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Lorlatinib

CAT: 0013-GTR19163173-02Size: 2 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19163173-02Size:2 mg
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Description
A novel CNS-penetrant, ATP-competitive inhibitor of ALK/ROS1 with IC50 of 0.07/0.025 nM respectively; also inhibits ALK L1196M (IC50=0.7 nM) and exhibits selectivity >100-fold for ROS1 over 204 kinases; inhibits crizotinib-resistant mutant ROS1G2032R and ROS1L2026M and orally available in vivo.Lung Cancer Phase 3 Clinical (In Vitro) :Lorlatinib (PF-06463922) demonstrates significant cell activity against ALK and a large set of ALK clinical mutations with IC50 ranging from 0.2 nM-77 nM. Lorlatinib significantly inhibits cell proliferation and induces cell apoptosis in the HCC78 human NSCLC cells harboring SLC34A2-ROS1 fusions and the BaF3-CD74-ROS1 cells expressing human CD74-ROS1. Lorlatinib also shows potent growth inhibitory activity and induces apoptosis in the NSCLC cells harboring either non-mutant ALK or mutant ALK fusions. (In Vivo) :In rats, Lorlatinib (PF-06463922) displays low plasma clearance, a moderate volume of distribution, a reasonable half-life, low propensity for p-glycoprotein 1-mediated efflux and a bioavailability of 100%. In vivo, Lorlatinib shows cytoreductive antitumor efficacy in the NIH3T3 xenograft models expressing human CD74-ROS1 and Fig-ROS1 via inhibition in ROS1 phosphorylation and the downstream signaling molecules, as well as inhibition of the cell cycle protein Cyclin D1 in tumors. Lorlatinib also demonstrates marked antitumor activity in mice bearing tumor xenografts expressing EML4-ALK, EML4-ALK-L1196M, EML4-ALK-G1269A, EML4-ALK-G1202R or NPM-ALK.
CAS Number
1454846-35-5
Product Name Alternative
PF-06463922 | PF 06463922 | PF06463922
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 28 mg/mL
Smiles
N#CC1=C (C (CN2C) =NN1C) C3=CN=C (N) C (O[C@H] (C) C4=CC (F) =CC=C4C2=O) =C3
Molecular Formula
C21H19FN6O2
Molecular Weight
406.413
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
2H-4,8-Methenopyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecine-3-carbonitrile, 7-amino-12-fluoro-10,15,16,17-tetrahydro-2,10,16-trimethyl-15-oxo-, (10R) -

Chemical Information

Lorlatinib

Lorlatinib is a cyclic ether that is 16,17-dihydro-2H-8,4-(metheno)pyrazolo[4,3-h][2,5,11]benzoxadiazacyclotetradecin-15(10H)-one substituted by methyl groups at positions 2 and 10R, and by cyano, amino and fluoro groups at positions 3, 7 and 12 respectively. It is a small molecule inhibitor of ALK and ROS1 kinase developed by Pfizer for the treatment of ALK-positive non-small cell lung cancer. It has a role as an antineoplastic agent and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is a nitrile, a member of benzamides, a member of pyrazoles, an aromatic ether, a cyclic ether, an organic heterotetracyclic compound, an aminopyridine, an azamacrocycle and a member of monofluorobenzenes.

CAS Number1454846-35-5
PubChem CID71731823
IUPAC Name(16R)-19-amino-13-fluoro-4,8,16-trimethyl-9-oxo-17-oxa-4,5,8,20-tetrazatetracyclo[16.3.1.02,6.010,15]docosa-1(22),2,5,10(15),11,13,18,20-octaene-3-carbonitrile
Molecular FormulaC21H19FN6O2
Molecular Weight406.4
XLogP1.5
Topological Polar Surface Area110
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count0
Heavy Atom Count30
Formal Charge0
Complexity700
SMILES
C[C@@H]1C2=C(C=CC(=C2)F)C(=O)N(CC3=NN(C(=C3C4=CC(=C(N=C4)N)O1)C#N)C)C
InChI
InChI=1S/C21H19FN6O2/c1-11-15-7-13(22)4-5-14(15)21(29)27(2)10-16-19(17(8-23)28(3)26-16)12-6-18(30-11)20(24)25-9-12/h4-7,9,11H,10H2,1-3H3,(H2,24,25)/t11-/m1/s1
InChIKey
IIXWYSCJSQVBQM-LLVKDONJSA-N
Chemical Structure
2D Structure
2D structure of Lorlatinib
CAS: 1454846-35-5
CID: 71731823
Formula: C21H19FN6O2
MW: 406.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight406.4
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count0
Exact Mass406.15535203
Monoisotopic Mass406.15535203
Topological Polar Surface Area110 Ų
Heavy Atom Count30
Formal Charge0
Complexity700
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes