chloramphenicol 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: 1.28
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 115.38
  • ALOGS: -2.85
  • ROTB: 6

  • Status: OFP

  • 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 ┬ÁM/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
Keratopathy 100.83 27.13 16 1639 290 46684117
Cholestasis of pregnancy 62.33 27.13 13 1642 1111 46683296
Parophthalmia 59.97 27.13 10 1645 249 46684158
Toxic anterior segment syndrome 54.01 27.13 13 1642 2124 46682283
Intraocular pressure increased 53.53 27.13 16 1639 5941 46678466
Conjunctival oedema 45.70 27.13 9 1646 576 46683831
Exophthalmos 45.14 27.13 10 1645 1135 46683272
Genital rash 41.19 27.13 8 1647 476 46683931
Eye swelling 40.93 27.13 18 1637 20085 46664322
Right ventricular hypertrophy 38.54 27.13 8 1647 667 46683740
Eye pain 32.40 27.13 17 1638 27923 46656484
Lip swelling 28.16 27.13 15 1640 25380 46659027
Pulmonary infarction 27.61 27.13 8 1647 2663 46681744

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
Keratopathy 56.80 35.29 9 879 195 29951395
Corneal oedema 51.20 35.29 11 877 1301 29950289

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 e.coli metabolites
CHEBI has role CHEBI:131604 mycoplasma genitalium metabolites

Drug Use (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

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
Streptokinase A Enzyme EC50 6.01 WOMBAT-PK
Chloramphenicol acetyltransferase Enzyme Kd 4.89 WOMBAT-PK
Probable HTH-type transcriptional regulator TtgR Unclassified Kd 4.88 WOMBAT-PK

External reference:

IDSource
4018199 VUID
N0000146533 NUI
D00104 KEGG_DRUG
4018199 VANDF
4021527 VANDF
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
2348 RXNORM
3887 MMSL
4406 MMSL
d00025 MMSL
002767 NDDF
372777009 SNOMEDCT_US
57191001 SNOMEDCT_US

Pharmaceutical products:

None