Rescinnamine
Identification
- Name
- Rescinnamine
- Accession Number
- DB01180
- 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Rescinnamine (DB01180)
- Weight
- Average: 634.716
Monoisotopic: 634.289030952 - Chemical Formula
- C35H42N2O9
- Synonyms
- 3,4,5-Trimethoxycinnamoyl methyl reserpate
- Rescinnamine
- Trimethoxy cinnamoyl reserpate de methyl
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
For the treatment of hypertension.
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism AAngiotensin-converting enzyme inhibitorHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Rescinnamine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The risk or severity of hyperkalemia can be increased when Rescinnamine is combined with Acebutolol. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Rescinnamine. Acemetacin The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Rescinnamine. Acetylsalicylic acid The therapeutic efficacy of Rescinnamine can be decreased when used in combination with Acetylsalicylic acid. Agrostis gigantea pollen The risk or severity of adverse effects can be increased when Rescinnamine is combined with Agrostis gigantea pollen. Agrostis stolonifera pollen The risk or severity of adverse effects can be increased when Rescinnamine is combined with Agrostis stolonifera pollen. Alclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Alclofenac is combined with Rescinnamine. Aldesleukin Aldesleukin may increase the hypotensive activities of Rescinnamine. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Rescinnamine. Alfuzosin Alfuzosin may increase the hypotensive activities of Rescinnamine. 
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- Not Available
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- International/Other Brands
- Tsuruselpi S
Categories
- ATC Codes
- C02LA52 — Rescinnamine and diuretics, combinations with other drugs
- C02LA — Rauwolfia alkaloids and diuretics in combination
- C02L — ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
- C02 — ANTIHYPERTENSIVES
- C — CARDIOVASCULAR SYSTEM
- C02LA — Rauwolfia alkaloids and diuretics in combination
- C02L — ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
- C02 — ANTIHYPERTENSIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Agents Acting on the Renin-Angiotensin System
- Agents causing angioedema
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alkaloids
- Angiotensin-Converting Enzyme Inhibitors
- Antiadrenergic Agents, Centrally Acting
- Antihypertensive Agents
- Heterocyclic Compounds, Fused-Ring
- Indole Alkaloids
- Indoles
- Secologanin Tryptamine Alkaloids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Yohimbine alkaloids
- Sub Class
- Not Available
- Direct Parent
- Yohimbine alkaloids
- Alternative Parents
- Corynanthean-type alkaloids / Beta carbolines / Cinnamic acid esters / Coumaric acids and derivatives / 3-alkylindoles / Styrenes / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers show 16 more
- Substituents
- 3-alkylindole / Alkyl aryl ether / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 38 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- Q6W1F7DJ2D
- CAS number
- 24815-24-5
- InChI Key
- SZLZWPPUNLXJEA-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[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]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
References
- General References
- Not Available
- External Links
- KEGG Drug
- D00198
- KEGG Compound
- C06540
- PubChem Compound
- 32681
- PubChem Substance
- 46507786
- ChemSpider
- 4444446
- 9259
- ChEBI
- 28572
- ChEMBL
- CHEMBL1668
- ZINC
- ZINC000004097185
- Therapeutic Targets Database
- DAP000910
- PharmGKB
- PA164768818
- Wikipedia
- Rescinnamine
- MSDS
- Download (52.7 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 238.5 °C PhysProp logP 3.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00349 mg/mL ALOGPS logP 4.48 ALOGPS logP 4.07 ChemAxon logS -5.3 ALOGPS pKa (Strongest Acidic) 16.29 ChemAxon pKa (Strongest Basic) 7.56 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 117.78 Å2 ChemAxon Rotatable Bond Count 11 ChemAxon Refractivity 171.16 m3·mol-1 ChemAxon Polarizability 69.65 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9144 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (13.2 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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with our fully connected ADMET & drug target dataset.
Accelerate your drug discovery research with our ADMET & drug target dataset
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- 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...
- Gene Name
- ACE
- Uniprot ID
- P12821
- Uniprot Name
- Angiotensin-converting enzyme
- Molecular Weight
- 149713.675 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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:17016423]
- 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:16431399]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51