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aztreonam 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
monobactam antibiotics	279	78110-38-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cayston aztreonam azonam azthreonam aztreon monobactam nebactam primbactam aztreonam lysine azactam	A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms. Molecular weight: 435.43 Formula: C13H17N5O8S2 CLOGP: -0.36 LIPINSKI: 1 HAC: 13 HDO: 4 TPSA: 201.58 ALOGS: -3.34 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cayston
aztreonam
azonam
azthreonam
aztreon
monobactam
nebactam
primbactam
aztreonam lysine
azactam

A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.

Molecular weight: 435.43
Formula: C13H17N5O8S2
CLOGP: -0.36
LIPINSKI: 1
HAC: 13
HDO: 4
TPSA: 201.58
ALOGS: -3.34
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.23	g	Inhal.solution
4	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	10 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	68 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	305.44 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	1 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.18 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1.50 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.40 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.50 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 31, 1986	FDA	BRISTOL MYERS SQUIBB

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
Infective pulmonary exacerbation of cystic fibrosis	1676.40	24.32	346	6253	7563	50590962
Cystic fibrosis	421.16	24.32	93	6506	2771	50595754
Death	259.26	24.32	261	6338	325118	50273407
Lung transplant	215.92	24.32	54	6545	2771	50595754
Pulmonary function test decreased	211.00	24.32	55	6544	3333	50595192
Haemoptysis	207.19	24.32	89	6510	25484	50573041
Hospitalisation	194.70	24.32	117	6482	67820	50530705
Cystic fibrosis respiratory infection suppression	125.33	24.32	23	6576	257	50598268
Respiratory failure	110.68	24.32	93	6506	91088	50507437
Cough	98.36	24.32	138	6461	241126	50357399
Pseudomonas infection	97.15	24.32	39	6560	9391	50589134
Lung disorder	81.18	24.32	58	6541	44741	50553784
Off label use	78.46	24.32	183	6416	474243	50124282
Sputum increased	64.06	24.32	19	6580	1848	50596677
Infection	60.26	24.32	92	6507	172862	50425663
Bronchial secretion retention	54.55	24.32	16	6583	1497	50597028
Distal intestinal obstruction syndrome	54.42	24.32	12	6587	353	50598172
Sinus operation	52.74	24.32	16	6583	1680	50596845
Bacterial disease carrier	49.67	24.32	13	6586	798	50597727
Bronchiectasis	49.52	24.32	25	6574	10258	50588267
Eosinophilia	47.86	24.32	30	6569	18622	50579903
Pneumonia	45.78	24.32	130	6469	378271	50220254
Drug reaction with eosinophilia and systemic symptoms	45.13	24.32	34	6565	28390	50570135
Forced expiratory volume decreased	44.65	24.32	18	6581	4376	50594149
Pancreatic failure	43.95	24.32	12	6587	866	50597659
Transplant	42.62	24.32	11	6588	639	50597886
Pulmonary haemorrhage	37.89	24.32	18	6581	6474	50592051
Nonspecific reaction	35.59	24.32	12	6587	1767	50596758
Chest discomfort	34.61	24.32	51	6548	92671	50505854
Superinfection	33.89	24.32	12	6587	2044	50596481
Bronchospasm	33.43	24.32	22	6577	14832	50583693
Treatment noncompliance	32.93	24.32	29	6570	30121	50568404
Productive cough	32.23	24.32	37	6562	52657	50545868
Pathogen resistance	27.88	24.32	14	6585	5675	50592850
Drug resistance	26.40	24.32	21	6578	18968	50579557
Pneumothorax	25.00	24.32	18	6581	14016	50584509

