ABROCITINIB

ID: ALA3655081

Chembl Id: CHEMBL3655081

Max Phase: Approved

First Approval: 2021

Molecular Formula: C14H21N5O2S

Molecular Weight: 323.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Abrocitinib | Cibinqo | Pf-04965842 | PF-04965842

Trade Names(1): Cibinqo

Canonical SMILES:  CCCS(=O)(=O)N[C@H]1C[C@@H](N(C)c2ncnc3[nH]ccc23)C1

Standard InChI:  InChI=1S/C14H21N5O2S/c1-3-6-22(20,21)18-10-7-11(8-10)19(2)14-12-4-5-15-13(12)16-9-17-14/h4-5,9-11,18H,3,6-8H2,1-2H3,(H,15,16,17)/t10-,11+

Standard InChI Key:  IUEWXNHSKRWHDY-PHIMTYICSA-N

Alternative Forms

1. Parent:

   

   ALA3655081

   ABROCITINIB

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 323.42

Molecular Weight (Monoisotopic): 323.1416

AlogP: 1.25

#Rotatable Bonds: 6

Polar Surface Area: 90.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.47

CX Basic pKa: 6.45

CX LogP: 0.83

CX LogD: 0.79

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -1.27

References

1. Unpublished dataset, 

2.  (2015)  Pyrrolo[2,3-D]pyrimidine derivatives, 

3. Vazquez ML, Kaila N, Strohbach JW, Trzupek JD, Brown MF, Flanagan ME, Mitton-Fry MJ, Johnson TA, TenBrink RE, Arnold EP, Basak A, Heasley SE, Kwon S, Langille J, Parikh MD, Griffin SH, Casavant JM, Duclos BA, Fenwick AE, Harris TM, Han S, Caspers N, Dowty ME, Yang X, Banker ME, Hegen M, Symanowicz PT, Li L, Wang L, Lin TH, Jussif J, Clark JD, Telliez JB, Robinson RP, Unwalla R..  (2018)  Identification of N-{cis-3-[Methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclobutyl}propane-1-sulfonamide (PF-04965842): A Selective JAK1 Clinical Candidate for the Treatment of Autoimmune Diseases.,  61  (3): [PMID:29298069] [10.1021/acs.jmedchem.7b01598]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Hansen BB, Jepsen TH, Larsen M, Sindet R, Vifian T, Burhardt MN, Larsen J, Seitzberg JG, Carnerup MA, Jerre A, Mølck C, Lovato P, Rai S, Nasipireddy VR, Ritzén A..  (2020)  Fragment-Based Discovery of Pyrazolopyridones as JAK1 Inhibitors with Excellent Subtype Selectivity.,  63  (13): [PMID:32462873] [10.1021/acs.jmedchem.0c00359]

6. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

7. Unpublished dataset, 

8. WHO Anatomical Therapeutic Chemical Classification, 

9. Raghuvanshi R, Bharate SB..  (2022)  Recent Developments in the Use of Kinase Inhibitors for Management of Viral Infections.,  65  (2.0): [PMID:33539089] [10.1021/acs.jmedchem.0c01467]

10. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

11. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]

12. European Medicines Agency, 

Source

Source(9):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• BindingDB Database
• WHO Anatomical Therapeutic Chemical Classification
• EUbOPEN Chemogenomic Library
• IMI-CARE SARS-CoV-2 Data
• European Medicines Agency