Rescinnamine

Last updated
Rescinnamine
Rescinnamine.svg
Rescinnamine.png
Clinical data
Trade names Moderil, Cinnasil, Anaprel
Other namesmethyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.042.232 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C35H42N2O9
Molar mass 634.726 g·mol−1
3D model (JSmol)
  • [H][C@]26C[C@@H](OC(=O)/C=C/c1cc(OC)c(OC)c(OC)c1)[C@H](OC)[C@@H](C(=O)OC)[C@@]2([H])C[C@]5([H])c4[nH]c3cc(OC)ccc3c4CCN5C6
  • InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1 Yes check.svgY
  • Key:SZLZWPPUNLXJEA-QEGASFHISA-N Yes check.svgY
   (verify)

Rescinnamine, known by the brand names Moderil, Cinnasil, and Anaprel, is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

It is a vinca alkaloid obtained from Rauvolfia serpentina [1] and other species of Rauvolfia . [2]

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

<span class="mw-page-title-main">Apocynaceae</span> Dogbane and oleander family of flowering plants

Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

<i>Catharanthus</i> Genus of flowering plants

Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".

<span class="mw-page-title-main">Laboratoires Pierre Fabre</span>

Laboratoires Pierre Fabre is a French multinational pharmaceutical and cosmetics company. The company had a consolidated turnover of 1.978 billion euros in 2012. It is headquartered in the city of Castres, Midi-Pyrénées, France.

<span class="mw-page-title-main">Vincristine</span> Chemical compound; chemotherapy medication

Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's disease, neuroblastoma, and small cell lung cancer among others. It is given intravenously.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<i>Vinca</i> Genus of flowering plants

Vinca is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus Catharanthus.

<i>Rauvolfia serpentina</i> Species of plant

Rauvolfia serpentina, the Indian snakeroot, devil pepper, or serpentine wood, is a species of flower in the milkweed family Apocynaceae. It is native to the Indian subcontinent and East Asia.

<i>Catharanthus roseus</i> Species of flowering plant in the family Apocynaceae

Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a perennial species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but grown elsewhere as an ornamental and medicinal plant. It is a source of the drugs vincristine and vinblastine, used to treat cancer. It was formerly included in the genus Vinca as Vinca rosea.

<i>Vinca minor</i> Species of flowering plant in the dogbane family

Vinca minor is a species of flowering plant in the dogbane family, native to central and southern Europe, from Portugal and France north to the Netherlands and the Baltic States, east to the Caucasus, and also southwestern Asia in Turkey. Other vernacular names used in cultivation include small periwinkle, common periwinkle, and sometimes in the United States, myrtle or creeping myrtle.

<i>Vinca</i> alkaloid

Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus and other vinca plants. They block beta-tubulin polymerization in a dividing cell.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<span class="mw-page-title-main">Vindesine</span> Chemical compound

Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus. Like the natural and semisynthetic vinca alkaloids derived from this plant, vindesine is an inhibitor of mitosis that is used as a chemotherapy drug. By inhibiting mitosis, vinedsine blocks the proliferation of cells, particularly the rapidly proliferation cells of certain types of cancer. It is used, generally in combination with other chemotherapeutic drugs, in the treatment of various malignancies such as leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.

<span class="mw-page-title-main">Ajmaline</span> Chemical compound

Ajmaline is an alkaloid that is classified as a 1-A antiarrhythmic agent. It is often used to induce arrhythmic contraction in patients suspected of having Brugada syndrome. Individuals suffering from Brugada syndrome will be more susceptible to the arrhythmogenic effects of the drug, and this can be observed on an electrocardiogram as an ST elevation.

<span class="mw-page-title-main">Akuammine</span> Chemical compound

Akuammine (vincamajoridine) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida, commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid plant products with pharmacological properties.

<span class="mw-page-title-main">Vinflunine</span> Chemical compound

Vinflunine is a novel fluorinated vinca alkaloid derivative undergoing research for the treatment of bladder cancer. It was originally discovered by the team of the Professor Jean-Claude Jacquesy, developed by Laboratoires Pierre Fabre and was licensed to Bristol-Myers Squibb for development in certain countries, including the United States.

<span class="mw-page-title-main">Corynanthine</span> Chemical compound

Corynanthine, also known as rauhimbine, is an alkaloid found in the Rauvolfia and Corynanthe genera of plants. It is one of the two diastereoisomers of yohimbine, the other being rauwolscine. It is also related to ajmalicine.

<span class="mw-page-title-main">Ajmalicine</span> Chemical compound

Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. 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. It is an alkaloid found naturally in various plants such as Rauvolfia spp., Catharanthus roseus, and Mitragyna speciosa.

<span class="mw-page-title-main">Akuammicine</span> Alkaloid

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

<span class="mw-page-title-main">Vinervine</span> Vinca alkaloid

Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

References

  1. FIFE R, MACLAURIN JC, WRIGHT JH (December 1960). "Rescinnamine in treatment of hypertension in hospital clinic and in general practice". British Medical Journal. 2 (5216): 1848–50. doi:10.1136/bmj.2.5216.1848. PMC   2098607 . PMID   13699407.
  2. Balsevich J, Constabel F, Kurz WG (1982). "Alkaloids of Vinca major cv. Variegata". Planta Med. 44 (2): 91–3. doi:10.1055/s-2007-971409. PMID   17402086.