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
Infective pulmonary exacerbation of cystic fibrosis	889.77	24.65	205	4581	6031	29563710
Cystic fibrosis	350.48	24.65	74	4712	1418	29568323
Lung transplant	277.98	24.65	63	4723	1693	29568048
Hospitalisation	135.02	24.65	87	4699	45901	29523840
Death	114.49	24.65	200	4586	341884	29227857
Pulmonary function test decreased	88.47	24.65	31	4755	4132	29565609
Cystic fibrosis respiratory infection suppression	87.93	24.65	17	4769	203	29569538
Haemoptysis	80.30	24.65	54	4732	30496	29539245
Pseudomonas infection	74.61	24.65	36	4750	10816	29558925
Eosinophilia	72.60	24.65	45	4741	22116	29547625
Respiratory failure	61.46	24.65	77	4709	97054	29472687
Sputum increased	55.35	24.65	18	4768	1909	29567832
Cystic fibrosis related diabetes	50.65	24.65	10	4776	134	29569607
Productive cough	49.99	24.65	41	4745	31218	29538523
Infection	48.75	24.65	61	4725	76690	29493051
Hepatic cytolysis	46.46	24.65	24	4762	8323	29561418
Pathogen resistance	41.36	24.65	22	4764	8094	29561647
Infective exacerbation of bronchiectasis	39.90	24.65	10	4776	414	29569327
Lung disorder	38.73	24.65	35	4751	30327	29539414
Leukocytosis	38.63	24.65	30	4756	21112	29548629
Rash maculo-papular	34.97	24.65	30	4756	24259	29545482
Condition aggravated	34.28	24.65	74	4712	146221	29423520
Distal intestinal obstruction syndrome	33.76	24.65	8	4778	261	29569480
Off label use	32.14	24.65	114	4672	300686	29269055
Forced expiratory volume decreased	31.05	24.65	13	4773	2800	29566941
Drug reaction with eosinophilia and systemic symptoms	29.43	24.65	29	4757	27963	29541778
Cough	27.28	24.65	62	4724	126665	29443076

FDA Adverse Event Reporting System (Geriatric)

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
Infective pulmonary exacerbation of cystic fibrosis	1984.85	20.89	437	9182	11359	64477754
Cystic fibrosis	569.02	20.89	126	9493	3308	64485805
Lung transplant	395.37	20.89	97	9522	4011	64485102
Pulmonary function test decreased	244.15	20.89	73	9546	6388	64482725
Haemoptysis	223.69	20.89	120	9499	48928	64440185
Death	210.22	20.89	305	9314	482400	64006713
Hospitalisation	198.02	20.89	129	9490	75078	64414035
Cystic fibrosis respiratory infection suppression	149.73	20.89	29	9590	382	64488731
Pseudomonas infection	129.64	20.89	60	9559	17823	64471290
Eosinophilia	124.49	20.89	75	9544	38001	64451112
Sputum increased	103.19	20.89	33	9586	3602	64485511
Respiratory failure	89.48	20.89	115	9504	161068	64328045
Off label use	88.21	20.89	249	9370	632557	63856556
Distal intestinal obstruction syndrome	81.75	20.89	19	9600	619	64488494
Cough	74.82	20.89	149	9470	301999	64187114
Lung disorder	74.34	20.89	66	9553	60634	64428479
Drug reaction with eosinophilia and systemic symptoms	72.53	20.89	62	9557	54155	64434958
Forced expiratory volume decreased	65.70	20.89	28	9591	6839	64482274
Infective exacerbation of bronchiectasis	63.58	20.89	16	9603	732	64488381
Pancreatic failure	61.70	20.89	18	9601	1442	64487671
Bronchiectasis	57.18	20.89	32	9587	14108	64475005
Pathogen resistance	55.16	20.89	30	9589	12513	64476600
Pneumonia	53.75	20.89	194	9425	559382	63929731
Productive cough	51.58	20.89	59	9560	73144	64415969
Sinus operation	50.63	20.89	16	9603	1679	64487434
Bacterial disease carrier	45.25	20.89	13	9606	986	64488127
Hepatic cytolysis	44.15	20.89	27	9592	14022	64475091
Cystic fibrosis related diabetes	43.32	20.89	9	9610	172	64488941
Transplant	42.35	20.89	12	9607	866	64488247
Bronchial secretion retention	40.65	20.89	15	9604	2512	64486601
Rash maculo-papular	40.25	20.89	42	9577	46984	64442129
Drug resistance	38.70	20.89	36	9583	35066	64454047
Pneumonia pseudomonal	37.23	20.89	17	9602	4886	64484227
Toxic epidermal necrolysis	36.95	20.89	36	9583	37130	64451983
Nonspecific reaction	32.62	20.89	12	9607	1991	64487122
Condition aggravated	32.19	20.89	125	9494	372301	64116812
Leukocytosis	31.03	20.89	33	9586	37707	64451406
Toxicity to various agents	31.02	20.89	8	9611	363505	64125608
Chest discomfort	30.74	20.89	59	9560	116047	64373066
Disease complication	29.96	20.89	14	9605	4241	64484872
Pneumothorax	28.89	20.89	26	9593	24272	64464841
Bronchospasm	27.36	20.89	24	9595	21658	64467455
Toxic skin eruption	25.66	20.89	22	9597	19262	64469851
Treatment noncompliance	25.60	20.89	32	9587	43450	64445663
Sputum discoloured	25.05	20.89	21	9598	17835	64471278
Superinfection	24.95	20.89	12	9607	3874	64485239
Fall	24.56	20.89	16	9603	416810	64072303
Bronchopulmonary aspergillosis allergic	23.79	20.89	9	9610	1613	64487500
Dyspnoea	23.48	20.89	185	9434	718489	63770624
Cystic fibrosis hepatic disease	21.75	20.89	4	9615	39	64489074
Pain in extremity	21.74	20.89	9	9610	303076	64186037
Fatigue	20.89	20.89	51	9568	748679	63740434

