chloramphenicol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT2,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PLK1,PRKDC,SIK2,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 52
kinase-selectivity-class AXL,GRK2,MAP2K6,PDK1,STK33,TEK 6
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 139.72 27.31 58 4630 38552 90585207
Cardiospasm 113.85 27.31 28 4660 3418 90620341
Palmoplantar keratoderma 113.36 27.31 28 4660 3479 90620280
Sleep terror 106.66 27.31 28 4660 4436 90619323
Pruritus genital 106.08 27.31 28 4660 4530 90619229
Atrial tachycardia 98.50 27.31 28 4660 5962 90617797
Carotid artery occlusion 96.92 27.31 28 4660 6314 90617445
Tension headache 92.25 27.31 28 4660 7481 90616278
Anosmia 84.78 27.31 28 4660 9820 90613939
Immunisation 83.42 27.31 20 4668 2193 90621566
Keratopathy 81.34 27.31 16 4672 692 90623067
Subarachnoid haemorrhage 78.86 27.31 31 4657 17873 90605886
Facial pain 76.79 27.31 28 4660 13154 90610605
Pain of skin 71.37 27.31 28 4660 16054 90607705
Vasculitis 65.26 27.31 29 4659 22664 90601095
Eye pruritus 64.45 27.31 31 4657 28996 90594763
Tinnitus 63.72 27.31 35 4653 43067 90580692
Blindness 60.89 27.31 29 4659 26539 90597220
Muscle twitching 60.34 27.31 28 4660 24174 90599585
Angioedema 60.15 27.31 39 4649 64837 90558922
Ventricular tachycardia 59.79 27.31 28 4660 24680 90599079
Diplopia 55.79 27.31 28 4660 28686 90595073
Transient ischaemic attack 50.25 27.31 30 4658 43146 90580613
Disturbance in attention 45.33 27.31 29 4659 47080 90576679
Intentional product misuse 40.49 27.31 35 4653 89569 90534190
Insomnia 40.07 27.31 66 4622 333408 90290351
Hallucination 36.54 27.31 29 4659 65930 90557829
Genital rash 35.78 27.31 8 4680 645 90623114
Right ventricular hypertrophy 34.00 27.31 8 4680 809 90622950
Vulvovaginal candidiasis 33.20 27.31 11 4677 3889 90619870
Cognitive disorder 33.17 27.31 28 4660 69379 90554380
Tachycardia 31.87 27.31 40 4648 157633 90466126
Nasal oedema 27.58 27.31 11 4677 6573 90617186
Dry skin 27.46 27.31 28 4660 88045 90535714
Blood glucose increased 27.39 27.31 29 4659 95217 90528542

