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

Stem definition	Drug id	CAS RN
antibiotics, produced by Streptomyces strains	668	81103-11-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: clarithromycin 6-O-Methylerythromycin A biaxin clamicin clathromycin	A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation. Molecular weight: 747.96 Formula: C38H69NO13 CLOGP: 2.39 LIPINSKI: 2 HAC: 14 HDO: 4 TPSA: 182.91 ALOGS: -3.54 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

clarithromycin
6-O-Methylerythromycin A
biaxin
clamicin
clathromycin

A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.

Molecular weight: 747.96
Formula: C38H69NO13
CLOGP: 2.39
LIPINSKI: 2
HAC: 14
HDO: 4
TPSA: 182.91
ALOGS: -3.54
ROTB: 8

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.50	g	O
1	g	P

ADMET properties:

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Property	Value	Reference
CL (Clearance)	7.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	55 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	35 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	2.80 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	2 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	11.14 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	1.50 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.23 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Oct. 31, 1991	FDA	ABBVIE

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 interaction	973.00	11.40	1085	53346	228046	63206545
Macular degeneration	510.20	11.40	296	54135	24080	63410511
Drug hypersensitivity	401.17	11.40	846	53585	309841	63124750
Abortion spontaneous	340.10	11.40	299	54132	46896	63387695
Erythema multiforme	182.76	11.40	112	54319	10057	63424534
Dysgeusia	171.70	11.40	206	54225	46504	63388087
Chronic sinusitis	165.91	11.40	115	54316	12728	63421863
Paraesthesia oral	161.13	11.40	133	54298	19123	63415468
Labelled drug-drug interaction medication error	159.21	11.40	114	54317	13285	63421306
Swollen tongue	155.84	11.40	170	54261	34630	63399961

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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
Drug interaction	807.07	11.63	1103	36988	224843	34693997
Labelled drug-drug interaction medication error	262.00	11.63	177	37914	14762	34904078
Immunosuppressant drug level increased	195.06	11.63	106	37985	5949	34912891
Death	164.76	11.63	117	37974	397932	34520908
Rhabdomyolysis	122.06	11.63	245	37846	67918	34850922
Drug level increased	113.44	11.63	130	37961	21966	34896874
Paradoxical drug reaction	100.58	11.63	56	38035	3295	34915545
Drug resistance	84.84	11.63	122	37969	25805	34893035
Oesophageal perforation	81.40	11.63	35	38056	1164	34917676
Lip swelling	79.83	11.63	93	37998	15987	34902853

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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
Drug interaction	1625.62	10.91	2058	79779	413125	79249426
Labelled drug-drug interaction medication error	417.52	10.91	292	81545	27358	79635193
Immunosuppressant drug level increased	222.74	10.91	130	81707	8897	79653654
Death	203.39	10.91	170	81667	566344	79096207
Completed suicide	201.02	10.91	13	81824	245754	79416797
Rhabdomyolysis	199.36	10.91	370	81467	102761	79559790
Drug hypersensitivity	181.09	10.91	695	81142	298221	79364330
Lip swelling	176.70	10.91	214	81623	40697	79621854
Dysgeusia	171.25	10.91	250	81587	56927	79605624
Erythema multiforme	162.46	10.91	139	81698	17512	79645039

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A02BD04	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD05	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD06	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD07	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD09	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD11	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD12	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	A02BD14	ALIMENTARY TRACT AND METABOLISM DRUGS FOR ACID RELATED DISORDERS DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD) Combinations for eradication of Helicobacter pylori
ATC	J01FA09	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS Macrolides
CHEBI has role	CHEBI:35703	Xenobiotic

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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
Acute otitis media	indication	3110003
Haemophilus Influenzae Acute Otitis Media	indication	19021002
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Streptococcal tonsillitis	indication	41582007
Pneumonia due to Mycoplasma pneumoniae	indication	46970008
Bacterial pneumonia	indication	53084003	DOID:874
Acute maxillary sinusitis	indication	68272006	DOID:2050
Haemophilus influenzae pneumonia	indication	70036007
Acute bacterial sinusitis	indication	75498004
Pulmonary Mycobacterium avium complex infection	indication	186342000

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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	12.66	acidic
pKa2	8.65	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
500MG;500MG;EQ 20MG BASE	VOQUEZNA TRIPLE PAK	PHATHOM	N215152	May 3, 2022	DISCN	CAPSULE, TABLET, TABLET	ORAL	May 3, 2027	NEW CHEMICAL ENTITY
500MG;500MG;EQ 20MG BASE	VOQUEZNA TRIPLE PAK	PHATHOM	N215152	May 3, 2022	DISCN	CAPSULE, TABLET, TABLET	ORAL	May 3, 2032	GENERATING ANTIBIOTIC INCENTIVES NOW

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	4.23		WOMBAT-PK

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External reference:

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ID	Source
CTY	PDB_CHEM_ID
003608	NDDF
10903	IUPHAR_LIGAND_ID
203729	RXNORM
387487009	SNOMEDCT_US
3947	MMSL
4020086	VUID
4020086	VANDF
4462	MMSL
6252	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1930	TABLET, FILM COATED, EXTENDED RELEASE	500 mg	ORAL	ANDA	26 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1930	TABLET, FILM COATED, EXTENDED RELEASE	500 mg	ORAL	ANDA	26 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1930	TABLET, FILM COATED, EXTENDED RELEASE	500 mg	ORAL	ANDA	26 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1931	TABLET, FILM COATED	250 mg	ORAL	ANDA	28 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1931	TABLET, FILM COATED	250 mg	ORAL	ANDA	28 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1932	TABLET, FILM COATED	500 mg	ORAL	ANDA	28 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1932	TABLET, FILM COATED	500 mg	ORAL	ANDA	28 sections
clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0591-2805	TABLET, FILM COATED, EXTENDED RELEASE	500 mg	ORAL	ANDA	26 sections
clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0591-2805	TABLET, FILM COATED, EXTENDED RELEASE	500 mg	ORAL	ANDA	26 sections
Clarithromycin	HUMAN PRESCRIPTION DRUG LABEL	1	0781-1961	TABLET	250 mg	ORAL	ANDA	29 sections

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