CEFIDEROCOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H34ClN7O10S2
Molecular Weight	752.215
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(C[N+]4(CCNC(=O)C3=C(Cl)C(O)=C(O)C=C3)CCCC4)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C(O)=O)\C5=CSC(N)=N5)C([O-])=O

InChI

InChIKey=DBPPRLRVDVJOCL-FQRUVTKNSA-N

InChI=1S/C30H34ClN7O10S2/c1-30(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/h5-6,13,20,26H,3-4,7-12H2,1-2H3,(H7-,32,33,34,35,36,39,40,41,42,44,45,46,47)/t20-,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C30H34ClN7O10S2
Molecular Weight	752.215
Charge	0
Count

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

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 1579 inducer 768	inhibitor 1752	inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2B6 799 CYP2C8 901 CYP2C19 1463 CYP2E1 876 OATP1B1 781 MATE1 304 P-gp 1437 BCRP 691 BSEP 401 OAT1 595 OAT3 636 OCT1 506 OCT2 638 OATP1B3 700 MATE2 261	OAT1 320 OAT3 333 OCT2 348 MATE1 132 MATE2 94 P-gp 1527	CYP1A2 689 CYP2B6 538

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BCRP 765	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
BSEP 402	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 1673	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 985	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2B6 985	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 1909	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE1 306	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
OATP1B1 796	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
P-gp 1626	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=64 Page: 64.0	no
MATE2 261	inhibitor 3240 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 599	inhibitor 3240 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 638	inhibitor 3240 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 709	inhibitor 3240 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 523	inhibitor 3240 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 639	inhibitor 3240 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 132	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
MATE2 94	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT1 320	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OAT3 333	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
OCT2 348	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209445Orig1s000MultidisciplineR.pdf#page=84 Page: 84.0	yes
P-gp 1527	substrate 3326 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 1632	inhibitor 1613 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 `Thu Jul 06 16:10:45 UTC 2023` Edited by `admin` on `Thu Jul 06 16:10:45 UTC 2023`
Record UNII	SZ34OMG6E8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFIDEROCOL

Official Name

English

(6R,7R)-7-[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetamido]-3-({1-[2-(2-chloro-3,4-dihydroxybenzamido)ethyl]pyrrolidin-1-ium-1-yl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Systematic Name

English

CEFIDEROCOL [MI]

Common Name

English

S-649266

Code

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)-, INNER SALT

Systematic Name

English

GSK2696266

Code

English

CEFIDEROCOL [USAN]

Common Name

English

Cefiderocol [WHO-DD]

Common Name

English

cefiderocol [INN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548666