Details of the Drug

General Information of Drug (ID: DMDRKH2)

Drug Name

Thiamphenicol

Synonyms

thiamphenicol; 15318-45-3; Thiophenicol; Thiamcol; (+)-Thiamphenicol; Raceophenidol; Dextrosulphenidol; Thiamphenicolum; D-Thiocymetin; D-Thiophenicol; Thiocymetin (TN); Armai (TN); Thiocymetin; Tiamfenicolo [DCIT]; UNII-FLQ7571NPM; Tiamfenicol [INN-Spanish]; Thiamphenicol (Thiophenicol); Macphenicol; C12H15Cl2NO5S; Urfamycine; Igralin; Hyrazin; Dexawin; Rincrol; Neomyson; Urfamicina; Thiamphenicolum [INN-Latin]; Descocin; Masatirin; Efnicol; SW 5063; Unaseran-D; Thiamphenicol [USAN:INN:BAN:JAN]; EINECS 239-355-3; RACEPHENICOL; WIN-5063-2

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

356.2

Topological Polar Surface Area (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 120.3075 micromolar/kg/day [2]

Chemical Identifiers

Formula: C12H15Cl2NO5S
IUPAC Name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
Canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChI: InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1
InChIKey: OTVAEFIXJLOWRX-NXEZZACHSA-N

Cross-matching ID

PubChem CID: 27200
ChEBI ID: CHEBI:32215
CAS Number: 15318-45-3
DrugBank ID: DB08621
TTD ID: D03YLZ
VARIDT ID: DR01326

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 23S ribosomal RNA (Bact 23S rRNA)	TTLFGBV	NOUNIPROTAC	Modulator	[3]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
3	The fused TrpEG from Streptomyces venezuelae is an anthranilate synthase, not a 2-amino-2-deoxyisochorismate [corrected] (ADIC) synthase. Ethn Dis. 2008 Spring;18(2 Suppl 2):S2-9-13.
4	Active Mediated Transport of Chloramphenicol and Thiamphenicol in a Calu-3 Lung Epithelial Cell Model. J Pharm Sci. 2018 Apr;107(4):1178-1184.
5	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
6	MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
7	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
8	Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
9	Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
10	Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
11	Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
12	Company report (JMI Laboratories)
13	Inhibition of peptide bond formation by pleuromutilins: the structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin. Mol Microbiol. 2004 Dec;54(5):1287-94.
14	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
15	Genome sequencing of linezolid-resistant Streptococcus pneumoniae mutants reveals novel mechanisms of resistance. Genome Res. 2009 Jul;19(7):1214-23.
16	The apicoplast as an antimalarial drug target. Drug Resist Updat. 2001 Jun;4(3):145-51.
17	Has nature already identified all useful antibacterial targets Curr Opin Microbiol. 2008 Oct;11(5):387-92.
18	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
19	Ribosomal RNA is the target for oxazolidinones, a novel class of translational inhibitors. RNA. 1999 Jul;5(7):939-46.
20	EDP-420, a Bicyclolide (Bridged Bicyclic Macrolide), Is Active against Mycobacterium avium. Antimicrob Agents Chemother. 2007 May; 51(5): 1666-1670.