U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O4
Molecular Weight 368.4263
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITRAPHYLLINE

SMILES

[H][C@@]12C[C@]3([H])C(=CO[C@@H](C)[C@@]3([H])CN1CC[C@]24C(=O)NC5=CC=CC=C45)C(=O)OC

InChI

InChIKey=JMIAZDVHNCCPDM-DAFCLMLCSA-N
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/24841968|https://www.ncbi.nlm.nih.gov/pubmed/19724995|https://www.ncbi.nlm.nih.gov/pubmed/23975868|https://www.ncbi.nlm.nih.gov/pubmed/22846434|https://www.ncbi.nlm.nih.gov/pubmed/16445836

Mitraphylline is the major pentacyclic oxindolic alkaloid presented in Uncaria tomentosa. It has traditionally been used to treat disorders including arthritis, heart disease, cancer, and other inflammatory diseases. It is also present in the leaves of the tree Mitragyna speciosa, commonly known as kratom, herb which is traditionally used to treat withdrawal symptoms associated with opiate addiction. However, the specific role and the mechanism of action of mitraphylline is not clear. Current research is focusing on mitraphylline as a new promising anticancer and anti-inflammatory agent. Its antiproliferative and cytotoxic effects and in vivo efficacy to induce apoptosis has been studied in human breast cancer, sarcoma, bladder cancer as well as lymphoblastic leukaemia cell lines. As a new candidate for inflammatory disease therapies mitraphylline has been studied in vitro in LPS-activated human primary neutrophils and Its activity against cytokines involved in inflammation process was tested in a murine model in vivo. In mice mitraphylline inhibited around 50% of the release of interleukins 1α, 1β, 17, and TNF-α. It also reduced about 40% of the production of interleukin 4 (IL-4). Mitraphylline was stable in simulated gastric fluid but unstable in simulated intestinal fluid (13.6 % degradation) and was metabolized by human liver microsomes with half-live of 50 min.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines.
2010 Feb
Evaluation of in vitro absorption, distribution, metabolism, and excretion (ADME) properties of mitragynine, 7-hydroxymitragynine, and mitraphylline.
2014 May
Pharmacological effects of mitraphylline from Uncaria tomentosa in primary human monocytes: Skew toward M2 macrophages.
2015 Jul 21
Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils.
2016 Feb 15

Sample Use Guides

Mice received mitraphylline once a day for 3 days at 30 mg/kg/day
Route of Administration: Oral
In vitro use: At 5 - 40 uM mitraphylline inhibited the growth of human Ewing's sarcoma MHH-ES-1 and breast cancer MT-3 cell lines in a dose-dependent manner. The IC50 17.15 uM for MHH-ES-1 and 11.80 uM for MT-3 for 30 hours.
Name Type Language
MITRAPHYLLINE
Common Name English
MITRAPHILLINE
Common Name English
RUBRADININE
Common Name English
FORMOSANAN-16-CARBOXYLIC ACID, 19-METHYL-2-OXO-, METHYL ESTER, (19.ALPHA.)-
Systematic Name English
AJMALICINE OXINDOLE B
Common Name English
MITRAPHYLLIN
Common Name English
SPIRO(3H-INDOLE-3,6'(4'AH)-(1H)PYRANO(3,4-F)INDOLIZINE)-4'-CARBOXYLIC ACID, 1,2,5',5'A,7',8',10',10'A-OCTAHYDRO-1'-METHYL-2-OXO-, METHYL ESTER, (1'S,3R,4'AS,5'AS,10'AR)-
Systematic Name English
MITRAPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC]
Common Name English
RUBRADININ
Common Name English
Code System Code Type Description
SMS_ID
100000127752
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
CAS
509-80-8
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-106-0
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
PUBCHEM
94160
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
EVMPD
SUB33848
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
FDA UNII
1H9SRL2456
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
WIKIPEDIA
Mitraphylline
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID50198926
Created by admin on Thu Jul 06 16:20:38 UTC 2023 , Edited by admin on Thu Jul 06 16:20:38 UTC 2023
PRIMARY