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Identification
Name Rescinnamine
Accession Number DB01180 (APRD00112)
Type small molecule
Groups approved
Description

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Methyl Trimethoxycinnamoylreserpate
  • Recinnamine
  • Rescinnamin
  • Reserpinene
  • Reserpinin
  • Reserpinine
  • Trimethoxycinnamoyl Methyl Reserpate
Brand names
  • Anapral
  • Anaprel
  • Apolon
  • Apoterin
  • Apoterin S
  • Cartric
  • Cinamine
  • Cinatabs
  • Cinnaloid
  • Cinnasil
  • Moderil
  • Normorescina
  • Paresinan
  • Raupyrol
  • Raurescin
  • Raurescine
  • Recitensina
  • Rescaloid
  • Rescamin
  • Rescidan
  • Rescin
  • Rescinpal
  • Rescisan
  • Rescitens
  • Resealoid
  • Resipal
  • Reskinnamin
  • Rozex
  • Scinnamina
  • Tenamine
  • Tsuruselpi S
  • Tuareg
Brand name mixtures Not Available
Categories
  • Antihypertensive Agents
CAS number 24815-24-5
Weight Average: 634.716
Monoisotopic: 634.289030952
Chemical Formula C35H42N2O9
InChI Key InChIKey=SZLZWPPUNLXJEA-LAFLMMDJSA-N
InChI
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/t20-,24+,26-,29-,31+,34+/m1/s1
Plain Text
IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
SMILES
[H][C@]12C[C@@H](OC(=O)C=CC3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=C3C=CC(OC)=C1)C2
Plain Text
Mass Spec show (13.2 KB)
Taxonomy
Kingdom Organic
Classes
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Alkanes and Alkenes
  • Acetates
  • Indoles and Indole Derivatives
  • Monolignols
  • Phenols and Derivatives
  • Phenylpropenes
  • Pyrroles
  • Alkaloids and Alkaloid Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Catechols
  • Heterocyclic compounds
  • Aromatic compounds
  • Cinnamaldehydes
  • Anisoles
  • Tryptamines and Derivatives
  • Imines
  • (Iso)quinolines and Derivatives
  • Styrene Derivatives
  • Phenyl Esters
  • Piperidines
  • Cinnamates
Pharmacology
Indication For the treatment of hypertension.
Pharmacodynamics Used to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.
Mechanism of action Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00155 Rescinnamine Pathway SMP00155
Pharmacoeconomics
Manufacturers
  • Panray corp sub ormont drug and chemical co inc
  • Pfizer laboratories div pfizer inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 238.5 oC
Experimental Properties
Property Value Source
logP 3.5 PhysProp
Predicted Properties
Property Value Source
water solubility 3.49e-03 g/l ALOGPS
logP 4.48 ALOGPS
logP 4.07 ChemAxon Molconvert
logS -5.26 ALOGPS
pKa 16.54 ChemAxon Molconvert
hydrogen acceptor count 8 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 117.78 ChemAxon Molconvert
rotatable bond count 11 ChemAxon Molconvert
refractivity 171.16 ChemAxon Molconvert
polarizability 69.65 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00198 Link_out
KEGG Compound C06540 Link_out
PubChem Compound 5280954 Link_out
PubChem Substance 46507786 Link_out
ChemSpider 30295 Link_out
ChEBI 28572 Link_out
ChEMBL 28572 Link_out
Therapeutic Targets Database DAP000910 Link_out
PharmGKB PA451235 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Rescinnamine Link_out
ATC Codes
  • C02AA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (52.7 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Angiotensin-converting enzyme

Pharmacological action: yes
Actions: inhibitor

Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator

Organism class: human
UniProt ID: P12821 Link_out
Gene: ACE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Azhar I, Mazhar F, Manzar QN, Hussain I, Shamim S: Colorimetric determination of indolic drugs. Pak J Pharm Sci. 2005 Apr;18(2):48-51. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:09

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.