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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H22Cl2FN5O
Molecular Weight 450.337
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Crizotinib, (S)-

SMILES

C[C@H](OC1=CC(=CN=C1N)C2=CN(N=C2)C3CCNCC3)C4=C(Cl)C=CC(F)=C4Cl

InChI

InChIKey=KTEIFNKAUNYNJU-LBPRGKRZSA-N
InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H22Cl2FN5O
Molecular Weight 450.337
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(S)-crizotinib was discovered as an attractive chemical entity for further pre-clinical evaluation, and small-molecule inhibitors of MTH1 as a promising novel class of anticancer agents.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
7,8-dihydro-8-oxoguanine triphosphatase
2
Target ID: P36639
Gene ID: 4521.0
Gene Symbol: NUDT1
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 72.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Stereospecific targeting of MTH1 by (S)-crizotinib as an anticancer strategy.
2014-04-10

Sample Use Guides

In Vivo Use Guide
mouse xenograft: (S)-crizotinib 50mg/kg p.o., q.d (1 tablet by mouth once a day) was administered for 26 days
Route of Administration: Oral
In Vitro Use Guide
(S)-crizotinib (in concentrations: 500 nM, 2 uM and 5 uM) efficiently inhibited colony formation of SW480 and KRAS mutated PANC1 (human pancreatic carcinoma) cells. In vitro Kd measurements indicated that (S)-crizotinib was considerably less potent than the (R)-enantiomer against the established targets ALK, MET and ROS1.
Substance Class Chemical
Created
by admin
on Wed Apr 02 19:25:52 GMT 2025
Edited
by admin
on Wed Apr 02 19:25:52 GMT 2025
Record UNII
4SF5Q86VXC
Record Status Validated (UNII)
Record Version
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Name Type Language
(S)-Crizotinib
Preferred Name English
Crizotinib, (S)-
Common Name English
3-[(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1H-pyrazol-4-yl]-2-pyridinamine
Systematic Name English
(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine
Systematic Name English
2-Pyridinamine, 3-[(1S)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1H-pyrazol-4-yl]-
Systematic Name English
Code System Code Type Description
CAS
1374356-45-2
Created by admin on Wed Apr 02 19:25:52 GMT 2025 , Edited by admin on Wed Apr 02 19:25:52 GMT 2025
PRIMARY
PUBCHEM
56671814
Created by admin on Wed Apr 02 19:25:52 GMT 2025 , Edited by admin on Wed Apr 02 19:25:52 GMT 2025
PRIMARY
FDA UNII
4SF5Q86VXC
Created by admin on Wed Apr 02 19:25:52 GMT 2025 , Edited by admin on Wed Apr 02 19:25:52 GMT 2025
PRIMARY
Related Record Type Details
Structure of Crizotinib, (R,S)-
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