Erlotinib HCl (OSI-744) - Moligand™,≥99% , Epidermal growth factor receptor erbB1 inhibitor, CAS No.183319-69-9, Epidermal growth factor receptor erbB1 inhibitor

CAS: 183319-69-9 Cat. No.: E129310 Molecular Weight: 429.9 EC Number: 620-491-0

GRADE & PURITY Moligand™, ≥99%

Synonyms

HCl, Erlotinib | KS-1202 | CP-358,774-01 | ERLOTINIB HYDROCHLORIDE [MI] | N-(3-ETHENYLPHENYL)-6,7-BIS(2-METHOXYETHOXY)-4-QUINAZOLINAMINE HYDROCHLORIDE | Tarceva (Erlotinib Hydrochloride) | GTTBEUCJPZQMDZ-UHFFFAOYSA-N | CHEBI:53509 | ERLOTINIB HYDROCHLORID

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product Description
Erlotinib hydrochloride is an antineoplastic drug. It regulates mechanistic target of rapamycin (mTOR) inhibition, epidermal growth factor receptor down-regulation and epidermal interstitial transformation (EMT) suppression. Erlotinib Hydrochloride (CP-358774 Hydrochloride) inhibits purified EGFR kinase with an IC50 of 2 nM.

Product Application
Erlotinib hydrochloride has been used to activate mitochondrial fragmentation in a human PANC-1 pancreatic cancer cell line. 

Specifications

Synonyms

HCl, Erlotinib | KS-1202 | CP-358, 774-01 | ERLOTINIB HYDROCHLORIDE [MI] | N-(3-ETHENYLPHENYL)-6, 7-BIS(2-METHOXYETHOXY)-4-QUINAZOLINAMINE HYDROCHLORIDE | Tarceva (Erlotinib Hydrochloride) | GTTBEUCJPZQMDZ-UHFFFAOYSA-N | CHEBI:53509 | ERLOTINIB HYDROCHLORID

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

Erlotinib hydrochloride is an inhibitor of the receptor tyrosine kinase EGFR (epidermal growth factor receptor). It is used clinically for the treatment of non-small cell lung cancer (NSCLC) and in combination for metastatic pancreatic cancer.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Epidermal growth factor receptor erbB1 inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC.Cl
• IUPAC Name: N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine;hydrochloride
• InChIKey: GTTBEUCJPZQMDZ-UHFFFAOYSA-N
• INCHI: 1S/C22H23N3O4.ClH/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22;/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25);1H
• Isomeric SMILES: COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC.Cl
• Alternate CAS: 183319-69-9
• NSC Number: 718781
• MeSH Entry Terms: 11C erlotinib;11C-erlotinib;358,774, CP;358774, CP;CP 358,774;CP 358774;CP-358,774;CP-358774;CP358,774;CP358774;erlotinib;erlotinib HCl;erlotinib hydrochloride;HCl, Erlotinib;Hydrochloride, Erlotinib;N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-
• Molecular Weight: 429.9
• Reaxy-Rn: 8813963
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8813963&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazanaphthalenes
      • Subclass Benzodiazines
        • Level5 Quinazolines
          • Level6 Quinazolinamines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazanaphthalenes
• Subclass: Benzodiazines
• Intermediate Tree Nodes: Quinazolines
• Direct Parent: Quinazolinamines
• Alternative Parents: Aniline and substituted anilines Aminopyrimidines and derivatives Alkyl aryl ethers Imidolactams Heteroaromatic compounds Secondary amines Dialkyl ethers Azacyclic compounds Acetylides Organopnictogen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Quinazolinamine - Aniline or substituted anilines - Alkyl aryl ether - Aminopyrimidine - Monocyclic benzene moiety - Pyrimidine - Benzenoid - Imidolactam - Heteroaromatic compound - Dialkyl ether - Ether - Acetylide - Secondary amine - Azacycle - Organooxygen compound - Organonitrogen compound - Amine - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Hydrochloride - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
• External Descriptors: hydrochloride - terminal acetylenic compound

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

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ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)

Discover Target: ERBB2

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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HT-29 (80576 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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SF-295 (48000 Activities)

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SK-LU-1 (435 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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NCI-H322M (45589 Activities)

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HCT-116 (91556 Activities)

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HOP-92 (41141 Activities)

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Hs-578T (29457 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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IGROV-1 (47897 Activities)

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KB (17409 Activities)

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LOX IMVI (44321 Activities)

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HOP-62 (47048 Activities)

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MDA-MB-435 (38290 Activities)

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MDA-N (28205 Activities)

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MDA-MB-231 (73002 Activities)

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SNB-75 (44215 Activities)

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NCI-H23 (49055 Activities)

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SF-539 (44845 Activities)

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SW-620 (52400 Activities)

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HCT-15 (51914 Activities)

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BRAF Tclin Serine/threonine-protein kinase B-raf (11587 Activities)

Discover Target: BRAF

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Associated Targets(non-human)

Mus musculus (284745 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Brain (1 Activities)

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Plasma (328 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (3 mg/ml), methanol (sparingly), water (<1 mg/ml), and ethanol (<1 mg/ml).
• Sensitivity: Moisture sensitive;Air sensitive; Heat sensitive
• Melt Point(°C): 228 °C
• Molecular Weight: 429.900 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 429.146 Da
• Monoisotopic Mass: 429.146 Da
• Topological Polar Surface Area: 74.700 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 525.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Yun Zheng, Qiong Zhao, Jing Lin, Xiaoyang Dai, Chenyu Zhu, Yujie Wang, Hongye Fu.  (2022)  Xijiao Dihuang decoction relieves the erlotinib-induced dermatitis.  EXPERIMENTAL CELL RESEARCH,      [PMID:36435221] [10.1016/j.yexcr.2022.113437]

2. Yuping Liu, Xiangliang Jiang, Yue Gu, Yan Chen.  (2019)  Preventive effect of Diallyl Trisulfide on cutaneous toxicities induced by EGFR inhibitor.  INTERNATIONAL IMMUNOPHARMACOLOGY,      [PMID:30682720] [10.1016/j.intimp.2019.01.023]

3. Yueying Zhang, Dan Gao, Shangfu Li, Weili Wei, Jinshun Lin, Yuyang Jiang.  (2019)  1,5-Diaminonaphthalene functionalized carbon nanodots as a novel matrix for the analysis of small molecules by matrix-assisted laser desorption/ionization mass spectrometry.  Analytical Methods,  11  (8): (1131-1136).  [PMID:] [10.1039/C8AY02665C]

4. Xiaolan Zhou, Xiaofeng Zhu, Weixu Wang, Jing Wang, Haimei Wen, Yuqi Zhao, Jiayu Zhang, Qiushi Xu, Zhaozhao Zhao, Ting Ni.  (2025)  Comprehensive Cellular Senescence Evaluation to Aid Targeted Therapies.  Research,      [PMID:39822281] [10.34133/research.0576]