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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H19FN6O2
Molecular Weight 406.413
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORLATINIB

SMILES

C[C@H]1OC2=CC(=CN=C2N)C3=C(C#N)N(C)N=C3CN(C)C(=O)C4=CC=C(F)C=C14

InChI

InChIKey=IIXWYSCJSQVBQM-LLVKDONJSA-N
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

HIDE SMILES / InChI
Molecular Formula C21H19FN6O2
Molecular Weight 406.413
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:12:10 UTC 2023
Edited
by admin
on Sat Dec 16 02:12:10 UTC 2023
Record UNII
OSP71S83EU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORLATINIB
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
LORBRENA
Brand Name English
PF-06463922
Code English
lorlatinib [INN]
Common Name English
LORLATINIB [JAN]
Common Name English
(10R)-7-AMINO-12-FLUORO-2,10,16-TRIMETHYL-15-OXO-10,15,16,17-TETRAHYDRO-2H-4,8- METHENOPYRAZOLO(4,3-H)(2,5,11)BENZOXADIAZACYCLOTETRADECINE-3-CARBONITRILE
Systematic Name English
LORLATINIB [USAN]
Common Name English
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)-
Systematic Name English
Lorlatinib [WHO-DD]
Common Name English
LORLATINIB [MI]
Common Name English
LORLATINIB [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C141136
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
FDA ORPHAN DRUG 481015
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
WHO-ATC L01XE44
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
Code System Code Type Description
CAS
1454846-35-5
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
SMS_ID
100000166974
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID201027944
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
NCI_THESAURUS
C113655
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
DRUG BANK
DB12130
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
INN
10278
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
DRUG CENTRAL
5302
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
PUBCHEM
71731823
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
USAN
CD-57
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
MERCK INDEX
m12113
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
LACTMED
Lorlatinib
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
RXCUI
2103164
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
DAILYMED
OSP71S83EU
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
ChEMBL
CHEMBL3286830
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
FDA UNII
OSP71S83EU
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
EVMPD
SUB181272
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
CHEBI
143117
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
WIKIPEDIA
Lorlatinib
Created by admin on Sat Dec 16 02:12:10 UTC 2023 , Edited by admin on Sat Dec 16 02:12:10 UTC 2023
PRIMARY
Related Record Type Details
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A3
METABOLIC ENZYME -> SUBSTRATE
MINOR
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
OAT-3
TRANSPORTER -> INHIBITOR
ANAPLASTIC LYMPHOMA KINASE 1151TINS
TARGET -> INHIBITOR
Ki
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
ANAPLASTIC LYMPHOMA KINASE
TARGET -> INHIBITOR
INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
In vitro, protein binding of lorlatinib to human plasma proteins, including serum albumin and α1-acid glycoprotein, was 66% at a concentration of 2.4 μM.
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
Structure of LORLATINIB ACETATE
SALT/SOLVATE -> PARENT
PROTO-ONCOGENE TYROSINE-PROTEIN KINASE ROS
TARGET -> INHIBITOR
IC50
ANAPLASTIC LYMPHOMA KINASE F1174L
TARGET -> INHIBITOR
Ki
ANAPLASTIC LYMPHOMA KINASE L1152R
TARGET -> INHIBITOR
Ki
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
OCT-1
TRANSPORTER -> INHIBITOR
POTASSIUM VOLTAGE-GATED CHANNEL SUBFAMILY H MEMBER 2
OFF TARGET->NON-INHIBITOR
did not predict QTc prolongation, by inhibition of the hERG channel at clinically relevant concentrations
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
MINOR
OAT-1
TRANSPORTER -> INHIBITOR
SODIUM CHANNEL PROTEIN TYPE 5 SUBUNIT ALPHA
OFF TARGET->NON-INHIBITOR
failed to inhibit L-type calcium channel, or Nav1.5 sodium current at clinically relevant concentrations.
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INDUCER
ACTIVATOR
ANAPLASTIC LYMPHOMA KINASE C1156Y
TARGET -> INHIBITOR
Ki
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
MINOR
ANAPLASTIC LYMPHOMA KINASE S1206Y
TARGET -> INHIBITOR
Ki
ANAPLASTIC LYMPHOMA KINASE G1269A
TARGET -> INHIBITOR
Ki
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of LORLATINIB
EXCRETED UNCHANGED
Following a single oral 100 mg dose of radiolabeled lorlatinib, 48% of the radioactivity was recovered in urine (< 1% as unchanged) and 41% in feces (about 9% as unchanged).
FECAL; URINE
ANAPLASTIC LYMPHOMA KINASE L1196M
TARGET -> INHIBITOR
Ki
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
Ki
ANAPLASTIC LYMPHOMA KINASE G1202R
TARGET -> INHIBITOR
Ki
Related Record Type Details
Structure of PF- 06895751
METABOLITE INACTIVE -> PARENT
Related Record Type Details
Structure of LORLATINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Cmax PHARMACOKINETIC ROUTE OF ADMINSTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC SINGLE DOSE

ORAL

Blood-to-plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC SINGLE DOSE

ORAL

Biological Half-life PHARMACOKINETIC SINGLE DOSE

INTRAVENOUS

Volume of Distribution PHARMACOKINETIC SINGLE DOSE

INTRAVENOUS

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