Chloramphenicol

Summary

Chloramphenicol is a broad spectrum antibiotic that is effective confronting a multifariousness of susceptible and serious bacterial infections simply is not frequently used considering of its high gamble of os marrow toxicity.

Brand Names

Chloromycetin

Generic Proper noun
Chloramphenicol
DrugBank Accession Number
DB00446
Groundwork

An antibiotic get-go isolated from cultures of Streptomyces venequelae in 1947 merely now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibody to be discovered. Information technology acts past interfering with bacterial protein synthesis and is mainly bacteriostatic. (From Martindale, The Extra Pharmacopoeia, 29th ed, p106)

Type
Small-scale Molecule
Groups
Approved, Vet approved
Construction

Weight
Boilerplate: 323.129
Monoisotopic: 322.012326918
Chemical Formula
C11H12Cl2Northward2Ofive
Synonyms
  • Chloramphénicol
  • Chloramphenicol
  • Chloramphenicolum
  • Chlornitromycin
  • Cloramfenicol
  • Cloranfenicol
  • D-(−)-2,two-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-nitrophenylethyl)acetamide
  • D-(−)-threo-1-p-nitrophenyl-two-dichloroacetylamino-ane,three-propanediol
  • Laevomycetinum
  • Levomicetina
  • Levomycetin
External IDs
  • NSC-3069
Indication

Used in handling of cholera, as information technology destroys the vibrios and decreases the diarrhea. It is effective confronting tetracycline-resistant vibrios. Information technology is besides used in eye drops or ointment to treat bacterial conjunctivitis.

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Associated Weather condition
  • Acne
  • Allergic Conjunctivitis (Air-conditioning)
  • Bacterial Conjunctivitis
  • Bacterial Conjunctivitis caused by susceptible leaner
  • Bacterial Infections
  • Bacterial Keratitis
  • Bacterial dacryocystitis
  • Bacterial diarrhoea
  • Keratitis
  • Ocular Inflammation
  • Trachoma
  • Anterior center segment inflammation
  • Bacterial blepharitis
  • Bacterial corneal ulcers
  • Non-purulent ophthalmic infections caused past susceptible bacteria
  • Superficial ocular infections
  • Swelling of the optics
Associated Therapies
  • Pare disinfection
Contraindications & Blackbox Warnings

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Pharmacodynamics

Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is at present produced synthetically. Chloramphenicol is constructive against a wide variety of microorganisms, but due to serious side-effects (e.1000., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used confronting highly susceptible organisms. Chloramphenicol stops bacterial growth past binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis.

Mechanism of action

Chloramphenicol is lipid-soluble, allowing it to lengthened through the bacterial jail cell membrane. It then reversibly binds to the L16 protein of the 50S subunit of bacterial ribosomes, where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl transferase activity), thus inhibiting peptide bail germination and subsequent protein synthesis.

Target Actions Organism
U50S ribosomal poly peptide L16

inhibitor

 Escherichia coli (strain K12)
UDr hemagglutinin structural subunit

antagonist

 Escherichia coli
UComplement decay-accelerating factor

other

 Humans
Absorption

Rapidly and completely absorbed from gastrointestinal tract post-obit oral assistants (bioavailability eighty%). Well absorbed following intramuscular administration (bioavailability 70%). Intraocular and some systemic absorption also occurs later topical application to the heart.

Volume of distribution

Not Available

Protein binding

Plasma poly peptide binding is 50-60% in adults and 32% is premature neonates.

Metabolism

Hepatic, with xc% conjugated to inactive glucuronide.

Route of elimination

Not Available

One-half-life

Half-life in adults with normal hepatic and renal function is one.v - 3.5 hours. In patients with impaired renal part half-life is iii - four hours. In patients with severely impaired hepatic function half-life is 4.6 - 11.6 hours. Half-life in children 1 month to sixteen years erstwhile is 3 - 6.5 hours, while half-life in infants 1 to 2 days old is 24 hours or longer and is highly variable, especially in low birth-weight infants.

Clearance

Non Available

Adverse Furnishings

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Toxicity

Oral, mouse: LD50 = 1500 mg/kg; Oral, rat: LD50 = 2500 mg/kg. Toxic reactions including fatalities have occurred in the premature and newborn; the signs and symptoms associated with these reactions have been referred to as the gray syndrome. Symptoms include (in order of appearance) intestinal amplification with or without emesis, progressive pallid cyanosis, vasomotor collapse ofttimes accompanied by irregular respiration, and decease within a few hours of onset of these symptoms.

Pathways
Pathway Category
Chloramphenicol Activeness Pathway Drug action
Pharmacogenomic Effects/ADRs
Not Available
Drug Interactions

This data should not exist interpreted without the assistance of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily hateful no interactions exist.

  • Approved
  • Vet approved
  • Nutraceutical
  • Illicit
  • Withdrawn
  • Investigational
  • Experimental
  • All Drugs
Drug Interaction

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interactions in your software
Abatacept The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Abatacept.
Abciximab The hazard or severity of bleeding can be increased when Abciximab is combined with Chloramphenicol.
Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Chloramphenicol.
Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Chloramphenicol.
Acalabrutinib The metabolism of Acalabrutinib tin exist decreased when combined with Chloramphenicol.
Acenocoumarol The serum concentration of Acenocoumarol can exist increased when it is combined with Chloramphenicol.
Acetohexamide The metabolism of Acetohexamide tin be decreased when combined with Chloramphenicol.
Acetylsalicylic acid The risk or severity of haemorrhage tin exist increased when Acetylsalicylic acid is combined with Chloramphenicol.
Acyclovir The excretion of Acyclovir tin be decreased when combined with Chloramphenicol.
Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Chloramphenicol.
Food Interactions
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Drug production information from 10+ global regions

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dosage, grade, labeller, route of administration, and marketing period.

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International/Other Brands
Brochlor (Sanofi-Aventis) / Chloramex (Actavis) / Chlorocid (Egyt) / Chlorocol / Chlorsig (Sigma) / Fenicol (Alcon) / Globenicol / Halomycetin (Wabosan) / Oleomycetin / Sificetina (SIFI)
Make Name Prescription Products
Proper name Dosage Strength Route Labeller Marketing Start Marketing Terminate Region Image
Cebenicol Oph Liq 0.4% Liquid .4 % Ophthalmic Chauvin Pharma Inc. 1992-12-31 1997-07-15 Canada flag
Chloramphenicol Solution 0.5 % Ophthalmic Pharma Stulln Inc. 1994-12-31 Non applicable Canada flag
Chloramphenicol Ointment ane % w/w Ophthalmic; Topical Pharma Stulln Inc. 1994-12-31 2019-11-23 Canada flag
Chloromycetin Ointment 10 mg/1g Ophthalmic PARKE-DAVIS 2006-10-08 Not applicative US flag
Chloromycetin Oph Ont one% Ointment one % Ophthalmic Parke Davis Partitioning, Warner Lambert Canada Inc. 1951-12-31 1999-04-08 Canada flag
Chloromycetin Oph Soln 0.5% Liquid .five % Ophthalmic Parke Davis Division, Warner Lambert Canada Inc. 1971-12-31 1997-08-25 Canada flag
Chloromycetin Otic Solution / drops five mg/1mL Auricular (otic) Monarch Pharmaceuticals, Inc. 1953-03-30 2002-02-12 US flag
Chloroptic Dps 0.5% Solution / drops .5 % Ophthalmic Allergan 1963-12-31 2011-08-04 Canada flag
Chloroptic Oph Ont i% Ointment 10 mg / g Ophthalmic Allergan 1988-12-31 2011-08-04 Canada flag
Econochlor Ointment x mg/1g Ophthalmic ALCON LABORATORIES, INC. 2006-09-12 Not applicative US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Showtime Marketing End Region Epitome
Novo-chlorocap Cap 250mg Sheathing 250 mg / cap Oral Novopharm Express 1966-12-31 2005-08-ten Canada flag
Odan-chloramphenicol Liquid 0.v mg / mL Ophthalmic Odan Laboratories Ltd 1985-12-31 Not applicative Canada flag
Odan-chloramphenicol Ointment 10 mg / grand Ophthalmic Odan Laboratories Ltd 1992-12-31 Not applicable Canada flag
PMS-chloramphenicol Ophthalmic Soln 0.five% Solution / drops .5 % Ophthalmic Pharmascience Inc 1992-12-31 2016-10-28 Canada flag
Over the Counter Products
Proper name Dosage Strength Route Labeller Marketing Commencement Marketing Terminate Region Epitome
OPTIVIS OPHTHALMIC OINTMENT Ointment 1 %due west/due west Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 2004-04-04 Not applicative Thailand flag
VANAFEN OPTHALMIC OINTMENT Ointment 1 %w/w Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 1986-06-08 Not applicable Thailand flag
VENAFEN-S Heart Drib Liquid five mg/1ml Ophthalmic บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 1985-02-06 Not applicable Thailand flag
ขี้ผึ้ง ยูนีซัน Ointment ane %west/w Topical บริษัท ยูนีซัน จำกัด 1985-06-eighteen Not applicative Thailand flag
ขี้ผึ้งโคลฟามีน ใส่แผล Ointment 1 %west/due west Topical บริษัท แลชแมน จำกัด จำกัด 1987-03-17 Not applicable Thailand flag
คลอรอฟ ยาหยอดตา Liquid 5 mg/1ml Ophthalmic บริษัท แสงไทยกำปะนี จำกัด 1985-08-23 Not applicable Thailand flag
คลอร์ - ไพแร็ด Ointment one %due west/w Topical บริษัท สหการโอสถ (1996) จำกัด จำกัด 1996-11-07 Not applicable Thailand flag
คลออ๊อฟ ขี้ผึ้งป้ายตา Ointment 1 %w/w Ophthalmic บริษัท แสงไทยกำปะนี จำกัด 1985-01-29 Not applicable Thailand flag
คลอแรม ออยต์เมนท์ Ointment one %w/due west Topical บริษัท สหแพทย์เภสัช จำกัด 1986-05-27 Non applicable Thailand flag
พิซาลิน ออยเมนท์ Ointment 1 %w/westward Topical บริษัท 2 เอ็ม.(เมด-เมเกอร์) จำกัด จำกัด 1988-06-28 Not applicable Thailand flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Showtime Marketing End Region Image
Actinac Pwr Chloramphenicol (forty mg / yard) + Allantoin (24 mg / g) + Hydrocortisone acetate (forty mg / 1000) + Nicoboxil (24 mg / g) + Octasulfur (320 mg / g) Powder Topical Roussel Canada Inc. 1978-12-31 1996-09-09 Canada flag
Actinac Pws Chloramphenicol (forty mg / one thousand) + Allantoin (24 mg / thou) + Hydrocortisone acetate (forty mg / thousand) + Nicoboxil (24 mg / chiliad) + Octasulfur (320 mg / g) Pulverisation, for solution Topical Hoechst Roussel Canada Inc. 1994-12-31 2001-07-twenty Canada flag
Ophthocort Ont Chloramphenicol (10 mg / g) + Hydrocortisone acetate (5 mg / g) + Polymyxin B sulfate (5000 unit / chiliad) Ointment Ophthalmic Parke Davis Partition, Warner Lambert Canada Inc. 1958-12-31 1998-04-07 Canada flag
Pentamycetin/hc Chloramphenicol (10 mg / yard) + Hydrocortisone acetate (10 mg / g) Ointment Auricular (otic); Ophthalmic Sandoz Canada Incorporated 1992-12-31 2019-08-01 Canada flag
Pentamycetin/hc Chloramphenicol (2 mg / mL) + Hydrocortisone acetate (10 mg / mL) Suspension Auricular (otic); Ophthalmic Sandoz Canada Incorporated 1992-12-31 2019-08-01 Canada flag
Sopamycetin/hc Ointment Chloramphenicol (ten mg / g) + Hydrocortisone acetate (x mg / g) Ointment Auricular (otic); Ophthalmic Laboratoires Charton Laboratories 1992-12-31 1999-01-xvi Canada flag
Sopamycetin/hc Ont Chloramphenicol (.ii %) + Hydrocortisone acetate (1 %) Ointment Auricular (otic); Ophthalmic Laboratoires Charton Laboratories 1988-12-31 1999-01-16 Canada flag
Sopamycetin/hc Susp Chloramphenicol (.two %) + Hydrocortisone acetate (i %) Solution / drops Ophthalmic Laboratoires Charton Laboratories 1988-12-31 1999-01-16 Canada flag
คลอแรมเฟนิคอล เอ.เอ็น.บี. 250 มก. Chloramphenicol (250 MG/2ML) + Lidocaine (30 MG/2ML) Solution บริษัท เอ.เอ็น.บี.ลาบอราตอรี่ (อำนวยเภสัช) จำกัด จำกัด 1985-12-07 Not applicable Thailand flag
คอร์ทิคอร์ท-ซี Chloramphenicol (x MG/1G) + Hydrocortisone (ten MG/1G) Cream ห้างหุ้นส่วนจำกัด โรงงานเลิศสิงห์เภสัชกรรม 1997-06-06 Non applicable Thailand flag
ATC Codes
D06AX02 — Chloramphenicol
  • D06AX — Other antibiotics for topical employ
  • D06A — ANTIBIOTICS FOR TOPICAL Utilize
  • D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
  • D — DERMATOLOGICALS
S02AA01 — Chloramphenicol
  • S02AA — Antiinfectives
  • S02A — ANTIINFECTIVES
  • S02 — OTOLOGICALS
  • S — SENSORY ORGANS
D10AF03 — Chloramphenicol
  • D10AF — Antiinfectives for handling of acne
  • D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL Utilize
  • D10 — ANTI-ACNE PREPARATIONS
  • D — DERMATOLOGICALS
S01AA01 — Chloramphenicol
  • S01AA — Antibiotics
  • S01A — ANTIINFECTIVES
  • S01 — OPHTHALMOLOGICALS
  • S — SENSORY ORGANS
G01AA05 — Chloramphenicol
  • G01AA — Antibiotics
  • G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
  • G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
  • Thousand — GENITO URINARY Organization AND SEX HORMONES
J01BA01 — Chloramphenicol
  • J01BA — Amphenicols
  • J01B — AMPHENICOLS
  • J01 — ANTIBACTERIALS FOR SYSTEMIC Employ
  • J — ANTIINFECTIVES FOR SYSTEMIC Apply
S03AA08 — Chloramphenicol
  • S03AA — Antiinfectives
  • S03A — ANTIINFECTIVES
  • S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
  • South — SENSORY ORGANS
Drug Categories
  • Alcohols
  • Amphenicols
  • Anti-Acne Preparations
  • Anti-Acne Preparations for Topical Use
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Utilize
  • Antibiotics for Topical Use
  • Antiinfectives for Systemic Apply
  • Antiinfectives for Treatment of Acne
  • Benzene Derivatives
  • Cytochrome P-450 CYP2C19 Inhibitors
  • Cytochrome P-450 CYP2C19 Inhibitors (strong)
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors (force unknown)
  • Cytochrome P-450 CYP3A5 Inhibitors
  • Cytochrome P-450 CYP3A5 Inhibitors (forcefulness unknown)
  • Cytochrome P-450 CYP3A7 Inhibitors
  • Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
  • Cytochrome P-450 Enzyme Inhibitors
  • Dermatologicals
  • Enzyme Inhibitors
  • Genito Urinary System and Sex activity Hormones
  • Glycols
  • Gynecological Antiinfectives and Antiseptics
  • Immunosuppressive Agents
  • Myelosuppressive Agents
  • Nitro Compounds
  • Nitrobenzenes
  • OAT1/SLC22A6 inhibitors
  • Ophthalmological and Otological Preparations
  • Ophthalmologicals
  • Otologicals
  • Propylene Glycols
  • Poly peptide Synthesis Inhibitors
  • Sensory Organs
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known every bit nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Course
Nitrobenzenes
Direct Parent
Nitrobenzenes
Alternative Parents
Nitroaromatic compounds / Secondary alcohols / Propargyl-blazon ane,3-dipolar organic compounds / Organic oxoazanium compounds / Carboximidic acids / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic zwitterions / Organic oxides / Hydrocarbon derivatives / Aromatic alcohols / Alkyl chlorides show 4 more
Substituents
Booze / Alkyl chloride / Alkyl halide / Allyl-type ane,3-dipolar organic compound / Aromatic booze / Aromatic homomonocyclic compound / C-nitro chemical compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Nitroaromatic compound / Nitrobenzene / Organic 1,3-dipolar compound / Organic nitro compound / Organic nitrogen compound / Organic oxide / Organic oxoazanium / Organic oxygen compound / Organic zwitterion / Organochloride / Organohalogen chemical compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Propargyl-type i,iii-dipolar organic chemical compound / Secondary booze show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organochlorine compound (CHEBI:17698) / Aromatic compounds (C00918)
Afflicted organisms
  • Enteric bacteria and other eubacteria
  • Gram negative and gram positive bacteria
  • Streptococcus pneumoniae
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Enterococcus faecium
UNII
66974FR9Q1
CAS number
56-75-7
InChI Key
WIIZWVCIJKGZOK-RKDXNWHRSA-N
InChI

InChI=1S/C11H12Cl2N2O5/c12-10(13)eleven(xviii)xiv-eight(five-16)9(17)6-1-iii-7(4-two-6)15(19)xx/h1-4,8-ten,xvi-17H,5H2,(H,xiv,18)/t8-,ix-/m1/s1

IUPAC Name

2,2-dichloro-N-[(1R,2R)-ane,3-dihydroxy-ane-(iv-nitrophenyl)propan-ii-yl]acetamide

SMILES

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

Synthesis Reference

Guang-Zhong Wu, Wanda I. Tormos, "Disproportionate process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates." U.South. Patent US5352832, issued May, 1992.

US5352832
General References
  1. Bhutta ZA, Niazi SK, Suria A: Chloramphenicol clearance in typhoid fever: implications for therapy. Indian J Pediatr. 1992 Mar-Apr;59(ii):213-nine. [Commodity]
  2. Wali SS, Macfarlane JT, Weir WR, Cleland PG, Ball PA, Hassan-King One thousand, Whittle HC, Greenwood BM: Unmarried injection handling of meningococcal meningitis. ii. Long-acting chloramphenicol. Trans R Soc Trop Med Hyg. 1979;73(6):698-702. [Article]
  3. Puddicombe JB, Wali SS, Greenwood BM: A field trial of a single intramuscular injection of long-interim chloramphenicol in the treatment of meningococcal meningitis. Trans R Soc Trop Med Hyg. 1984;78(3):399-403. [Article]
  4. Pecoul B, Varaine F, Keita Yard, Soga One thousand, Djibo A, Soula G, Abdou A, Etienne J, Rey M: Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis. Lancet. 1991 October v;338(8771):862-six. [Article]
  5. Nathan N, Borel T, Djibo A, Evans D, Djibo Southward, Corty JF, Guillerm M, Alberti KP, Pinoges Fifty, Guerin PJ, Legros D: Ceftriaxone as effective as long-acting chloramphenicol in brusk-grade handling of meningococcal meningitis during epidemics: a randomised non-inferiority study. Lancet. 2005 Jul 23-29;366(9482):308-13. [Article]
Homo Metabolome Database
HMDB0014589
KEGG Drug
D00104
KEGG Compound
C00918
PubChem Compound
5959
PubChem Substance
46505318
ChemSpider
5744
BindingDB
23447
RxNav
2348
ChEBI
17698
ChEMBL
CHEMBL130
ZINC
ZINC000000113382
Therapeutic Targets Database
DAP001356
PharmGKB
PA448927
PDBe Ligand
CLM
RxList
RxList Drug Folio
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloramphenicol
PDB Entries
1cla / 1k01 / 1nji / 1qhs / 1qhy / 1usq / 2jkj / 2jkl / 2uxp / 2xat … show 23 more
FDA label
MSDS
Clinical Trials
Stage Status Purpose Conditions Count
four Completed Treatment Ophthalmopathy , Lacrimal System 1
0 Terminated Treatment Osteomyelitis 1
Not Available Completed Not Available Antibiotic Resistant Infection / Bacterial Infections / Surgical Site Infections 1
Manufacturers
  • John j ferrante
  • Ivax pharmaceuticals inc sub teva pharmaceuticals the states
  • Parkedale pharmaceuticals inc
  • Armenpharm ltd
  • Parke davis pharmaceutical research div warner lambert co
  • Altana inc
  • Pharmafair inc
  • Allergan pharmaceutical
  • Alcon laboratories inc
  • Akorn inc
  • Optopics laboratories corp
  • Elkins sinn div ah robins co inc
  • App pharmaceuticals llc
  • Gruppo lepetit spa sub merrell dow pharmaceuticals inc
  • Angus chemical co
Packagers
  • Akorn Inc.
  • APP Pharmaceuticals
  • Darby Dental Supply Co. Inc.
  • Full general Injectables and Vaccines Inc.
  • Gruppo Lepetit SPA
  • Ivax Pharmaceuticals
  • Medisca Inc.
  • Professional Compounding Centers America LLC
  • Spectrum Pharmaceuticals
Dosage Forms
Form Road Strength
Pulverisation Topical
Powder, for solution Topical
Capsule Oral 250 mg
Syrup Oral
Suppository
Gel Conjunctival
Ointment Conjunctival
Solution / drops Conjunctival
Suspension / drops Conjunctival
Intermission / drops Conjunctival 0.5 %
Liquid Ophthalmic .4 %
Ointment Ophthalmic
Insert Vaginal 250 MG
Insert Vaginal 500 MG
Sheathing Oral
Cream
Ointment Ophthalmic; Topical 1 % westward/westward
Solution Ophthalmic 0.five %
Ointment Ophthalmic
Solution Auricular (otic) 5 %
Solution Auricular (otic) 5 % west/five
Solution Ophthalmic 25 mg/5ml
Injection, powder, for solution Intravenous; Parenteral ane M
Suspension Oral
Ointment Ophthalmic 10 mg/1g
Capsule, liquid filled Oral 250 mg
Ointment Ophthalmic ane %
Liquid Ophthalmic .five %
Solution / drops Auricular (otic) 5 mg/1mL
Solution / drops Ophthalmic .five %
Ointment Ophthalmic x mg / g
Break / drops Ophthalmic
Capsule, coated Oral 250 mg
Injection, pulverization, for solution Intravenous 1 Grand/10ML
Ointment
Injection, powder, for solution Parenteral one thousand mg
Solution / drops Ophthalmic
Cream
Solution / drops Auricular (otic)
Ointment Conjunctival; Ophthalmic
Solution Ophthalmic 5 mg/1mL
Insert Vaginal 0.25 g
Solution Auricular (otic) 2.5 mg
Ointment Topical
Injection, solution Intramuscular; Intravenous
Ointment 1 % w/w
Solution / drops Ophthalmic; Topical .5 %
Solution Ophthalmic 0.5 % w/five
Solution / drops Ophthalmic 0.5 %W/Five
Capsule Oral 250 mg / cap
Liquid Ophthalmic 0.v mg / mL
Ointment Ophthalmic ten mg/thousand
Solution Ophthalmic 5.0 mg/ml
Solution Ophthalmic two.5 mg / mL
Solution Ophthalmic 5 mg / mL
Suspension Auricular (otic); Ophthalmic
Solution / drops Auricular (otic)
Solution / drops Ophthalmic
Tablet, coated Oral
Ointment Ophthalmic .2 %
Solution / drops Auricular (otic) 5 %
Solution / drops Ophthalmic .two %
Ointment Auricular (otic); Ophthalmic
Solution Conjunctival; Ophthalmic
Solution / drops Ophthalmic 0.5 % W/Five
Cream; ointment
Solution / drops
Solution Ophthalmic 5 MG/ML
Solution Conjunctival; Ophthalmic 5 mg
Ointment Topical i %w/w
Ointment Topical ii %w/w
Liquid Ophthalmic 5 mg/1ml
Capsule Oral 100 mg
Solution
Liquid Ophthalmic
Liquid Auricular (otic) 10 mg/1ml
Tablet, coated Oral 100 mg
Liquid Auricular (otic) l mg/1ml
Liquid Auricular (otic)
Tablet 250 mg
Ointment Ophthalmic one %w/w
Prices
Unit description Toll Unit of measurement
Chloramphen na succ 1 gm vial 28.74USD vial
Chloramphenicol palm powder two.52USD g
Chloramphenicol crystals i.32USD g

