Chloramphenicol

Amphenicol-class Antibacterial — DERMATOLOGICALS

Key facts

Chloramphenicol is an ofm drug in the Amphenicol-class Antibacterial class catalogued in DrugCentral. It was first approved by the FDA in 1950. DrugCentral lists 4 molecular targets, including ska, cat and ttgR. Recorded indications include Bacterial infection of skin, Bacteroides Brain Abscess, Boutonneuse fever and Disease caused by rickettsiae.

• Approval status: ofm (first approved 1950 by the FDA).
• Drug class: Amphenicol-class Antibacterial.
• Molecular targets: ska, cat, ttgR and CYP3A4 (4 listed in DrugCentral).
• Indications: Bacterial infection of skin, Bacteroides Brain Abscess, Boutonneuse fever, Disease caused by rickettsiae and H. Influenzae Meningitis and others.
• ATC code: D06AX02 (Other antibiotics for topical use).
• Molecular formula: C11H12Cl2N2O5; molecular weight 323.13 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (11)

• Bacterial infection of skin
• Bacteroides Brain Abscess
• Boutonneuse fever
• Disease caused by rickettsiae
• H. Influenzae Meningitis
• Meningococcal meningitis
• Otitis externa
• Paratyphoid fever
• Streptococcal meningitis
• Superficial Ocular Infection
• Typhoid fever

Off-label uses (11)

• Anthrax
• Bacterial conjunctivitis
• Bacterial keratitis
• Blepharoconjunctivitis
• Exposure keratoconjunctivitis
• Gas gangrene caused by clostridium perfringens
• Gastrointestinal anthrax
• Infective blepharitis
• Inhalational anthrax
• Mastoidectomy Cavity Infections
• Neuropathic corneal ulcer

Contraindications (15)

• Acute intermittent porphyria
• Anemia
• Anemia due to enzyme deficiency
• Aplastic anemia
• Bone marrow depression
• Breastfeeding (mother)
• Disease of liver
• Granulocytopenic disorder
• Hypoplastic anemia
• Kidney disease
• Optic neuritis
• Paroxysmal nocturnal hemoglobinuria
• Peripheral nerve disease
• Significant Bleeding
• Thrombocytopenic disorder

Mechanism & targets

• Established pharmacologic class: Amphenicol-class Antibacterial

Molecular targets (4)

Target	Gene	Action	Activity
Streptokinase A	ska	unknown	EC50 6.01
Chloramphenicol acetyltransferase	cat	unknown	Kd 4.89
Probable HTH-type transcriptional regulator TtgR	ttgR	unknown	Kd 4.88
Cytochrome P450 3A4	CYP3A4	unknown	IC50 4.25

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1950-12-08	FDA	—	PARKEDALE

ATC classification

ATC code	Therapeutic hierarchy
D06AX02	DERMATOLOGICALS › ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE › ANTIBIOTICS FOR TOPICAL USE › Other antibiotics for topical use
D10AF03	DERMATOLOGICALS › ANTI-ACNE PREPARATIONS › ANTI-ACNE PREPARATIONS FOR TOPICAL USE › Antiinfectives for treatment of acne
G01AA05	GENITO URINARY SYSTEM AND SEX HORMONES › GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS › ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS › Antibiotics
J01BA01	ANTIINFECTIVES FOR SYSTEMIC USE › ANTIBACTERIALS FOR SYSTEMIC USE › AMPHENICOLS › Amphenicols
S01AA01	SENSORY ORGANS › OPHTHALMOLOGICALS › ANTIINFECTIVES › Antibiotics
S02AA01	SENSORY ORGANS › OTOLOGICALS › ANTIINFECTIVES › Antiinfectives
S03AA08	SENSORY ORGANS › OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS › ANTIINFECTIVES › Antiinfectives

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Appendicolith	210.6
Myasthenia gravis	188.2
Hyperphosphataemia	180.0
Analgesic therapy	173.2
Drug therapy	168.1
Appendicitis	165.6
Sleep disorder therapy	158.3
Ventricular fibrillation	143.0
Blood phosphorus increased	142.2
Anticoagulant therapy	141.0
Antacid therapy	140.6
Keratopathy	138.9

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Chloramphenicol is on its molecule page.

• Molecular formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular weight: 323.13 g/mol
• CAS number: 56-75-7
• InChIKey: WIIZWVCIJKGZOK-RKDXNWHRSA-N
• PubChem CID: 5959

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Chloramphenicol used for?

DrugCentral lists the following indications for Chloramphenicol: Bacterial infection of skin, Bacteroides Brain Abscess, Boutonneuse fever, Disease caused by rickettsiae, H. Influenzae Meningitis, Meningococcal meningitis, Otitis externa and Paratyphoid fever and others.

How does Chloramphenicol work?

Its molecular targets in DrugCentral include ska, cat, ttgR and CYP3A4.

When was Chloramphenicol first approved?

Chloramphenicol was first approved by the FDA in 1950.

What drug class does Chloramphenicol belong to?

Chloramphenicol is in the Amphenicol-class Antibacterial class.

What is the chemical formula of Chloramphenicol?

Chloramphenicol has the molecular formula C11H12Cl2N2O5 and a molecular weight of 323.13 g/mol.

Sources

• DrugCentral drug card 589 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL130 — compound record and bioactivity
• PubChem CID 5959 — chemical identifiers
• DrugBank DB00446 — drug record
• FDA UNII 66974FR9Q1 — substance identity
• DailyMed: FDA labels for Chloramphenicol — current prescribing information (label search)
• UniProt P08684 (CYP3A4) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.