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Chemistry

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Also known as: Shr0302, 1445987-21-2, Ivarmacitinib [usan], Unii-k6k4b9z5tv, K6k4b9z5tv, (3as,6ar)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxamide
Molecular Formula
C18H22N8O2S
Molecular Weight
414.5  g/mol
InChI Key
DNBCBAXDWNDRNO-FOSCPWQOSA-N
FDA UNII
K6K4B9Z5TV

Ivarmacitinib
1 2D Structure

Ivarmacitinib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3aS,6aR)-N-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxamide
2.1.2 InChI
InChI=1S/C18H22N8O2S/c1-25(15-13-3-4-19-14(13)20-9-21-15)12-5-10-7-26(8-11(10)6-12)18(27)23-17-22-16(28-2)24-29-17/h3-4,9-12H,5-8H2,1-2H3,(H,19,20,21)(H,22,23,24,27)/t10-,11+,12?
2.1.3 InChI Key
DNBCBAXDWNDRNO-FOSCPWQOSA-N
2.1.4 Canonical SMILES
CN(C1CC2CN(CC2C1)C(=O)NC3=NC(=NS3)OC)C4=NC=NC5=C4C=CN5
2.1.5 Isomeric SMILES
CN(C1C[C@@H]2CN(C[C@@H]2C1)C(=O)NC3=NC(=NS3)OC)C4=NC=NC5=C4C=CN5
2.2 Other Identifiers
2.2.1 UNII
K6K4B9Z5TV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cyclopenta(c)pyrrole-2(1h)-carboxamide, Hexahydro-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl-7h-pyrrolo(2,3-d)pyrimidin-4-ylamino)-, (3a Alpha,5 Alpha,6a Alpha)-

2. Ivarmacitinib Sulfate

3. Shr0302

4. Shr0302 Base

2.3.2 Depositor-Supplied Synonyms

1. Shr0302

2. 1445987-21-2

3. Ivarmacitinib [usan]

4. Unii-k6k4b9z5tv

5. K6k4b9z5tv

6. (3as,6ar)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxamide

7. Shr-0302

8. Shr0302 Base

9. Ivarmacitinib [inn]

10. Shr0302 Free Base

11. Shr-0302 Free Base

12. Schembl15077696

13. Schembl15077710

14. Schembl16191633

15. Gtpl11878

16. Ex-a5101

17. Who 11823

18. Ncgc00687790-01

19. Ac-36766

20. Example 34 [wo2013091539a1]

21. Hy-112724

22. Cs-0062969

23. Us9527851, 34

24. Us9527851, 74

25. (3ar,5s,6as)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl (7h-pyrrolo(2,3- D)pyrimidin-4-yl)amino) Hexahydrocyclopenta(c)pyrrole-2(1h)-carboxamide

26. (3ar,5s,6as)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl (7h-pyrrolo(2,3-d)pyrimidin-4-yl)amino) Hexahydrocyclopenta(c)pyrrole-2(1h)-carboxamide

27. (3ar,6as)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxamide

28. Cyclopenta(c)pyrrole-2(1h)-carboxamide, Hexahydro-n-(3-methoxy-1,2,4- Thiadiazol-5-yl)-5-(methyl-7h-pyrrolo(2,3-d)pyrimidin-4-ylamino)-, (3a.alpha.,5.alpha.,6a.alpha.)-

29. Cyclopenta(c)pyrrole-2(1h)-carboxamide, Hexahydro-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl-7h-pyrrolo(2,3-d)pyrimidin-4-ylamino)-, (3aalpha,5alpha,6aalpha)-

30. Rel-(3ar,5s,6as)-n-(3-methoxy-1,2,4-thiadiazol-5-yl)-5-(methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1h)-carboxamide

2.4 Create Date
2013-08-05
3 Chemical and Physical Properties
Molecular Weight 414.5 g/mol
Molecular Formula C18H22N8O2S
XLogP32.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass414.15864315 g/mol
Monoisotopic Mass414.15864315 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count29
Formal Charge0
Complexity600
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

API SUPPLIERS

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01

Jiangsu Hengrui Medicine

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Discovery on Target
Not Confirmed
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Jiangsu Hengrui Medicine

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Discovery on Target
Not Confirmed
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Drugs in Development

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Details:

ARQ-255 (ivarmacitinib) is a topical Janus kinase 1 (JAK1) inhibitor suspension formulated as a potential topical treatment for alopecia areata.


Lead Product(s): Ivarmacitinib

Therapeutic Area: Dermatology Brand Name: ARQ-255

Study Phase: Phase IProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable September 05, 2024

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01

Luxepack
Not Confirmed
Luxepack
Not Confirmed

Details : ARQ-255 (ivarmacitinib) is a topical Janus kinase 1 (JAK1) inhibitor suspension formulated as a potential topical treatment for alopecia areata.

Brand Name : ARQ-255

Molecule Type : Small molecule

Upfront Cash : Not Applicable

September 05, 2024

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Details:

SHR0302, an investigational selective Janus kinase type 1 (JAK1) inhibitor, met primary and key secondary endpoints in Reistone Biopharma's Phase 2 Clinical Study (AMBER2) for the treatment of patients with moderate to severe ulcerative colitis (UC).


Lead Product(s): Ivarmacitinib

Therapeutic Area: Gastroenterology Brand Name: SHR0302

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable January 20, 2021

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02

Luxepack
Not Confirmed
Luxepack
Not Confirmed

Details : SHR0302, an investigational selective Janus kinase type 1 (JAK1) inhibitor, met primary and key secondary endpoints in Reistone Biopharma's Phase 2 Clinical Study (AMBER2) for the treatment of patients with moderate to severe ulcerative colitis (UC).

Brand Name : SHR0302

Molecule Type : Small molecule

Upfront Cash : Not Applicable

January 20, 2021

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Details:

SHR0302 monotherapy achieved positive results on reaching primary endpoints with statistical significance, delivering significant improvements in skin clearance. Several late stage clinical studies are on-going in Ulcerative Colitis, Crohn's disease, etc.


Lead Product(s): Ivarmacitinib

Therapeutic Area: Dermatology Brand Name: SHR0302

Study Phase: Phase IIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable October 26, 2020

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03

Luxepack
Not Confirmed
Luxepack
Not Confirmed

Details : SHR0302 monotherapy achieved positive results on reaching primary endpoints with statistical significance, delivering significant improvements in skin clearance. Several late stage clinical studies are on-going in Ulcerative Colitis, Crohn's disease, etc...

Brand Name : SHR0302

Molecule Type : Small molecule

Upfront Cash : Not Applicable

October 26, 2020

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Full Screen ViewFULL SCREEN VIEW Click here to open all results in a new tab [this preview display 10 results]

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