Chloramphenicol

Details

• Internal ID: 61e2ca35-49e2-4786-8e3c-08011e86d366
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Nitrobenzenes
• IUPAC Name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• SMILES (Canonical): C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
• InChI Key: WIIZWVCIJKGZOK-RKDXNWHRSA-N
• Popularity: 60,163 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular Weight: 323.13 g/mol
• Exact Mass: 322.0123269 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 56-75-7
• Chlornitromycin
• Levomycetin
• Levomicetina
• Chlorocid
• Chloroamphenicol
• Alficetyn
• Chloramex
• Globenicol
• Halomycetin
• Oleomycetin
• Amphicol
• Chlorocol
• Fenicol
• D-Chloramphenicol
• Mychel
• Chloramficin
• Chloramfilin
• Chloronitrin
• Enteromycetin
• Amseclor
• Aquamycetin
• Austracil
• Austracol
• Chemicetin
• Chemicetina
• Chlomycol
• Chloramsaar
• Chlorocaps
• Chloroptic
• Cidocetine
• Cloramicol
• Econochlor
• Juvamycetin
• Kemicetine
• Leukomyan
• Leukomycin
• Novomycetin
• Ophthochlor
• Sificetina
• Catilan
• Klorita
• Biophenicol
• Chloricol
• Ciplamycetin
• Cloramficin
• Cloramidina
• Cloromisan
• Comycetin
• Cylphenicol
• Detreomycine
• Doctamicina
• Embacetin
• Erbaplast
• Farmicetina
• Intramycetin
• Ismicetina
• Isophenicol
• Laevomycetinum
• Loromisin
• Mastiphen
• Mediamycetine
• Micochlorine
• Microcetina
• Novophenicol
• Rivomycin
• Sintomicetina
• Stanomycetin
• Synthomycetin
• Ambofen
• Anacetin
• Biocetin
• Chlomin
• Clorocyn
• Desphen
• Emetren
• Ertilen
• Glorous
• Kamaver
• Paraxin
• Enicol
• Isopto fenicol
• Chlora-tabs
• Chloramphenicolum
• Chloroject L
• Chlorocidin C tetran
• Cloramfenicol
• Novochlorocap
• Chloromax
• Oftalent
• Pantovernil
• Romphenil
• Septicol
• Mycinol
• Opclor
• Otophen
• Cloroamfenicolo
• Chlorofair
• Optomycin
• Cloranfenicol
• Tifomycine
• Treomicetina
• Unimycetin
• Tevcocin
• Veticol
• Viceton
• 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• Chloramphenicol crystalline
• I 337A
• Chloroptic S.O.P.
• NCI-C55709
• U-6062
• 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
• (-)-chloramphenicol
• D-(-)-threo-1-p-Nitrophenyl-2-dichloroacetylamino-1,3-propanediol
• DTXSID7020265
• NSC3069
• NSC-3069
• D-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenylethyl)acetamide
• D-(-)-threo-1-p-Nitrophenyl-2-dichloracetamido-1,3-propanediol
• CHEBI:17698
• Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,R*))-
• 66974FR9Q1
• 9-hydroxy-9-phenylxanthene
• DTXCID90265
• Kloramfenikol
• 2,2-Dichloro-N-((1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide
• Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]-
• Chlorsig
• Sno Phenicol
• Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-
• Amphenicols
• 2,2-DICHLORO-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)ACETAMIDE
• Chlorbiotic
• Kernispray
• Brochlor
• Klorafect
• Viceton Tablets
• Anacetin Tablets
• Medichol Tablets
• Mychel-Vet Tabs
• Brolene antibiotic
• Mychel-Vet Injection
• Golden eye antibiotic
• Tubilux infected eyes
• Chloramphenicol Capsules
• RefChem:6406
• GlyTouCan:G11009BX
• Mychel-Vet Capsules (50 mg)
• Chloromycetin Ophthalmic Ointment
• G11009BX
• Chloramphenicol 1% Ophthalmic, Vetrocloricin Ophthalmic Ointment
• Chloromycetin Tablets 100 mg, Chloromycetin Tablets 250 mg, Chloromycetin Tablets 500 mg
• 200-287-4
• (R-(R*,R*))-2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)acetamide
• 9-phenyl-9h-xanthen-9-ol
• NSC-16331
• Xanthen-9-ol, 9-phenyl-
• Chloromycetin
• Detreomycin
• Amphenicol
• Chlorocide
• Kemicetina
• Levomitsetin
• Chlorocidin C
• Klorocid S
• Dextromycetin
• Chlorasol
• Chlorovules
• Clorosintex
• Hortfenicol
• Isicetin
• Medichol
• Micloretin
• Micoclorina
• Normimycin V
• Mychel-Vet
• Chloramfenikol
• Otachron
• Pentamycetin
• Quemicetina
• Ronphenil
• Chloro-25 vetag
• Sintomicetine R
• Sno-Phenicol
• Synthomycetine
• D-(-)-Chloramphenicol
• Chloromycetny
• D-(-)-threo-Chloramphenicol
• C11H12Cl2N2O5
• Tiromycetin
• Leukamycin
• Loromisan
• Tifomycin
• D-threo-Chloramphenicol
• Tega-Cetin
• DL-Chloramphenicol
• NSC 3069
• CAF
• Chloramphenicol-[ring-3,5-3H]
• D(-)-threo-Chloramphenicol
• Cloramfen
• Chloramphenicol (Chloromycetin)
• Ak-chlor
• 125440-98-4
• MFCD00078159
• D-(-)-threo-1-(4-Nitrophenyl)-2-dichloroacetamido-1,3-propanediol
• Myclocin
• Cloramfenicolo
• Syntomycin
• D-(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol
• D-threo-(1R,2R)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol
• NCGC00091011-05
• CAF (pharmaceutical)
• Chloramfenikol [Czech]
• Chloramphenicol 10 microg/mL in Acetonitrile
• Chloromycetny [Polish]
• Cloramfenicolo [DCIT]
• D-threo-N-(1,1'-Dihydroxy-1-p-nitrophenylisopropyl)dichloroacetamide
• 2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)-2-propyl]acetamide
• Chlorbiotic (Veterinary)
• Chloramphenicol 100 microg/mL in Ethyl acetate
• Cloroamfenicolo [Italian]
• Elase-Chloromycetin
• Gloveticol
• Mycochlorin
• Ocuphenicol
• Sintomicetin
• Tyfomycine
• Chlorocin
• Halcetin
• Levocin
• Levoplast
• Levosin
• Levovetin
• Soluthor
• Chloramphenicol, d-
• Cloramfenicol [INN-Spanish]
• Chloramphenicolum [INN-Latin]
• Ophtochlor
• Synthomycine
• Tevcosin
• Opelor
• D(-)-threo-2-Dichloroacetamido-1-p-nitrophenyl-1,3-propanediol
• Acetamide, 2,2-dichloro-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-
• Econochlor (TN)
• N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-2,2-dichloroace tamide
• Amphicol (TN)
• Ophthocort (Salt/Mix)
• ACETAMIDE, 2,2-DICHLORO-N-[(1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL]-
• SMR000471851
• Chloromyxin (Salt/Mix)
• Chloromycetin (TN)
• CCRIS 3922
• HSDB 3027
• SR-01000761450
• 2787-09-9
• EINECS 200-287-4
• Elase-Chloromycetin (Salt/Mix)
• BRN 2225532
• chioramphenicol
• Umimycin
• Chloramphenicol & VRC3375
• Chloramphenicole
• Chloromycetin;
• Chloronitrin;
• Enteromycetin;
• Sintomicetin;
• Chemicetin;
• Chlorcetin;
