Deuruxolitinib
C17H18N6, 314.422
Fda approved Leqselvi, 7/25/2024, To treat severe alopecia areata
C-21543, CTP 543, CTP-543, CTP543
(3r)-3-(2,2,3,3,4,4,5,5-d8)cyclopentyl-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)propanenitrile
1h-pyrazole-1-propanenitrile, .beta.-(cyclopentyl-2,2,3,3,4,4,5,5-d8)-4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-, (.beta.r)-D8-ruxolitinib
| Ingredient | UNII | CAS | InChI Key |
|---|---|---|---|
| Deuruxolitinib phosphate | 8VJ43S4LCM | 2147706-60-1 | JFMWPOCYMYGEDM-NTVOUFPTSA-N |
unii
0CA0VSF91Y
Deuruxolitinib, sold under the brand name Leqselvi, is a medication used for the treatment of alopecia areata.[1] It is a Janus kinase inhibitor selective for JAK1 and JAK2.[2] Although the relative effectiveness of deuruxolitinib and another Janus kinase inhibitor—baricitinib—for alopecia areata may vary depending on the population studied, both drugs are more effective than alternative treatments.[3]
Deuruxolitinib was approved for medical use in the United States in July 2024.[1][4]
Medical uses
Deuruxolitinib is indicated for the treatment of adults with severe alopecia areata.[1]
Side effects
The FDA prescribing label for deuruxolitinib contains a boxed warning for serious infections; malignancies; cardiovascular death, myocardial infarction, and stroke; and thrombosis.[5]
Society and culture
Names
Deuruxolitinib is the international nonproprietary name[6] and the United States Adopted Name.[7]
SYN
20240108633METHOD FOR PREVENTING OR TREATING DISEASE OR CONDITION ASSOCIATED WITH ANTITUMOR AGENT
20240058345TREATMENT OF HAIR LOSS DISORDERS WITH DEUTERATED JAK INHIBITORS
2023553253重水素化ＪＡＫ阻害剤による脱毛障害の治療のためのレジメン
20230390292REGIMENS FOR THE TREATMENT OF HAIR LOSS DISORDERS WITH DEUTERATED JAK INHIBITORS
20230322787PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED JAK INHIBITORS
1020230093504중수소화된 JAK 억제제를 이용한 탈모 장애의 치료를 위한 요법
WO/2023/018954TREATMENT OF JAK-INHIBITION-RESPONSIVE DISORDERS WITH PRODRUGS OF JAK INHIBITORS
2022171838TREATMENT OF ALOPECIA CAUSED BY DEUTERATED JAK INHIBITOR
2022171838TREATMENT OF ALOPECIA CAUSED BY DEUTERATED JAK INHIBITOR
20220226327Combination therapy comprising JAK pathway inhibitor and rock inhibitor
20220213105PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED JAK INHIBITORS
20220202834JAK inhibitor with a vitamin D analog for treatment of skin diseases
20210387991Deuterated JAK inhibitor and uses thereof SUN
WO/2020/163653PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED JAK INHIBITORS CONCERT
20200222408TREATMENT OF HAIR LOSS DISORDERS WITH DEUTERATED JAK INHIBITORS
2019516684Treatment of Hair Loss Disorders with Deuterated JAK Inhibitors
PATENT
US20210387991
USE OF COMPD NOT SYNTHESIS
https://patentscope.wipo.int/search/en/detail.jsf?docId=US344953814&_cid=P12-M0XGHQ-19840-2
Example 1
Synthesis of Compound 10
| HRMS: Agilent 6530 Q-TOF LC/MS system with electrospray ionization in positive mode. The measured time-of-flight mass-to-charge ratio (m/z) is 333.22839 (theoretical value=333.22735). |
| Clinical data | |
|---|---|
| Trade names | Leqselvi |
| Other names | CTP-543 |
| License data | US DailyMed: Deuruxolitinib |
| Routes of administration | By mouth |
| Drug class | Janus kinase inhibitor |
| ATC code | None |
| Legal status | |
| Legal status | US: ℞-only[1] |
| Identifiers | |
| showIUPAC name | |
| CAS Number | 1513883-39-0as phosphate: 2147706-60-1 |
| PubChem CID | 72704611as phosphate: 154572727 |
| DrugBank | DB18847 |
| ChemSpider | 115010950 |
| UNII | 0CA0VSF91Yas phosphate: 8VJ43S4LCM |
| KEGG | D11866as phosphate: D11867 |
| ChEMBL | ChEMBL4594381 |
| Chemical and physical data | |
| Formula | C17H18N6 |
| Molar mass | 306.373 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| showSMILES | |
References
