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{{Use dmy dates|date=November 2019}}
{{Infobox drug
{{Infobox drug
| drug_name =
| drug_name =
| INN =
| INN =
| type =<!-- empty -->
| type =<!-- empty -->
⚫
| IUPAC_name = (2''S'')-1-''N''-[4-Methyl-5-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl]-1,3-thiazol-2-yl]pyrrolidine-1,2-dicarboxamide
| image = Alpelisib.svg
| image = Alpelisib.svg
| alt =
| alt =
| caption =
| caption =

<!-- Clinical data -->
<!-- Clinical data -->
| pronounce =
| pronounce =
| tradename = Piqray
| tradename = Piqray
| Drugs.com =
| Drugs.com = {{drugs.com|monograph|alpelisib}}
| MedlinePlus =
| MedlinePlus = a619036
| licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) -->
| licence_EU = <!-- EMA uses INN (or special INN_EMA) -->
| DailyMedID = Alpelisib
⚫
| licence_US = Piqray
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| pregnancy_AU_comment =
| pregnancy_AU_comment =
| pregnancy_US = <!-- A/B/C/D/X/N -->
| pregnancy_US = N
| pregnancy_US_comment =
| pregnancy_category=
| pregnancy_category=
| dependency_liability =
⚫
| routes_of_administration =
| addiction_liability =
⚫
| routes_of_administration = [[By mouth|Oral]]
⚫
| class =
⚫
| ATCvet =
| ATC_prefix = L01
| ATC_suffix = XX65
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III -->
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| 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 = <!-- 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 = Rx-only
| legal_US_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status = <!-- Free text -->
| legal_status = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->
<!-- Pharmacokinetic data -->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| metabolites =
| metabolites =
| onset =
| onset =
| elimination_half-life =
| elimination_half-life =
| duration_of_action =
| duration_of_action =
| excretion =
| excretion =

<!-- Identifiers -->
<!-- Identifiers -->
| CAS_number = 1217486-61-7
| CAS_number = 1217486-61-7
| class =
| CAS_supplemental =
⚫
| ATCvet =
⚫
| ATC_prefix = L01
⚫
| ATC_suffix = XX65
| PubChem = 56649450
| PubChem = 56649450
| PubChemSubstance = 347828332
| IUPHAR_ligand =
| DrugBank = DB12015
| ChemSpiderID = 28424123
| UNII = 08W5N2C97Q
| UNII = 08W5N2C97Q
| DrugBank =
| KEGG =
| ChEBI = 93752
| ChEMBL = 2396661
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = BYL719
| synonyms = BYL719

