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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

Iloprost
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 Weight 360.5 g/mol
Molecular Formula C22H32O4
XLogP32.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass360.23005950 g/mol
Monoisotopic Mass360.23005950 g/mol
Topological Polar Surface Area77.8 Ų
Heavy Atom Count26
Formal Charge0
Complexity606
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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


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.


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Looking for 78919-13-8 / Iloprost API manufacturers, exporters & distributors?

Iloprost manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Iloprost API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Iloprost manufacturer or Iloprost supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Iloprost manufacturer or Iloprost supplier.

PharmaCompass also assists you with knowing the Iloprost API Price utilized in the formulation of products. Iloprost API Price is not always fixed or binding as the Iloprost Price is obtained through a variety of data sources. The Iloprost Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Iloprost

Synonyms

Ciloprost, Ventavis, Endoprost, Ilomedin, 78919-13-8, Iloprostum

Cas Number

78919-13-8

Unique Ingredient Identifier (UNII)

JED5K35YGL

About Iloprost

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.

78919-13-8 Manufacturers

A 78919-13-8 manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of 78919-13-8, including repackagers and relabelers. The FDA regulates 78919-13-8 manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. 78919-13-8 API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of 78919-13-8 manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

78919-13-8 Suppliers

A 78919-13-8 supplier is an individual or a company that provides 78919-13-8 active pharmaceutical ingredient (API) or 78919-13-8 finished formulations upon request. The 78919-13-8 suppliers may include 78919-13-8 API manufacturers, exporters, distributors and traders.

click here to find a list of 78919-13-8 suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

78919-13-8 USDMF

A 78919-13-8 DMF (Drug Master File) is a document detailing the whole manufacturing process of 78919-13-8 active pharmaceutical ingredient (API) in detail. Different forms of 78919-13-8 DMFs exist exist since differing nations have different regulations, such as 78919-13-8 USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A 78919-13-8 DMF submitted to regulatory agencies in the US is known as a USDMF. 78919-13-8 USDMF includes data on 78919-13-8's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The 78919-13-8 USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of 78919-13-8 suppliers with USDMF on PharmaCompass.

78919-13-8 WC

A 78919-13-8 written confirmation (78919-13-8 WC) is an official document issued by a regulatory agency to a 78919-13-8 manufacturer, verifying that the manufacturing facility of a 78919-13-8 active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting 78919-13-8 APIs or 78919-13-8 finished pharmaceutical products to another nation, regulatory agencies frequently require a 78919-13-8 WC (written confirmation) as part of the regulatory process.

click here to find a list of 78919-13-8 suppliers with Written Confirmation (WC) on PharmaCompass.

78919-13-8 NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing 78919-13-8 as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for 78919-13-8 API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture 78919-13-8 as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain 78919-13-8 and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a 78919-13-8 NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of 78919-13-8 suppliers with NDC on PharmaCompass.

78919-13-8 GMP

78919-13-8 Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of 78919-13-8 GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right 78919-13-8 GMP manufacturer or 78919-13-8 GMP API supplier for your needs.

78919-13-8 CoA

A 78919-13-8 CoA (Certificate of Analysis) is a formal document that attests to 78919-13-8's compliance with 78919-13-8 specifications and serves as a tool for batch-level quality control.

78919-13-8 CoA mostly includes findings from lab analyses of a specific batch. For each 78919-13-8 CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

78919-13-8 may be tested according to a variety of international standards, such as European Pharmacopoeia (78919-13-8 EP), 78919-13-8 JP (Japanese Pharmacopeia) and the US Pharmacopoeia (78919-13-8 USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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