cefoxitin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, cefalosporanic acid derivatives	550	35607-66-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cefoxitin cefoxitin sodium cephoxitin cefoxitin sodium salt	A semisynthetic cephamycin antibiotic resistant to beta-lactamase. Molecular weight: 427.45 Formula: C16H17N3O7S2 CLOGP: -0.81 LIPINSKI: 0 HAC: 10 HDO: 3 TPSA: 148.26 ALOGS: -3.34 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cefoxitin
cefoxitin sodium
cephoxitin
cefoxitin sodium salt

A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

Molecular weight: 427.45
Formula: C16H17N3O7S2
CLOGP: -0.81
LIPINSKI: 0
HAC: 10
HDO: 3
TPSA: 148.26
ALOGS: -3.34
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
6	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	1000 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	85 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	401.04 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.17 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	3.60 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.73 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.81 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Oct. 18, 1978	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Systemic mastocytosis	112.45	32.98	15	870	148	46685029
Catatonia	49.66	32.98	12	873	3750	46681427
Drug resistance	46.61	32.98	16	869	17352	46667825
Drug reaction with eosinophilia and systemic symptoms	38.33	32.98	16	869	29532	46655645
Mycobacterium abscessus infection	37.70	32.98	7	878	619	46684558

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Mycobacterium abscessus infection	82.23	42.15	14	732	574	29951158
Drug reaction with eosinophilia and systemic symptoms	58.06	42.15	23	723	28465	29923267

Pharmacologic Action:

Source	Code	Description
ATC	J01DC01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Second-generation cephalosporins
FDA CS	M0003827	Cephalosporins
FDA EPC	N0000175488	Cephalosporin Antibacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
CHEBI has role	CHEBI:36047	antibacterial drugs

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Septicemia due to Escherichia coli	indication	9323009
Bacterial septicemia	indication	10001005	DOID:0040085
Gonorrhea	indication	15628003	DOID:7551
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Acute gonococcal cervicitis	indication	20943002	DOID:10615
Staphylococcal pneumonia	indication	22754005
Streptococcal septicemia	indication	29577008
Postoperative infection	indication	33910007
Pneumonia due to Streptococcus	indication	34020007
Peritonitis	indication	48661000
Pneumonia due to Escherichia coli	indication	51530003
Bacterial pneumonia	indication	53084003	DOID:874
Klebsiella cystitis	indication	60867007
Acute gonococcal endometritis	indication	65295003	DOID:7527
Haemophilus influenzae pneumonia	indication	70036007
Infection due to Escherichia coli	indication	71057007
Rhinoscleroma	indication	72409005	DOID:11336
Abscess of lung	indication	73452002	DOID:0060317
Abdominal abscess	indication	75100008
Endometritis	indication	78623009	DOID:1002
Septicemia due to Bacteroides	indication	79587009
Infection of bone	indication	111253001
Female genital tract infection	indication	125585007
Infectious disease of abdomen	indication	128070006
Bacterial infection due to Klebsiella pneumoniae	indication	186435004
Female pelvic cellulitis	indication	280486004
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Streptococcus pyogenes infection	indication	302809008
Bacterial urinary infection	indication	312124009
Infectious disorder of joint	indication	363162000
Infection due to Staphylococcus aureus	indication	406602003
Osteomyelitis due to Staphylococcus aureus	indication	428783003
Sepsis due to Staphylococcus aureus	indication	448417001
Peptostreptococcus infection	indication	135341000119101
Skin and Skin Structure Clostridium Infection	indication
Klebsiella Pneumoniae Peritonitis	indication
Staphylococcus Lung Abscess	indication
Prevention of Perioperative Infection	indication
Bacteroides Pelvic Inflammatory Disease	indication
Vaginal Hysterectomy Infection Prevention	indication
Peptococcus Pelvic Inflammatory Disease	indication
Transurethral Prostatectomy Infection Prevention	indication
Skin and Skin Structure Peptococcus Infection	indication
Peptococcus Pelvic Cellulitis	indication
Clostridium Pelvic Inflammatory Disease	indication
Intra-Abdominal Klebsiella Abscess	indication
Klebsiella Lung Abscess	indication
Skin and Skin Structure Proteus Infection	indication
Clostridium Endometritis	indication
Clostridium Peritonitis	indication
E. Coli Peritonitis	indication
Haemophilus Influenzae Lung Abscess	indication
Peptococcus Endometritis	indication
Morganella Morganii Urinary Tract Infection	indication
Staphylococcus Epidermidis Skin and Skin Structure Infection	indication
Bacteroides Lung Abscess	indication
Peptostreptococcus Endometritis	indication
Streptococcus Lung Abscess	indication
Inflammatory Disease of Female Pelvic Organs	indication
Intra-Abdominal E. Coli Abscess	indication
Pelvic Inflammatory Disease with Neisseria Gonorrhea	indication
Clostridium Pelvic Cellulitis	indication
Peptostreptococcus Pelvic Inflammatory Disease	indication
Peptostreptococcus Pelvic Cellulitis	indication
Bacteroides Pelvic Cellulitis	indication
Staphylococcus Aureus Joint Infection	indication
E. Coli Pelvic Cellulitis	indication
E. Coli Endometritis	indication
E. Coli Pelvic Inflammatory Disease	indication
Bacteroides Pneumonia	indication
Bacteroides Endometritis	indication
Infection Prevention for GI Surgery	indication
Intra-Abdominal Clostridium Abscess	indication
Intra-Abdominal Bacteroides Abscess	indication
Group B Streptococcus Pelvic Inflammatory Disease	indication
Neisseria Gonorrhea Pelvic Cellulitis	indication
Skin and Skin Structure Bacteroides Fragilis Infection	indication
Cesarean Section Infection Prevention	indication
Bacteroides Peritonitis	indication
Providencia Urinary Tract Infection	indication
E. Coli Lung Abscess	indication
Acute gonococcal urethritis	off-label use	29864006
Gonorrhea of rectum	off-label use	42746002
Colitis	contraindication	64226004	DOID:0060180
Kidney disease	contraindication	90708001	DOID:557
Pseudomembranous enterocolitis	contraindication	397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.54	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Bacterial penicillin-binding protein	Enzyme	DACA_ECOLI DACB_ECOLI DACC_ECOLI FTSI_ECOLI PBP2_ECOLI PBPA_ECOLI PBPB_ECOLI	INHIBITOR			CHEMBL	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_CLOPE				WOMBAT-PK
Streptokinase A	Enzyme	STRP_STRP1		EC50	5.48	WOMBAT-PK
Beta-lactamase	Enzyme	BLAC_BACLI				WOMBAT-PK
Beta-lactamase	Enzyme	B2ZTR6_ACIBA		Ki	7	CHEMBL
Beta-lactamase	Enzyme	D6NSM8_ACIBA		Ki	6.30	CHEMBL
Beta-lactamase	Enzyme	A2RP81_CITFR		Ki	6.85	CHEMBL

