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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H40N2
Molecular Weight 356.5878
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CONESSINE

SMILES

[H][C@]12CC[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]13CN(C)[C@H]2C)N(C)C

InChI

InChIKey=GPLGAQQQNWMVMM-MYAJQUOBSA-N
InChI=1S/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19+,20+,21-,22-,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H40N2
Molecular Weight 356.5878
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Conessine is a plant steroid alkaloid that acts as a potent and specific antagonist of histamine H3 receptors. Conessine displayed high affinity at both rat and human H3 receptors (pKi = 7.61 and 8.27) and generally high selectivity against other sites, including histamine receptors H1, H2, and H4. Conessine was found to efficiently penetrate the CNS and reach very high brain concentrations. Although the very slow CNS clearance and strong binding to adrenergic receptors discouraged focus on conessine itself for further development, its potency and novel steroid-based skeleton motivated further chemical investigation. Modification based on introducing diversity at the 3-nitrogen position generated a new series of H3 antagonists with higher in vitro potency, improved target selectivity, and more favorable drug-like properties. Conessine also has high affinity for the adrenergic receptors. Conessine has being shown to possess anti-malarial activity. In India conessine finds therapeutic use for treatment of dysentery and helminthic disorders.

CNS Activity

Curator's Comment: Conessine was found to efficiently penetrate the CNS and reach very high brain concentrations. Conessine has sedative, central nervous system depressant activities.

Approval Year

PubMed

PubMed

TitleDatePubMed
Squalamine: an aminosterol antibiotic from the shark.
1993 Feb 15
Déjà vu guides the way to new antimicrobial steroid.
1993 Feb 19
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Highly enantioselective construction of fused pyrrolidine systems that contain a quaternary stereocenter: concise formal synthesis of (+)-conessine.
2004 May 3
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Antibacterial activities of the extracts and conessine from Holarrhena floribunda G. Don. (Apocynaceae).
2007 Feb 16
Patents

Patents

Sample Use Guides

Mice: Conessine significantly reduced parasitaemia (at 10 mg/kg exhibited 88.95% parasite inhibition) in P. berghei-infected mice. Conessine was administered orally to mice of different groups for four days
Route of Administration: Oral
Conessine showed in vitro anti-plasmodial activity with its IC₅₀ value 1.9 ug/ml and 1.3 ug/ml using schizont maturation and pLDH assay respectively. The compound showed cytotoxity IC₅₀= 14 ug/ml against L6 cells of rat skeletal muscle myoblast.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:05:24 UTC 2023
Edited
by admin
on Sat Dec 16 17:05:24 UTC 2023
Record UNII
EZ38J9BBDF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONESSINE
INN   MI  
INN  
Official Name English
NSC-119994
Code English
conessine [INN]
Common Name English
CONESSINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
Code System Code Type Description
CHEBI
27965
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-897-2
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
CAS
546-06-5
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL191703
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
FDA UNII
EZ38J9BBDF
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
PUBCHEM
441082
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
EVMPD
SUB06803MIG
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
MESH
C007111
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
NCI_THESAURUS
C79899
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
NSC
119994
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
WIKIPEDIA
CONESSINE
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
INN
443
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
MERCK INDEX
m3750
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6046000
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
SMS_ID
100000084247
Created by admin on Sat Dec 16 17:05:24 UTC 2023 , Edited by admin on Sat Dec 16 17:05:24 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY