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

Stem definition	Drug id	CAS RN
	589	56-75-7

Description:

Molecule	Description
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

Molecule

Description

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:

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

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

Drug Use (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

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	Type	Activity value (-log[M])	Bioact source
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN	IC50	4.25	WOMBAT-PK
Streptokinase A	Enzyme		STRP_STRP1	EC50	6.01	WOMBAT-PK
Chloramphenicol acetyltransferase	Enzyme		CAT_SALTI	Kd	4.89	WOMBAT-PK
Probable HTH-type transcriptional regulator TtgR	Unclassified		TTGR_PSEPK	Kd	4.88	WOMBAT-PK

External reference:

ID	Source
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