<!-- Chemical and physical data -->
<!-- Chemical and physical data -->
⚫
| IUPAC_name = (2''S'')-1-''N''-[4-Methyl-5-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl]-1,3-thiazol-2-yl]pyrrolidine-1,2-dicarboxamide
⚫
| C=19|H=22|F=3|N=5|O=2|S=1
| chemical_formula =
⚫
| StdInChIKey = STUWGJZDJHPWGZ-LBPRGKRZSA-N
⚫
| C=19 | H=22 | F=3 | N=5 | O=2 | S=1
⚫
| StdInChI=1S/C19H22F3N5O2S/c1-10-14(11-6-7-24-13(9-11)18(2,3)19(20,21)22)30-16(25-10)26-17(29)27-8-4-5-12(27)15(23)28/h6-7,9,12H,4-5,8H2,1-3H3,(H2,23,28)(H,25,26,29)/t12-/m0/s1
| molecular_weight =
| SMILES = CC1=C(SC(=N1)NC(=O)N2CCCC2C(=O)N)C3=CC(=NC=C3)C(C)(C)C(F)(F)F
| Jmol =
⚫
| StdInChI = 1S/C19H22F3N5O2S/c1-10-14(11-6-7-24-13(9-11)18(2,3)19(20,21)22)30-16(25-10)26-17(29)27-8-4-5-12(27)15(23)28/h6-7,9,12H,4-5,8H2,1-3H3,(H2,23,28)(H,25,26,29)/t12-/m0/s1
| StdInChI_comment =
⚫
| StdInChIKey = STUWGJZDJHPWGZ-LBPRGKRZSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}
}}
<!-- Definition and medical uses -->
<!-- Definition and medical uses -->
'''Alpelisib''' ([[International Nonproprietary Name|INN]]; development code '''BYL719'''; brand name '''Piqray''') is a medication sold by Novartis and used to treat certain types of [[breast cancer]].<ref name=FDA2019/> It is used together with [[fulvestrant]].<ref name=FDA2019>{{cite web |title=FDA approves first PI3K inhibitor for breast cancer |url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-pi3k-inhibitor-breast-cancer |website=FDA |accessdate=29 May 2019 |language=en |date=24 May 2019}}</ref> It is taken by mouth.<ref name=FDA2019/>
'''Alpelisib''' ([[International Nonproprietary Name|INN]]; development code '''BYL719'''; brand name '''Piqray''') is a medication sold by Novartis and used to treat certain types of [[breast cancer]].<ref name=FDA2019/> It is used together with [[fulvestrant]].<ref name=FDA2019>{{cite press release |title=FDA approves first PI3K inhibitor for breast cancer | url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-pi3k-inhibitor-breast-cancer | website=U.S. [[Food and Drug Administration]] (FDA) | accessdate=29 May 2019 | date=24 May 2019 | archive-url=https://web.archive.org/web/20191125012114/https://www.fda.gov/news-events/press-announcements/fda-approves-first-pi3k-inhibitor-breast-cancer | archive-date=25 November 2019 | url-status=live }}{{PD-notice}}</ref> It is taken by mouth.<ref name=FDA2019/>


<!-- Side effects and mechanism -->
<!-- Side effects and mechanism -->
Common side effects include high blood sugar, kidney problems, diarrhea, rash, low blood cells, liver problems, pancreatitis, vomiting, and hair loss.<ref name=FDA2019/> It is an alpha-specific [[PI3K inhibitor]].<ref name=FDA2019/><ref>{{Cite journal | doi = 10.1056/NEJMoa1813904 | pmid = 31091374 | title = Alpelisib for PIK3CA-Mutated, Hormone Receptor–Positive Advanced Breast Cancer | journal = New England Journal of Medicine | volume = 380 | issue = 20 | pages = 1929–1940 | year = 2019 | last1 = André | first1 = Fabrice | last2 = Ciruelos | first2 = Eva | last3 = Rubovszky | first3 = Gabor | last4 = Campone | first4 = Mario | last5 = Loibl | first5 = Sibylle | last6 = Rugo | first6 = Hope S. | last7 = Iwata | first7 = Hiroji | last8 = Conte | first8 = Pierfranco | last9 = Mayer | first9 = Ingrid A. | last10 = Kaufman | first10 = Bella | last11 = Yamashita | first11 = Toshinari | last12 = Lu | first12 = Yen-Shen | last13 = Inoue | first13 = Kenichi | last14 = Takahashi | first14 = Masato | last15 = Pápai | first15 = Zsuzsanna | last16 = Longin | first16 = Anne-Sophie | last17 = Mills | first17 = David | last18 = Wilke | first18 = Celine | last19 = Hirawat | first19 = Samit | last20 = Juric | first20 = Dejan | author21 = SOLAR-1 Study Group | author22 = the SOLAR-1 Study Group }}</ref> It was approved for medical use in the United States in May of 2019.<ref name=FDA2019/>
Common side effects include high blood sugar, kidney problems, diarrhea, rash, low blood cells, liver problems, pancreatitis, vomiting, and hair loss.<ref name=FDA2019/> It is an alpha-specific [[PI3K inhibitor]].<ref name=FDA2019/><ref>{{Cite journal | doi = 10.1056/NEJMoa1813904 | pmid = 31091374 | title = Alpelisib for PIK3CA-Mutated, Hormone Receptor–Positive Advanced Breast Cancer | journal = New England Journal of Medicine | volume = 380 | issue = 20 | pages = 1929–1940 | year = 2019 | last1 = André | first1 = Fabrice | last2 = Ciruelos | first2 = Eva | last3 = Rubovszky | first3 = Gabor | last4 = Campone | first4 = Mario | last5 = Loibl | first5 = Sibylle | last6 = Rugo | first6 = Hope S. | last7 = Iwata | first7 = Hiroji | last8 = Conte | first8 = Pierfranco | last9 = Mayer | first9 = Ingrid A. | last10 = Kaufman | first10 = Bella | last11 = Yamashita | first11 = Toshinari | last12 = Lu | first12 = Yen-Shen | last13 = Inoue | first13 = Kenichi | last14 = Takahashi | first14 = Masato | last15 = Pápai | first15 = Zsuzsanna | last16 = Longin | first16 = Anne-Sophie | last17 = Mills | first17 = David | last18 = Wilke | first18 = Celine | last19 = Hirawat | first19 = Samit | last20 = Juric | first20 = Dejan | author21 = SOLAR-1 Study Group | author22 = the SOLAR-1 Study Group }}</ref> It was approved for medical use in the United States in May 2019.<ref name=FDA2019/>