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Patents
Not Available
Land
Solid
Experimental Properties
Property Value Source
melting point (°C) 171 Bartz, Q.R.; U.Southward. Patent 2,483,871; October four, 1949; assigned to Parke, Davis & Company Crooks, H.Thou., Jr., Rebstock, M.C., Controulis, J. and Bartz, Q.R.; U.Due south. Patent 2,483,884; October iv, 1949; assigned to Parke, Davis & Company. Ehrlich, J., Smith, R.Chiliad. and Penner, Yard.A.; U.Due south. Patent two,483,892; Oct 4, 1949; assigned to Parke, Davis & Company. Carrara, G.; U.S. Patent 2,776,312; January 1, 1957 Slack, R.; U.S. Patent 2,786,870; March 26, 1957; assigned to Parke, Davis & Company.
water solubility 2500 mg/50 (at 25 °C) MERCK Index (2001)
logP 1.14 HANSCH,C ET AL. (1995)
logS -2.11 ADME Inquiry, USCD
Caco2 permeability -iv.69 ADME Research, USCD
Predicted Properties
Property Value Source
Water Solubility 0.461 mg/mL ALOGPS
logP 1.xv ALOGPS
logP 0.88 ChemAxon
logS -2.8 ALOGPS
pKa (Strongest Acidic) viii.69 ChemAxon
pKa (Strongest Bones) -2.eight ChemAxon
Physiological Accuse 0 ChemAxon
Hydrogen Acceptor Count five ChemAxon
Hydrogen Donor Count three ChemAxon
Polar Surface Area 112.7 Å2 ChemAxon
Rotatable Bail Count 6 ChemAxon
Refractivity 72.2 one thousand3·mol-one ChemAxon
Polarizability 28.13 Å3 ChemAxon
Number of Rings i ChemAxon
Bioavailability 1 ChemAxon
Rule of V Yes ChemAxon
Ghose Filter Yes ChemAxon
Veber's Dominion No ChemAxon
MDDR-similar Dominion No ChemAxon
Predicted ADMET Features
Property Value Probability
Human being Abdominal Absorption + 0.9157
Blood Brain Barrier + 0.9366
Caco-2 permeable + 0.7367
P-glycoprotein substrate Non-substrate 0.7305
P-glycoprotein inhibitor I Not-inhibitor 0.9216
P-glycoprotein inhibitor Two Non-inhibitor 0.8822
Renal organic cation transporter Not-inhibitor 0.9477
CYP450 2C9 substrate Non-substrate 0.7775
CYP450 2D6 substrate Not-substrate 0.8934
CYP450 3A4 substrate Non-substrate 0.5936
CYP450 1A2 substrate Not-inhibitor 0.9046
CYP450 2C9 inhibitor Non-inhibitor 0.9071
CYP450 2D6 inhibitor Non-inhibitor 0.9231
CYP450 2C19 inhibitor Inhibitor 0.8994
CYP450 3A4 inhibitor Not-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682
Ames exam Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.5483
Biodegradation Ready biodegradable 0.5053
Rat acute toxicity 2.2247 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9658
hERG inhibition (predictor II) Non-inhibitor 0.8764

ADMET data is predicted using admetSAR, a costless tool for evaluating chemical ADMET properties. (23092397)

