Drug Information

General Information
Drug ID
DR00304
Drug Name
Sorafenib
Synonyms
4(4-{3-[4-Chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N(sup 2)-methylpyridine-2-carboxamide; 4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide; 4-(4-(3-(4-chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxyllic acid methyamide-4-methylbenzenesulfonate; 4-(4-{3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido}phenoxy)-N(sup 2)-methylpyridine-2-carboxamide; 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide; 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide; 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide; 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-2-pyridinecarboxamide; 4-{4-[({[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]AMINO}CARBONYL)AMINO]PHENOXY}-N-METHYLPYRIDINE-2-CARBOXAMIDE; N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea; N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcar bamoyl)-4-pyridyloxy)phenyl)urea; N-[4-Chloro-3-(trifluoromethyl)phenyl]-N'-[4-[2-(N-methylcarbamoyl)-4-pyridyloxy]phenyl]urea; Nexavar; Nexavar (TN); Sorafenib (INN); Sorafenib (Pan-TK inhibitor); Sorafenib [INN]; Sorafenibum
Drug Type
Small molecular drug
Indication Hepatocellular carcinoma [ICD11:2C12.02] Approved [1]
Renal cell carcinoma [ICD11:2C90] Approved [1]
Differentiated thyroid cancer [ICD11:2D10] Approved [1]
Pancreatic cancer [ICD11:2C10] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C21H16ClF3N4O3
Canonical SMILES
CNC(=O)C1=NC=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F
InChI
InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChIKey
MLDQJTXFUGDVEO-UHFFFAOYSA-N
CAS Number
CAS 284461-73-0
Pharmaceutical Properties Molecular Weight 464.8 Topological Polar Surface Area 92.4
Heavy Atom Count 32 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
XLogP
4.1
PubChem CID
216239
PubChem SID
103420820 ,103904444 ,104178872 ,113461200 ,117695450 ,117871124 ,12015507 ,124767621 ,124893320 ,124893321 ,124893322 ,124893323 ,124893324 ,125346960 ,14720365 ,14834034 ,30419984 ,46505329 ,46516901 ,50069824 ,50070560 ,50071324 ,50100118 ,50112741 ,53787819 ,53799234 ,56312334 ,56312336 ,56312338 ,56312517 ,56312519 ,56312521 ,56394953 ,57399755 ,68529952 ,74382940 ,75518900 ,7886069 ,81092852 ,833589 ,833590 ,85174603 ,85285882 ,85845166 ,91148447 ,92718861 ,93581025 ,9372814 ,96025209 ,99443909
ChEBI ID
ChEBI:50924
TTD Drug ID
D0W5HK
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [5]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [6]
RALBP1 Transporter Info RalBP1-associated Eps domain-containing protein 2 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data RALBP1 Transporter Info Km =10.4 microM Human kidney cancer cells (Caki-2)-RALBP1 [7]
References
1 Sorafenib was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Perceived parental guan and school adjustment among Chinese early adolescents: The moderating role of interdependent self-construal. J Adolesc. 2019 Feb;71:18-27.
3 Double-transduced MDCKII cells to study human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) interplay in drug transport across the blood-brain barrier. Mol Pharm. 2011 Apr 4;8(2):571-82.
4 Multidrug resistance protein 2 implicates anticancer drug-resistance to sorafenib. Biol Pharm Bull. 2011;34(3):433-5.
5 Contribution of OATP1B1 and OATP1B3 to the disposition of sorafenib and sorafenib-glucuronide. Clin Cancer Res. 2013 Mar 15;19(6):1458-66.
6 Breast cancer resistance protein and P-glycoprotein limit sorafenib brain accumulation. Mol Cancer Ther. 2010 Feb;9(2):319-26.
7 Rlip76 transports sunitinib and sorafenib and mediates drug resistance in kidney cancer. Int J Cancer. 2010 Mar 15;126(6):1327-38.

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