Compounds > rhazinilam
Page last updated: 2024-11-07

rhazinilam

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Description

rhazinilam: tetracyclic structure comprises phenyl-pyrrole bridged by a nine-membered lactam ring; novel alkaloid isolated from Aspidosperma quebrachoblanco leaves; possesses mild analgesic activity in mice; RN given refers to (8aR-(8aR*,14aR*))-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AspidospermagenusA plant genus of the family APOCYNACEAE. It contains ellipticine.[MeSH]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID11312435
CHEMBL ID302501
SCHEMBL ID4908273
MeSH IDM0053643

Synonyms (6)

Synonym
rhazinilam
CHEMBL302501
SCHEMBL4908273
Q18394240
(12r)-12-ethyl-8,16-diazatetracyclo[10.6.1.0?,?.0??,??]nonadeca-1(19),2,4,6,17-pentaen-9-one
(12r)-12-ethyl-8,16-diazatetracyclo[10.6.1.02,7.016,19]nonadeca-1(19),2,4,6,17-pentaen-9-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1393116Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at S phase at 1 uM incubated for 72 hrs by flow cytometry (Rvb = 18.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID311667Cytotoxicity against vincristine-resistant human KB/VJ300 cells2007Journal of natural products, Nov, Volume: 70, Issue:11
Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.
AID1393124Inhibition of IL6 production in anti-CD3/anti-CD28 antibody-stimulated human T cells at 0.2 to 5 uM incubated for 48 hrs by ELISA2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393107Immunosuppressive activity in human T cells assessed as reduction in alloantigen stimulation-induced cell proliferation incubated for 72 hrs by CFSE based flow cytometry2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393112Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G0/G1 phase at 0.2 uM incubated for 72 hrs by flow cytometry (Rvb = 66.6%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393119Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at S phase at 5 uM incubated for 72 hrs by flow cytometry (Rvb = 18.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393114Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G2/M phase at 0.2 uM incubated for 72 hrs by flow cytometry (Rvb = 15.3%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393115Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G0/G1 phase at 1 uM incubated for 72 hrs by flow cytometry (Rvb = 66.6%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393129Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD69 expression at 1 uM incubated for 24 hrs by flow cytometry (Rvb = 41.2%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393109Cytotoxicity in human PBMC cells assessed as reduction in cell viability at 20 to 320 uM incubated for 72 hrs by CCK8 assay2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393126Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD25 expression at 5 uM incubated for 24 hrs by flow cytometry (Rvb = 69.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393111Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD69 expression at 0.2 to 5 uM incubated for 24 hrs by flow cytometry2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393128Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD69 expression at 0.2 uM incubated for 24 hrs by flow cytometry (Rvb = 41.2%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393105Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD25 expression at 0.2 uM incubated for 24 hrs by flow cytometry (Rvb = 69.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393110Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD25 expression at 0.2 to 5 uM incubated for 24 hrs by flow cytometry2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393117Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G2/M phase at 1 uM incubated for 72 hrs by flow cytometry (Rvb = 15.3%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393104Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD25 expression at 1 uM incubated for 24 hrs by flow cytometry (Rvb = 69.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393120Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G2/M phase at 5 uM incubated for 72 hrs by flow cytometry (Rvb = 15.3%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID421700Cytotoxicity against human HT-29 cells after 96 hrs by microplate reader assay2009Journal of natural products, Feb-27, Volume: 72, Issue:2
Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea.
AID1393113Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at S phase at 0.2 uM incubated for 72 hrs by flow cytometry (Rvb = 18.1%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393118Induction of cell cycle arrest in anti-CD3/anti-CD28 antibody-stimulated human T cells assessed as accumulation at G0/G1 phase at 5 uM incubated for 72 hrs by flow cytometry (Rvb = 66.6%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393125Inhibition of IL17 production in anti-CD3/anti-CD28 antibody-stimulated human T cells at 0.2 to 5 uM incubated for 48 hrs by ELISA2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID421699Cytotoxicity against human A549 cells after 96 hrs by microplate reader assay2009Journal of natural products, Feb-27, Volume: 72, Issue:2
Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea.