==History==
In May 2019, alpelisib was approved in the United States for use in combination with the endocrine therapy fulvestrant, to treat postmenopausal women, and men, with hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative, PIK3CA-mutated, advanced or metastatic breast cancer following progression on or after an endocrine-based regimen.<ref name=FDA2019 />

The U.S. [[Food and Drug Administration]] (FDA) also approved the companion diagnostic test, therascreen PIK3CA RGQ PCR Kit, to detect the PIK3CA mutation in a tissue and/or a liquid biopsy.<ref name=FDA2019 />

The efficacy of alpelisib was studied in the SOLAR-1 trial (NCT02437318), a randomized trial of 572 postmenopausal women and men with HR-positive, HER2-negative, advanced or metastatic breast cancer whose cancer had progressed while on or after receiving an aromatase inhibitor.<ref name=FDA2019 /><ref name="FDA Snapshot">{{cite web | title=Drug Trials Snapshots: Piqray | website=U.S. [[Food and Drug Administration]] (FDA) | date=14 June 2019 | url=https://www.fda.gov/drugs/drug-trials-snapshots-piqray | archive-url=https://web.archive.org/web/20191125013110/https://www.fda.gov/drugs/drug-trials-snapshots-piqray | archive-date=25 November 2019 | url-status=live | access-date=24 November 2019}}</ref>

The FDA granted the application for alpelisib [[priority review]] designation and granted approval of Piqray to Novartis. The FDA granted approval of the therascreen PIK3CA RGQ PCR Kit to Qiagen Manchester, Ltd.<ref name=FDA2019 />


==References==
==References==
{{reflist}}
{{reflist}}


==External links==
⚫
{{pharma-stub}}
* {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/alpelisib | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Alpelisib }}


{{portal bar | Pharmacy and pharmacology}}

⚫
[[Category:Amides]]
[[Category:Phosphoinositide 3-kinase inhibitors]]
[[Category:Phosphoinositide 3-kinase inhibitors]]
⚫
[[Category:Ureas]]
[[Category:Pyridines]]
[[Category:Pyridines]]
[[Category:Pyrrolidines]]
[[Category:Pyrrolidines]]
[[Category:Thiazoles]]
[[Category:Thiazoles]]
[[Category:Trifluoromethyl compounds]]
[[Category:Trifluoromethyl compounds]]
[[Category:Amides]]
[[Category:Ureas]]

