Cobimetinib

Cobimetinib
Clinical data
Pronunciation	/ˌkoʊbɪˈmɛtɪnɪb/ KOH-bim-ET-i-nib
Trade names	Cotellic
Other names	GDC-0973, XL-518
AHFS/Drugs.com	Monograph
MedlinePlus	a615057
License data	US DailyMed: Cobimetinib;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
ATC code	L01EE02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	reported from 28% to 46%
Protein binding	95%
Metabolism	Intestinal and low Liver clearance (mostly CYP3A4 oxidation and UGT2B7 glucuronidation)
Elimination half-life	44 hours (mean)
Excretion	Feces (76–77%), urine (17.9–18%) (after oral and IV administration)
Identifiers
	IUPAC name (S)-[3,4-Difluoro-2-(2-fluoro-4-iodophenylamino)phenyl] [3-hydroxy-3-(piperidin-2-yl)azetidin-1-yl] methanone;
CAS Number	934660-93-2;
PubChem CID	16222096;
IUPHAR/BPS	7626;
DrugBank	DB05239 ;
ChemSpider	17349374;
UNII	ER29L26N1X;
KEGG	D10405; D10615;
ChEBI	CHEBI:90851 ;
ChEMBL	ChEMBL2146883;
CompTox Dashboard (EPA)	DTXSID60239435 ;
Chemical and physical data
Formula	C21H21F3IN3O2
Molar mass	531.318 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCN[C@@H](C1)C2(CN(C2)C(=O)C3=C(C(=C(C=C3)F)F)NC4=C(C=C(C=C4)I)F)O;
	InChI InChI=1S/C21H21F3IN3O2/c22-14-6-5-13(19(18(14)24)27-16-7-4-12(25)9-15(16)23)20(29)28-10-21(30,11-28)17-3-1-2-8-26-17/h4-7,9,17,26-27,30H,1-3,8,10-11H2/t17-/m0/s1; Key:BSMCAPRUBJMWDF-KRWDZBQOSA-N;

Cobimetinib, sold under the brand name Cotellic, is an anti-cancer medication used to treat melanoma and histiocytic neoplasms. Cobimetinib is a MEK inhibitor. Cobimetinib is marketed by Genentech.

The most common side effects include diarrhea, rash, nausea (feeling sick), vomiting, pyrexia (fever), photosensitivity (light sensitivity) reaction, abnormal results for certain liver function tests (increased levels of alanine aminotransferase, aspartate aminotransferase) and abnormal results for an enzyme related to muscle breakdown (creatine phosphokinase).

Cobimetinib was approved for medical use in the United States in November 2015.

Clinical data

Pronunciation	/ˌkoʊbɪˈmɛtɪnɪb/ KOH-bim-ET-i-nib
Trade names	Cotellic
Other names	GDC-0973, XL-518
AHFS/Drugs.com	Monograph
MedlinePlus	a615057
License data	US DailyMed: Cobimetinib
Pregnancy category	AU: D
Routes of administration	By mouth
ATC code	L01EE02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	reported from 28% to 46%
Protein binding	95%
Metabolism	Intestinal and low Liver clearance (mostly CYP3A4 oxidation and UGT2B7 glucuronidation)
Elimination half-life	44 hours (mean)
Excretion	Feces (76–77%), urine (17.9–18%) (after oral and IV administration)
Identifiers
IUPAC name (S)-[3,4-Difluoro-2-(2-fluoro-4-iodophenylamino)phenyl] [3-hydroxy-3-(piperidin-2-yl)azetidin-1-yl] methanone
CAS Number	934660-93-2
PubChem CID	16222096
IUPHAR/BPS	7626
DrugBank	DB05239^Y
ChemSpider	17349374
UNII	ER29L26N1X
KEGG	D10405 D10615
ChEBI	CHEBI:90851^Y
ChEMBL	ChEMBL2146883
CompTox Dashboard (EPA)	DTXSID60239435
Chemical and physical data
Formula	C₂₁H₂₁F₃IN₃O₂
Molar mass	531.318 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CCN[C@@H](C1)C2(CN(C2)C(=O)C3=C(C(=C(C=C3)F)F)NC4=C(C=C(C=C4)I)F)O
InChI InChI=1S/C21H21F3IN3O2/c22-14-6-5-13(19(18(14)24)27-16-7-4-12(25)9-15(16)23)20(29)28-10-21(30,11-28)17-3-1-2-8-26-17/h4-7,9,17,26-27,30H,1-3,8,10-11H2/t17-/m0/s1 Key:BSMCAPRUBJMWDF-KRWDZBQOSA-N