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 |
|---|---|
|
Synonyms:
|
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)
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 3 | g | O |
| 3 | g | P |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Dec. 8, 1950 | FDA | PARKEDALE |
FDA Adverse Event Reporting System (Female)
| 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 |
|---|---|---|---|---|---|---|
| Keratopathy | 99.94 | 31.88 | 16 | 1226 | 452 | 50603430 |
| Genital rash | 44.63 | 31.88 | 8 | 1234 | 447 | 50603435 |
| Lip swelling | 43.74 | 31.88 | 18 | 1224 | 24718 | 50579164 |
| Right ventricular hypertrophy | 41.64 | 31.88 | 8 | 1234 | 654 | 50603228 |
| Eye swelling | 36.77 | 31.88 | 15 | 1227 | 20129 | 50583753 |
FDA Adverse Event Reporting System (Male)
| 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 |
|---|---|---|---|---|---|---|
| Keratopathy | 46.45 | 35.28 | 8 | 690 | 370 | 29573459 |
FDA Adverse Event Reporting System (Geriatric)
| 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 |
|---|---|---|---|---|---|---|
| Keratopathy | 141.30 | 28.22 | 24 | 2015 | 756 | 64495937 |
| Lip swelling | 50.05 | 28.22 | 23 | 2016 | 31884 | 64464809 |
| Genital rash | 37.44 | 28.22 | 8 | 2031 | 861 | 64495832 |
| Right ventricular hypertrophy | 34.11 | 28.22 | 8 | 2031 | 1312 | 64495381 |
| Eye swelling | 31.63 | 28.22 | 15 | 2024 | 22266 | 64474427 |
| Premature baby | 31.32 | 28.22 | 9 | 2030 | 3263 | 64493430 |
| Potentiating drug interaction | 30.98 | 28.22 | 11 | 2028 | 7841 | 64488852 |
| Hypopyon | 30.65 | 28.22 | 7 | 2032 | 1022 | 64495671 |
| Vulvovaginal candidiasis | 30.30 | 28.22 | 8 | 2031 | 2122 | 64494571 |
| Congenital bowing of long bones | 30.29 | 28.22 | 4 | 2035 | 20 | 64496673 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| 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 |
| 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|
| 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 | ||
| 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
| Species | Use | Relation |
|---|---|---|
| Cats | Bacterial conjunctivitis | Indication |
| Dogs | Respiratory tract infections | Indication |
| Dogs | Urinary tract infections | Indication |
| Dogs | Bacterand enteritis | Indication |
| Dogs | Tonsillitis | Indication |
🐶 Veterinary products
| Product | Applicant | Ingredients |
|---|---|---|
| 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 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:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA 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:
| ID | Source |
|---|---|
| 4018199 | VUID |
| N0000146533 | NUI |
| D00104 | KEGG_DRUG |
| 2348 | RXNORM |
| 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 |
| 3887 | MMSL |
| 4406 | MMSL |
| d00025 | MMSL |
| 002767 | NDDF |
| 372777009 | SNOMEDCT_US |
| 57191001 | SNOMEDCT_US |
Pharmaceutical products:
None