Natural Product (NP) Details

General Information of the NP (ID: NP0515)
Name
Iloprost
Synonyms
ILOPROST; Ciloprost; Ventavis; Iloprostum; 78919-13-8; ZK 36374; ZK-36374; CHEMBL494; CHEBI:63916; [3H]-Iloprost; Endoprost; Ilomedin; Ventavis (TN); ZK 00036374; (16R,S)-methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I2; 73873-87-7; (5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]hexahydropentalen-2(1H)-ylidene]pentanoic acid; Iloprostum [Latin]; SR-05000001498; Iloprost [USAN:INN:BAN]; Ilomedine; BAY Q6256; Iloprost (USAN/INN); SCHEMBL6083382; Iloprost, >=98% (HPLC); BAY-q-6256; DTXSID2041046; BDBM23954; HMS2090A19; HY-A0096; SH-401; (16R,S)-Methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I(sub 2); AKOS024456922; CS-5586; DB01088; (E)-5-(3aS,4R,5R,6aS)-5-Hydroxy-4((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-inyl)perhydropentalen-2-yliden)valeriansaeure; K395; Pentanoic acid, 5-(hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)-pentalenylidene)-; ZK-00036374; D02721; ACETICACID2-TERT-BUTYL-4-METHYLPHENYLESTER; J-502615; SR-05000001498-1; SR-05000001498-2; BRD-A45664787-001-01-4; BRD-A45664787-001-02-2; Q20817139; (1S,2R,3R,5S)-7-[(E)-4-carboxybutylidene]-2-[(3S,1E)-3-hydroxy-4-methyl-6-octyne-1-enyl]-3-hydroxybicyclo[3.3.0]octane; (5E)-5-[(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-ynyl]-2(1H)-pentalenylidene]pentanoic acid; (E)-(3aS,4R,5R,6aS)-Hexahydro-5-hydroxy-4-((E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl)-delta(sup 2(1H),delta)-pentalenevaleric acid; (Z)-5-((3aS,4R,5R,6aS)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)hexahydropentalen-2(1H)-ylidene)pentanoic acid; 5-[(2E,3aS,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoic acid
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Pulmonary hypertension [ICD-11: BB01] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.386
 
MDCK Permeability
 -5.109
 
PAMPA
 +++
 
HIA
 +++
 
Distribution
VDss
 -0.408
 
PPB
 58.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - -
HLM Stability
 - - -
 
Excretion
CLplasma
 7.841
 
T1/2
 1.341
Toxicity
DILI
 -
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 ++
 
Respiratory
 +++
 
Human Hepatotoxicity
 +
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 -
 
Genotoxicity
 -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C22H32O4
PubChem CID
5311181
Canonical SMILES
CC#CCC(C)C(C=CC1C(CC2C1CC(=CCCCC(=O)O)C2)O)O
InChI
1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1
InChIKey
HIFJCPQKFCZDDL-ACWOEMLNSA-N
CAS Number
CAS 78919-13-8
ChEBI ID
CHEBI:63916
TTD Drug ID
D05ZTH
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Montelukast      Asthma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression IL6  Molecule Info 
Pathway MAP
                    Experimental
                    Result(s)		 Combined use of iloprost and montelukast may reduce ischemic damage in transient spinal cord ischemia and may provide better neurological outcome.
Target and Pathway
Target(s) Prostaglandin E2 receptor EP2 (PTGER2)  Molecule Info  [3]
KEGG Pathway cAMP signaling pathway Click to Show/Hide
2 Neuroactive ligand-receptor interaction
3 Inflammatory mediator regulation of TRP channels
4 Renin secretion
5 Pathways in cancer
Reactome Prostanoid ligand receptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 Ovarian Infertility Genes
4 Small Ligand GPCRs
5 GPCR ligand binding
6 GPCR downstream signaling
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1966).
Reference 2 Efficacy of iloprost and montelukast combination on spinal cord ischemia/reperfusion injury in a rat model. J Cardiothorac Surg. 2013 Apr 4;8:64.
Reference 3 Exploration of prostanoid receptor subtype regulating estradiol and prostaglandin E2 induction of spinophilin in developing preoptic area neurons. Neuroscience. 2007 May 25;146(3):1117-27.
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