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J01DF01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Monobactams
FDA CS	M0014030	Monobactams
FDA EPC	N0000175493	Monobactam Antibacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
CHEBI has role	CHEBI:36047	antibacterial drugs
CHEBI has role	CHEBI:50696	PBP3 inhibitor
CHEBI has role	CHEBI:88188	allergenic drug

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Septicemia due to Escherichia coli	indication	9323009
Infection due to Pseudomonas aeruginosa	indication	11218009
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Pneumonia due to Pseudomonas	indication	41381004
Peritonitis	indication	48661000
Lower respiratory tract infection	indication	50417007
Pneumonia due to Escherichia coli	indication	51530003
Klebsiella cystitis	indication	60867007
Urinary tract infectious disease	indication	68566005
Haemophilus influenzae pneumonia	indication	70036007
Infection due to Escherichia coli	indication	71057007
Bacterial infection due to Serratia	indication	71120004
Rhinoscleroma	indication	72409005	DOID:11336
Endometritis	indication	78623009	DOID:1002
Septicemia due to Serratia	indication	82091000
Female genital tract infection	indication	125585007
Infectious disease of abdomen	indication	128070006
Infection due to Enterobacteriaceae	indication	128945009
Bacterial infection due to Klebsiella pneumoniae	indication	186435004
Proteus pneumonia	indication	195888009
Bacterial peritonitis	indication	197171003
Proteus septicemia	indication	300986008
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Bacterial urinary infection	indication	312124009
Sepsis due to Pseudomonas	indication	448813005
Sepsis due to Gram negative bacteria	indication	449082003
Gram-Negative Aerobic Bacillary Pneumonia	indication
Serratia Urinary Tract Infection	indication
E. Coli Pelvic Inflammatory Disease	indication
Enterobacter Pneumonia	indication
Citrobacter Urinary Tract Infection	indication
Skin and Skin Structure Proteus Infection	indication
Skin and Skin Structure Pseudomonas Aeruginosa Infection	indication
Haemophilus Influenzae Bronchitis	indication
E. Coli Bronchitis	indication
Respiratory Cystic Fibrosis with Pseudomonas aeruginosa Colonization	indication
Skin and Skin Structure Serratia Infection	indication
Inflammatory Disease of Female Pelvic Organs	indication
Proteus Pelvic Inflammatory Disease	indication
E. Coli Endometritis	indication
Enterobacter Cloacae Bronchitis	indication
Serratia Bronchitis	indication
Pseudomonas Aeruginosa Bronchitis	indication
Citrobacter Peritonitis	indication
Aerobic Gram-Negative Bacteremia	indication
E. Coli Peritonitis	indication
Enterobacter Endometritis	indication
Skin and Skin Structure Citrobacter Infection	indication
Serratia Peritonitis	indication
Enterobacter Pelvic Inflammatory Disease	indication
Klebsiella Endometritis	indication
Pseudomonas Aeruginosa Urinary Tract Infection	indication
Klebsiella Pelvic Inflammatory Disease	indication
Bacterial Exacerbation of Acute Bronchitis	indication
Proteus Bronchitis	indication
Proteus Endometritis	indication
Klebsiella Pneumoniae Peritonitis	indication
Bronchospasm	contraindication	4386001
Kidney disease	contraindication	90708001	DOID:557
Disease of liver	contraindication	235856003	DOID:409
Pseudomembranous enterocolitis	contraindication	397683000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.44	acidic
pKa2	2.83	Basic

