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Iloprost

Iloprost

Synopsis, Chemistry

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Also known as: Ciloprost, Ventavis, Endoprost, Ilomedin, 78919-13-8, Iloprostum

Molecular Formula

C₂₂H₃₂O₄

Molecular Weight

360.5 g/mol

InChI Key

HIFJCPQKFCZDDL-ACWOEMLNSA-N

FDA UNII

JED5K35YGL

An eicosanoid, derived from the cyclooxygenase pathway of arachidonic acid metabolism. It is a stable and synthetic analog of EPOPROSTENOL, but with a longer half-life than the parent compound. Its actions are similar to prostacyclin. Iloprost produces vasodilation and inhibits platelet aggregation.

Iloprost is a Prostacycline.

1 2D Structure

Iloprost

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid

2.1.2 InChI

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

2.1.3 InChI Key

HIFJCPQKFCZDDL-ACWOEMLNSA-N

2.1.4 Canonical SMILES

CC#CCC(C)C(C=CC1C(CC2C1CC(=CCCCC(=O)O)C2)O)O

2.1.5 Isomeric SMILES

CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)O

2.2 Other Identifiers

2.2.1 UNII

JED5K35YGL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ciloprost

2. Ventavis

3. Zk 36374

4. Zk-36374

5. Zk36374

2.3.2 Depositor-Supplied Synonyms

1. Ciloprost

2. Ventavis

3. Endoprost

4. Ilomedin

5. 78919-13-8

6. Iloprostum

7. Zk-36374

8. Jed5k35ygl

9. Zk 36374

10. Chembl494

11. Chebi:63916

12. Zk 00036374

13. (5e)-5-[(3as,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]pentanoic Acid

14. [3h]-iloprost

15. Ventavis (tn)

16. Zk-00036374

17. 73873-87-7

18. (16r,s)-methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I2

19. 15(r)-iloprost

20. (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

21. Iloprostum [latin]

22. Sr-05000001498

23. Unii-jed5k35ygl

24. Iloprost [usan:inn:ban]

25. Ilomedine

26. Bay Q6256

27. Iloprost [usan]

28. Iloprost (usan/inn)

29. Iloprost [inn]

30. Iloprost [jan]

31. Iloprost [mi]

32. Iloprost [vandf]

33. Iloprost [mart.]

34. Iloprost [who-dd]

35. Iloprost [ema Epar]

36. Iloprost [orange Book]

37. Schembl6083382

38. Iloprost, >=98% (hplc)

39. Bay-q-6256

40. Dtxsid2041046

41. Bdbm23954

42. Hms2090a19

43. 85026-51-3

44. Ex-a6213

45. Hy-a0096

46. Sh-401

47. (16r,s)-methyl-18,18,19,19-tetradehydro-6a-carbaprostaglandin I(sub 2)

48. Akos024456922

49. Cs-5586

50. Db01088

51. (e)-5-(3as,4r,5r,6as)-5-hydroxy-4((e)-(3s,4rs)-3-hydroxy-4-methyl-1-octen-6-inyl)perhydropentalen-2-yliden)valeriansaeure

52. Pentanoic Acid, 5-(hexahydro-5-hydroxy-4-(3-hydroxy-4-methyl-1-octen-6-ynyl)-2(1h)-pentalenylidene)-

53. D02721

54. E-1030

55. Aceticacid2-tert-butyl-4-methylphenylester

56. J-502615

57. Sr-05000001498-1

58. Sr-05000001498-2

59. Brd-a45664787-001-01-4

60. Brd-a45664787-001-02-2

61. Q20817139

62. (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

63. (5e)-(3as,4r,5r,6as)-5-hydroxy-4-((1e)-(3s,4rs)-3-hydroxy-4-methyloct-1-en-6-ynyl)-hexahydropentalen-2(1h)-ylidene)pentanoic Acid

64. (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

65. (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

66. (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

67. 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

68. Pentanoic Acid, 5-((3as,4r,5r,6as)-hexahydro-5-hydroxy-4-((1e,3s)-3-hydroxy-4-methyl-1-octen-6-ynyl)-2(1h)-pentalenylidene)-, (5e)-

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₂O₄
Molecular Weight	360.5 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Exact Mass	360.23005950 g/mol
Monoisotopic Mass	360.23005950 g/mol
Topological Polar Surface Area	77.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	606
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used for the treatment of pulmonary arterial hypertension.

FDA Label

Treatment of patients with primary pulmonary hypertension, classified as New York Heart Association functional class III, to improve exercise capacity and symptoms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Iloprost is a synthetic analogue of prostacyclin PGI2 that dilates systemic and pulmonary arterial vascular beds. It was shown to affect platelet aggregation, but whether this effect contributes to its vasodilatory action has not been elucidated. There are two diastereoisomers of iloprost and the 4S isomer is reported to exhibit a higher potency in dilating blood vessels compared to the 4R isomer.

5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ILOPROST

5.3.2 FDA UNII

JED5K35YGL

5.3.3 Pharmacological Classes

Prostaglandins I [CS]; Prostacycline [EPC]

5.4 ATC Code

B01AC11

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AC - Platelet aggregation inhibitors excl. heparin

B01AC11 - Iloprost

5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed with bioavailability of 63%

Volume of Distribution

0.7 to 0.8 L/kg

Clearance

20 mL/min/kg [Normal subjects]

5.6 Metabolism/Metabolites

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

5.7 Biological Half-Life

20-30 minutes

5.8 Mechanism of Action

Iloprost is a second generation structural analog of prostacyclin (PGI) with about ten-fold greater potency than the first generation stable analogs, such as carbaprostacyclin. Iloprost binds with equal affinity to human prostacyclin (Prostanoid IP) and prostaglandin EP1 receptors. Iloprost constricts the ilium and fundus circular smooth muscle as strongly as prostaglandin E2 (PGE2) itself. Iloprost inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets. In whole animals, iloprost acts as a vasodilator, hypotensive, antidiuretic, and prolongs bleeding time. All of these properties help to antagonize the pathological changes that take place in the small pulmonary arteries of patients with pulmonary hypertension.