• Chloroptic;
• Detreomycin;
• Gloveticol;
• Kemicetine;
• Levomycetin;
• Ophthochlor;
• Synthomycin;
• AI3-25003
• Alficetyn;
• Chlorocid;
• Flamycin;
• Halcetin;
• Paraxin;
• Chlorocidin C;
• UNII-66974FR9Q1
• Normimycin V;
• CAS-56-75-7
• Chloramphenicol RS
• NCGC00094620-01
• D-(-)-threo-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl))-p-nitrophenethylacetamide
• D-(-)-threo-2,2-Dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)]-p-nitrophenethylacetamide
• Chloramphenicol CRS
• Chloramphenicol [USP:INN:BAN:JAN]
• Prestwick3_000031
• Chloramphenicol (Standard)
• CHEMBL130
• Epitope ID:114066
• Pork muscle-Chloramphenicol
• CHLORAMPHENICOL [MI]
• SCHEMBL16111
• BSPBio_000121
• CHLORAMPHENICOL [INN]
• CHLORAMPHENICOL [JAN]
• WLN: WNR DYQY1QMVYGG
• 4-13-00-02742 (Beilstein Handbook Reference)
• MLS001055372
• MLS001066397
• MLS001332385
• MLS001332386
• MLS002222155
• BIDD:GT0145
• CHLORAMPHENICOL [HSDB]
• CHLORAMPHENICOL [IARC]
• DivK1c_000544
• Pork muscle - Chloramphenicol
• CHLORAMPHENICOL [VANDF]
• BPBio1_000135
• CHLORAMPHENICOL [MART.]
• CHLORAMPHENICOLUM [HPUS]
• CHLORAMPHENICOL [USP-RS]
• CHLORAMPHENICOL [WHO-DD]
• CHLORAMPHENICOL [WHO-IP]
• D-(-)-threo-1-(p-Nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol
• D-(-)-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol
• BDBM23447
• Chloramphenicol, gamma-irradiated
• GTPL10901
• HMS501L06
• HY-B0239R
• KBio1_000544
• MSK7001
• NINDS_000544
• 754 - Chloramphenicol in seafood
• Chloramphenicol (JP18/USP/INN)
• GLXC-07915
• HMS2090M15
• HMS2095G03
• HMS2269N06
• HMS3712G03
• Chloramphenicol, >=98% (HPLC)
• Acetamide, 2,2-dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl)-, D-(-)-threo-
• Acetamide, 2,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-
• D-(-)-threo-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide
• D-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol
• HY-B0239
• RKL10087
• CHLORAMPHENICOL [GREEN BOOK]
• Tox21_111306
• Tox21_400061
• CHLORAMPHENICOL [ORANGE BOOK]
• EBC-07470
• MSK7001-100A
• s1677
• SBB057728
• CHLORAMPHENICOL [EP MONOGRAPH]
• AKOS005111001
• Chloramphenicol for peak identification
• MSK7001-1000A
• Porcine muscle-Chloramphenicol (blank)
• AC09460
• CCG-220031
• CHLORAMPHENICOL [USP MONOGRAPH]
• DB00446
• EBC-656093
• CHLORAMPHENICOLUM [WHO-IP LATIN]
• D-threo-(-)-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide
• IDI1_000544
• SMP1_000065
• NCGC00091011-01
• NCGC00091011-02
• NCGC00091011-03
• NCGC00091011-04
• NCGC00091011-06
• NCGC00091011-08
• NCGC00091011-09
• NCGC00091011-20
• Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (theta-(theta,theta))-
• AS-14683
• NCI60_002620
• Porcine muscle - Chloramphenicol (blank)
• ST024743
• Chloramphenicol for peak identification CRS
• OPHTHOCORT COMPONENT CHLORAMPHENICOL
• Chloramphenicol, puriss., 98.0-102.0%
• CHLOROMYXIN COMPONENT CHLORAMPHENICOL
• AB00374860
• C2255
• Chloramphenicol, tested according to Ph.Eur.