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
Peptidoglycan synthase FtsI	Enzyme	FTSI_ECOLI	INHIBITOR	IC50	5.74	WOMBAT-PK	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_ECOLI	INHIBITOR	IC50	5.32	WOMBAT-PK	CHEMBL
Penicillin-binding protein 1B	Enzyme	PBPB_ECOLI	INHIBITOR	IC50	4.32	WOMBAT-PK	CHEMBL
Beta-lactamase	Enzyme	A4ZYU9_ECOLX		IC50	7.49	CHEMBL
Efflux transporter; SugE	Transporter	Q3S5C3_SALNE		IC50	8.22	CHEMBL
Beta-lactamase	Enzyme	Q48435_KLEPN		IC50	8.22	CHEMBL
Beta-lactamase	Enzyme	B2ZTR6_ACIBA		Ki	8.15	CHEMBL
AmpC	Unclassified	Q83TT7_ECOLX		IC50	7.22	CHEMBL
Beta-lactamase	Enzyme	D6NSM8_ACIBA		Ki	5.52	CHEMBL
Penicillin-binding protein 1A	Enzyme	PBPA_PSEAE		IC50	5.48	CHEMBL
Beta-lactamase	Enzyme	A2RP81_CITFR		Ki	5.70	CHEMBL

External reference:

ID	Source
D00240	KEGG_DRUG
827611-49-4	SECONDARY_CAS_RN
1272	RXNORM
C0004521	UMLSCUI
CHEBI:161680	CHEBI
CHEMBL158	ChEMBL_ID
CHEMBL3833340	ChEMBL_ID
D001398	MESH_DESCRIPTOR_UI
DB00355	DRUGBANK_ID
10763	IUPHAR_LIGAND_ID
5159	INN_ID
G2B4VE5GH8	UNII
5742832	PUBCHEM_CID
167898	MMSL
170132	MMSL
2813	MMSL
4239	MMSL
d00067	MMSL
002807	NDDF
013342	NDDF
4017762	VANDF
4037186	VANDF
AZR	PDB_CHEM_ID
373297006	SNOMEDCT_US
387386004	SNOMEDCT_US
409132008	SNOMEDCT_US
409133003	SNOMEDCT_US
69918003	SNOMEDCT_US
734461007	SNOMEDCT_US
90614001	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
AZACTAM	HUMAN PRESCRIPTION DRUG LABEL	1	0003-2560	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAMUSCULAR	NDA	21 sections
AZACTAM	HUMAN PRESCRIPTION DRUG LABEL	1	0003-2570	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAMUSCULAR	NDA	21 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	0409-0829	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	23 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	0409-0830	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	23 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-401	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections
Aztreonam	HUMAN PRESCRIPTION DRUG LABEL	1	63323-402	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	2 g	INTRAMUSCULAR	ANDA	24 sections