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Properties

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Taxonomy

Vismodegib

Targets (1)Enzymes (4)Carriers (2)Transporters (2)Biointeractions (8)

Identification

Name

Vismodegib

Accession Number

DB08828

Type

Small Molecule

Groups

Approved, Investigational

Description

Vismodegib inhibits the hedgehog signalling pathway and is indicated for treatment of adult basal cell carcinoma. FDA approved on Jan 30, 2012.

Structure

Similar Structures

Synonyms

Vismodegib
Vismodégib
Vismodegibum

External IDs

GDC-0449 / RG-3616

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Erivedge	Capsule	150 mg	Oral	Hoffmann La Roche	2013-08-09	Not applicable
Erivedge	Capsule	150 mg/1	Oral	Genentech, Inc.	2012-01-30	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

UNII

25X868M3DS

CAS number

879085-55-9

Weight

Average: 421.297
Monoisotopic: 420.010218428

Chemical Formula

C₁₉H₁₄Cl₂N₂O₃S

InChI Key

BPQMGSKTAYIVFO-UHFFFAOYSA-N

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)

IUPAC Name

2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide

SMILES

CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1

Pharmacology

Indication

Vismodegib is used for treating locally advanced or metastatic basal cell carcinoma in patients whose carcinoma has recurred after surgery, and in patients who are not candidates for surgery or radiation.

Associated Conditions

Pharmacodynamics

Vismodegib selectively binds to and inhibits the transmembrane protein Smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway.

Mechanism of action

Mutations of the Hedgehog pathway may results in uncontrolled proliferation of skin basal cells. Vismodegib binds to and inhibits the transmembrane protein Smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway.

Target	Actions	Organism
ASmoothened homolog	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The absolute bioavailability of a single dose is 31.8%. Absorption is saturable and is not affected by food.

Volume of distribution

Vismodegib has a volume of distribution of 16.4 to 26.6 L.

Protein binding

Vismodegib is highly protein bound with plasma protein binding at about 99%. Vismodegib binds to the plasma proteins, albumin and alpha-1-acid glycoprotein (saturable bnding).

Metabolism

The main metabolic enzymes are CYP2C9 and CYP3A4, however more than 98% of total systemic vismodegib is not metabolized. Metabolic pathways of vismodegib in humans include oxidation, glucuronidation, and pyridine ring cleavage. The two most abundant oxidative metabolites recovered in feces are produced in vitro by recombinant CYP2C9 and CYP3A4/5.

Route of elimination

Vismodegib is mostly excreted unchanged, and the main route of elimination is by the feces (82%) and the urine accounts for 4.4%.

Half life

The half-life after a single dose is 12 days, and after continuous daily dosing is 4 days.

Clearance

Not Available

Toxicity

Increased risk of embryo-fetal death and significant birth defects. Common adverse event include muscle spasms, alopecia, dysgeusia, weight loss, fatigue, nausea, diarrhea, decreased appetite, constipation, arthralgias, vomiting, and ageusia.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Vismodegib.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Vismodegib.
Abatacept	The metabolism of Vismodegib can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Vismodegib can be increased when it is combined with Abemaciclib.
Abiraterone	The metabolism of Vismodegib can be decreased when combined with Abiraterone.
Acebutolol	The serum concentration of Vismodegib can be increased when it is combined with Acebutolol.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Vismodegib.
Acetaminophen	The serum concentration of Vismodegib can be increased when it is combined with Acetaminophen.
Acetohexamide	The metabolism of Acetohexamide can be decreased when combined with Vismodegib.
Acetyl sulfisoxazole	The metabolism of Vismodegib can be decreased when combined with Acetyl sulfisoxazole.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Food does not affect absorption.

References

General References

Von Hoff DD, LoRusso PM, Rudin CM, Reddy JC, Yauch RL, Tibes R, Weiss GJ, Borad MJ, Hann CL, Brahmer JR, Mackey HM, Lum BL, Darbonne WC, Marsters JC Jr, de Sauvage FJ, Low JA: Inhibition of the hedgehog pathway in advanced basal-cell carcinoma. N Engl J Med. 2009 Sep 17;361(12):1164-72. doi: 10.1056/NEJMoa0905360. Epub 2009 Sep 2. [PubMed:19726763]
Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017]

External Links

KEGG Drug: D09992
PubChem Compound: 24776445
PubChem Substance: 175427109
ChemSpider: 23337846
BindingDB: 50249522
ChEBI: 66903
ChEMBL: CHEMBL473417
PharmGKB: PA166048558
HET: VIS
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Vismodegib

