Glasdegib (PF-04449913) - Moligand™, ≥98% , Smoothened homolog antagonist, CAS No.1095173-27-5, Smoothened homolog antagonist

CAS: 1095173-27-5 Cat. No.: G413714 Molecular Weight: 374.44 EC Number: 813-776-8

GRADE & PURITY Moligand™, ≥98%

Synonyms

Q27077810 | N-[(2R,4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-N'-(4-cyanophenyl)urea | AC-35176 | L01XX63 | Prestwick0_000101 | UNII-K673DMO5H9 | 1-((2R,4R)-2-(1H-benzo[d]iMidazol-2-yl)-1-Methylpiperidin-4-yl)-3-(4-cyanophenyl)urea | EX-A858 | D

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Glasdegib (PF-04449913) is a potent, and orally bioavailableSmoothened (Smo)inhibitor withIC50of 5 nM. Phase 2.

Targets

Smoothened 5 nM

In vitro

In vitro microsomal assays, PF-04449913 have high clearance in rat and low clearance in dog and human, without inhibiting any of the major cytochrome P450 isoforms.

In vivo

In rat and dog, PF-04449913 shows high clearance, and good oral bioavailability.

Specifications

Synonyms

Q27077810 | N-[(2R, 4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-N'-(4-cyanophenyl)urea | AC-35176 | L01XX63 | Prestwick0_000101 | UNII-K673DMO5H9 | 1-((2R, 4R)-2-(1H-benzo[d]iMidazol-2-yl)-1-Methylpiperidin-4-yl)-3-(4-cyanophenyl)urea | EX-A858 | D

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Glasdegib (PF-04449913) is a potent, and orally bioavailable Smoothened (Smo) inhibitor with IC50 of 5 nM. Phase 2.

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

ANTAGONIST

Mechanism of action

Smoothened homolog antagonist

Purity

≥98%

Product Properties

• ALogP: 2.363
• hba_count: 2
• HBD Count: 3
• Rotatable Bond: 3

Names and Identifiers

• Pubchem Sid: 488200773
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488200773
• Canonical Smiles: CN1CCC(CC1C2=NC3=CC=CC=C3N2)NC(=O)NC4=CC=C(C=C4)C#N
• IUPAC Name: 1-[(2R,4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-3-(4-cyanophenyl)urea
• InChIKey: SFNSLLSYNZWZQG-VQIMIIECSA-N
• INCHI: 1S/C21H22N6O/c1-27-11-10-16(24-21(28)23-15-8-6-14(13-22)7-9-15)12-19(27)20-25-17-4-2-3-5-18(17)26-20/h2-9,16,19H,10-12H2,1H3,(H,25,26)(H2,23,24,28)/t16-,19-/m1/s1
• Isomeric SMILES: CN1CC[C@H](C[C@@H]1C2=NC3=CC=CC=C3N2)NC(=O)NC4=CC=C(C=C4)C#N
• Molecular Weight: 374.44
• Reaxy-Rn: 50424442
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=50424442&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass N-phenylureas

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: N-phenylureas
• Intermediate Tree Nodes: Not available
• Direct Parent: N-phenylureas
• Alternative Parents: Benzimidazoles Benzonitriles Aralkylamines Piperidines Imidazoles Heteroaromatic compounds Ureas Trialkylamines Nitriles Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-phenylurea - Benzimidazole - Benzonitrile - Aralkylamine - Piperidine - Azole - Imidazole - Heteroaromatic compound - Urea - Tertiary aliphatic amine - Tertiary amine - Organoheterocyclic compound - Azacycle - Carbonitrile - Nitrile - Amine - Organonitrogen compound - Organooxygen compound - Cyanide - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
• External Descriptors: Not available

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)

SMO Tclin Smoothened homolog (1 Activities)

Discover Target: SMO

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)

Discover Target: CYP2C8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Caco-2 (12174 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMO Tclin Smoothened homolog (1371 Activities)

Discover Target: SMO

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver microsomes (16955 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Salmonella typhimurium (15756 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Canis familiaris (36305 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasma (328 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 74 mg/mL (197.62 mM); Water: Insoluble; Ethanol: Insoluble
• DMSO(mg / mL) Max Solubility: 47
• DMSO(mM) Max Solubility: 125.5207777
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 374.400 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 374.186 Da
• Monoisotopic Mass: 374.186 Da
• Topological Polar Surface Area: 96.800 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 595.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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: 1