Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1698)
Drug Name
Vismodegib
Synonyms
Vismodegib; Vismodegib (GDC-0449); Erivedge; GDC 0449; GDC-0449; GDC-0449 (Vismodegib); GDC0449; HhAntag691; 2-Chloro-N-[4-chloro-3-(2-pyridinyl)phenyl]-4-(methylsulfonyl)benzamide; 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide; 2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide; 2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-(methylsulfonyl)benzamide; 25X868M3DS; 879085-55-9; AK-77261; C19H14Cl2N2O3S; CHEBI:66903; CHEMBL473417; NSC755986; UNII-25X868M3DS
Indication Melanoma [ICD11: 2C30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 421.3 Topological Polar Surface Area 84.5
Heavy Atom Count 27 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
24776445
PubChem SID
49701104 ; 56182549 ; 99431642 ; 99436972 ; 103596069 ; 104103799 ; 124756985 ; 124950698 ; 125163790 ; 126582948 ; 126723724 ; 131408297 ; 131480672 ; 134221782 ; 134964405 ; 135261181 ; 135264774 ; 135626713 ; 135693359 ; 135727390 ; 136367283 ; 136367935 ; 136920328 ; 137209785 ; 137275857 ; 139063406 ; 143499146 ; 144074933 ; 144116004 ; 152105953 ; 152237711 ; 152258215 ; 152344224 ; 160645549 ; 160647051 ; 160828460 ; 162011920 ; 162037423 ; 162201437 ; 163093562 ; 163390565 ; 164041956 ; 164193932 ; 164766132 ; 167250332 ; 170498924 ; 172919842 ; 174531169 ; 175265446 ; 175427109
ChEBI ID
ChEBI:66903
CAS Number
879085-55-9
TTD Drug ID
D03EDQ
Formula
C19H14Cl2N2O3S
Canonical SMILES
CS(=O)(=O)C1=CC(=C(C=C1)C(=O)NC2=CC(=C(C=C2)Cl)C3=CC=CC=N3)Cl
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Vismodegib metabolite M1 DM005280
156028129
Unclear 1 [3] , [4] , [5]
Vismodegib metabolite M14 DM005282
156028028
Oxidation - Hydrolyzationn 1 [3] , [4] , [5]
Vismodegib metabolite M18 DM005277
156028037
Oxidation - Oxidationn 1 [3] , [4]
Vismodegib metabolite M3 DM005276
156028055
Oxidation - Hydrolyzationn 1 [3] , [4] , [5]
Vismodegib metabolite M13 DM005278
156028048
Oxidation - Oxidationn 2 [3] , [4]
Vismodegib metabolite M18 DM005277
156028037
Oxidation - Oxidationn 2 [3] , [4] , [5]
Vismodegib metabolite M4 DM005281
155929053
Conjugation - Glucuronidation 2 [3] , [4] , [5]
Vismodegib metabolite M5 DM005279
156028049
Conjugation - Glucuronidation 2 [3] , [4] , [5]
Vismodegib metabolite M13 DM005278
156028048
Oxidation - Oxidationn 3 [3] , [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005655 Vismodegib Vismodegib metabolite M3 Oxidation - Hydrolyzationn CYP2C9 [3], [4], [5]
MR005659 Vismodegib Vismodegib metabolite M1 Unclear CYP3A4. CYP3A5 ... [3], [4], [5]
MR005661 Vismodegib Vismodegib metabolite M18 Oxidation - Oxidationn Unclear [3], [4]
MR005662 Vismodegib Vismodegib metabolite M14 Oxidation - Hydrolyzationn Unclear [3], [4], [5]
MR005660 Vismodegib metabolite M1 Vismodegib metabolite M4 Conjugation - Glucuronidation UGT [3], [4], [5]
MR005656 Vismodegib metabolite M3 Vismodegib metabolite M18 Oxidation - Oxidationn Unclear [3], [4], [5]
MR005658 Vismodegib metabolite M3 Vismodegib metabolite M5 Conjugation - Glucuronidation UGT [3], [4], [5]
MR005657 Vismodegib metabolite M18 Vismodegib metabolite M13 Oxidation - Oxidationn Unclear [3], [4], [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3] , [4] , [5]
References
1 Vismodegib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7.
3 A single dose mass balance study of the Hedgehog pathway inhibitor vismodegib (GDC-0449) in humans using accelerator mass spectrometry
4 Absorption, distribution, metabolism, and excretion of [1?C]GDC-0449 (vismodegib), an orally active hedgehog pathway inhibitor, in rats and dogs: a unique metabolic pathway via pyridine ring opening
5 Preclinical assessment of the absorption, distribution, metabolism and excretion of GDC-0449 (2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide), an orally bioavailable systemic Hedgehog signalling pathway inhibitor

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