ATC Codes

L01XX43 — Vismodegib

AHFS Codes

10:00.00 — Antineoplastic Agents

PDB Entries

5l7i

FDA label

Download (211 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Basal Cell Carcinoma of the Skin / Recurrent Skin Cancer	1
0	Completed	Treatment	Prostate Cancer	1
0	Unknown Status	Treatment	Pancreatic Adenocarcinoma Resectable	1
1	Active Not Recruiting	Treatment	Adult Solid Neoplasm / Pancreatic Acinar Cell Carcinoma / Pancreatic Ductal Adenocarcinoma / Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer / Stage IV Pancreatic Cancer AJCC v6 and v7	1
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Treatment	Acinar Cell Adenocarcinoma of the Pancreas / Duct Cell Adenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific	1
1	Completed	Treatment	Agnogenic Myeloid Metaplasia	1
1	Completed	Treatment	Basal Cell Carcinoma (BCC)	1
1	Completed	Treatment	DS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Idiopathic Pulmonary Fibrosis (IPF)	1
1	Completed	Treatment	Malignancies / Solid Cancers	1
1	Completed	Treatment	Recurrent Childhood Medulloblastoma	1
1	Completed	Treatment	Solid Cancers	2
1	Completed	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
1	Terminated	Treatment	Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma	1
1, 2	Active Not Recruiting	Treatment	Neoplasms, Malignant	1
1, 2	Completed	Treatment	Adenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer	1
1, 2	Completed	Treatment	Adult Alveolar Soft Part Sarcoma / Adult Angiosarcoma / Adult Desmoplastic Small Round Cell Tumor / Adult Epithelioid Hemangioendothelioma / Adult Epithelioid Sarcoma / Adult Extraskeletal Myxoid Chondrosarcoma / Adult Extraskeletal Osteosarcoma / Adult Fibrosarcoma / Adult Leiomyosarcoma / Adult Liposarcoma / Adult Malignant Mesenchymoma / Adult Malignant Peripheral Nerve Sheath Tumor / Adult Rhabdomyosarcoma / Adult Synovial Sarcoma / Adult Unclassified Pleomorphic Sarcoma / Chondrosarcomas / Clear Cell Sarcoma of the Kidney / Conjunctival Kaposi Sarcoma / Dermatofibrosarcoma Protuberans / Gastrointestinal Stromal Tumors / Metastatic Bone Sarcomas / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Ovarian Sarcoma / Recurrent Adult Soft Tissue Sarcoma / Recurrent Adult Unclassified Pleomorphic Sarcoma of Bone / Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Recurrent Kaposi's Sarcoma / Recurrent Osteosarcoma / Recurrent Uterine Corpus Sarcoma / Small Intestine Leiomyosarcoma / Stage III Adult Soft Tissue Sarcoma / Stage III Uterine Sarcoma / Stage IV Adult Soft Tissue Sarcoma / Stage IV Uterine Sarcoma / Unclassified Pleomorphic Sarcoma of Bone	1
1, 2	Completed	Treatment	Skin Basal Cell Carcinoma	1
1, 2	Recruiting	Treatment	Glioblastoma, Adult	1
1, 2	Terminated	Treatment	Activation of the Sonic Hedgehog (SHH) Pathway / Histologically Confirmed Medulloblastoma	1
1, 2	Terminated	Treatment	Adenocarcinoma, Prostate / Stage IIA Prostate Cancer / Stage IIA Prostate Cancer AJCC v7 / Stage IIB Prostate Cancer / Stage IIB Prostate Cancer AJCC v7	1
2	Active Not Recruiting	Treatment	Basal Cell Carcinoma (BCC)	2
2	Active Not Recruiting	Treatment	Chondrosarcoma, Mesenchymal / Chondrosarcomas / Clear Cell Chondrosarcoma / Dedifferentiated Chondrosarcoma / Metastatic Chondrosarcoma / Primary Central Chondrosarcoma	1
2	Active Not Recruiting	Treatment	Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer	1
2	Active Not Recruiting	Treatment	Stomach Neoplasms	1
2	Completed	Treatment	Adenocarcinoma of the Stomach / Adenocarcinomas of the Gastroesophageal Junction / Advanced Gastric Cancer / Recurrent Gastric Cancer / Stage IIIA Gastric Cancer / Stage IIIB Gastric Cancer / Stage IIIC Gastric Cancer	1
2	Completed	Treatment	Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor	1
2	Completed	Treatment	Adult Medulloblastoma	1
2	Completed	Treatment	Basal Cell Carcinoma (BCC)	7
2	Completed	Treatment	Basal Cell Carcinoma (BCC) / Metastatic Colorectal Cancer (MCRC) / Ovarian Cancer	1
