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Revision as of 11:02, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 469541507 of page Treprostinil for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 14:42, 14 June 2024 edit ActivelyDisinterested (talk | contribs)Extended confirmed users50,211 edits Duplicates {{CS1 config}}, clearing CS1 message 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{More citations needed|date=October 2021}}
{{Drugbox
{{Use dmy dates|date=February 2020}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 431682874
| verifiedrevid = 477864833
| IUPAC_name = (1''R'',2''R'',3a''S'',9a''S'')-<nowiki>-1''H''-benzinden-5-yl]<br>oxy]acetic acid
| image = Treprostinil.svg | image = Treprostinil.svg
| width = 250
| alt =
| image2 = Treprostinil2.png | image2 = Treprostinil2.png
| alt2 =


<!--Clinical data--> <!-- Clinical data -->
| pronounce =
| tradename = Remodulin, Tyvaso
| tradename = Remodulin, Orenitram, Tyvaso, others
| Drugs.com = {{drugs.com|CONS|treprostinil}}
| Drugs.com = {{drugs.com|monograph|treprostinil-sodium}}
| MedlinePlus = a600042
| pregnancy_category = B | MedlinePlus =
| DailyMedID = Treprostinil
| pregnancy_AU = B3
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = ], ], ], ]
| class =
| ATC_prefix = B01
| ATC_suffix = AC21
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment = <ref name="Remodulin FDA label">{{cite web | title=Remodulin- treprostinil injection, solution; Sterile diluent for remodulin- water injection, solution | website=DailyMed | date=9 October 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6c80bb38-e8db-4138-9f0d-dbbf9c673185 | access-date=21 May 2024}}</ref><ref name="Orenitram FDA label">{{cite web | title=Orenitram- treprostinil tablet, extended release; Orenitram- treprostinil kit | website=DailyMed | date=7 November 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8ed2003a-c801-411e-831e-d06079bb0d7c | access-date=21 May 2024}}</ref><ref name="Tyvaso FDA label">{{cite web | title=Tyvaso- treprostinil inhalant | website=DailyMed | date=8 December 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cbc31ab1-a80f-4b50-a3b1-39910b0fb609 | access-date=21 May 2024}}</ref><ref name="Tyvaso DPI FDA label">{{cite web | title=Tyvaso DPI- treprostinil inhalant; Tyvaso DPI- treprostinil kit | website=DailyMed | date=26 January 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ddc3d400-bcb3-4b09-aae2-0768b10a5b0f | access-date=21 May 2024}}</ref>
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Trepulmix EPAR" />
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = ] or ], inhalation


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = approximately 100% | bioavailability = ~100%
| protein_bound =
| metabolism = Treprostinil is substantially metabolized by the liver, but the involved enzymes are not currently known. Five metabolites (HU1 through HU5) have been described thus far. Based on the results of in vitro human hepatic cytochrome P450 studies, Remodulin does not inhibit CYP-1A2, 2C9, 2C19, 2D6, 2E1, or 3A. Whether Remodulin induces these enzymes has not been studied.
| metabolism = Substantially metabolized by the ]
| metabolites =
| onset =
| elimination_half-life = 4 hours | elimination_half-life = 4 hours
| duration_of_action =
| excretion = Urine (79 % of administered dose is excreted in the urine as 4% unchanged drug and 64% as identified metabolites); feces (13%)
| excretion = Urine (79% of administered dose is excreted as 4% unchanged drug and 64% as identified metabolites); feces (13%)


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 289480-64-4 --> | CAS_number = 81846-19-7
| ATC_prefix = B01 | CAS_supplemental =
| ATC_suffix = AC21
| PubChem = 6918140 | PubChem = 6918140
| IUPHAR_ligand = 5820
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00374 | DrugBank = DB00374
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5293353 | ChemSpiderID = 5293353
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RUM6K67ESG | UNII = RUM6K67ESG
| ChEBI_Ref = {{ebicite|changed|EBI}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D06213
| KEGG2_Ref = {{keggcite|changed|kegg}}
| KEGG2 = D08628
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50861 | ChEBI = 50861
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201254 --> | ChEMBL = 1201254
| C=23 | H=34 | O=5 | NIAID_ChemDB =
| PDB_ligand =
| molecular_weight = relative molecular weight is 390.52 g/mol.
| synonyms =
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

<!-- Chemical and physical data -->
| IUPAC_name = (1''R'',2''R'',3a''S'',9a''S'')-<nowiki>-1''H''-benzinden-5-yl]oxy]acetic acid
| C=23 | H=34 | O=5
| SMILES =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1 | StdInChI = 1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PAJMKGZZBBTTOY-ZFORQUDYSA-N | StdInChIKey = PAJMKGZZBBTTOY-ZFORQUDYSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

'''Treprostinil''', sold under the brand names '''Remodulin''' for infusion, '''Orenitram''' for oral, and '''Tyvaso''' for inhalation, is a ] that is used for the treatment of ].<ref name="pmid23259441">{{cite journal | vauthors = Torres F, Rubin LJ | title = Treprostinil for the treatment of pulmonary arterial hypertension | journal = Expert Review of Cardiovascular Therapy | volume = 11 | issue = 1 | pages = 13–25 | date = January 2013 | pmid = 23259441 | doi = 10.1586/erc.12.160 | s2cid = 29661141 }}</ref>

Treprostinil was approved for use in the United States in May 2002.<ref name="Remodulin FDA approval">{{cite web | title=Drug Approval Package: Remodulin (Treprostinil Sodium) NDA #021272 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-272_Remodulin.cfm | access-date=9 April 2020}}</ref>