King B, Mesinkovska N, Mirmirani P, Bruce S, Kempers S, Guttman-Yassky E, Roberts JL, McMichael A, Colavincenzo M, Hamilton C, Braman V, Cassella JV: Phase 2 randomized, dose-ranging trial of CTP-543, a selective Janus Kinase inhibitor, in moderate-to-severe alopecia areata. J Am Acad Dermatol. 2022 Aug;87(2):306-313. doi: 10.1016/j.jaad.2022.03.045. Epub 2022 Mar 29. [Article]Yan T, Wang T, Tang M, Liu N: Comparative efficacy and safety of JAK inhibitors in the treatment of moderate-to-severe alopecia areata: a systematic review and network meta-analysis. Front Pharmacol. 2024 Apr 10;15:1372810. doi: 10.3389/fphar.2024.1372810. eCollection 2024. [Article]Barati Sedeh F, Michaelsdottir TE, Henning MAS, Jemec GBE, Ibler KS: Comparative Efficacy and Safety of Janus Kinase Inhibitors Used in Alopecia Areata: A Systematic Review and Meta-analysis. Acta Derm Venereol. 2023 Jan 25;103:adv00855. doi: 10.2340/actadv.v103.4536. [Article]Sardana K, Bathula S, Khurana A: Which is the Ideal JAK Inhibitor for Alopecia Areata – Baricitinib, Tofacitinib, Ritlecitinib or Ifidancitinib – Revisiting the Immunomechanisms of the JAK Pathway. Indian Dermatol Online J. 2023 Jun 28;14(4):465-474. doi: 10.4103/idoj.idoj_452_22. eCollection 2023 Jul-Aug. [Article]FDA Approved Drug Products: LEQSELVI (deuruxolitinib) tablets, for oral use [Link]AJMC: FDA Approves Deuruxolitinib for Alopecia Areata [Link]
^ Jump up to:a b c d “Archived copy” (PDF). Archived (PDF) from the original on 29 July 2024. Retrieved 26 July 2024.
- ^ King, Brett; Mesinkovska, Natasha; Mirmirani, Paradi; Bruce, Suzanne; Kempers, Steve; Guttman-Yassky, Emma; et al. (August 2022). “Phase 2 randomized, dose-ranging trial of CTP-543, a selective Janus Kinase inhibitor, in moderate-to-severe alopecia areata”. Journal of the American Academy of Dermatology. 87 (2): 306–313. doi:10.1016/j.jaad.2022.03.045. ISSN 1097-6787. PMID 35364216. S2CID 247866262.
- ^ SEDEH, Farnam Barati; MICHAELSDÓTTIR, Thorunn Elísabet; HENNING, Mattias Arvid Simon; JEMEC, Gregor Borut Ernst; IBLER, Kristina Sophie (25 January 2023). “Comparative Efficacy and Safety of Janus Kinase Inhibitors Used in Alopecia Areata: A Systematic Review and Meta-analysis”. Acta Dermato-Venereologica. 103: 4536. doi:10.2340/actadv.v103.4536. ISSN 0001-5555. PMC 10391778. PMID 36695751.
- ^ “U.S. FDA Approves Leqselvi (deuruxolitinib), an Oral JAK Inhibitor for the Treatment of Severe Alopecia Areata” (Press release). Sun Pharmaceutical. 25 July 2024. Archived from the original on 26 July 2024. Retrieved 26 July 2024 – via PR Newswire.
- ^ http://www.leqselvi.com/&a=Prescribing Information
- ^ World Health Organization (2021). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 86”. WHO Drug Information. 35 (3). hdl:10665/346562.
- ^ “Deuruxolitinib”. American Medical Association. Retrieved 27 July 2024.
Further reading
Passeron T, King B, Seneschal J, Steinhoff M, Jabbari A, Ohyama M, et al. (2023). “Inhibition of T-cell activity in alopecia areata: recent developments and new directions”. Frontiers in Immunology. 14: 1243556. doi:10.3389/fimmu.2023.1243556. PMC 10657858. PMID 38022501.
External links
- “Deuruxolitinib (Code C175770)”. NCI Thesaurus.
- “Deuruxolitinib Phosphate (Code C175771)”. NCI Thesaurus.
- Clinical trial number NCT04518995 for “Study to Evaluate the Efficacy and Safety of CTP-543 in Adults With Moderate to Severe Alopecia Areata (THRIVE-AA1) (THRIVE-AA1)” at ClinicalTrials.gov
- Clinical trial number NCT04797650 for “Study to Evaluate the Efficacy and Safety of CTP-543 in Adults With Moderate to Severe Alopecia Areata (THRIVE-AA2) (THRIVE-AA2)” at ClinicalTrials.gov
////Deuruxolitinib, alopecia areata, Leqselvi , approvals 2024, fda 2024, C-21543, CTP 543, CTP-543, CTP543, UNII-0CA0VSF91Y, WHO 11622