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

Stem definition	Drug id	CAS RN
	589	56-75-7

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: chloramphenicol chlorocidin cloramphenicol	An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106) Molecular weight: 323.13 Formula: C11H12Cl2N2O5 CLOGP: 1.03 LIPINSKI: 0 HAC: 7 HDO: 3 TPSA: 115.38 ALOGS: -2.85 ROTB: 6 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

chloramphenicol
chlorocidin
cloramphenicol

An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)

Molecular weight: 323.13
Formula: C11H12Cl2N2O5
CLOGP: 1.03
LIPINSKI: 0
HAC: 7
HDO: 3
TPSA: 115.38
ALOGS: -2.85
ROTB: 6

Status: OFM

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

Drug dosage:

Dose	Unit	Route
3	g	O
3	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	82 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	5 %	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	4.60 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	309.47 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	2.50 mg/mL	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	2.40 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	0.94 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.34 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 8, 1950	FDA	PARKEDALE

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
Lip swelling	100.11	31.61	43	3249	31020	63454710
Cardiospasm	91.69	31.61	21	3271	1886	63483844
Palmoplantar keratoderma	90.62	31.61	21	3271	1986	63483744
Pruritus genital	84.79	31.61	21	3271	2633	63483097
Sleep terror	84.59	31.61	21	3271	2659	63483071
Keratopathy	83.53	31.61	16	3276	600	63485130
Atrial tachycardia	75.03	31.61	21	3271	4219	63481511
Carotid artery occlusion	72.92	31.61	21	3271	4673	63481057
Tension headache	70.85	31.61	21	3271	5165	63480565
Anosmia	65.06	31.61	21	3271	6839	63478891

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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
Appendicolith	136.94	49.87	39	1741	8562	34946589
Appendicitis	116.06	49.87	39	1741	14768	34940383
Ventricular fibrillation	99.37	49.87	39	1741	22915	34932236
Cardiogenic shock	93.78	49.87	39	1741	26579	34928572
Stress	92.11	49.87	40	1740	30307	34924844
Blood phosphorus increased	79.38	49.87	25	1755	7696	34947455
Ascites	75.79	49.87	40	1740	46531	34908620
Myasthenia gravis	73.54	49.87	23	1757	6917	34948234
Abdominal distension	72.55	49.87	42	1738	58450	34896701
Blood uric acid increased	70.04	49.87	24	1756	9600	34945551

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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
Appendicolith	128.84	28.79	39	4965	8512	79730872
Keratopathy	120.39	28.79	25	4979	1169	79738215
Appendicitis	94.95	28.79	39	4965	20755	79718629
Lip swelling	86.62	28.79	45	4959	40866	79698518
Ventricular fibrillation	81.91	28.79	40	4964	31886	79707498
Cardiogenic shock	68.93	28.79	39	4965	41875	79697509
Blood phosphorus increased	66.98	28.79	25	4979	10322	79729062
Cardiospasm	62.60	28.79	18	4986	3283	79736101
Palmoplantar keratoderma	60.50	28.79	18	4986	3698	79735686
Myasthenia gravis	59.64	28.79	23	4981	10376	79729008

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D06AX02	DERMATOLOGICALS ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE ANTIBIOTICS FOR TOPICAL USE Other antibiotics for topical use
ATC	D10AF03	DERMATOLOGICALS ANTI-ACNE PREPARATIONS ANTI-ACNE PREPARATIONS FOR TOPICAL USE Antiinfectives for treatment of acne
ATC	G01AA05	GENITO URINARY SYSTEM AND SEX HORMONES GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS Antibiotics
ATC	J01BA01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE AMPHENICOLS Amphenicols
ATC	S01AA01	SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFECTIVES Antibiotics
ATC	S02AA01	SENSORY ORGANS OTOLOGICALS ANTIINFECTIVES Antiinfectives
ATC	S03AA08	SENSORY ORGANS OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS ANTIINFECTIVES Antiinfectives
CHEBI has role	CHEBI:33281	antibiotics
CHEBI has role	CHEBI:36047	antibacterial drugs
CHEBI has role	CHEBI:48001	protein synthesis inhibitors

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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
Otitis externa	indication	3135009
Streptococcal meningitis	indication	4510004	DOID:11574
Typhoid fever	indication	4834000	DOID:13258
Disease caused by rickettsiae	indication	37246009
Paratyphoid fever	indication	85904008	DOID:3055
Bacterial infection of skin	indication	128936008
Boutonneuse fever	indication	186774005	DOID:14095
Meningococcal meningitis	indication	192644005
Superficial Ocular Infection	indication
H. Influenzae Meningitis	indication

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🐶 Veterinary Drug Use

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Species	Use	Relation
Cats	Bacterial conjunctivitis	Indication
Dogs	Respiratory tract infections	Indication
Dogs	Urinary tract infections	Indication
Dogs	Bacterand enteritis	Indication
Dogs	Tonsillitis	Indication

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🐶 Veterinary products

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Product	Applicant	Ingredients
Anacetin Tablets	Cronus Pharma Specialities India Private Limited	1
Chloramphenicol 1% Ophthalmic, Vetrocloricin Ophthalmic Ointment	Dechra, Ltd.	1
Chloramphenicol Capsules	Pharmaceutical Ventures, Ltd.	1
Chloromycetin Ophthalmic Ointment	Zoetis Inc.	1
Chloromycetin Tablets 100 mg, Chloromycetin Tablets 250 mg, Chloromycetin Tablets 500 mg	Zoetis Inc.	1
Medichol Tablets	Cronus Pharma Specialities India Private Limited	1
Mychel-Vet Capsules (50 mg)	Zoetis Inc.	1
Mychel-Vet Injection	Zoetis Inc.	1
Mychel-Vet Tabs	Zoetis Inc.	1
Tevcocin	Cronus Pharma Specialities India Private Limited	1

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.75	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN	IC50	4.25	WOMBAT-PK
Chloramphenicol acetyltransferase	Enzyme		CAT_SALTI	Kd	4.89	WOMBAT-PK
Streptokinase A	Enzyme		STRP_STRP1	EC50	6.01	WOMBAT-PK
Probable HTH-type transcriptional regulator TtgR	Unclassified		TTGR_PSEPK	Kd	4.88	WOMBAT-PK

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External reference:

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ID	Source
CLM	PDB_CHEM_ID
002767	NDDF
10901	IUPHAR_LIGAND_ID
2348	RXNORM
372777009	SNOMEDCT_US
3887	MMSL
4018199	VUID
4018199	VANDF
4021527	VANDF
4406	MMSL

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Pharmaceutical products:

None