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

Stem definitionDrug idCAS RN
589 56-75-7

Description:

MoleculeDescription

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:

DoseUnitRoute
3 g O
3 g P

ADMET properties:

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

Approvals:

DateAgencyCompanyOrphan
Dec. 8, 1950 FDA PARKEDALE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Immunisation 62.00 31.61 14 3278 1179 63484551
Facial pain 56.19 31.61 21 3271 10540 63475190
Pain of skin 54.22 31.61 21 3271 11613 63474117
Eye pruritus 54.10 31.61 24 3268 18647 63467083
Subarachnoid haemorrhage 53.42 31.61 22 3270 14261 63471469
Insomnia 49.08 31.61 58 3234 215194 63270536
Vasculitis 48.28 31.61 22 3270 18187 63467543
Blindness 44.60 31.61 22 3270 21677 63464053
Muscle twitching 43.60 31.61 21 3271 19647 63466083
Ventricular tachycardia 43.29 31.61 21 3271 19958 63465772
Tinnitus 42.06 31.61 25 3267 35603 63450127
Diplopia 39.87 31.61 21 3271 23707 63462023
Angioedema 37.59 31.61 26 3266 47939 63437791
Genital rash 36.93 31.61 8 3284 556 63485174
Vulvovaginal candidiasis 35.40 31.61 11 3281 3164 63482566
Right ventricular hypertrophy 35.18 31.61 8 3284 695 63485035
Disturbance in attention 33.01 31.61 22 3270 38167 63447563

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Multiple organ dysfunction syndrome 57.40 49.87 40 1740 76526 34878625
Hyponatraemia 54.63 49.87 40 1740 82651 34872500
Abdominal pain 50.25 49.87 51 1729 163567 34791584

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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
Blood uric acid increased 57.40 28.79 24 4980 13336 79726048
Sleep terror 57.27 28.79 18 4986 4440 79734944
Pruritus genital 57.16 28.79 18 4986 4468 79734916
Ascites 52.32 28.79 41 4963 75521 79663863
Atrial tachycardia 48.98 28.79 18 4986 7115 79732269
Tension headache 48.78 28.79 18 4986 7193 79732191
Stress 48.33 28.79 40 4964 79572 79659812
Carotid artery occlusion 47.75 28.79 18 4986 7629 79731755
Hyponatraemia 47.32 28.79 57 4947 177791 79561593
Anosmia 45.21 28.79 18 4986 8826 79730558
Facial pain 42.60 28.79 19 4985 12331 79727053
Immunisation 41.91 28.79 12 4992 2155 79737229
Abdominal distension 39.68 28.79 43 4961 119607 79619777
Pain of skin 39.54 28.79 19 4985 14594 79724790
Multiple organ dysfunction syndrome 39.50 28.79 43 4961 120203 79619181
Eye pruritus 38.90 28.79 21 4983 20549 79718835
Vulvovaginal candidiasis 35.86 28.79 11 4993 2503 79736881
Incorrect route of product administration 33.30 28.79 23 4981 34906 79704478
Muscle twitching 32.69 28.79 20 4984 24744 79714640
Genital rash 30.63 28.79 8 4996 1020 79738364
Insomnia 30.61 28.79 55 4949 245115 79494269
Subarachnoid haemorrhage 30.37 28.79 19 4985 24446 79714938
Vasculitis 29.92 28.79 19 4985 25083 79714301
Drug therapy 29.40 28.79 8 4996 1193 79738191
Endophthalmitis 29.13 28.79 12 4992 6416 79732968

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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
FDA EXT N0000175479 Amphenicols
FDA EPC N0000175480 Amphenicol-class Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
CHEBI has role CHEBI:33281 antibiotics
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:48001 protein synthesis inhibitors
CHEBI has role CHEBI:76971 Escherichia coli metabolites
CHEBI has role CHEBI:131604 Mycoplasma genitalium metabolites
CHEBI has role CHEBI:176497 geroprotectors

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

DiseaseRelationSNOMED_IDDOID
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
Bacteroides Brain Abscess indication
Inhalational anthrax off-label use 11389007
Exposure keratoconjunctivitis off-label use 14366000 DOID:9461
Blepharoconjunctivitis off-label use 68659002 DOID:2456
Gastrointestinal anthrax off-label use 111798006 DOID:13386
Bacterial conjunctivitis off-label use 128350005 DOID:9700
Neuropathic corneal ulcer off-label use 231901007
Gas gangrene caused by clostridium perfringens off-label use 266093005
Infective blepharitis off-label use 312219000
Bacterial keratitis off-label use 314557000
Anthrax off-label use 409498004 DOID:7427
Mastoidectomy Cavity Infections off-label use
Paroxysmal nocturnal hemoglobinuria contraindication 1963002 DOID:0060284
Hypoplastic anemia contraindication 41614006
Optic neuritis contraindication 66760008 DOID:1210
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Acute intermittent porphyria contraindication 234422006 DOID:3890
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Peripheral nerve disease contraindication 302226006
Aplastic anemia contraindication 306058006 DOID:12449
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Granulocytopenic disorder contraindication 417672002
Significant Bleeding contraindication




🐶 Veterinary Drug Use

SpeciesUseRelation
Cats Bacterial conjunctivitis Indication
Dogs Respiratory tract infections Indication
Dogs Urinary tract infections Indication
Dogs Bacterand enteritis Indication
Dogs Tonsillitis Indication

🐶 Veterinary products

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

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.75 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Cytochrome P450 3A4 Enzyme IC50 4.25 WOMBAT-PK
Chloramphenicol acetyltransferase Enzyme Kd 4.89 WOMBAT-PK
Streptokinase A Enzyme EC50 6.01 WOMBAT-PK
Probable HTH-type transcriptional regulator TtgR Unclassified Kd 4.88 WOMBAT-PK

External reference:

IDSource
4018199 VUID
N0000146533 NUI
D00104 KEGG_DRUG
2348 RXNORM
C0008168 UMLSCUI
CHEBI:17698 CHEBI
CLM PDB_CHEM_ID
CHEMBL130 ChEMBL_ID
DB00446 DRUGBANK_ID
D002701 MESH_DESCRIPTOR_UI
5959 PUBCHEM_CID
10901 IUPHAR_LIGAND_ID
977 INN_ID
66974FR9Q1 UNII
3887 MMSL
4406 MMSL
d00025 MMSL
002767 NDDF
372777009 SNOMEDCT_US
57191001 SNOMEDCT_US
4018199 VANDF
4021527 VANDF

Pharmaceutical products:

None