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
Myasthenia gravis 154.40 53.06 60 4547 16077 42600651
Appendicolith 142.93 53.06 54 4553 13402 42603326
Hyperphosphataemia 137.44 53.06 52 4555 12952 42603776
Appendicitis 127.10 53.06 56 4551 20557 42596171
Stress 115.11 53.06 67 4540 44145 42572583
Analgesic therapy 110.38 53.06 37 4570 6487 42610241
Hypophosphataemia 107.26 53.06 50 4557 20895 42595833
Drug therapy 107.21 53.06 36 4571 6344 42610384
Ventricular fibrillation 104.02 53.06 55 4552 30068 42586660
Activated partial thromboplastin time prolonged 100.58 53.06 44 4563 15859 42600869
Neuralgia 100.55 53.06 51 4556 25596 42591132
Blood phosphorus increased 100.36 53.06 41 4566 12484 42604244
Incorrect route of product administration 97.23 53.06 49 4558 24256 42592472
Sleep disorder therapy 96.76 53.06 34 4573 6860 42609868
Multiple organ dysfunction syndrome 95.61 53.06 81 4526 96954 42519774
Blood uric acid increased 95.04 53.06 42 4565 15505 42601223
Anticoagulant therapy 94.01 53.06 30 4577 4505 42612223
Antacid therapy 92.85 53.06 30 4577 4687 42612041
Cardiogenic shock 87.44 53.06 52 4555 35588 42581140
Congenital hiatus hernia 84.93 53.06 30 4577 6144 42610584
Abdominal distension 83.46 53.06 66 4541 71669 42545059
Blood calcium increased 79.26 53.06 31 4576 8423 42608305
Ascites 78.79 53.06 58 4549 56620 42560108
Blood cholesterol increased 76.16 53.06 43 4564 26698 42590030
Ulcer 74.21 53.06 36 4571 16405 42600323
End stage renal disease 73.97 53.06 36 4571 16522 42600206
Sleep disorder 73.19 53.06 52 4555 48043 42568685
Swelling 71.45 53.06 54 4553 54831 42561897
Hyponatraemia 71.10 53.06 70 4537 101392 42515336
Drug intolerance 70.79 53.06 63 4544 80361 42536367
Bronchopulmonary aspergillosis allergic 69.61 53.06 24 4583 4574 42612154
Diabetes mellitus 67.11 53.06 54 4553 60033 42556695
Blood test abnormal 66.62 53.06 31 4576 12875 42603853
Troponin increased 66.31 53.06 35 4572 19027 42597701
Hyperlipidaemia 65.07 53.06 36 4571 21480 42595248
Dry mouth 65.04 53.06 45 4562 39834 42576894
Bacterial infection 61.46 53.06 38 4569 27841 42588887
Gout 61.24 53.06 38 4569 28017 42588711
Chronic obstructive pulmonary disease 60.66 53.06 52 4555 63062 42553666
Intentional product misuse 57.46 53.06 50 4557 61850 42554878
Thrombosis 56.97 53.06 52 4555 68459 42548269
Pleuritic pain 56.10 53.06 23 4584 7054 42609674
Iron deficiency 55.33 53.06 26 4581 11035 42605693
General physical health deterioration 54.45 53.06 74 4533 151172 42465556

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 181.78 29.59 61 8982 14194 110566062
Myasthenia gravis 178.87 29.59 67 8976 21444 110558812
Hyperphosphataemia 162.07 29.59 58 8985 16323 110563933
Appendicitis 147.33 29.59 63 8980 28401 110551855
Analgesic therapy 146.00 29.59 44 8999 7240 110573016
Drug therapy 141.67 29.59 43 9000 7248 110573008
Sleep disorder therapy 132.16 29.59 41 9002 7430 110572826
Blood phosphorus increased 125.37 29.59 48 8995 16292 110563964
Ventricular fibrillation 124.90 29.59 63 8980 41250 110539006
Anticoagulant therapy 123.20 29.59 36 9007 5325 110574931
Antacid therapy 122.40 29.59 36 9007 5448 110574808
Hypophosphataemia 116.39 29.59 56 8987 33126 110547130
Blood uric acid increased 115.87 29.59 49 8994 21480 110558776
Activated partial thromboplastin time prolonged 114.07 29.59 49 8994 22319 110557937
Keratopathy 110.29 29.59 25 9018 1348 110578908
Neuralgia 107.16 29.59 60 8983 48418 110531838
Multiple organ dysfunction syndrome 107.11 29.59 93 8950 151617 110428639
Incorrect route of product administration 106.66 29.59 66 8977 63995 110516261
Lip swelling 99.37 29.59 58 8985 50609 110529647
Congenital hiatus hernia 96.78 29.59 31 9012 6228 110574028
Cardiogenic shock 95.26 29.59 59 8984 57279 110522977
Stress 94.00 29.59 74 8969 105274 110474982
Intentional product misuse 90.83 29.59 80 8963 132824 110447432
End stage renal disease 90.02 29.59 41 9002 21432 110558824
Hyponatraemia 87.33 29.59 98 8945 217555 110362701
Ascites 84.53 29.59 66 8977 92742 110487514
Blood calcium increased 80.55 29.59 36 9007 18004 110562252
Hyperlipidaemia 75.51 29.59 43 9000 35805 110544451
Gout 74.71 29.59 43 9000 36523 110543733
Troponin increased 74.49 29.59 40 9003 29726 110550530
Iron deficiency 70.33 29.59 33 9010 18443 110561813
Bronchopulmonary aspergillosis allergic 69.12 29.59 26 9017 8400 110571856
Diabetes mellitus 68.23 29.59 60 8983 99321 110480935
Cardiospasm 66.26 29.59 22 9021 4945 110575311
Ulcer 65.67 29.59 42 9001 43074 110537182
Bacterial infection 65.58 29.59 43 9000 45993 110534263
Blood test abnormal 64.88 29.59 36 9007 28518 110551738
Palmoplantar keratoderma 64.51 29.59 22 9021 5365 110574891
Chronic obstructive pulmonary disease 63.39 29.59 60 8983 109098 110471158
Abdominal distension 62.06 29.59 74 8969 175029 110405227
Transient ischaemic attack 61.51 29.59 47 8996 63935 110516321
Pruritus genital 60.39 29.59 22 9021 6500 110573756
Sleep terror 60.10 29.59 22 9021 6588 110573668
Thrombosis 59.83 29.59 58 8985 108604 110471652
Atrial tachycardia 53.09 29.59 22 9021 9156 110571100
Pleuritic pain 52.85 29.59 26 9017 16114 110564142
Carotid artery occlusion 52.22 29.59 22 9021 9543 110570713
Tension headache 52.10 29.59 22 9021 9596 110570660
Aortic stenosis 51.80 29.59 24 9019 13035 110567221
Sleep disorder 48.66 29.59 70 8973 198574 110381682
Total lung capacity decreased 47.84 29.59 19 9024 7095 110573161
Benign prostatic hyperplasia 47.01 29.59 25 9018 18209 110562047
Anosmia 46.62 29.59 22 9021 12450 110567806
Immunisation 46.08 29.59 15 9028 3168 110577088
Facial pain 45.19 29.59 23 9020 15316 110564940
Micturition urgency 42.91 29.59 24 9019 19296 110560960
Pain of skin 42.10 29.59 24 9019 20005 110560251
Pulmonary embolism 41.83 29.59 68 8975 214406 110365850
Somnolence 39.74 29.59 80 8963 297369 110282887
Bacteroides infection 39.22 29.59 13 9030 2906 110577350
Aspiration 37.45 29.59 26 9017 30507 110549749
Respiratory symptom 37.15 29.59 20 9023 14925 110565331
Sepsis 35.62 29.59 81 8962 327265 110252991
Breath sounds abnormal 34.40 29.59 23 9020 25381 110554875
Eye pruritus 33.53 29.59 25 9018 32750 110547506
Subarachnoid haemorrhage 33.43 29.59 24 9019 29678 110550578
Muscle twitching 33.26 29.59 24 9019 29911 110550345
Lung opacity 32.95 29.59 17 9026 11635 110568621
Lower respiratory tract infection 32.00 29.59 65 8978 243041 110337215
Cardiovascular disorder 31.77 29.59 21 9022 22739 110557517
Vulvovaginal candidiasis 30.11 29.59 11 9032 3274 110576982