Mass Spec (NIST)
Download (ten.ix KB)
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Bachelor
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Bachelor
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Non Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Bachelor
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Non Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Non Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0kmi-0945000000-40a09f3f9528bd669823
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0udi-0900000000-64dbb16119292f4410e2
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0udi-0900000000-5c8fbcad8e93fa9f2906
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0uk9-1900000000-4c6518583a7488591aa3
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-00di-1900000000-00574ed667d64b4a45e9
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-00di-1900000000-d4ac63e9260ab31ac6b1
LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-0zml-0933000000-4ae209b29cb52d4e3844
LC-MS/MS Spectrum - LC-ESI-QTOF , negative LC-MS/MS splash10-056r-0933000000-74ff5ec451e56526d425
MS/MS Spectrum - Linear Ion Trap , negative LC-MS/MS splash10-0a4l-0590000000-90d108018a0f99815fb7
MS/MS Spectrum - Linear Ion Trap , negative LC-MS/MS splash10-0a4l-0690000000-161f2afa43298fd3437a
LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-0uk9-0923000000-86308db0ec59b40b1533
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-05fr-0094000000-ad8da59124745b38a76f
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-00di-0390000000-06fcf307f2fdb79741ad
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-014i-1940000000-be07d702045f4d3e05ac
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-014i-1910000000-55a74a828c3c9750ee1c
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-0159-2900000000-bf685c17ab79583133ee
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-0159-4900000000-e6f6ccbfffe89c345365
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-00di-0191000000-41f70006e2b4e5f8d8aa
LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-014i-0960000000-d64346c38bebc079f066
MS/MS Spectrum - Linear Ion Trap , positive LC-MS/MS splash10-0f89-0491000000-c7e13efc8c7ed0e68cff
MS/MS Spectrum - Linear Ion Trap , positive LC-MS/MS splash10-0f89-0492000000-4b6f8c10f6acc0f02196
MS/MS Spectrum - , positive LC-MS/MS splash10-014i-0920000000-96bfb1c31d89e3f10caf
LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-0600-0592000000-129db104bb506af06de0

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological activeness

Unknown

Actions

Inhibitor

General Function
Trna binding
Specific Function
This protein binds direct to 23S ribosomal RNA and is located at the A site of the peptidyltransferase center. It contacts the A and P site tRNAs. It has an essential role in subunit assembly, wh...
Factor Name
rplP
Uniprot ID
P0ADY7
Uniprot Name
50S ribosomal poly peptide L16
Molecular Weight
15281.125 Da
References
  1. Murray IA, Cann PA, Twenty-four hour period PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition by chloramphenicol acetyltransferase: engineering science and structural assay of a high affinity fusidic acid binding site. J Mol Biol. 1995 December fifteen;254(5):993-1005. [Article]
  2. Nierhaus D, Nierhaus KH: Identification of the chloramphenicol-binding protein in Escherichia coli ribosomes by partial reconstitution. Proc Natl Acad Sci U South A. 1973 Aug;70(eight):2224-8. [Article]
  3. Baxter RM, Ganoza MC, Zahid Due north, Chung DG: Reconstruction of peptidyltransferase activity on 50S and 70S ribosomal particles by peptide fragments of poly peptide L16. Eur J Biochem. 1987 Mar 16;163(three):473-ix. [Article]
Kind
Protein
Organism
Escherichia coli
Pharmacological action

Unknown

Deportment

Antagonist

General Part
Not Available
Specific Function
Hemagglutinins of uropathogenic E.coli mediate adherence to the upper urinary tract. These adhesins bind to the Dr blood group antigen and also agglutinate man erythrocytes in the presence of D-g...
Gene Name
draA
Uniprot ID
P24093
Uniprot Proper name
Dr hemagglutinin structural subunit
Molecular Weight
17058.095 Da
References
  1. Swanson TN, Bilge SS, Nowicki B, Moseley SL: Molecular structure of the Dr adhesin: nucleotide sequence and mapping of receptor-binding domain past utilise of fusion constructs. Infect Immun. 1991 Jan;59(1):261-8. [Commodity]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Deportment

Other

Full general Function
Virus receptor activeness
Specific Function
This protein recognizes C4b and C3b fragments that condense with jail cell-surface hydroxyl or amino groups when nascent C4b and C3b are locally generated during C4 and c3 activation. Interaction of daf...
Gene Name
CD55
Uniprot ID
P08174
Uniprot Name
Complement disuse-accelerating gene
Molecular Weight
41399.79 Da
References
  1. Pettigrew D, Anderson KL, Billington J, Cota Eastward, Simpson P, Urvil P, Rabuzin F, Roversi P, Nowicki B, du Merle L, Le Bouguenec C, Matthews S, Lea SM: High resolution studies of the Afa/Dr adhesin DraE and its interaction with chloramphenicol. J Biol Chem. 2004 Nov v;279(45):46851-7. Epub 2004 Aug 24. [Article]
  2. Korotkova N, Chattopadhyay S, Tabata TA, Beskhlebnaya Five, Vigdorovich V, Kaiser BK, Strong RK, Dykhuizen DE, Sokurenko EV, Moseley SL: Selection for functional multifariousness drives accumulation of point mutations in Dr adhesins of Escherichia coli. Mol Microbiol. 2007 April;64(1):180-94. [Commodity]

