Details of the Drug

General Information of Drug (ID: DM5IXKQ)

Drug Name

Vismodegib

Synonyms

879085-55-9; GDC-0449; Erivedge; 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide; Vismodegib (GDC-0449); HhAntag691; GDC0449; GDC 0449; UNII-25X868M3DS; CHEMBL473417; CHEBI:66903; 25X868M3DS; NSC755986; AK-77261; 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-(methylsulfonyl)benzamide; C19H14Cl2N2O3S; 2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide; 2-chloro-n-(4-chloro-3-(2-pyridinyl)phenyl)-4-(methylsulfonyl)benzamide; Erivedge (TN); Vismodegib (SHH inhibitor); Gdc-0449

Indication

Disease Entry	ICD 11	Status	REF
Basal cell carcinoma	2C32	Approved	[1], [2]
Primitive neuroectodermal tumour medulloblastoma	2A00.11	Phase 2	[3]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

421.3

Topological Polar Surface Area (xlogp)

3.8

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [4]
Bioavailability: The bioavailability of drug is 31.8% [5]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.01 mL/min/kg [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 12 days [6]
Metabolism: The drug is not metabolised [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.01% [6]
Vd: The volume of distribution (Vd) of drug is 16.4-26.6 L [7]

Chemical Identifiers

Formula: C19H14Cl2N2O3S
IUPAC Name: 2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide
Canonical SMILES: CS(=O)(=O)C1=CC(=C(C=C1)C(=O)NC2=CC(=C(C=C2)Cl)C3=CC=CC=N3)Cl
InChI: InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)
InChIKey: BPQMGSKTAYIVFO-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 24776445
ChEBI ID: CHEBI:66903
CAS Number: 879085-55-9
DrugBank ID: DB08828
TTD ID: D03EDQ
VARIDT ID: DR00234
INTEDE ID: DR1698
ACDINA ID: D00730

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Smoothened homolog (SMO)	TT8J1S3	SMO_HUMAN	Modulator	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[8]
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Basal cell carcinoma

ICD Disease Classification

2C32

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Smoothened homolog (SMO)	DTT	SMO	4.01E-06	-0.18	-0.35
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	4.91E-03	-1.59E-01	-3.84E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.29E-36	-3.75E-01	-1.06E+00

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Vismodegib (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Vismodegib caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[33]
SODIUM CITRATE	DMHPD2Y	Minor	Decreased absorption of Vismodegib due to altered gastric pH caused by SODIUM CITRATE.	Discovery agent [N.A.]	[34]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Eisenoxyd	E00585	56841934	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
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⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Vismodegib 150 mg capsule	150 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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