• NS00000500
• SW198497-2
• C00918
• D00104
• AB00374860-13
• AB00374860-14
• AB00374860_15
• Chloramphenicol, meets USP testing specifications
• F492377
• Q274515
• Chloramphenicol Solution in Acetonitrile, 1000ug/mL
• Chloramphenicol Solution in Acetonitrile, 100ug/mL
• Chloramphenicol, VETRANAL(TM), analytical standard
• ELASE-CHLOROMYCETIN COMPONENT CHLORAMPHENICOL
• SR-01000761450-2
• SR-01000761450-3
• SR-01000761450-5
• BRD-K08111712-001-02-7
• BRD-K08111712-001-14-2
• BRD-K08111712-001-16-7
• CHLOROPTIC-P S.O.P. COMPONENT CHLORAMPHENICOL
• Z2065671241
• Chloramphenicol, BioReagent, suitable for plant cell culture
• Chloramphenicol, certified reference material, TraceCERT(R)
• CHLOROMYCETIN HYDROCORTISONE COMPONENT CHLORAMPHENICOL
• 724 - Chloramphenicol, Florfenicol, Thiamphenicol in chicken
• Chloramphenicol, British Pharmacopoeia (BP) Reference Standard
• Chloramphenicol, European Pharmacopoeia (EP) Reference Standard
• Chloramphenicol, United States Pharmacopeia (USP) Reference Standard
• D-(-)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol
• D-threo-1-(p-Nitrophenyl)-2-(dichloroacetylamino)-1,3-propanediol
• 2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide-(1R,2R)
• Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]
• Chloramphenicol, Biotechnology Performance Certified, suitable for plant cell culture
• D-(-)-2,2-Dichloro-N-(.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenyl-ethyl)acetamide
• 2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(hydroxy(oxido)amino)phenyl)ethyl)acetamide, (1R, 2R)-
• Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R*,R*)-(+-)-
• Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, D-threo-(-)-
• Acetamide,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-,D-(-)-threo-
• Acetamide,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]-
• D-(-)-threo-alpha, alpha-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide
• D-THREO-(-)-2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-NITROPHENETHYL)ACETAMIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7284	72.84%
Caco-2	-	0.6684	66.84%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7057	70.57%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8696	86.96%
P-glycoprotein inhibitior	-	0.9477	94.77%
P-glycoprotein substrate	-	0.8550	85.50%
CYP3A4 substrate	-	0.6193	61.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9397	93.97%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5400	54.00%
Carcinogenicity (trinary)	Non-required	0.7280	72.80%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.9727	97.27%
Skin irritation	-	0.7073	70.73%
Skin corrosion	-	0.9051	90.51%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8548	85.48%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	-	0.5556	55.56%
skin sensitisation	-	0.8221	82.21%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5839	58.39%
Acute Oral Toxicity (c)	III	0.7521	75.21%
Estrogen receptor binding	-	0.6670	66.70%
Androgen receptor binding	+	0.5528	55.28%
Thyroid receptor binding	-	0.6439	64.39%
Glucocorticoid receptor binding	+	0.5772	57.72%
Aromatase binding	-	0.8515	85.15%
PPAR gamma	-	0.8545	85.45%
Honey bee toxicity	-	0.9092	90.92%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7653	76.53%
Fish aquatic toxicity	+	0.7455	74.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1255126	O15151	Protein Mdm4	96.33%	90.20%
CHEMBL4040	P28482	MAP kinase ERK2	95.08%	83.82%
CHEMBL2581	P07339	Cathepsin D	94.26%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.80%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.31%	99.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.96%	92.88%
CHEMBL3902	P09211	Glutathione S-transferase Pi	87.69%	93.81%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	87.45%	89.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.25%	96.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.90%	91.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.95%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	83.36%	94.73%
CHEMBL2069	P21731	Thromboxane A2 receptor	83.35%	92.62%
CHEMBL4208	P20618	Proteasome component C5	81.83%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.37%	86.92%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	80.84%	92.29%
CHEMBL221	P23219	Cyclooxygenase-1	80.15%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5959
• LOTUS: LTS0172894
• wikiData: Q274515