CEFIDEROCOL SULFATE TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	3C30H35ClN7O10S2.4C7H7O3S.O4S.3H.H2O
Molecular Weight	3061.545
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 9
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure of CEFIDEROCOL SULFATE TOSYLATE

Structure Search

SMILES

[H+].[H+].[H+].O.[O-]S([O-])(=O)=O.CC1=CC=C(C=C1)S([O-])(=O)=O.CC2=CC=C(C=C2)S([O-])(=O)=O.CC3=CC=C(C=C3)S([O-])(=O)=O.CC4=CC=C(C=C4)S([O-])(=O)=O.CC(C)(O\N=C(/C(=O)N[C@H]5[C@H]6SCC(C[N+]8(CCNC(=O)C7=CC=C(O)C(O)=C7Cl)CCCC8)=C(N6C5=O)C(O)=O)C9=CSC(N)=N9)C(O)=O.CC(C)(O\N=C(/C(=O)N[C@H]%10[C@H]%11SCC(C[N+]%13(CCNC(=O)C%12=CC=C(O)C(O)=C%12Cl)CCCC%13)=C(N%11C%10=O)C(O)=O)C%14=CSC(N)=N%14)C(O)=O.CC(C)(O\N=C(/C(=O)N[C@H]%15[C@H]%16SCC(C[N+]%18(CCNC(=O)C%17=CC=C(O)C(O)=C%17Cl)CCCC%18)=C(N%16C%15=O)C(O)=O)C%19=CSC(N)=N%19)C(O)=O

InChI

InChIKey=QNMVZYPDWLKAJC-RXVBEKIDSA-N

InChI=1S/3C30H34ClN7O10S2.4C7H8O3S.H2O4S.H2O/c3*1-30(2,28(46)47)48-36-19(16-13-50-29(32)34-16)24(42)35-20-25(43)37-21(27(44)45)14(12-49-26(20)37)11-38(8-3-4-9-38)10-7-33-23(41)15-5-6-17(39)22(40)18(15)31;4*1-6-2-4-7(5-3-6)11(8,9)10;1-5(2,3)4;/h3*5-6,13,20,26H,3-4,7-12H2,1-2H3,(H7-,32,33,34,35,36,39,40,41,42,44,45,46,47);4*2-5H,1H3,(H,8,9,10);(H2,1,2,3,4);1H2/t3*20-,26-;;;;;;/m111....../s1