External reference:

ID	Source
4019665	VUID
N0000147757	NUI
D00913	KEGG_DRUG
33564-30-6	SECONDARY_CAS_RN
4017965	VANDF
4019665	VANDF
C0007557	UMLSCUI
CHEBI:209807	CHEBI
CFX	PDB_CHEM_ID
CHEMBL996	ChEMBL_ID
CHEMBL1200530	ChEMBL_ID
DB01331	DRUGBANK_ID
D002440	MESH_DESCRIPTOR_UI
441199	PUBCHEM_CID
10937	IUPHAR_LIGAND_ID
3397	INN_ID
6OEV9DX57Y	UNII
203118	RXNORM
33155	MMSL
37872	MMSL
4380	MMSL
82774	MMSL
d00094	MMSL
002722	NDDF
004843	NDDF
372780005	SNOMEDCT_US
57670008	SNOMEDCT_US
84165004	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9876	INJECTION, POWDER, FOR SOLUTION	10 g	INTRAVENOUS	ANDA	27 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9877	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	26 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9878	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	26 sections
Cefoxitin and Dextrose	HUMAN PRESCRIPTION DRUG LABEL	1	0264-3123	INJECTION, SOLUTION	1 g	INTRAVENOUS	NDA	24 sections
Cefoxitin and Dextrose	HUMAN PRESCRIPTION DRUG LABEL	1	0264-3125	INJECTION, SOLUTION	2 g	INTRAVENOUS	NDA	24 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	25021-109	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	25021-110	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	25 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	25021-111	INJECTION, POWDER, FOR SOLUTION	10 g	INTRAVENOUS	ANDA	27 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	44567-245	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	44567-245	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	44567-246	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	44567-246	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	44567-247	INJECTION, POWDER, FOR SOLUTION	10 g	INTRAVENOUS	ANDA	24 sections
Cefoxitin	Human Prescription Drug Label	1	63323-341	POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	Human Prescription Drug Label	1	63323-341	POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	Human Prescription Drug Label	1	63323-342	POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	Human Prescription Drug Label	1	63323-342	POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	23 sections
Cefoxitin	HUMAN PRESCRIPTION DRUG LABEL	1	66288-4100	INJECTION, POWDER, FOR SOLUTION	100 g	INTRAVENOUS	ANDA	27 sections