AID311668Cytotoxicity against vincristine-resistant human KB/VJ300 cells in presence of 0.121 uM vincristine2007Journal of natural products, Nov, Volume: 70, Issue:11
Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.
AID1393130Effect on anti-CD3/anti-CD28 antibody-induced cell activation in human T cells assessed as effect on CD69 expression at 5 uM incubated for 24 hrs by flow cytometry (Rvb = 41.2%)2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID311666Cytotoxicity against vincristine-resistant human KB cells2007Journal of natural products, Nov, Volume: 70, Issue:11
Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.
AID1393106Immunosuppressive activity in human T cells assessed as reduction in anti-CD3/anti-CD28 antibody-induced cell proliferation incubated for 72 hrs by CFSE based flow cytometry2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
AID1393108Cytotoxicity in human T cells assessed as reduction in cell viability at 20 to 320 uM incubated for 72 hrs by CCK8 assay2017Journal of natural products, 04-28, Volume: 80, Issue:4
Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (6.06)18.7374
1990's2 (6.06)18.2507
2000's15 (45.45)29.6817
2010's12 (36.36)24.3611
2020's2 (6.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9710sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		7.4720elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
phosphoric acid
phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.		7.110phosphoric acidsalgal metabolite;
fertilizer;
human metabolite;
NMR chemical shift reference compound;
solvent
spermine
[no description available]		1.9710polyazaalkane;
tetramine		antioxidant;
fundamental metabolite;
immunosuppressive agent
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		1.9510benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
vincristine
[no description available]		2.0310acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
phenylephrine
Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.		2.1110phenols;
phenylethanolamines;
secondary amino compound		alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		2.0110alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
dimethylformamide
Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.		1.9710formamides;
volatile organic compound		geroprotector;
hepatotoxic agent;
polar aprotic solvent
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		2.7430pyrrole;
secondary amine
propadiene
[no description available]		2.0310allenes
3-ethylpyridine
3-ethylpyridine: structure given in Merck		7.1110pyridines
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		3.2860metal allergen;
nickel group element atom;
platinum group metal atom
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		7.4620copper group element atom;
elemental gold
zinc sulfate
Zinc Sulfate: A compound given in the treatment of conditions associated with zinc deficiency such as acrodermatitis enteropathica. Externally, zinc sulfate is used as an astringent in lotions and eye drops. (Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Englewood, CO, 1995). zinc sulfate : A metal sulfate compound having zinc(2+) as the counterion.		1.9710metal sulfate;
zinc molecular entity		fertilizer
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		1.9510benzenes;
phenyl acetates
alkenes
[no description available]		2.110
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.1310glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.6930taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
quebrachamine
quebrachamine: an indole alkaloid; isolated from Aspidosperma tree; structure given in first source		7.0510alkaloid
7-acetyltaxol
7-acetyltaxol: structure given in first source		1.9710
docetaxel
[no description available]		2.0510hydrate;
secondary alpha-hydroxy ketone		antineoplastic agent
allocolchicine
allocolchicine: not allo-isomer of colchicine; structure given in first source; RN given refers to (S)-isomer		2.0110
griseofulvin
Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.		1.97101-benzofurans;
antibiotic antifungal drug;
benzofuran antifungal drug;
organochlorine compound;
oxaspiro compound		antibacterial agent;
Penicillium metabolite
tacrolimus
Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.		2.1510macrolide lactambacterial metabolite;
immunosuppressive agent
rhazinicine
rhazinicine: structure in first source		7.9940
maytansine
Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.		1.9810alpha-amino acid ester;
carbamate ester;
epoxide;
maytansinoid;
organic heterotetracyclic compound;
organochlorine compound		antimicrobial agent;
antimitotic;
antineoplastic agent;
plant metabolite;
tubulin modulator
aspidospermidine
aspidospermidine: structure in first source		2.0710Aspidosperma alkaloid;
indole alkaloid fundamental parent
iproniazid
rhazinal: from the stem extracts of a Malayan Kopsia teoi; displays potent and unusual anti-mitotic property; structure in first source		2.4720
leuconolam
leuconolam: structure given in first source		3.9330monoterpenoid indole alkaloid
leuconoxine
leuconoxine: from Leuconotis eugenefolia; structure in first source		7.110alkaloidmetabolite
guanosine diphosphate
Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.		2.1310guanosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		2.7230guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0310
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0310