HIDE SMILES / InChI

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
138 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/209445s000lbl.pdf	2 g 3 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFIDEROCOL unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
89.7 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/209445s000lbl.pdf	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEFIDEROCOL unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1184 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/209445s000lbl.pdf	2 g 3 times / day multiple, intravenous dose: 2 g route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFIDEROCOL unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
386 mg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/209445s000lbl.pdf	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEFIDEROCOL unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 g 3 times / day multiple, intravenous Recommended Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf	unhealthy, 18 to 93 years Health Status: unhealthy Age Group: 18 to 93 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf	Disc. AE: Diarrhea, Drug hypersensitivity... Other AEs: Diarrhea, Infusion site reactions... AEs leading to discontinuation/dose reduction: Diarrhea (0.3%) Drug hypersensitivity (0.3%) Hepatic enzymes increased (0.3%) Death (grade 5, 0.3%) Other AEs: Diarrhea (4%) Infusion site reactions (4%) Constipation (3%) Rash (3%) Candidiasis (2%) Cough (2%) Elevated liver enzymes (2%) Headache (2%) Hypokalemia (2%) Nausea (2%) Vomiting (2%) Thrombocytosis (<2%) Congestive heart failure (<2%) Bradycardia (<2%) Atrial fibrillation (<2%) Abdominal pain (<2%) Dry mouth (<2%) Stomatitis (<2%) Pyrexia (<2%) Peripheral edema (<2%) Cholelithiasis (<2%) Cholecystitis (<2%) Gallbladder pain (<2%) Drug hypersensitivity (<2%) Clostridium difficile infection (<2%) Prothrombin time prolonged (<2%) Red blood cells urine positive (<2%) Creatine phosphokinase increased (<2%) Decreased appetite (<2%) Hypocalcemia (<2%) Fluid overload (<2%) Dysgeusia (<2%) Seizure (<2%) Dyspnea (<2%) Pleural effusion (<2%) Pruritis (<2%) Insomnia (<2%) Restlessness (<2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf
1 g 1 times / day single, intravenous Dose: 1 g, 1 times / day Route: intravenous Route: single Dose: 1 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27874971/	unhealthy, mean age 60.1 years Health Status: unhealthy Age Group: mean age 60.1 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27874971/	Disc. AE: Urticaria... AEs leading to discontinuation/dose reduction: Urticaria (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/27874971/
2 g 3 times / day multiple, intravenous Recommended Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf	unhealthy, median age - 67 years Health Status: unhealthy Age Group: median age - 67 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf	Disc. AE: Death, Elevated liver enzymes... Other AEs: Elevated liver enzymes, Hypokalemia... AEs leading to discontinuation/dose reduction: Death (grade 5, 26.4%) Elevated liver enzymes Other AEs: Elevated liver enzymes (16%) Hypokalemia (11%) Diarrhea (9%) Hypomagnesemia (5%) Atrial fibrillation (5%) Thrombocytopenia (<4%) Thrombocytosis (<4%) Myocardial infarction (<4%) Atrial flutter (<4%) Nausea (<4%) Vomiting (<4%) Abdominal pain (<4%) Cholecystitis (<4%) Cholestasis (<4%) Clostridium difficile infection (<4%) Oral candidiasis (<4%) Prothrombin time prolonged (<4%) Activated partial thromboplastin time (<4%) Hypocalcemia (<4%) Hyperkalemia (<4%) Seizure (<4%) Acute interstitial nephritis (<4%) Cough (<4%) Rash (<4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/209445s002lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 OATP1B1 1079 MATE1 415 P-gp 1741 BCRP 910 BSEP 550 OAT1 725 OAT3 747 OCT1 620 OCT2 779 OATP1B3 961 MATE2 267	OAT1 395 OAT3 391 OCT2 434 MATE1 182 MATE2 98 P-gp 2052	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE1 416	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE2 267	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0
OCT1 656	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	yes	no (co-administration study) Comment: The results from a clinical drug-drug interaction study indicate that cefiderocol had no clinically meaningful effects on the PK of furosemide (substrate for OAT1 and OAT3), metformin (for OCT1, OCT2, and MATE2- K), and rosuvastatin (for OATP1B3). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0

Drug as victim

Target	Modality	Activity
MATE1 182	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
MATE2 98	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=49 Page: 49.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA01EOPK	https://www.aablocks.com/goods/Goods/detail?id=AA01EOPK
Angel Pharmatech	AG103023	http://www.angelpharmatech.com/1225208-94-5.html
BOC Sciences	1225208-94-5	https://www.bocsci.com/cefiderocol-cas-1225208-94-5-item-475177.html
Chem Scene	CS-0016784	http://www.chemscene.com/1225208-94-5.html
Chemspace	CSSB00161189600	https://chem-space.com/CSSB00161189600
eNovation Chemicals	D666623	https://www.enovationchem.com/ProductDetails.asp?ProductID=D666623
Hairui	CEJL016	http://www.hairuichem.com/en/product/1225208-94-5.html
MedChem Express	HY-17628	https://www.medchemexpress.com/cefiderocol.html
Smolecule	S523086	http://www.smolecule.com/products/s523086
Smolecule	S879858	https://www.smolecule.com/products/s879858
THE BioTek	bt-263321	https://www.thebiotek.com/product/inhibitors/bt-263321

Name

Type

Language

FETROJA

Preferred Name

English

CEFIDEROCOL SULFATE TOSYLATE

Official Name

English

S-649266D

Code

English

CEFIDEROCOL TOSILATE SULFATE HYDRATE [JAN]

Common Name

English

CEFIDEROCOL SULFATE TOSYLATE [MI]

Common Name

English

GSK-2696266D

Code

English

CEFIDEROCOL SULFATE TOSYLATE [ORANGE BOOK]

Common Name

English

CEFIDEROCOL SULFATE TOSYLATE [USAN]

Common Name

English

PYRROLIDINIUM, 1-(((6R,7R)-7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-((1-CARBOXY-1-METHYLETHOXY)IMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-1-(2-((2-CHLORO-3,4-DIHYDROXYBENZOYL)AMINO)ETHYL)-, 4-METHYLBENZENESULFONATE SULF

Systematic Name

English

Cefiderocol sulfate tosylate [WHO-DD]

Common Name

English

CEFIDEROCOL TOSILATE SULFATE HYDRATE

Common Name

English

GSK2696266D

Code

English

Code System Code Type Description

RXCUI

2265863