| Revision as of 05:02, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{drugbox}} taken from revid 456677534 of page Ajmalicine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 03:41, 8 September 2024 edit 98.178.241.102 (talk) Navbox. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 456676199 |
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| verifiedrevid = 477316195 |
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| IUPAC_name = (19α)-16,17-didehydro- 19-methyloxayohimban- 16-carboxylic acid methyl ester |
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| IUPAC_name = (19α)-16,17-didehydro- 19-methyloxayohimban- 16-carboxylic acid methyl ester |
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| image = Ajmalicine.png |
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| image = ] |
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| image2 = ] |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CAS_number = <!-- blanked - oldvalue: 483-04-5 --> |
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| UNII = 4QJL8OX71Z |
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| CAS_number = 483-04-5 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| ChEBI = 2524 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 123325 |
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| ChEMBL = 123325 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=21 | H=24 | N=2 | O=3 |
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| C=21 | H=24 | N=2 | O=3 |
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| smiles = O=C(OC)\C4=C\OC(C5CN3CCc1c(c2ccccc12)C3CC45)C |
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| molecular_weight = 352.43 g/mol |
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| smiles = O=C(OC)\C4=C\OC(C5CN3CCc1c(nc2ccccc12)C3CC45)C |
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| InChI = 1/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3 |
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| InChIKey = GRTOGORTSDXSFK-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1 |
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| StdInChI = 1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GRTOGORTSDXSFK-XJTZBENFSA-N |
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| StdInChIKey = GRTOGORTSDXSFK-XJTZBENFSA-N |
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| melting_point = 262.5 |
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| melting_high = 263 |
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}} |
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}} |
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'''Ajmalicine''', also known as '''δ-yohimbine''' or '''raubasine''', is an ] ] used in the treatment of high ].<ref name="isbn0-306-45465-3">{{cite book | vauthors = Wink M, Roberts MW | chapter = Compartmentation of alkaloid synthesis, transport. and storage | title = Alkaloids: biochemistry, ecology, and medicinal applications | publisher = Plenum Press | location = New York | year = 1998 | isbn = 0-306-45465-3 | chapter-url = https://books.google.com/books?id=bMCzyrAtrvYC&q=ajmalicine&pg=PA451 }}</ref> It has been marketed under numerous brand names including '''Card-Lamuran''', '''Circolene''', '''Cristanyl''', '''Duxil''', '''Duxor''', '''Hydroxysarpon''', '''Iskedyl''', '''Isosarpan''', '''Isquebral''', '''Lamuran''', '''Melanex''', '''Raunatin''', '''Saltucin Co''', '''Salvalion''', and '''Sarpan'''.<ref name="isbn0-306-45465-3"/> It is an ] found ] in various plants such as '']'' spp., '']'', and '']''.<ref name="isbn0-306-45465-3"/><ref name="pmid17401876">{{cite journal | vauthors = Kurz WG, Chatson KB, Constabel F, Kutney JP, Choi LS, Kolodziejczyk P, Sleigh SK, Stuart KL, Worth BR | display-authors = 6 | title = Alkaloid Production in Catharanthus roseus cell cultures VIII | journal = Planta Medica | volume = 42 | issue = 1 | pages = 22–31 | date = May 1981 | pmid = 17401876 | doi = 10.1055/s-2007-971541 | s2cid = 28177495 }}</ref><ref name="pmid19731590">{{cite journal | vauthors = León F, Habib E, Adkins JE, Furr EB, McCurdy CR, Cutler SJ | title = Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A | journal = Natural Product Communications | volume = 4 | issue = 7 | pages = 907–910 | date = July 2009 | pmid = 19731590 | pmc = 9255435 | doi = 10.1177/1934578X0900400705 | s2cid = 37709142 | doi-access = free }}</ref> |
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Ajmalicine is ] related to ], ], and other ] ]s.<ref>{{cite book | vauthors = Roberts MF |title=Alkaloids: Biochemistry, Ecology, and Medicinal Applications |date=1998-06-30 |publisher=Springer Science & Business Media |isbn=978-0-306-45465-3 |language=en}}</ref> Like ], it acts as a ] ] with preferential actions over ]s, underlying its hypotensive rather than hypertensive effects.<ref name="isbn0-306-45465-3"/><ref name="pmid6099269">{{cite journal | vauthors = Roquebert J, Demichel P | title = Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine | journal = European Journal of Pharmacology | volume = 106 | issue = 1 | pages = 203–205 | date = October 1984 | pmid = 6099269 | doi = 10.1016/0014-2999(84)90698-8 }}</ref> |
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Additionally, it is a very strong inhibitor of the ] liver enzyme, which is responsible for the breakdown of many drugs. Its binding affinity at this receptor is 3.30 nM.<ref name="pmid8487254">{{cite journal | vauthors = Strobl GR, von Kruedener S, Stöckigt J, Guengerich FP, Wolff T | title = Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 9 | pages = 1136–1145 | date = April 1993 | pmid = 8487254 | pmc = | doi = 10.1021/jm00061a004 }} </ref> |
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== Biosynthesis == |
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Two moieties are involved in the biosynthesis of ajmalicine, the terpenoid moiety and the indole moiety.<ref name="issn10214437">{{cite journal | vauthors = Chang K, Chen M, Zeng L, Lan X, Wang Q, Liao Z | title = Abscisic Acid Enhanced Ajmalicine Biosynthesis in Hairy Roots of Rauvolfia verticillata by Upregulating Expression of the MEP Pathway Genes | journal = Russian Journal of Plant Physiology | volume = 61 | issue = 1 | pages = 136–141 | year = 2014 | issn = 1021-4437 | doi = 10.1134/S102144371401004X | s2cid = 255013940 }}</ref> The terpenoid moiety is synthesized by the MEP pathway. The MEP pathway starts with pyruvate and D-glyceraldehyde-3-phosphate, followed by the involvement of DXS, DXR, MCT, MECS, HDS, and HDR genes. This results in isopentenyl diphosphate and dimethylallyl diphosphate which are then synthesized into secologanin. The indole moiety is brought about by the indole pathway, where tryptophan decarboxylase (TDC) catalyzes the formation of tryptamine from tryptophan. Strictosidine synthase (STR) then catalyzes the formation of strictosidine from the intermediates of the previous pathways. Strictosidine is the common precursor for all terpenoid indole alkaloids. Ajmalicine is finally synthesized under catalysis of strictosidine glucosidase (SGD). |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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{{Antihypertensives}} |
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{{Adrenergic receptor modulators}} |
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{{Tryptamines}} |
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{{Antihypertensive-stub}} |