CAS 78919-13-8|ciloprost|Iloprost|iloprost|2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate|Ventavis

General Information

Structure

Molecular Formula

C₃₀H₃₈O₅

Molecular Mass

478.61972

Exact Mass

478.27192432

Charge

InChI

InChI=1S/C30H38O5/c1-3-4-10-21(2)27(31)16-15-25-26-18-22(17-24(26)19-28(25)32)11-8-9-14-30(34)35-20-29(33)23-12-6-5-7-13-23/h5-7,11-13,15-16,21,24-28,31-32H,8-10,14,17-20H2,1-2H3/b16-15+,22-11-

InChIKey

CZUMMMDKQYRZDP-JCAXBLPDSA-N

Canonic Smiles

CC#CCC(C(/C=C/C1C(O)CC2C1C/C(=C\CCCC(=O)OCC(=O)c1ccccc1)/C2)O)C

Isomeric Smiles

OC1C(C2C(C1)C/C(=C/CCCC(=O)OCC(=O)c1ccccc1)/C2)/C=C/C(O)C(CC#CC)C

Calculated Properties

JChem

Acid pKa

13.723218

H Acceptors

H Donor

LogD (pH = 5.5)

4.942495

LogD (pH = 7.4)

4.942495

Log P

4.942495

Molar Refractivity

139.853

Polarizability

53.542786

Polar Surface Area

83.83

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

5.04

LOG S

-5.38

Solubility (Water)

2.00e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

ciloprost

Synonyms

Iloprostiloprost

IUPAC name

2-oxo-2-phenylethyl 5-[(2Z)-5-hydroxy-4-[(1E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-octahydropentalen-2-ylidene]pentanoate

Brand Name

Ventavis

Names and Identifiers

Registration numbers

PubChem CID

6443959

PubChem SID

16096442246507818

CAS Number

78919-13-8

Registration numbers

Properties

Physical Property

Solubility

Very slightly soluble

Hydrophobicity(logP)

4.8

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB01088

Drug Groups

approved; investigational

Description

Iloprost is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It is used to treat pulmonary arterial hypertension (PAH).

Indication

Used for the treatment of pulmonary arterial hypertension.

Pharmacology

Iloprost is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It also affects platelet aggregation but the relevance of this effect to the treatment of pulmonary hypertension is unknown. The two diastereoisomers of iloprost differ in their potency in dilating blood vessels, with the 4S isomer substantially more potent than the 4R isomer.

Toxicity

Overdoses can lead to hypotension, headache, flushing, nausea, vomiting, and diarrhea.

Affected Organisms

Humans and other mammals

Biotransformation

Primarily hepatic. Iloprost is metabolized principally via beta-oxidation of the carboxyl side chain.

Absorption

Rapidly absorbed with bioavailability of 63%

Half Life

20-30 minutes

Protein Binding

60%