2	Completed	Treatment	Basal Cell Nevus Syndrome / Gorlin's Syndrome	2
2	Completed	Treatment	Cutaneous Malignancy / Locally Advanced Basal Cell Carcinoma / Skin Cancers	1
2	Completed	Treatment	Extensive Stage Small Cell Lung Cancer / Extensive Stage Small Cell Lung Carcinoma / Recurrent Small Cell Lung Carcinoma / Refractory Small cell lung cancer	1
2	Completed	Treatment	Keratocystic Odontogenic Tumor	1
2	Completed	Treatment	Metastatic Colorectal Cancer (MCRC)	1
2	Completed	Treatment	Ovarian Cancer	1
2	Completed	Treatment	Pancreatic Cancer Metastatic	1
2	Completed	Treatment	Recurrent Childhood Medulloblastoma	1
2	Not Yet Recruiting	Treatment	Basal Cell Nevus Syndrome	1
2	Recruiting	Treatment	Advanced Malignant Neoplasm / Advanced Malignant Solid Neoplasm / Bladder Carcinoma / Carcinoma, Breast / Carcinoma, Colorectal / Carcinoma, Pancreatic / Cervical Carcinoma / Colon Carcinoma / Endometrial Carcinoma / Esophageal Carcinoma / Gastric Carcinoma / Gliomas / Head and Neck Carcinoma / Liver and Intrahepatic Bile Duct Carcinoma / Lung, Carcinoma / Malignant Lymphomas / Malignant Uterine Neoplasm / Melanoma / Ovarian Carcinoma / Plasma Cell Myeloma / Prostate Cancer / Rectal Carcinoma / Recurrent Bladder Carcinoma / Recurrent Breast Carcinoma / Recurrent Cervical Carcinoma / Recurrent Colon Carcinoma / Recurrent Colorectal Carcinoma / Recurrent Esophageal Carcinoma / Recurrent Gastric Carcinoma / Recurrent Gliomas / Recurrent Head and Neck Carcinoma / Recurrent Liver Carcinoma / Recurrent Lung Carcinoma / Recurrent Lymphoma / Recurrent Malignant Solid Neoplasm / Recurrent Melanoma / Recurrent Ovarian Carcinoma / Recurrent Pancreatic Carcinoma / Recurrent Plasma Cell Myeloma / Recurrent Prostate Carcinoma / Recurrent Rectal Carcinoma / Recurrent Skin Carcinoma / Recurrent Solid Neoplasm / Recurrent Thyroid Gland Carcinoma / Recurrent Uterine Corpus Carcinoma / Refractory Lymphomas / Refractory Malignant Neoplasm / Refractory Malignant Solid Neoplasm / Refractory Plasma Cell Myeloma / Renal Carcinoma / Skin Carcinoma / Solid Neoplasms / Thyroid Gland Carcinoma / Uterine Corpus Cancer	1
2	Recruiting	Treatment	Advanced Solid Tumors / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL)	1
2	Recruiting	Treatment	Basal Cell Carcinoma (BCC)	1
2	Recruiting	Treatment	Biliary Cancer / Bladder Cancers / Neoplasms / Salivary Cancer / Tumors, Solid	1
2	Recruiting	Treatment	Breast Cancer	1
2	Recruiting	Treatment	Cancer of Unknown Primary Site	1
2	Recruiting	Treatment	Leukemia Acute Myeloid Leukemia (AML)	1
2	Recruiting	Treatment	Malignancies / Neoplasms / Tumors	1
2	Recruiting	Treatment	Medulloblastomas	1
2	Suspended	Treatment	Intracranial Meningioma / NF2 Gene Mutation / Recurrent Meningiomas	1
2	Terminated	Prevention	Basal Cell Carcinoma (BCC)	1
2	Terminated	Treatment	"Indolent" Non-hodgkin Lymphoma / Chronic Lymphocytic Leukaemia (CLL) / Indolent Non-Hodgkin's Lymphomas / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Primary Central Nervous System Lymphoma (PCNSL)	1
2	Terminated	Treatment	Myelodysplastic Syndromes, Myelogenous Leukemia, Acute	1
2	Terminated	Treatment	Pancreatic Ductal Adenocarcinoma	1
2	Terminated	Treatment	Pontine Glioma	1
2	Withdrawn	Treatment	Idiopathic Pulmonary Fibrosis (IPF)	1
4	Approved for Marketing	Not Available	Basal Cell Carcinoma (BCC)	1
4	Recruiting	Treatment	Basal Cell Carcinoma (BCC)	1
4	Recruiting	Treatment	Locally Advanced Basal Cell Carcinoma / Metastatic Basal cell carcinoma	1
Not Available	Active Not Recruiting	Not Available	Basal Cell Carcinoma (BCC)	1
Not Available	Completed	Not Available	Basal Cell Carcinoma (BCC) / Locally Advanced Basal Cell Carcinoma	1
Not Available	Terminated	Treatment	Chronic Graft Versus Host Disease / Progressive cGVHD	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Capsule	Oral	150 mg/1
Capsule	Oral	150 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US9278961	No	2016-03-08	2028-12-15
US7888364	No	2011-02-15	2028-11-11

