Beraprost

Beraprost

Systematic (IUPAC) name
2,3,3a,8b-tetrahydro-2-hydroxy-1-(3-hydroxy-4- methyl-1-octen-6-ynyl)-1H-cyclopenta(b)benzofuran- 5-butanoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Routes	Oral
Pharmacokinetic data
Bioavailability	50–70%
Metabolism	Unknown
Half-life	35–40 minutes
Excretion	?
Identifiers
CAS number	88430-50-6 88475-69-8
ATC code	B01AC19
PubChem	CID 5282428
IUPHAR ligand	1967
ChemSpider	5293169^Y
UNII	35E3NJJ4O6^Y
Chemical data
Formula	C₂₄H₃₀O₅
Mol. mass	398.492 g/mol
InChI 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^Y Key:CTPOHARTNNSRSR-APJZLKAGSA-N^Y
Y(what is this?) (verify)

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.

Clinical pharmacology

As an analogue of prostacyclin PGI₂, 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.

Dosage and administration

Beraprost is administered orally as a pill.

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab • Eptifibatide • Tirofiban

ADP receptor/P2Y₁₂ inhibitors	thienopyridines (Clopidogrel, Prasugrel, Ticlopidine) • nucleotide/nucleoside analogs (Cangrelor, Elinogrel, Ticagrelor)

Prostaglandin analogue (PGI2)	Beraprost • Prostacyclin • Iloprost • Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# • Aloxiprin • Carbasalate calcium • Indobufen • Triflusal

Thromboxane inhibitors	thromboxane synthase inhibitors (Dipyridamole, Picotamide) • receptor antagonist (Terutroban^†)

Phosphodiesterase inhibitors	Cilostazol • Dipyridamole • Triflusal

Other	Cloricromen • Ditazole

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

coumarins: Acenocoumarol • Coumatetralyl • Dicoumarol • Ethyl biscoumacetate • Phenprocoumon • Warfarin^#

1,3-Indandiones: Clorindione • Diphenadione • Phenindione

other: Tioclomarol

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	low-molecular-weight heparin (Bemiparin, Certoparin, Dalteparin, Enoxaparin, Nadroparin, Parnaparin, Reviparin, Tinzaparin) oligosaccharides (Fondaparinux, Idraparinux) heparinoid (Danaparoid, Sulodexide, Dermatan sulfate)

Direct Xa inhibitors	xabans (Apixaban, Betrixaban, Edoxaban, Otamixaban, Rivaroxaban)

Direct thrombin (II) inhibitors

bivalent: Hirudin (Bivalirudin, Lepirudin, Desirudin)

univalent: Argatroban • Dabigatran • Melagatran^‡ • Ximelagatran^‡

Other

REG1 • Defibrotide • Ramatroban • Antithrombin III • Protein C (Drotrecogin alfa)

Thrombolytic drugs/
fibrinolytics

plasminogen activators: r-tPA (Alteplase, Reteplase, Tenecteplase) • UPA (Urokinase, Saruplase) • Streptokinase^# • Anistreplase • Monteplase

other serine endopeptidases: Ancrod • Fibrinolysin

Brinase

Non-medicinal

Citrate • EDTA • Oxalate

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: MYL

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

Medications used in the management of pulmonary arterial hypertension (B01, C02)

Prostacyclin analogues	Beraprost, Epoprostenol, Iloprost, Treprostinil

Endothelin receptor antagonists	Ambrisentan, Bosentan, Sitaxentan

PDE5 inhibitors	Sildenafil, Tadalafil

Adjunctive therapy	Calcium channel blockers, Diuretics, Digoxin, Oxygen therapy, Warfarin

Autacoids, unsaturated fatty acids: Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG) and
analogues

Precursor

H₂

Active

D/J	D₂

E/F	E₂ (Dinoprostone): Enprostil · Sulprostone E₁ (Alprostadil): Misoprostol · Gemeprost F_2α (Dinoprost): Bimatoprost · Carboprost · Latanoprost · Tafluprost · Travoprost · Unoprostone

I	I₂ (Prostacyclin/Epoprostenol): Beraprost · Iloprost · Treprostinil

Thromboxanes (TX)

A₂ · B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide

Initial	A₄ · B₄

SRS-A	C₄ · D₄ · E₄

Nonclassic

Lipoxins (A₄, B₄) · Virodhamine

By function

bronchoconstriction (PGF_2α, TXA₂, LTC₄, LTD₄, LTE₄)

vasoconstriction (PGF_2α, TXA₂, TXB₂) · vasodilation (PGE₂, PGI₂, LTC₄, LTD₄, LTE₄)

platelets: induce (TXA₂) inhibit (PGD₂, PGI₂) · leukocytes: induce (TXA₂, LTB₄) inhibit (PGD₂, PGE₂)

fever stimulation: (PGE₂)

labor stimulation: (PGE₂ (Dinoprostone), PGF_2α (Dinoprost))

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i