⚫
{{pharma-stub}}

Revision as of 01:47, 25 November 2019

Alpelisib
Clinical data
Trade namesPiqray
Other namesBYL719
AHFS/Drugs.comMonograph
MedlinePlusa619036
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
  • (2S)-1-N-[4-Methyl-5-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl]-1,3-thiazol-2-yl]pyrrolidine-1,2-dicarboxamide
CAS Number
PubChem CID
PubChem SID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.233.704 Edit this at Wikidata
Chemical and physical data
FormulaC19H22F3N5O2S
Molar mass441.47 g·mol−1
3D model (JSmol)
  • CC1=C(SC(=N1)NC(=O)N2CCCC2C(=O)N)C3=CC(=NC=C3)C(C)(C)C(F)(F)F
  • InChI=1S/C19H22F3N5O2S/c1-10-14(11-6-7-24-13(9-11)18(2,3)19(20,21)22)30-16(25-10)26-17(29)27-8-4-5-12(27)15(23)28/h6-7,9,12H,4-5,8H2,1-3H3,(H2,23,28)(H,25,26,29)/t12-/m0/s1
  • Key:STUWGJZDJHPWGZ-LBPRGKRZSA-N

Alpelisib (INN; development code BYL719; brand name Piqray) is a medication sold by Novartis and used to treat certain types of breast cancer.[1] It is used together with fulvestrant.[1] It is taken by mouth.[1]

Common side effects include high blood sugar, kidney problems, diarrhea, rash, low blood cells, liver problems, pancreatitis, vomiting, and hair loss.[1] It is an alpha-specific PI3K inhibitor.[1][2] It was approved for medical use in the United States in May 2019.[1]

History

In May 2019, alpelisib was approved in the United States for use in combination with the endocrine therapy fulvestrant, to treat postmenopausal women, and men, with hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative, PIK3CA-mutated, advanced or metastatic breast cancer following progression on or after an endocrine-based regimen.[1]

The U.S. Food and Drug Administration (FDA) also approved the companion diagnostic test, therascreen PIK3CA RGQ PCR Kit, to detect the PIK3CA mutation in a tissue and/or a liquid biopsy.[1]

The efficacy of alpelisib was studied in the SOLAR-1 trial (NCT02437318), a randomized trial of 572 postmenopausal women and men with HR-positive, HER2-negative, advanced or metastatic breast cancer whose cancer had progressed while on or after receiving an aromatase inhibitor.[1][3]

The FDA granted the application for alpelisib priority review designation and granted approval of Piqray to Novartis. The FDA granted approval of the therascreen PIK3CA RGQ PCR Kit to Qiagen Manchester, Ltd.[1]

References

  1. ^ a b c d e f g h i j "FDA approves first PI3K inhibitor for breast cancer". U.S. Food and Drug Administration (FDA) (Press release). 24 May 2019. Archived from the original on 25 November 2019. Retrieved 29 May 2019.Public Domain This article incorporates text from this source, which is in the public domain.
  2. ^ André, Fabrice; Ciruelos, Eva; Rubovszky, Gabor; Campone, Mario; Loibl, Sibylle; Rugo, Hope S.; Iwata, Hiroji; Conte, Pierfranco; Mayer, Ingrid A.; Kaufman, Bella; Yamashita, Toshinari; Lu, Yen-Shen; Inoue, Kenichi; Takahashi, Masato; Pápai, Zsuzsanna; Longin, Anne-Sophie; Mills, David; Wilke, Celine; Hirawat, Samit; Juric, Dejan; SOLAR-1 Study Group; the SOLAR-1 Study Group (2019). "Alpelisib for PIK3CA-Mutated, Hormone Receptor–Positive Advanced Breast Cancer". New England Journal of Medicine. 380 (20): 1929–1940. doi:10.1056/NEJMoa1813904. PMID 31091374.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  3. ^ "Drug Trials Snapshots: Piqray". U.S. Food and Drug Administration (FDA). 14 June 2019. Archived from the original on 25 November 2019. Retrieved 24 November 2019.

External links

  • "Alpelisib". Drug Information Portal. U.S. National Library of Medicine.
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