Beraprost: Difference between revisions

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{{Short description|Chemical compound}}
{{Refimprove|date=June 2007}}
{{drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
| Watchedfields = changed
⚫
| UNII = 35E3NJJ4O6 verifiedrevid = 407866856
| verifiedrevid = 447623508
|
|IUPAC_name = 2,3,3''a'',8''b''-tetrahydro-2-hydroxy-1-(3-hydroxy-4-<br>methyl-1-octen-6-ynyl)-1''H''-cyclopenta(''b'')benzofuran-<br>5-butanoic acid<!--lacking stereo descriptors-->
| IUPAC_name = 4-<nowiki/>{(1''R'',2''R'',3a''S'',8b''S'')-2-Hydroxy-1-[(1''E'',3''S'')-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2,3,3a,8b-tetrahydro-1''H''-benzo[''b'']cyclopenta[''d'']furan-5-yl}butanoic acid
| image = Beraprost.svg
| image = Beraprost.svg
| width = 250
| width = 300

⚫
| CAS_number=88430-50-6
<!--Clinical data-->
⚫
| CAS_supplemental={{CAS|88475-69-8}} (sodium salt)
| tradename =
⚫
| ATC_prefix=B01
| Drugs.com = {{drugs.com|international|beraprost}}
⚫
| ATC_suffix=AC19
⚫
| pregnancy_category =
| PubChem=5282428<!--free base-->
⚫
| legal_status =
⚫
| IUPHAR_ligand = 1967
⚫
| routes_of_administration = Oral
| DrugBank=

⚫
| C = 24 | H = 30 | O = 5
<!--Pharmacokinetic data-->
| molecular_weight = 398.492 g/mol
| bioavailability= 50–70%
| bioavailability = 50–70%
| metabolism = Unknown
| metabolism = Unknown
| elimination_half-life= 35–40 minutes
| elimination_half-life = 35–40 minutes
⚫
| excretion =
⚫
| pregnancy_category =

⚫
| routes_of_administration= Oral
<!--Identifiers-->
⚫
| excretion = ?
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| legal_status = ?
⚫
| CAS_number = 88430-50-6
⚫
| CAS_supplemental = {{CAS|88475-69-8}}
⚫
| ATC_prefix = B01
⚫
| ATC_suffix = AC19
| ChEBI = 135633
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1207745
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5293169
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CTPOHARTNNSRSR-APJZLKAGSA-N
| PubChem = 6917951
⚫
| IUPHAR_ligand = 1967
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 35E3NJJ4O6

<!--Chemical data-->
⚫
| C=24 | H=30 | O=5
| smiles = CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)O)O)O
}}
}}


'''Beraprost''' is a pharmaceutical drug used in several Asian countries, including Japan and South Korea, as a [[vasodilator]] and antiplatelet agent.<ref name=drugs>{{Cite web | url = https://www.drugs.com/international/beraprost.html | title = Beraprost | publisher = [[drugs.com]]}}</ref> It is classified as a [[prostacyclin]] analog.<ref name=drugs/><ref>{{cite journal | vauthors = Melian EB, Goa KL | title = Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension | journal = Drugs | volume = 62 | issue = 1 | pages = 107–33 | date = 2002 | pmid = 11790158 | doi = 10.2165/00003495-200262010-00005 }}</ref>
⚫
'''Beraprost''' is a synthetic analogue of [[prostacyclin]], under [[clinical trials]] for the treatment of [[pulmonary hypertension]]. It is also being studied for use in avoiding [[reperfusion injury]].

⚫
It has been studied for the treatment of [[pulmonary hypertension]] and for use in avoiding [[reperfusion injury]].


==Clinical pharmacology==
==Clinical pharmacology==
As an analogue of prostacyclin PGI<sub>2</sub>, beraprost effects [[vasodilation]], which in turn lowers the [[blood pressure]]. Beraprost also inhibits [[platelet]] aggregation, though the role this phenomenon may play in relation to pulmonary hypertension has yet to be determined.
As an analog of prostacyclin PGI<sub>2</sub>, beraprost affects [[vasodilation]], which in turn lowers [[blood pressure]]. Beraprost also inhibits [[platelet]] aggregation, though the role this phenomenon may play in relation to pulmonary hypertension has yet to be determined.


==Dosage and administration==
==Dosage and administration==
Beraprost is administered orally as a pill.
Beraprost is administered orally as a pill available in strength of 20 mcg. Dose ranges from 60 to 180 mcg in divided doses after meals.

==References==
{{reflist}}



{{Antithrombotics}}
{{Antithrombotics}}
{{PAH rx}}
{{PAH rx}}
{{Prostaglandins}}
{{Prostaglandins}}
{{Prostanoidergics}}


[[Category:Prostaglandins]]
[[Category:Prostaglandins]]
[[Category:Alkynes]]
[[Category:Alkyne derivatives]]
[[Category:Alkenes]]
[[Category:Alkene derivatives]]
[[Category:Alcohols]]
[[Category:Secondary alcohols]]


{{blood-drug-stub}}

[[es:Iloprost]]

Latest revision as of 18:37, 24 April 2024

Beraprost
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Bioavailability50–70%
MetabolismUnknown
Elimination half-life35–40 minutes
Identifiers
  • 4-{(1R,2R,3aS,8bS)-2-Hydroxy-1-[(1E,3S)-3-hydroxy-4-methyl-1-octen-6-yn-1-yl]-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl}butanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H30O5
Molar mass398.499 g·mol−1
3D model (JSmol)
  • CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)O)O)O
  • InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1 checkY
  • Key:CTPOHARTNNSRSR-APJZLKAGSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Beraprost is a pharmaceutical drug used in several Asian countries, including Japan and South Korea, as a vasodilator and antiplatelet agent.[1] It is classified as a prostacyclin analog.[1][2]

It has been studied for the treatment of pulmonary hypertension and for use in avoiding reperfusion injury.

Clinical pharmacology[edit]

As an analog of prostacyclin PGI2, beraprost affects vasodilation, which in turn lowers blood pressure. Beraprost also inhibits platelet aggregation, though the role this phenomenon may play in relation to pulmonary hypertension has yet to be determined.

Dosage and administration[edit]

Beraprost is administered orally as a pill available in strength of 20 mcg. Dose ranges from 60 to 180 mcg in divided doses after meals.

References[edit]

  1. ^ a b "Beraprost". drugs.com.
  2. ^ Melian EB, Goa KL (2002). "Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension". Drugs. 62 (1): 107–33. doi:10.2165/00003495-200262010-00005. PMID 11790158.


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