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	0.1 μg/mL and is pH dependent	FDA label
logP	2.7	FDA label
pKa	3.8	FDA label

Predicted Properties

Property	Value	Source
Water Solubility	0.00173 mg/mL	ALOGPS
logP	4.22	ALOGPS
logP	3.93	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.81 m³·mol^-1	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9547
Blood Brain Barrier	+	0.9387
Caco-2 permeable	+	0.6048
P-glycoprotein substrate	Non-substrate	0.8443
P-glycoprotein inhibitor I	Non-inhibitor	0.8663
P-glycoprotein inhibitor II	Non-inhibitor	0.9558
Renal organic cation transporter	Non-inhibitor	0.8925
CYP450 2C9 substrate	Non-substrate	0.6009
CYP450 2D6 substrate	Non-substrate	0.63
CYP450 3A4 substrate	Non-substrate	0.5083
CYP450 1A2 substrate	Non-inhibitor	0.6067
CYP450 2C9 inhibitor	Inhibitor	0.9078
CYP450 2D6 inhibitor	Non-inhibitor	0.6638
CYP450 2C19 inhibitor	Inhibitor	0.8515
CYP450 3A4 inhibitor	Inhibitor	0.8452
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9282
Ames test	Non AMES toxic	0.8271
Carcinogenicity	Non-carcinogens	0.6746
Biodegradation	Not ready biodegradable	0.9956
Rat acute toxicity	2.0840 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9973
hERG inhibition (predictor II)	Non-inhibitor	0.8224

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00di-0212900000-190a5fdca2d781122e92

Taxonomy

Description: This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Anilides
Direct Parent: Benzanilides
Alternative Parents: Phenylpyridines / 2-halobenzoic acids and derivatives / Benzamides / Benzenesulfonyl compounds / Benzoyl derivatives / Chlorobenzenes / Aryl chlorides / Vinylogous halides / Sulfones / Heteroaromatic compounds
show 8 more
Substituents: Benzanilide / 2-phenylpyridine / 2-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzenesulfonyl group / Benzoyl / Chlorobenzene / Halobenzene
show 23 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: sulfone, benzamides, pyridines, monochlorobenzenes (CHEBI:66903)

Targets

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	7	N/A	N/A	22268551
Ki (nM)	16.2	N/A	N/A	23063522

Details1. Smoothened homolog

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Wnt-protein binding
Specific Function: G protein-coupled receptor that probably associates with the patched protein (PTCH) to transduce the hedgehog's proteins signal. Binding of sonic hedgehog (SHH) to its receptor patched is thought t...
Gene Name: SMO
Uniprot ID: Q99835
Uniprot Name: Smoothened homolog
Molecular Weight: 86395.95 Da

References

Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017]

Enzymes

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017]
Vismodegib FDA Label [File]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017]

Details3. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

Details4. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Fellner C: Vismodegib (erivedge) for advanced Basal cell carcinoma. P T. 2012 Dec;37(12):670-82. [PubMed:23319845]
Vismodegib [File]

Carriers

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	1.20E+05	N/A	N/A	21438527
Kd (nM)	1.30E+05	N/A	N/A	21438527
Kd (nM)	5.50E+03	N/A	N/A	21438527
Kd (nM)	6.00E+03	N/A	N/A	21438527

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

Details2. Alpha-1-acid glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name: ORM1
Uniprot ID: P02763
Uniprot Name: Alpha-1-acid glycoprotein 1
Molecular Weight: 23511.38 Da

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017]

Details2. ATP-binding cassette sub-family G member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name: ABCG2
Uniprot ID: Q9UNQ0
Uniprot Name: ATP-binding cassette sub-family G member 2
Molecular Weight: 72313.47 Da

Drug created on January 04, 2013 14:48 / Updated on December 09, 2019 19:29

Vismodegib

Identification

Structure for Vismodegib (DB08828)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References

References

References

Carriers

Transporters

References