== Medical uses ==
Treprostinil is ] for the treatment of ] in people with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.<ref name="Remodulin FDA label" />

== Adverse effects ==
* Since treprostinil is a ], its antihypertensive effect may be compounded by other medications that affect the blood pressure, including ], ], and other vasodilating agents.<ref name="pmid27286723"/>
* Because of treprostinil's inhibiting effect on platelet aggregation, there is an increased risk of bleeding, especially among patients who are also taking ]s.<ref name="pmid27286723"/>
* It is not known whether treprostinil is excreted in breast milk. Caution is advised when administering this medication to nursing women.
* Caution is advised when administering treprostinil to patients who have ] or ].<ref name="pmid27286723"/>

Common side effects depending on route of administration:
* 85% of patients report pain or other reaction at the infusion site.<ref name="pmid27286723">{{cite journal | vauthors = Kumar P, Thudium E, Laliberte K, Zaccardelli D, Nelsen A | title = A Comprehensive Review of Treprostinil Pharmacokinetics via Four Routes of Administration | journal = Clinical Pharmacokinetics | volume = 55 | issue = 12 | pages = 1495–1505 | date = December 2016 | pmid = 27286723 | pmc = 5107196 | doi = 10.1007/s40262-016-0409-0 }}</ref>

== Administration ==

===For infusion===
Treprostinil may be administered as a continuous subcutaneous infusion or continuous intravenous infusion.<ref name="Remodulin FDA label" />

===Inhaled form===
The inhaled form of treprostinil was approved by the FDA in July 2009, and is sold under the brand name Tyvaso.<ref name="Tyvaso FDA label" /><ref name="Tyvaso DPI FDA label" />

===Oral form===
The oral form of treprostinil was approved by the FDA in December 2013, and is sold under the brand name Orenitram.<ref name="Orenitram FDA label" />

==History==
{{main|Prostacyclin#History}}
During the 1960s a UK research team, headed by Professor ] began to explore the role of ]s in ] and respiratory diseases. Working with a team from the Royal College of Surgeons, Vane discovered that aspirin and other oral anti-inflammatory drugs worked by inhibiting the synthesis of prostaglandins. This finding opened the door to a broader understanding of the role of prostaglandins in the body.

Vane and a team from the ] had identified a lipid mediator they called “PG-X,” which inhibited platelet aggregation. PG-X, which later would become known as prostacyclin, was 30 times more potent than any other known anti-aggregatory agent.{{citation needed|date=December 2015}}

By 1976, Vane and fellow researcher ] published the first paper on prostacyclin, in the scientific journal ''Nature''.<ref name=Moncada1976>{{cite journal | vauthors = Moncada S, Gryglewski R, Bunting S, Vane JR | title = An enzyme isolated from arteries transforms prostaglandin endoperoxides to an unstable substance that inhibits platelet aggregation | journal = Nature | volume = 263 | issue = 5579 | pages = 663–665 | date = October 1976 | pmid = 802670 | doi = 10.1038/263663a0 | s2cid = 4279030 | bibcode = 1976Natur.263..663M }}</ref>

Treprostinil (Remodulin) was approved for use in the United States in May 2002,<ref name="Remodulin FDA label" /><ref name="Remodulin FDA approval" /> and again in July 2018.<ref>{{cite web | title=Drug Approval Package: Remodulin | website=U.S. ] (FDA) | date=7 February 2019 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208276Orig1s000TOC.cfm | access-date=9 April 2020}}</ref> Tyvaso, the inhaled form of treprostinil, was approved for use in the United States in July 2009.<ref>{{cite web | title=Drug Approval Package: Tyvaso (Treprostinil) Inhalation Solution NDA #022387 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022387s000TOC.cfm | access-date=9 April 2020}}</ref> Orenitram was approved in December 2013.<ref>{{cite web | title=Drug Approval Package: Orenitram (Treprostinil) Extended Release Tablets NDA #203496 | website=U.S. ] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203496Orig1s000TOC.cfm | access-date=9 April 2020}}</ref>

Treprostinil (Trepulmix) was approved for use in the European Union in April 2020.<ref name="Trepulmix EPAR">{{cite web | title=Trepulmix EPAR | website=] (EMA) | date=29 January 2020 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/trepulmix | access-date=9 April 2020}}</ref>

== Research ==
Treprostinil therapy may be effective in treating ].<ref name="pmid23557362">{{cite journal | vauthors = Shapiro LS, Toledo-Garcia AE, Farrell JF | title = Effective treatment of malignant atrophic papulosis (Köhlmeier-Degos disease) with treprostinil--early experience | journal = Orphanet Journal of Rare Diseases | volume = 8 | pages = 52 | date = April 2013 | pmid = 23557362 | pmc = 3636001 | doi = 10.1186/1750-1172-8-52 | doi-access = free }}</ref>

== References ==
{{reflist}}

== Further reading ==
* {{cite journal | vauthors = Narine L, Hague LK, Walker JH, Vicente C, Schilz R, Desjardins O, Einarson TR, Iskedjian M | title = Cost-minimization analysis of treprostinil vs. epoprostenol as an alternate to oral therapy non-responders for the treatment of pulmonary arterial hypertension | journal = Current Medical Research and Opinion | volume = 21 | issue = 12 | pages = 2007–2016 | date = December 2005 | pmid = 16368052 | doi = 10.1185/030079905X75104 | s2cid = 13162585 | url = https://surface.syr.edu/cgi/viewcontent.cgi?article=1002&context=nsd }}

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