of the familySolanaceae includingDatura.[4] Its Mandarin Chinese name山莨菪 is given afterAnisodus tanguticus (Chinese:;pinyin:shān làng dàng).[5]

In rodents, anisodamine is more "selective" in its action compared to atropine. It poorly passes the blood-brain barrier and binds brain mAChR less tightly. In rodents, it exhibits weaker CNS effects,[6] causes lessmydriasis, but has approximately equal or slightly lower potency in blocking spasms and in reducing GI motility.[7] Chinese textbooks consider it to have a similar spectrum of effects on humans.[8] As a result, it (or rather, its synthetic racemic version) is widely used in China. It was added to China's national Essential Medicine List in 2012.[9]

See also

[edit]

References

[edit]
  1. ^Varma DR, Yue TL (March 1986)."Adrenoceptor blocking properties of atropine-like agents anisodamine and anisodine on brain and cardiovascular tissues of rats".British Journal of Pharmacology.87 (3):587–594.doi:10.1111/j.1476-5381.1986.tb10201.x.PMC 1916562.PMID 2879586.
  2. ^"Pharmacopoeia Search: "山莨菪碱"". 中国药典. Archived fromthe original on 2017-12-03.
  3. ^"消旋山莨菪碱滴眼液防治少年儿童假性近视的疗效分析".国际医药卫生导报 (in Chinese (China)).14 (15):67–68. 2008.doi:10.3760/cma.j.issn.1007-1245.2008.15.027.Archived from the original on 2023-03-27. Retrieved2017-12-03.
  4. ^Ye N, Li J, Gao C, Xie Y (August 2013). "Simultaneous determination of atropine, scopolamine, and anisodamine in Flos daturae by capillary electrophoresis using a capillary coated by graphene oxide".Journal of Separation Science.36 (16):2698–2702.doi:10.1002/jssc.201300304.PMID 23868645.
  5. ^"消旋山莨菪碱" (in Chinese (China)). 中国药典. Archived fromthe original on 2017-12-03. Retrieved3 December 2017.
  6. ^Zhang WW, Song MK, Cui YY, Wang H, Zhu L, Niu YY, et al. (October 2008). "Differential neuropsychopharmacological influences of naturally occurring tropane alkaloids anisodamine versus scopolamine".Neuroscience Letters.443 (3):241–245.doi:10.1016/j.neulet.2008.07.048.PMID 18672024.S2CID 2730169.
  7. ^Poupko JM, Baskin SI, Moore E (March 2007). "The pharmacological properties of anisodamine".Journal of Applied Toxicology.27 (2):116–121.doi:10.1002/jat.1154.PMID 17186568.
  8. ^DAI TJ, YU T, eds. (2016). "第八章 作用于胆碱受体药物 [8 Agents acting on acetylcholine receptors]".麻醉药理学 [Anesthesia Pharmacology] (in Chinese) (4 ed.). Beijing: 人民卫生出版社. p. 133.ISBN 978-7-117-22701-8.
  9. ^Zhang Y, Zou J, Wan F, Peng F, Peng C (May 2023)."Update on the sources, pharmacokinetics, pharmacological action, and clinical application of anisodamine".Biomedicine & Pharmacotherapy.161 114522.doi:10.1016/j.biopha.2023.114522.PMID 37002581.
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)
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