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Identification
NameRescinnamine
Accession NumberDB01180  (APRD00112)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
3,4,5-Trimethoxycinnamoyl methyl reserpateNot AvailableNot Available
RescinnamineNot AvailableNot Available
Trimethoxy cinnamoyl reserpate de methylNot AvailableNot Available
Tsuruselpi SNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Tsuruselpi SNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number24815-24-5
WeightAverage: 634.716
Monoisotopic: 634.289030952
Chemical FormulaC35H42N2O9
InChI KeySZLZWPPUNLXJEA-QEGASFHISA-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/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
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),4,6,8-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
Mass Specshow(13.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassYohimbine Alkaloids
SubclassNot Available
Direct parentYohimbine Alkaloids
Alternative parentsCorynanthean-type Alkaloids; Beta Carbolines; Coumaric Acids and Derivatives; Cinnamic Acids; Indoles; Phenylpropenes; Anisoles; Styrenes; Alkyl Aryl Ethers; Dicarboxylic Acids and Derivatives; Piperidines; Pyrroles; Enones; Tertiary Amines; Carboxylic Acid Esters; Polyamines; Enolates
Substituentspyridoindole; beta-carboline; coumaric acid or derivative; cinnamic acid; cinnamic acid or derivative; indole or derivative; indole; phenylpropene; anisole; phenol ether; styrene; alkyl aryl ether; dicarboxylic acid derivative; piperidine; benzene; pyrrole; enone; tertiary amine; carboxylic acid ester; polyamine; ether; carboxylic acid derivative; enolate; amine; organonitrogen compound
Classification descriptionThis compound belongs to the yohimbine alkaloids. These are compounds containing the pentacyclic yohimban skeleton.
Pharmacology
IndicationFor the treatment of hypertension.
PharmacodynamicsUsed 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 actionRescinnamine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Rescinnamine Action PathwayDrug actionSMP00155
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9604
Blood Brain Barrier + 0.9248
Caco-2 permeable + 0.6805
P-glycoprotein substrate Substrate 0.8163
P-glycoprotein inhibitor I Inhibitor 0.8826
P-glycoprotein inhibitor II Non-inhibitor 0.6553
Renal organic cation transporter Inhibitor 0.5
CYP450 2C9 substrate Non-substrate 0.8706
CYP450 2D6 substrate Non-substrate 0.9064
CYP450 3A4 substrate Substrate 0.7223
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9144
CYP450 3A4 substrate Non-inhibitor 0.8203
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7162
Ames test Non AMES toxic 0.9208
Carcinogenicity Non-carcinogens 0.9453
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.8345 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.697
hERG inhibition (predictor II) Non-inhibitor 0.678
Pharmacoeconomics
Manufacturers
  • Panray corp sub ormont drug and chemical co inc
  • Pfizer laboratories div pfizer inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point238.5 °CPhysProp
logP3.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00349ALOGPS
logP4.48ALOGPS
logP4.07ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.29ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area117.78 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity171.16 m3·mol-1ChemAxon
Polarizability69.65 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00198
KEGG CompoundC06540
PubChem Compound5280954
PubChem Substance46507786
ChemSpider30295
ChEBI28572
ChEMBLCHEMBL1668
Therapeutic Targets DatabaseDAP000910
PharmGKBPA164768818
WikipediaRescinnamine
ATC CodesC02AA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(52.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Angiotensin-converting enzyme

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Angiotensin-converting enzyme P12821 Details

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

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Drug created on June 13, 2005 07:24 / Updated on January 10, 2014 20:33