CEFIDEROCOL SULFATE TOSYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	3C30H35ClN7O10S2.4C7H7O3S.O4S.3H.H2O
Molecular Weight	3061.545
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
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.[H][C@]56SCC(C[N+]8(CCNC(=O)C7=C(Cl)C(O)=C(O)C=C7)CCCC8)=C(N5C(=O)[C@H]6NC(=O)C(=N/OC(C)(C)C(O)=O)\C9=CSC(N)=N9)C(O)=O.[H][C@]%10%11SCC(C[N+]%13(CCNC(=O)C%12=C(Cl)C(O)=C(O)C=C%12)CCCC%13)=C(N%10C(=O)[C@H]%11NC(=O)C(=N/OC(C)(C)C(O)=O)\C%14=CSC(N)=N%14)C(O)=O.[H][C@]%15%16SCC(C[N+]%18(CCNC(=O)C%17=C(Cl)C(O)=C(O)C=C%17)CCCC%18)=C(N%15C(=O)[C@H]%16NC(=O)C(=N/OC(C)(C)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

Molecular Formula	C7H7O3S
Molecular Weight	171.194
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	O4S
Molecular Weight	96.063
Charge	-2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C30H35ClN7O10S2
Molecular Weight	753.223
Charge	1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	H
Molecular Weight	1.0079
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 n = 300 Health Status: unhealthy Condition: Complicated Urinary Tract Infections Age Group: 18 to 93 years Sex: M+F Population Size: 300 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 n = 8 Health Status: unhealthy Condition: Gram-Negative Bacterial Infections Age Group: mean age 60.1 years Sex: M+F Population Size: 8 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 n = 148 Health Status: unhealthy Condition: Hospital-acquired Bacterial Pneumonia and Ventilator-associated Bacterial Pneumonia Age Group: median age - 67 years Sex: M+F Population Size: 148 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 1587 inducer 781	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882 OATP1B1 788 MATE1 306 P-gp 1461 BCRP 699 BSEP 402 OAT1 599 OAT3 642 OCT1 512 OCT2 647 OATP1B3 706 MATE2 263	OAT1 326 OAT3 339 OCT2 355 MATE1 135 MATE2 96 P-gp 1537	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE1 308	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE2 263	inhibitor 3277 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 603	inhibitor 3277 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 644	inhibitor 3277 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 715	inhibitor 3277 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 543	inhibitor 3277 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 648	inhibitor 3277 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 135	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
MATE2 96	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT1 326	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT3 339	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OCT2 355	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
P-gp 1537	substrate 3367 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 1647	inhibitor 1626 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
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
eNovation Chemicals	D666623	https://www.enovationchem.com/ProductDetails.asp?ProductID=D666623

Substance Class	Chemical Created by `admin` on `Sat Dec 16 14:50:57 UTC 2023` Edited by `admin` on `Sat Dec 16 14:50:57 UTC 2023`
Record UNII	TTP8LBP45D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

FETROJA

Brand 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