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 D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D011500 Protein Synthesis Inhibitors
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:48001 protein synthesis inhibitor
CHEBI has role CHEBI:66981 ophthalmology drug
CHEBI has role CHEBI:76971 <em>Escherichia coli</em> metabolite
CHEBI has role CHEBI:131604 <em>Mycoplasma genitalium</em> metabolite
CHEBI has role CHEBI:176497 geroprotector

Related Drugs by ATC class:

D06AX Other antibiotics for topical use 12 drugs
amikacinbacitracinfusidic acidgentamicinmupirocinneomycinozenoxacinretapamulinrifamycinrifaximintyrothricinvirginiamycin
D10AF Antiinfectives for treatment of acne 6 drugs
clindamycinerythromycinmeclocyclineminocyclinenadifloxacinsulfacetamide
G01AA Antibiotics 10 drugs
amphotericin Bcandicidincarfecillinclindamycinhachimycinmepartricinnatamycinnystatinoxytetracyclinepentamycin
J01BA Amphenicols 1 drug
thiamphenicol
S01AA Antibiotics 27 drugs
amikacinampicillinazidamfenicolazithromycinbacitracinbenzylpenicillincefmenoximecefuroximechlortetracyclinedibekacindihydrostreptomycinerythromycin show all 27 →
S02AA Antiinfectives 17 drugs
acetic acidaluminium acetotartrateboric acidcefmenoximechlorhexidineciprofloxacinclioquinolfosfomycingentamicinhydrogen peroxidemiconazoleneomycin show all 17 →
S03AA Antiinfectives 7 drugs
chlorhexidineciprofloxacingentamicinhexamidineneomycinPolymyxin Btetracycline

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 Transcription factor 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