Enzymes

Kind
Poly peptide
Organism
Escherichia coli
Pharmacological action

Unknown

Actions

Substrate

Full general Role
Chloramphenicol o-acetyltransferase activeness
Specific Role
This enzyme is an effector of chloramphenicol resistance in bacteria.
Gene Name
cat3
Uniprot ID
P00484
Uniprot Proper name
Chloramphenicol acetyltransferase 3
Molecular Weight
24993.32 Da
References
  1. Murray IA, Cann PA, Mean solar day PJ, Derrick JP, Sutcliffe MJ, Shaw WV, Leslie AG: Steroid recognition past chloramphenicol acetyltransferase: engineering and structural analysis of a high affinity fusidic acid binding site. J Mol Biol. 1995 Dec 15;254(v):993-1005. [Commodity]
  2. Derrick JP, Lian LY, Roberts GC, Shaw WV: Assay of the binding of 1,3-diacetylchloramphenicol to chloramphenicol acetyltransferase by isotope-edited 1H NMR and site-directed mutagenesis. Biochemistry. 1992 Sep 8;31(35):8191-v. [Article]
  3. Murray IA, Lewendon A, Shaw WV: Stabilization of the imidazole ring of His-195 at the agile site of chloramphenicol acetyltransferase. J Biol Chem. 1991 Jun 25;266(18):11695-eight. [Article]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action

Unknown

Actions

Substrate

General Function
Chloramphenicol o-acetyltransferase activity
Specific Part
This enzyme is an effector of chloramphenicol (Cm) resistance in bacteria. Acetylates Cm but not one-acetoxy-Cm.
Gene Name
true cat
Uniprot ID
P26841
Uniprot Name
Chloramphenicol acetyltransferase
Molecular Weight
23524.385 Da
References
  1. Potrykus J, Baranska S, Wegrzyn G: Inactivation of the acrA gene is partially responsible for chloramphenicol sensitivity of Escherichia coli CM2555 strain expressing the chloramphenicol acetyltransferase gene. Microb Drug Resist. 2002 Fall;8(3):179-85. [Article]
  2. Potrykus J, Wegrzyn One thousand: Chloramphenicol-sensitive Escherichia coli strain expressing the chloramphenicol acetyltransferase (true cat) gene. Antimicrob Agents Chemother. 2001 Dec;45(12):3610-ii. [Article]
  3. Navia MM, Capitano L, Ruiz J, Vargas M, Urassa H, Schellemberg D, Gascon J, Vila J: Typing and characterization of mechanisms of resistance of Shigella spp. isolated from feces of children under 5 years of age from Ifakara, Tanzania. J Clin Microbiol. 1999 Oct;37(10):3113-7. [Article]
Kind
Protein
Organism
Streptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
Pharmacological action

Unknown

Actions

Substrate

Full general Function
Kinase activeness
Specific Function
Inactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic's C-3' hydroxyl group.
Factor Name
Not Available
Uniprot ID
Q56148
Uniprot Proper noun
Chloramphenicol 3-O phosphotransferase
Molecular Weight
18816.255 Da
References
  1. Ellis J, Campopiano DJ, Izard T: Cubic crystals of chloramphenicol phosphotransferase from Streptomyces venezuelae in complex with chloramphenicol. Acta Crystallogr D Biol Crystallogr. 1999 May;55(Pt 5):1086-8. [Article]
  2. Izard T, Ellis J: The crystal structures of chloramphenicol phosphotransferase reveal a novel inactivation mechanism. EMBO J. 2000 Jun ane;19(eleven):2690-700. [Article]
  3. Mosher RH, Military camp DJ, Yang 1000, Brown MP, Shaw WV, Vining LC: Inactivation of chloramphenicol past O-phosphorylation. A novel resistance mechanism in Streptomyces venezuelae ISP5230, a chloramphenicol producer. J Biol Chem. 1995 November 10;270(45):27000-vi. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Deportment

Inhibitor

General Function
Steroid hydroxylase activeness
Specific Part
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug Southward-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Cistron Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in homo liver microsomes. Antimicrob Agents Chemother. 2003 November;47(11):3464-9. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Poly peptide
Organism
Humans
Pharmacological activeness

Unknown

Actions

Inhibitor

Full general Function
Vitamin d3 25-hydroxylase activity
Specific Office
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron send pathway. It performs a variety of oxidation react...
Gene Proper noun
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Park JY, Kim KA, Kim SL: Chloramphenicol is a potent inhibitor of cytochrome P450 isoforms CYP2C19 and CYP3A4 in human liver microsomes. Antimicrob Agents Chemother. 2003 November;47(11):3464-nine. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Poly peptide
Organism
Humans
Pharmacological activity

Unknown

Actions

Inhibitor

General Function
Oxygen bounden
Specific Function
Cytochromes P450 are a grouping of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Factor Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Tabular array of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological activeness

Unknown

Actions

Inhibitor

General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action

Unknown

Actions

Inhibitor

General Role
Sodium-independent organic anion transmembrane transporter activity
Specific Office
Involved in the renal emptying of endogenous and exogenous organic anions. Functions equally organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Cistron Proper name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Proper name
Solute carrier family 22 member half-dozen
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul North, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter i. J Pharmacol Exp Ther. 1999 Aug;290(ii):672-7. [Commodity]

Drug created at June 13, 2005 13:24 / Updated at October 04, 2022 23:16