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

Stem definition	Drug id	CAS RN
antibiotics, produced by Streptomyces strains	276	83905-01-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: CP-62993 CP 62993 azithromycin arzomicin aziromycin Azithromycin A azithromycin monohydrate azithromycin anhydrous azithromycin dihydrate azithromycin hydrate	A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis. Some evidence of in vitro activity against SARS-CoV-2 in infected Vero E6 and Caco-2 cells has been reported but clinical importance it is unclear. Only limited information available regarding the frequency and microbiology of bacterial pulmonary coinfections or superinfections in pacients with COVID-19. Molecular weight: 749.00 Formula: C38H72N2O12 CLOGP: 2.64 LIPINSKI: 2 HAC: 14 HDO: 5 TPSA: 180.08 ALOGS: -3.16 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

CP-62993
CP 62993
azithromycin
arzomicin
aziromycin
Azithromycin A
azithromycin monohydrate
azithromycin anhydrous
azithromycin dihydrate
azithromycin hydrate

A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis. Some evidence of in vitro activity against SARS-CoV-2 in infected Vero E6 and Caco-2 cells has been reported but clinical importance it is unclear. Only limited information available regarding the frequency and microbiology of bacterial pulmonary coinfections or superinfections in pacients with COVID-19.

Molecular weight: 749.00
Formula: C38H72N2O12
CLOGP: 2.64
LIPINSKI: 2
HAC: 14
HDO: 5
TPSA: 180.08
ALOGS: -3.16
ROTB: 7

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.30	g	O
0.50	g	P

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	69 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	6 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	44.50 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Bocci G, Oprea TI, Benet LZ
BA (Bioavailability)	34 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	33 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	10 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.88 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.07 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
March 10, 2000	PMDA	PFIZER
Nov. 1, 1991	FDA

FDA Adverse Event Reporting System (Female)

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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
Drug hypersensitivity	1374.75	10.01	2093	102752	308594	63075583
Infective pulmonary exacerbation of cystic fibrosis	784.34	10.01	352	104493	8465	63375712
Abortion incomplete	536.42	10.01	200	104645	2931	63381246
Off label use	525.04	10.01	2349	102496	672113	62712064
Premature delivery	403.07	10.01	361	104484	29920	63354257
Macular degeneration	335.13	10.01	296	104549	24080	63360097
Asthma	315.74	10.01	669	104176	126892	63257285
Contraindicated product administered	297.34	10.01	15	104830	217633	63166544
Cystic fibrosis	278.55	10.01	127	104718	3169	63381008
Normal labour	270.53	10.01	77	104768	440	63383737

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FDA Adverse Event Reporting System (Male)

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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
Off label use	1900.27	10.59	3160	67005	416364	34470402
Infective pulmonary exacerbation of cystic fibrosis	613.52	10.59	291	69874	6510	34880256
Electrocardiogram QT prolonged	436.27	10.59	472	69693	40480	34846286
Asthma	299.86	10.59	398	69767	42258	34844508
Drug ineffective for unapproved indication	276.65	10.59	287	69878	23428	34863338
Drug hypersensitivity	199.37	10.59	475	69690	80054	34806712
Product use in unapproved indication	198.93	10.59	602	69563	116897	34769869
Wheezing	154.60	10.59	289	69876	41113	34845653
Long QT syndrome	154.19	10.59	86	70079	2717	34884049
Immune reconstitution inflammatory syndrome	151.79	10.59	132	70033	8627	34878139

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FDA Adverse Event Reporting System (Geriatric)

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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
Off label use	2489.30	9.70	5216	139534	901999	78697639
Infective pulmonary exacerbation of cystic fibrosis	1130.82	9.70	524	144226	12327	79587311
Electrocardiogram QT prolonged	676.29	9.70	827	143923	89559	79510079
Drug hypersensitivity	636.89	9.70	1563	143187	297353	79302285
Asthma	540.58	9.70	918	143832	134177	79465461
Abortion incomplete	522.18	9.70	200	144550	2864	79596774
Drug ineffective for unapproved indication	411.16	9.70	486	144264	50752	79548886
Wheezing	354.32	9.70	704	144046	115960	79483678
Cystic fibrosis	328.20	9.70	154	144596	3726	79595912
Bronchiectasis	326.69	9.70	293	144457	22093	79577545

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J01FA10	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS Macrolides
ATC	J01RA07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	J01RA16	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	S01AA26	SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFECTIVES Antibiotics
FDA Chemical/Ingredient	N0000007529	Macrolides
FDA CS	M0028311	Macrolides
FDA EPC	N0000175935	Macrolide Antimicrobial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents

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

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Disease	Relation	SNOMED_ID	DOID
Haemophilus Influenzae Acute Otitis Media	indication	19021002
Acute gonococcal cervicitis	indication	20943002	DOID:10615
Acute gonococcal urethritis	indication	29864006
Bacterial blepharitis	indication	41446000	DOID:9423
Streptococcal tonsillitis	indication	41582007
Pneumonia due to Mycoplasma pneumoniae	indication	46970008
Bacterial pneumonia	indication	53084003	DOID:874
Haemophilus influenzae pneumonia	indication	70036007
Acute bacterial sinusitis	indication	75498004
Dacryocystitis	indication	85777005	DOID:9938

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.45	acidic
pKa2	8.87	Basic
pKa3	8.24	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 2GM BASE/BOT	ZMAX	PF PRISM CV	N050797	June 10, 2005	DISCN	FOR SUSPENSION, EXTENDED RELEASE	ORAL	6984403	Feb. 14, 2024	METHOD OF TREATING BACTERIAL INFECTIONS

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN		IC50	4.16	WOMBAT-PK
Motilin receptor	GPCR	O43193	MTLR_HUMAN	AGONIST	EC50	5.50	IUPHAR
Taste receptor type 2 member 4	GPCR	Q9NYW5	TA2R4_HUMAN	AGONIST	EC50	4.13	IUPHAR
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	3.39	WOMBAT-PK
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	3.70	WOMBAT-PK

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External reference:

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ID	Source
ZIT	PDB_CHEM_ID
003635	NDDF
117772-70-0	SECONDARY_CAS_RN
121470-24-4	SECONDARY_CAS_RN
1298839	RXNORM
387531004	SNOMEDCT_US
391805000	SNOMEDCT_US
4020019	VUID
4020019	VANDF
4020964	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0400	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	500 mg	INTRAVENOUS	NDA	29 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0400	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	500 mg	INTRAVENOUS	NDA	29 sections
ZITHROMAX	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3051	POWDER, FOR SUSPENSION	1 g	ORAL	NDA	31 sections
ZITHROMAX	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3051	POWDER, FOR SUSPENSION	1 g	ORAL	NDA	31 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3060	TABLET, FILM COATED	250 mg	ORAL	NDA	30 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3060	TABLET, FILM COATED	250 mg	ORAL	NDA	30 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3060	TABLET, FILM COATED	250 mg	ORAL	NDA	30 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3070	TABLET, FILM COATED	500 mg	ORAL	NDA	30 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3070	TABLET, FILM COATED	500 mg	ORAL	NDA	30 sections
Zithromax	HUMAN PRESCRIPTION DRUG LABEL	1	0069-3070	TABLET, FILM COATED	500 mg	ORAL	NDA	30 sections

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